The best movies of 1999 stand out for their unforgettable stories, superb performances, and influential impact on the film industry. This list was created based on crowd voting by thousands of movie fans, ensuring that the favorites truly reflect popular opinion. The criteria focus on movies released in theaters in 1999, showcasing iconic flicks from various genres that have left a lasting impression on audience members.
Notable mentions include genre-defining movies like The Matrix, which captivated viewers with groundbreaking special effects, and Fight Club, which delved into the psyche of disenchanted young men. The Sixth Sense shocked audiences with its twist ending, while comedies such as American Pie and Office Space provided laughter and commentary on teenage life and corporate drudgery. Toy Story 2 continued to warm hearts with the adventures of Woody and Buzz, and The Blair Witch Project innovated horror with its found-footage style.
Each movie on this list brings something unique. The Green Mile, starring Tom Hanks and Michael Clarke Duncan, moved viewers with its themes of justice and redemption. The Mummy, a blend of adventure and horror featuring Brendan Fraser, revived interest in ancient Egypt while entertaining with thrilling escapades. Being John Malkovich fascinated with its surreal take on identity, whereas Election offered a satirical look into high school politics. These good films that came out in 1999 differ not just in genre but in the way they push cinematic boundaries and invoke thought-provoking themes.
Dive into this list and vote for your favorites. Whether it's the action-packed sequences or heartwarming stories that resonate with you, casting your vote helps future viewers discover these gems. Rediscover the top movies from 1999 and help elevate the ones that made an impression on you.
- 1
An innovative blend of science fiction and action, The Matrix is a groundbreaking film that redefined genre cinema in 1999. Directed by Lana and Lilly Wachowski, this mind-bending story follows Neo (Keanu Reeves) as he uncovers the truth behind the simulated reality he inhabits - known as the Matrix - while leading a rebellion against oppressive machines controlling humanity. Boasting cutting-edge visual effects such as "bullet time" and providing thought-provoking philosophical concepts about existence itself, The Matrix has become a cornerstone of modern filmmaking revered by critics and fans alike.
- Released: 1999
- Directed by: Lilly Wachowski, Lana Wachowski
- 1Morpheus236 Votes
- 2Neo273 Votes
- 3Agent Smith292 Votes
- 4Trinity151 Votes
- 2
Fight Club, a distinct and powerful film directed by David Fincher, premiered in 1999 to widespread acclaim. Based on Chuck Palahniuk's novel of the same name, the movie stars Brad Pitt and Edward Norton as two disillusioned men who form an underground fighting club as an aggressive form of male bonding and emancipation from societal norms. The film's themes of consumerism, masculinity, and self-destruction are expertly woven into its provocative narrative, making it one of the standout movies of 1999. With its shocking twist ending, superb performances from its cast, and relentless pacing, Fight Club remains a must-watch for cinephiles worldwide.
- Released: 1999
- Directed by: David Fincher
- 3
Renowned for its shocking twist ending, M. Night Shyamalan's The Sixth Sense is a supernatural thriller that captivated audiences in 1999 with its chilling atmosphere and exceptional performances. Starring Bruce Willis as child psychologist Dr. Malcolm Crowe and Haley Joel Osment as troubled young Cole Sear, the film follows their attempts to uncover the cause of Cole's terrifying visions of deceased individuals. Showcasing deft direction, masterful storytelling, and captivating cinematography, The Sixth Sense remains an influential piece of modern cinema that keeps viewers guessing until its unforgettable conclusion.
- Released: 1999
- Directed by: M. Night Shyamalan
- 4
Based on Stephen King's bestselling novel and directed by Frank Darabont in 1999, The Green Mile is an emotionally powerful drama that examines themes such as redemption and sacrifice via extraordinary events at a Louisiana death row prison during the Great Depression. Tom Hanks stars as compassionate prison guard Paul Edgecomb who forms an unlikely bond with gentle giant inmate John Coffey (Michael Clarke Duncan), whose miraculous healing powers have profound consequences for those around him. Featuring stellar performances from its ensemble cast—including Oscar-nominated turns by Hanks and Duncan—The Green Mile is essential viewing for those seeking a poignant and engaging cinematic experience.
- Released: 1999
- Directed by: Frank Darabont
- 5
Bringing swashbuckling adventure and horror together in a thrilling package, Stephen Sommers' 1999 film The Mummy reinvigorated interest in Egyptology while delivering heart-pounding action sequences alongside chilling supernatural scares. Brendan Fraser stars as daring adventurer Rick O'Connell who, along with librarian Evelyn Carnahan (Rachel Weisz) and her brother Jonathan (John Hannah), inadvertently awakens ancient Egyptian priest Imhotep (Arnold Vosloo) from his cursed slumber leading to dire consequences for all involved. Encompassing romance, humor, and classic monster movie elements, The Mummy remains a beloved fan-favorite among action-adventure enthusiasts nearly two decades after its release.
- Released: 1999
- Directed by: Stephen Sommers
- 6
Office Space is a hilarious cult classic comedy directed by Mike Judge that delves into the soul-crushing monotony of corporate life through the eyes of beleaguered software engineer Peter Gibbons (Ron Livingston). Released in 1999, this witty satire lampoons office culture with relatable characters such as cubicle-dwelling everyman Milton Waddams (Stephen Root) and overbearing boss Bill Lumbergh (Gary Cole), showcasing the absurdity inherent within the daily grind for many employees worldwide. With its biting commentary on workplace frustrations and memorable quotes, Office Space endures as a compelling examination of the human condition within modern corporate America.
- Released: 1999
- Directed by: Mike Judge
- 1Ron Livingston20 Votes
- 2Stephen Root17 Votes
- 3Gary Cole13 Votes
- 4John C. McGinley10 Votes
- 7
Sam Mendes' directorial debut American Beauty is a powerful exploration of suburban ennui that earned five Academy Awards in 2000, including Best Picture. Kevin Spacey stars as Lester Burnham—a disillusioned advertising executive at the center of this darkly comedic family drama—who becomes infatuated with his teenage daughter's best friend (Mena Suvari) while simultaneously struggling with his crumbling marriage (Annette Bening). Showcasing masterful writing by Alan Ball and stellar performances from its ensemble cast, American Beauty expertly dissects themes such as materialism, self-discovery, and societal expectations amid a seemingly idyllic suburban landscape.
- Released: 1999
- Directed by: Sam Mendes
- 8
A quintessential coming-of-age comedy, American Pie burst onto screens in 1999 with its raunchy humor and endearing portrayal of teenage friendship. Directed by brothers Paul and Chris Weitz, this crowd-pleasing tale follows a group of high school friends—played by Jason Biggs, Chris Klein, Thomas Ian Nicholas, Eddie Kaye Thomas, and Seann William Scott—as they make a pact to lose their virginity on prom night. Featuring memorable scenes involving warm apple pastries and uproarious one-liners from characters such as Jim's Dad (Eugene Levy), American Pie has become a beloved classic within the teen-comedy genre.
- Released: 1999
- Directed by: Paul Weitz
- 9
Tim Burton's 1999 film adaptation of Washington Irving's classic tale The Legend of Sleepy Hollow, Sleepy Hollow stars Johnny Depp as Ichabod Crane, a New York City constable sent to investigate mysterious beheadings in the eponymous small town. With its atmospheric visuals, macabre Gothic aesthetic, and grisly horror sequences featuring Christopher Walken as the dreaded Headless Horseman, this stylish production is a delightfully spooky ride for fans of supernatural thrillers. Boasting unforgettable set designs and captivating performances from its ensemble cast—including Christina Ricci as love interest Katrina Van Tassel—Sleepy Hollow demonstrates why it ranks among Tim Burton’s most beloved cinematic endeavors.
- Released: 1999
- Directed by: Tim Burton
- 10
A modern-day retelling of William Shakespeare's The Taming of the Shrew, the 1999 romantic comedy 10 Things I Hate About You stars Julia Stiles, Heath Ledger, Joseph Gordon-Levitt, and Larisa Oleynik in a charming tale of teenage relationships and high school politics. Directed by Gil Junger, this delightful film features witty dialogue, appealing performances from its young cast, and an infectious soundtrack that resonated with audiences during its release. With Ledger's memorable rendition of "Can't Take My Eyes Off You" and Stiles' poignant delivery of her titular poem, 10 Things I Hate About You remains an enduring classic for fans of '90s cinema.
- Released: 1999
- Directed by: Gil Junger
- 1Jason Bateman - Walter Stratford130 Votes
- 2Dulé Hill - Mr. Morgan98 Votes
- 3Sam Rockwell - Mr. Chapin101 Votes
- 4Hailee Steinfeld - Mandella102 Votes
- 11
The Iron Giant premiered in 1999 to widespread acclaim for its heartwarming story about friendship between young Hogarth Hughes (Eli Marienthal) and an extraterrestrial robot who crash-lands near his small Maine town amid Cold War tensions. Directed by Brad Bird before his subsequent work on Pixar classics such as The Incredibles and Ratatouille, this animated film boasts a touching narrative, impressive visuals, and memorable voice performances from talents like Jennifer Aniston, Harry Connick Jr., and Vin Diesel. Earning praise for its themes of empathy, acceptance, and the importance of choosing one's path in life, The Iron Giant remains an enduring family favorite.
- Released: 1999
- Directed by: Brad Bird
- 12
In 1999, audiences were once again treated to the groovy exploits of British secret agent Austin Powers in Austin Powers: The Spy Who Shagged Me. Directed by Jay Roach and starring Mike Myers in multiple roles—including both titular character Austin and his nemesis Dr. Evil—this uproarious sequel continues the madcap adventures of everyone's favorite swinging spy as he travels back in time to recover his stolen mojo. With quotable lines, outrageous costumes, and unforgettable characters such as Mini-Me (Verne Troyer) and Felicity Shagwell (Heather Graham), this comedy sequel remains a beloved entry in the Austin Powers franchise.
- Released: 1999
- Directed by: Jay Roach
- 13
Galaxy Quest is a sci-fi comedy released in 1999 that lovingly parodies popular television series like Star Trek while maintaining its unique identity as an entertaining standalone film. Directed by Dean Parisot and featuring an ensemble cast including Tim Allen, Sigourney Weaver, Alan Rickman, Tony Shalhoub, Sam Rockwell, and Daryl Mitchell, this delightful romp follows former television space opera actors who are whisked away by aliens seeking their assistance against a deadly threat. Packed with witty humor, thrilling action sequences, and affectionate nods to genre tropes, Galaxy Quest has become a cult classic among fans of science fiction cinema.
- Released: 1999
- Directed by: Dean Parisot
- 14
Based on Patricia Highsmith's novel, The Talented Mr. Ripley is a psychological thriller released in 1999 that features exceptional performances from its star-studded cast including Matt Damon, Jude Law, Gwyneth Paltrow, Cate Blanchett, and Philip Seymour Hoffman. Directed by Anthony Minghella, this tense narrative follows the exploits of enigmatic Tom Ripley (Damon) as he becomes entangled in the lives of wealthy expatriates Dickie Greenleaf (Law) and his girlfriend Marge Sherwood (Paltrow) in 1950s Italy—leading to disastrous consequences for all involved. With its lush cinematography capturing picturesque settings and remarkable acting conveying nuanced characterizations, The Talented Mr. Ripley remains a gripping tale about ambition, obsession, and deception.
- Released: 1999
- Directed by: Anthony Minghella
- 15
Cruel Intentions is a deliciously dark teen drama released in 1999, loosely based on Pierre Choderlos de Laclos' novel Les Liaisons dangereuses. Directed by Roger Kumble and starring Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, and Selma Blair in career-defining roles, this sensual tale explores themes such as betrayal, manipulation, and self-discovery amid a backdrop of decadent New York City high society. Featuring sumptuous cinematography and a seductive soundtrack boasting hits such as The Verve's "Bitter Sweet Symphony," Cruel Intentions offers viewers a titillating glimpse into the twisted machinations of privileged adolescence.
- Released: 1999
- Directed by: Roger Kumble
- 16
From the irreverent minds behind the popular animated television series South Park comes South Park: Bigger, Longer & Uncut—a raunchy musical extravaganza that pushes boundaries with its biting satire and controversial humor. Released in 1999, this film co-directed by Trey Parker and Matt Stone sees the titular Colorado town embroiled in a dangerous conflict with Canada after parents blame their neighbors to the north for their children's exposure to profanity-laden entertainment. Featuring an Academy Award-nominated song ("Blame Canada") and a plethora of memorable musical numbers such as "Uncle F**ka" and "Kyle's Mom's a B***h," South Park: Bigger, Longer & Uncut remains an audacious achievement in animated satire.
- Released: 1999
- Directed by: Trey Parker
- 17
Spike Jonze's 1999 directorial debut Being John Malkovich is a surreal exploration of identity that introduced audiences to one of the most inventive cinematic minds in recent memory. Written by Charlie Kaufman, this mind-bending tale stars John Cusack as puppeteer Craig Schwartz who stumbles upon a portal leading into the mind of actor John Malkovich (playing himself), allowing individuals to inhabit his consciousness for brief periods. As Schwartz exploits this discovery for personal gain alongside his manipulative co-worker (Catherine Keener) and wife (Cameron Diaz), Being John Malkovich offers viewers a kaleidoscope of existential concepts deftly woven into an engaging narrative.
- Released: 1999
- Directed by: Spike Jonze
- 18
Double Jeopardy is a suspenseful crime thriller directed by Bruce Beresford that premiered in 1999 to audience acclaim for its engaging plot twists and standout performances by Ashley Judd and Tommy Lee Jones. Judd stars as Libby Parsons—a woman framed for her husband's murder—who discovers he is still alive upon her release from prison and resolves to exact justice without fear of further legal repercussions due to the titular legal concept preventing her from being tried twice for the same crime. Showcasing atmospheric cinematography and a tense cat-and-mouse narrative, Double Jeopardy remains an enthralling cinematic experience that keeps viewers on their toes.
- Released: 1999
- Directed by: Bruce Beresford
- 19
In 1999 director Troy Duffy made his feature debut with The Boondock Saints—a gritty action-thriller that attained cult status for its stylish violence, dark humor, and unconventional storytelling. Starring Sean Patrick Flanery and Norman Reedus as two Irish brothers who embark on a vigilante mission to rid Boston of evil under the guidance of their religious beliefs, this film showcases memorable performances from Willem Dafoe as an eccentric FBI agent hot on their trail. With its catchy dialogue and unforgettable action sequences, The Boondock Saints remains a beloved fixture within the realm of crime cinema.
- Released: 1999
- Directed by: Troy Duffy
- 20
Kevin Smith's irreverent take on religious dogma and organized faith manifested itself in his controversial 1999 film Dogma—a comedy that explores complex theological concepts through humor without forsaking sincerity or thoughtfulness. Boasting an all-star cast including Ben Affleck, Matt Damon, Chris Rock, Salma Hayek, Jason Lee, Alan Rickman, Linda Fiorentino—and the director himself reprising his role as Silent Bob—Dogma pokes fun at conventional biblical lore while examining more profound ideas about belief systems and devotion. Despite inciting backlash from certain religious groups upon its release due to perceived blasphemy, Dogma endures as an influential examination into matters of faith within contemporary cinema.
- Released: 1999
- Directed by: Kevin Smith
- 21
Adam Sandler stars as the lovable but irresponsible Sonny Koufax in Big Daddy—a heartwarming comedy released in 1999 about an unlikely father-son bond forged through unexpected circumstances. Directed by Dennis Dugan and featuring supporting roles from Joey Lauren Adams, Jon Stewart, Rob Schneider, and Steve Buscemi, this film follows Sonny as he learns valuable life lessons while caring for abandoned five-year-old Julian (Cole and Dylan Sprouse). With its mix of slapstick humor and genuine emotion showcasing Sandler's versatility as a comedic actor, Big Daddy has resonated with audiences as a charming exploration of parenthood and personal growth.
- Released: 1999
- Directed by: Dennis Dugan
- 22
A unique blend of war film and heist thriller, Three Kings arrived in theaters in 1999 under the direction of David O. Russell—offering viewers an engaging look at the aftermath of the Persian Gulf War as four American soldiers (George Clooney, Mark Wahlberg, Ice Cube, and Spike Jonze) embark upon a risky mission to steal gold bullion hidden by Saddam Hussein's regime. With its distinctive visual style characterized by high-contrast color grading and whip-fast editing that adds to the film's frenetic pacing alongside memorable performances from its ensemble cast conveying the complexities inherent within wartime moral dilemmas—the movie stands out as one of Russell's most accomplished works during his early career.
- Released: 1999
- Directed by: David O. Russell
- 23
Based on Susanna Kaysen's eponymous memoir, Girl, Interrupted is a compelling drama released in 1999 that features standout performances from Winona Ryder and Angelina Jolie—who won her first Academy Award for her role as sociopath Lisa Rowe. Directed by James Mangold, this film explores themes such as mental illness, self-discovery, and personal growth through the eyes of Kaysen (Ryder) during her stay at a psychiatric hospital during the late 1960s. Showcasing powerful acting alongside poignant storytelling grounded in real-life experiences, Girl, Interrupted offers viewers an intimate glimpse into the often misunderstood world of mental health treatment.
- Released: 1999
- Directed by: James Mangold
- 24
Paul Thomas Anderson's sprawling ensemble drama Magnolia premiered in 1999 to critical acclaim for its interwoven narratives exploring themes such as forgiveness, redemption, love amid loss—all set during one rainy day within California's San Fernando Valley region. Boasting an incredible cast including Tom Cruise, Julianne Moore, Philip Seymour Hoffman, William H. Macy, John C. Reilly, and Jason Robards in his final role before passing away—Cruise received an Academy Award nomination for his portrayal of self-help guru Frank T.J. Mackey. With its poignant storytelling featuring emotionally charged scenes set to a captivating score by Jon Brion, Magnolia remains a powerful examination of human connections within the fabric of everyday life.
- Released: 1999
- Directed by: Paul Thomas Anderson
- 25
Stanley Kubrick's final film before his untimely passing in 1999, Eyes Wide Shut is a provocative drama that examines themes of sexual desire, infidelity, and societal decadence through the eyes of Dr. Bill Harford (Tom Cruise) following his wife Alice's (Nicole Kidman) revelation of an intimate fantasy involving another man. As Bill embarks upon a dangerous journey into New York City's elite underworld of secret societies and hedonistic pleasures, Kubrick explores the dark recesses of human nature with masterful precision while employing visually arresting cinematography set against a haunting musical score composed by Jocelyn Pook. A controversial and polarizing piece upon release, Eyes Wide Shut remains an enigmatic cinematic masterpiece that continues to generate discussion among scholars and cinephiles alike.
- Released: 1999
- Directed by: Stanley Kubrick
- 1Nicole Kidman17 Votes
- 2Leelee Sobieski17 Votes
- 3Tom Cruise17 Votes
- 4Sydney Pollack17 Votes
- 26
Directed by Phillip Noyce in 1999, The Bone Collector is an engrossing thriller starring Denzel Washington as quadriplegic forensics expert Lincoln Rhyme tasked with solving a series of grisly murders inspired by obscure crime novels alongside rookie cop Amelia Donaghy (Angelina Jolie). As they work together to decipher cryptic clues left at each crime scene while forging an unlikely bond amid harrowing circumstances, Washington and Jolie deliver top-notch performances punctuating the film's tension-fueled atmosphere. The Bone Collector remains an exciting entry within the crime-thriller genre for its captivating premise and skilled execution.
- Released: 1999
- Directed by: Phillip Noyce
- 27
Varsity Blues is a 1999 sports drama directed by Brian Robbins that delves into the world of high school football culture within small-town Texas amid intense pressure for players to achieve success on the field at any cost. Starring James Van Der Beek as Jonathan "Mox" Moxon—a backup quarterback thrust into the spotlight following an injury to the team's star player—the film examines themes such as loyalty, courage under adversity, and the importance of maintaining integrity amid conflicting influences. With memorable performances from actors like Jon Voight and Paul Walker, Varsity Blues resonates with audiences as a compelling portrayal of contemporary American sports culture.
- Released: 1999
- Directed by: Brian Robbins
- 28After seeking the expertise of former "Big Tobacco" executive Jeffrey Wigand (Russell Crowe), seasoned TV producer Lowell Bergman (Al Pacino) suspects a story lies behind Wigand's reluctance to speak. As Bergman persuades Wigand to share his knowledge of industry secrets, the two must contend with the courts and the corporations that stand between them and exposing the truth. All the while, Wigand must struggle to maintain his family life amidst lawsuits and death threats.
- Released: 1999
- Directed by: Michael Mann
- 29
Payback is a gritty crime-thriller directed by Brian Helgeland that hit theaters in 1999 starring Mel Gibson as Porter—an anti-hero seeking vengeance against his former partner-in-crime Val Resnick (Gregg Henry) and crime syndicate boss Bronson (Kris Kristofferson) after they betray him during a heist gone awry. With shades of film noir permeating its dark atmosphere alongside sharp dialogue and brutal action sequences, Payback offers viewers an unrelenting tale of revenge featuring standout performances from Gibson as well as supporting roles played by Maria Bello, David Paymer, Bill Duke, and Lucy Liu.
- Released: 1999
- Directed by: Brian Helgeland
- 30
Disney's animated adaptation of Edgar Rice Burroughs' iconic character Tarzan premiered in 1999 to widespread acclaim for its stunning visual effects—particularly regarding fluid character motion achieved via groundbreaking computer-generated imagery combined with traditional hand-drawn animation techniques under directors Chris Buck and Kevin Lima. Featuring memorable songs by Phil Collins—including the Academy Award-winning "You'll Be in My Heart"—this heartwarming tale chronicles Tarzan's journey from orphaned infant raised by gorillas within the African jungle to discovering his true heritage as an English nobleman while navigating relationships with newfound love interest Jane Porter (voiced by Minnie Driver) and protective gorilla mother Kala (Glenn Close). With its rousing narrative, engaging characters, and breathtaking visuals set amidst lush jungle environments, Tarzan remains a beloved entry within Disney's animated canon.
- Released: 1999
- Directed by: Chris Buck, Kevin Lima
- 31
The Blair Witch Project is a revolutionary found-footage horror film that debuted in 1999 under the direction of Daniel Myrick and Eduardo Sánchez—contributing to the rise of viral marketing campaigns while leaving audiences terrified upon release due to its ambiguously authentic nature. Presented as a documentary-style account of three student filmmakers lost within Maryland's Black Hills Forest while investigating local legends surrounding purported supernatural occurrences involving a malevolent witch figure, this low-budget production capitalized on its unsettling atmosphere achieved through minimalistic techniques such as handheld camera work and improvised dialogue among its cast. The Blair Witch Project remains a landmark achievement within independent cinema that spawned countless imitations thanks to its innovative approach to storytelling.
- Released: 1999
- Directed by: Daniel Myrick, Eduardo Sánchez
- 32
Deep Blue Sea is a thrilling shark-infested action-horror film released in 1999 under the direction of Renny Harlin. The movie stars Saffron Burrows, Thomas Jane, LL Cool J, Michael Rapaport, Stellan Skarsgård, and Samuel L. Jackson as a team of researchers stationed at an underwater facility who find themselves fighting for their lives when their experiments on genetically enhanced mako sharks take a catastrophic turn. Featuring intense action sequences bolstered by innovative animatronics and CGI effects for its time—as well as memorable scenes such as Jackson's shocking mid-speech demise—Deep Blue Sea remains a suspenseful cinematic experience for fans of shark-infested mayhem.
- Released: 1999
- Directed by: Renny Harlin
- 33Four years ago, DAmato's (Al Pacino) Miami Sharks were at the top. Now, his team is struggling with three consecutive losses, sliding attendance, and aging heroes, particularly 39-year-old quarterback Jack "Cap" Rooney (Dennis Quaid). Off the field, DAmato is struggling with a failed marriage and estranged children, and is on a collision course with Christina Pagniacci (Cameron Diaz), the young president/co-owner of the Sharks organization.
- Released: 1999
- Directed by: Oliver Stone
- 34
Inspired by the true story of NASA engineer Homer Hickam, October Sky is a heartwarming drama released in 1999 that chronicles one young man's pursuit of his dream to become a rocket scientist despite facing seemingly insurmountable odds growing up in rural West Virginia amid socioeconomic hardship. Directed by Joe Johnston and starring Jake Gyllenhaal, Chris Cooper, Laura Dern, and Chris Owen, this uplifting tale showcases themes such as perseverance, self-determination, and the importance of supportive educators as it follows Hickam's journey from aspiring miner to accomplished aerospace engineer thanks to his unwavering passion for knowledge. Featuring stellar performances and an inspiring narrative grounded in real-life events, October Sky stands as a testament to the power of dreams and determination.
- Released: 1999
- Directed by: Joe Johnston
- 35
The Hurricane is a biographical sports drama directed by Norman Jewison in 1999 that tells the inspiring true story of Rubin "Hurricane" Carter—the professional boxer wrongfully convicted of triple homicide in 1966—and his subsequent quest for justice amidst racial prejudice and judicial corruption. Denzel Washington delivers a powerhouse performance as Carter which earned him an Academy Award nomination for Best Actor while showcasing themes such as perseverance against adversity, the impact of grassroots activism led by supporters Lesra Martin (Vicellous Reon Shannon) and Sam Chaiton (Liev Schreiber), and the transformative power of forgiveness within a flawed legal system.
- Released: 1999
- Directed by: Norman Jewison
- 36
Milos Forman directed this compelling biopic Man on the Moon in 1999 which delves into the enigmatic life and career of legendary comedic performer Andy Kaufman through an extraordinary portrayal by Jim Carrey that garnered critical acclaim for its uncanny accuracy. Chronicling Kaufman's breakthrough as Latka Gravas on television sitcom Taxi alongside his controversial wrestling antics and mysterious behavior that blurred the lines between reality and performance art, Man on the Moon offers viewers an intimate look at one of entertainment's most intriguing figures while questioning conventional notions surrounding fame and artistic integrity within popular culture.
- Released: 1999
- Directed by: Milos Forman
- 37Obi-Wan Kenobi (Ewan McGregor) is a young apprentice Jedi knight under the tutelage of Qui-Gon Jinn (Liam Neeson) ; Anakin Skywalker (Jake Lloyd), who will later father Luke Skywalker and become known as Darth Vader, is just a 9-year-old boy. When the Trade Federation cuts off all routes to the planet Naboo, Qui-Gon and Obi-Wan are assigned to settle the matter.
- Released: 1999
- Directed by: George Lucas
- 38
A delightful fusion of mobster movie tropes and comedic elements, Analyze This premiered in 1999 under director Harold Ramis as an entertaining romp featuring standout performances from Robert De Niro as mafia boss Paul Vitti who seeks therapy from mild-mannered psychiatrist Ben Sobol (Billy Crystal) to address his newly discovered anxiety issues. With its amusing premise offering a fresh take on the gangster film genre alongside sharp dialogue that highlights the comedic chemistry between De Niro and Crystal, Analyze This struck a chord with audiences and critics alike—proving itself a memorable entry within both actors' esteemed careers.
- Released: 1999
- Directed by: Harold Ramis
- 39
Alexander Payne's satirical comedy Election hit theaters in 1999, offering a biting look at high school politics and personal ambition through the eyes of ambitious overachiever Tracy Flick (Reese Witherspoon) as she vies for student body president against affable underdog Paul Metzler (Chris Klein) under the watchful eye of disillusioned teacher Jim McAllister (Matthew Broderick). With its razor-sharp screenplay, well-developed characters, and standout performances—particularly from Witherspoon in her breakout role—Election provided audiences with a hilarious glimpse into the cutthroat world of adolescent power struggles while proving itself a timeless classic within the genre.
- Released: 1999
- Directed by: Alexander Payne
- 40
In 1999, director John McTiernan helmed this stylish remake of the 1968 film The Thomas Crown Affair—starring Pierce Brosnan as debonair billionaire and art thief Thomas Crown alongside Rene Russo as cunning insurance investigator Catherine Banning. As these two formidable adversaries engage in a high-stakes cat-and-mouse game filled with thrilling heist sequences, luxurious settings, and undeniable chemistry that culminates in a passionate romance—the movie offers viewers an enticing blend of suspense, glamour, and intrigue that has since solidified its place among classic caper films.
- Released: 1999
- Directed by: John McTiernan
- 41
The Ninth Gate is a supernatural thriller directed by Roman Polanski that premiered in 1999 starring Johnny Depp as rare book dealer Dean Corso, who becomes embroiled in a dangerous quest to locate the titular demonic tome capable of summoning Satan himself. As Corso travels throughout Europe while encountering mysterious figures both human and otherworldly, The Ninth Gate showcases atmospheric cinematography that evokes classic horror cinema aesthetics through its shadowy visuals and eerie score composed by Wojciech Kilar. Though polarizing among audiences upon release due to its slow-burning narrative and unconventional conclusion, The Ninth Gate remains an intriguing entry within the realm of occult-themed cinema for viewers seeking a more cerebral exploration into matters of sacred texts and arcane knowledge.
- Released: 1999
- Directed by: Roman Polanski
- 42
Sofia Coppola's directorial debut The Virgin Suicides premiered in 1999, offering a haunting exploration of adolescence and suburban ennui through the eyes of five teenage sisters who succumb to inexplicable acts of self-destruction amid a seemingly idyllic environment. Based on Jeffrey Eugenides' novel and starring Kirsten Dunst, James Woods, Kathleen Turner, and Josh Hartnett among its talented cast, this ethereal drama features evocative cinematography that captures the dreamlike quality of its narrative alongside a mesmerizing score by French duo Air—contributing to an overall atmosphere of melancholic beauty that has resonated with audiences for decades.
- Released: 1999
- Directed by: Sofia Coppola
- 43With the millennium approaching, a series of disturbing signs suggests that Satan (Arnold Schwarzenegger) has returned to Earth and is walking the streets of New York City. It seems that Satan needs to find a woman who will bear his child, as the time for the arrival of the anti-Christ draws near.
- Released: 1999
- Directed by: Peter Hyams
- 44
Boys Don't Cry is a powerful drama based on the real-life story of Brandon Teena—a transgender man who was brutally murdered in Nebraska during December 1993 after his biological gender was revealed to acquaintances. Directed by Kimberly Peirce, this 1999 film features a career-defining performance by Hilary Swank in her Academy Award-winning role as Teena alongside strong supporting turns from Chloë Sevigny and Peter Sarsgaard. With its unflinching portrayal of violence against transgender individuals rooted in ignorance and prejudice, Boys Don't Cry offers an important glimpse into the struggles faced by those who defy societal norms in search of acceptance and love.
- Released: 1999
- Directed by: Kimberly Peirce
- 45
Kevin Bacon stars in Stir of Echoes—a chilling supernatural thriller directed by David Koepp in 1999 about a blue-collar worker who becomes haunted by terrifying visions following an ill-fated hypnosis session that unlocks his latent psychic abilities. As Tom Witzky (Bacon) delves deeper into the mystery surrounding his newfound gift while navigating his crumbling marriage and friendships amid increasingly disturbing encounters with malevolent forces—this film provides audiences with a gripping narrative filled with unexpected twists and expertly crafted scares that will keep them on the edge of their seats until its shocking conclusion.
- Released: 1999
- Directed by: David Koepp
- 46A Muslim ambassador exiled from his homeland, Ahmad ibn Fadlan (Antonio Banderas) finds himself in the company of Vikings. While the behavior of the Norsemen initially offends ibn Fadlan, the more cultured outsider grows to respect the tough, if uncouth, warriors. During their travels together, ibn Fadlan and the Vikings get word of an evil presence closing in, and they must fight the frightening and formidable force, which was previously thought to exist only in legend.
- Released: 1999
- Directed by: Michael Crichton, John McTiernan
- 47
Released in 1999, Entrapment is a suspenseful heist film directed by Jon Amiel that stars Sean Connery and Catherine Zeta-Jones as skilled thieves who become embroiled in a dangerous partnership while attempting to pull off the ultimate crime. With its exotic locations, thrilling action sequences—including an unforgettable laser-dodging scene—and palpable chemistry between its two charismatic leads, this movie offers audiences an exciting ride filled with twists and turns that keep viewers guessing until the final reveal. Despite receiving mixed reviews upon release, Entrapment has since garnered appreciation for its entertaining blend of romance and intrigue within the realm of high-stakes art theft.
- Released: 1999
- Directed by: Jon Amiel
- 48
Released in 1999, Blast from the Past is a charming romantic comedy directed by Hugh Wilson that offers a humorous look at culture shock and adapting to new surroundings when faced with unfamiliar experiences. Starring Brendan Fraser as Adam Webber—a young man who has spent his entire life living in an underground fallout shelter built by his paranoid father (Christopher Walken) during the height of Cold War panic—he emerges into present-day Los Angeles seeking supplies and unwittingly falls for quirky antique store owner Eve (Alicia Silverstone). With delightful performances from Fraser and Silverstone alongside an amusing premise exploring societal norms through fresh eyes, Blast from the Past is a lighthearted cinematic treat.
- Released: 1999
- Directed by: Hugh Wilson
- 49
Based on John Irving's novel and directed by Lasse Hallström in 1999, The Cider House Rules is a coming-of-age drama set during World War II that garnered critical acclaim for its sensitive exploration of complex themes such as self-discovery, love amid adversity, and moral ambiguity. Tobey Maguire stars as Homer Wells—an orphan raised within a rural Maine hospital who embarks upon his own path after forming a bond with a young couple (Charlize Theron and Paul Rudd)—while learning valuable life lessons from the institution's compassionate head doctor (Michael Caine) who imparts wisdom regarding the titular rules of the cider house. With its evocative storytelling, moving performances—Caine earned an Academy Award for his role—and picturesque cinematography that captures the beauty of its New England setting, The Cider House Rules remains a thought-provoking entry within contemporary cinema.
- Released: 1999
- Directed by: Lasse Hallström
- 50Private detective Tom Welles (Nicolas Cage) lives a normal life with his wife (Catherine Keener) and young daughter, until he receives a startling new case. A widow named Mrs. Christian (Myra Carter) has found what appears to be a snuff film among her late husband's belongings, and she wants Welles to determine if the movie is real or fake. Welles heads to California, where a video store employee (Joaquin Phoenix) helps him infiltrate the dangerous and depraved world of illegal porn movies.
- Released: 1999
- Directed by: Joel Schumacher
- 51When the body of Army Capt. Elizabeth Campbell (Leslie Stefanson) is found on a Georgia military base, two investigators, Warrant Officers Paul Brenner (John Travolta) and Sara Sunhill (Madeleine Stowe), are ordered to solve her murder. What they uncover is anything but clear-cut. Unseemly details emerge about Campbell's life, leading to allegations of a possible military coverup of her death and the involvement of her father, Lt. Gen. Joseph Campbell (James Cromwell).
- Released: 1999
- Directed by: Simon West
- 52
Adapted from E.B. White's beloved children's book, Stuart Little is a family-friendly adventure released in 1999 under director Rob Minkoff that tells the heartwarming tale of a charming anthropomorphic mouse (voiced by Michael J. Fox) who is adopted by a human family to join siblings George (Jonathan Lipnicki) and Martha Little (Anna Hoelck). Featuring state-of-the-art CGI effects for its time which brought Stuart to life alongside live-action co-stars Geena Davis and Hugh Laurie as well as impeccable voice talent including Nathan Lane as Snowbell the cat—this delightful romp offers viewers young and old alike an entertaining journey filled with fun, laughter, and valuable life lessons about acceptance, love, and the importance of family.
In the family-friendly adventure film, Stuart Little, a charming mouse named Stuart (voiced by Michael J. Fox) is adopted from an orphanage by the Little family. The parents, Mr. and Mrs. Little (Hugh Laurie and Geena Davis), treat him as their son, much to the chagrin of the family cat, Snowbell (Nathan Lane). As Stuart navigates life in a human world, he encounters various thrilling escapades that test his courage and wit. This film weaves elements of comedy, drama, and action into a heartwarming tale of acceptance and love; it's a delightful romp with memorable characters that young audiences will cherish.- Released: 1999
- Directed by: Rob Minkoff
- 53William Thacker (Hugh Grant) is a London bookstore owner whose humdrum existence is thrown into romantic turmoil when famous American actress Anna Scott (Julia Roberts) appears in his shop. A chance encounter over spilled orange juice leads to a kiss that blossoms into a full-blown affair. As the average bloke and glamorous movie star draw closer and closer together, they struggle to reconcile their radically different lifestyles in the name of love.
- Released: 1999
- Directed by: Roger Michell
- 1Julia Roberts7 Votes
- 2Hugh Grant7 Votes
- 3Hugh Bonneville8 Votes
- 4Emma Chambers5 Votes
- 54
In 1999, director Kinka Usher brought a new breed of superhero to the big screen with Mystery Men—a quirky comedy based on Bob Burden's comic book series starring Ben Stiller, Janeane Garofalo, Hank Azaria, William H. Macy, and Paul Reubens as an eclectic group of would-be crimefighters who must save their city from nefarious villain Casanova Frankenstein (Geoffrey Rush). Showcasing inventive visual effects, colorful characters with unique abilities such as "Furious" (Stiller), who channels his anger into fighting prowess and "The Shoveler" (Macy), who wields shovels like martial arts weapons—this film offers viewers an offbeat alternative to traditional superhero fare while providing plenty of laughs along the way.
- Released: 1999
- Directed by: Kinka Usher
- 55
A tongue-in-cheek homage to classic monster movies, Lake Placid debuted in 1999 as an entertaining creature-feature directed by Steve Miner that pits humans against nature in the form of a giant crocodile lurking within an idyllic Maine lake. Starring Bill Pullman, Bridget Fonda, Oliver Platt, Brendan Gleeson, and Betty White among its eclectic cast, this thrilling romp balances humor and horror while showcasing impressive special effects for its time. Despite receiving mixed reviews upon release due in part to its intentionally campy tone, Lake Placid has since gained cult status among fans who appreciate its cheeky approach to the genre.
- Released: 1999
- Directed by: Steve Miner
- 56Widowed when his FBI agent wife is killed by an extremist group, college professor Michael Faraday (Jeff Bridges) becomes obsessed with the culture of these groups -- especially when his new all-American neighbors, Oliver (Tim Robbins) and Cheryl Lang (Joan Cusack), start acting suspiciously. With each twist, the mystery deepens and questions loom as to whether Faraday is consumed by fear and driven by paranoia, or whether a lethal conspiracy has been born on Arlington Road.
- Released: 1999
- Directed by: Mark Pellington
- 57
She's All That is a delightful romantic comedy directed by Robert Iscove that captured the hearts of audiences in 1999. Starring Freddie Prinze Jr., Rachael Leigh Cook, Paul Walker, and Matthew Lillard, this modern-day Pygmalion retelling follows popular high school jock Zack Siler (Prinze Jr.) as he attempts to transform artsy outsider Laney Boggs (Cook) into prom queen material through an ill-conceived bet with fellow classmates. Boasting an infectious '90s soundtrack and memorable dance sequences choreographed by Fatima Robinson alongside endearing performances from its talented cast, She's All That remains a beloved staple for fans of teen romantic comedies.
- Released: 1999
- Directed by: Robert Iscove
- 58
Never Been Kissed is a charming romantic comedy directed by Raja Gosnell that debuted in 1999 starring Drew Barrymore as socially awkward journalist Josie Geller who goes undercover at her former high school to research teenage culture while grappling with unresolved insecurities from her own adolescence. As Josie navigates the choppy waters of popularity and unrequited love alongside unlikely allies such as her brother Rob (David Arquette) and dashing English teacher Sam Coulson (Michael Vartan), this heartwarming tale resonated with audiences through its depiction of relatable characters seeking acceptance amid life's trials and tribulations—ultimately proving itself a classic within the '90s teen comedy genre.
- Released: 1999
- Directed by: Raja Gosnell
- 59Bond (Pierce Brosnan) must race to defuse an international power struggle with the world's oil supply hanging in the balance. Elektra King (Sophie Marceau), is the daughter of a murdered oil tycoon whom Bond is assigned to protect. The villain is Renard (Robert Carlyle), who has a bullet lodged in his brain rendering him unable to feel pain. Also featuring nuclear weapons expert Dr. Christmas Jones (Denise Richards).
- Released: 1999
- Directed by: Michael Apted
- 60Grocery store clerk Simon (Desmond Askew) occasionally sells drugs from his cash register at work, so when soap opera actors Adam (Scott Wolf) and Zack (Jay Mohr) come looking for Ecstasy on a quiet Christmas Eve, they are surprised to find Ronna (Sarah Polley) covering his shift. Desperate for money, Ronna decides to become an impromptu drug dealer, unaware that Adam and Zack are secretly working for obsessed narcotics officer Burke (William Fichtner).
- Released: 1999
- Directed by: Doug Liman
- 61Deuce Bigalow (Rob Schneider) is a less than attractive, down on his luck aquarium cleaner. One day he wrecks the house of a gigolo and needs quick money to repair it. The only way he can make it is to become a gigolo himself, taking on an unusual mix of female clients. He encounters a couple of problems, though. He falls in love with one of his unusual clients, and a sleazy police officer is hot on his trail.
- Released: 1999
- Directed by: Mike Mitchell
- 62A retired farmer and widower in his 70s, Alvin Straight (Richard Farnsworth) learns one day that his distant brother Lyle (Harry Dean Stanton) has suffered a stroke and may not recover. Alvin is determined to make things right with Lyle while he still can, but his brother lives in Wisconsin, while Alvin is stuck in Iowa with no car and no driver's license. Then he hits on the idea of making the trip on his old lawnmower, thus beginning a picturesque and at times deeply spiritual odyssey.
- Released: 1999
- Directed by: David Lynch
- 63During the summer of 1977, a killer known as the Son of Sam keeps all of New York City on edge with a series of brutal murders. The philandering Vinny (John Leguizamo) unwittingly almost becomes a victim of the psychopath, and soon he and numerous people in his orbit -- including his wife, Dionna (Mira Sorvino), his punk-rocker friend, Ritchie (Adrien Brody), and aspiring porn star Ruby (Jennifer Esposito) -- are trying to figure out the identity of the killer, before it's too late.
- Released: 1999
- Directed by: Spike Lee
- 64When slacker teen Anton Tobias (Devon Sawa) has his right hand possessed by a demonic force, he finds that his life gets a lot more interesting. While Anton himself is an amiable guy, his hand proves to be an appendage of death, killing his two best buddies, Pnub (Elden Henson) and Mick (Seth Green), who return to life as wisecracking zombies. In addition to murdering those closest to him, Anton's evil hand significantly hinders his chances with lovely neighbor Molly (Jessica Alba).
- Released: 1999
- Directed by: Rodman Flender
- 65Richard Martin (Sam Neill) buys a gift, a new NDR-114 robot. The product is named Andrew (Robin Williams) by the youngest of the family's children. "Bicentennial Man" follows the life and times of Andrew, a robot purchased as a household appliance programmed to perform menial tasks. As Andrew begins to experience emotions and creative thought, the Martin family soon discovers they don't have an ordinary robot.
- Released: 1999
- Directed by: Chris Columbus
- 66
Luc Besson directed this historical epic The Messenger: The Story of Joan of Arc in 1999 which chronicles the life and legacy of France's patron saint through a powerful performance by Milla Jovovich in the titular role. Featuring an impressive supporting cast including John Malkovich, Faye Dunaway, and Dustin Hoffman as well as lavish production design that immerses viewers within medieval Europe during times of brutal conflict—the film offers a visually arresting look at one of history's most revered figures. Although met with mixed reviews upon release, The Messenger: The Story of Joan of Arc remains a compelling entry within the historical drama genre that showcases Besson's signature flair for grandiose storytelling.
- Released: 1999
- Directed by: Luc Besson
- 67During Prohibition, loudmouth Harlem grifter Ray (Eddie Murphy) and the no-nonsense Claude (Martin Lawrence) team up on a bootlegging mission to Mississippi that could bring them big bucks. But they run into trouble when a crooked lawman hits them with a phony murder charge. Ray and Claude are given life sentences and shipped off to jail, where they must think of a way to prove their innocence and avoid the brutal guards while battling their biggest enemies -- their opposing personalities.
- Released: 1999
- Directed by: Ted Demme
- 68After a disheartening and haunting career wears him down, New York City paramedic Frank Pierce (Nicolas Cage) begins to collapse under the strain of saving lives and witnessing deaths. Through the course of a few nights, three co-workers (John Goodman, Ving Rhames, Tom Sizemore) accompany Pierce as he grasps for sanity and pushes to be fired. Before Pierce falls off the edge, he still has a hope when he forms a friendship with a victim's daughter (Patricia Arquette).
- Released: 1999
- Directed by: Martin Scorsese
- 69Rock-loving teens and aspiring musicians Hawk (Edward Furlong), Lex (Giuseppe Andrews), Trip (James DeBello) and Jam (Sam Huntington) can't wait to see their favorite band, KISS, perform at an upcoming concert. However, when Jam's pious mother (Lin Shaye) finds the tickets to the event, she incinerates them, leaving the boys desperate for a way to see the show. In their attempts to see KISS, the lads endure misunderstandings, humiliation and violence, all just to see their beloved idols.
- Released: 1999
- Directed by: Adam Rifkin
- 70"Fantasia/2000" continues and builds upon Walt Disney's original idea with the creation of a new musical program interpreted by a group of distinguished Disney artists and storytellers. Adding to the fun and entertainment, celebrity hosts from the various arts appear on screen to introduce each of the segments. Included in that prestigious group are Steve Martin, Itzhak Perlman, Bette Midler, Quincy Jones, James Earl Jones, Penn & Teller and Angela Lansbury.
- Released: 1999
- Directed by: James Algar, Gaëtan Brizzi, Paul Brizzi, Hendel Butoy, Francis Glebas
- 71In the dark comedy Jawbreaker, a high school clique of popular girls, led by Courtney Shayne (Rose McGowan), accidentally murder their friend, Elizabeth Purr (Charlotte Ayanna), in a prank gone wrong. Marcie Fox (Julie Benz) and Julie Freeman (Rebecca Gayheart) are caught in the aftermath, while Fern Mayo (Judy Greer), an unnoticed classmate, becomes tangled in their web of secrets. As the shockwaves ripple through Reagan High School, power dynamics shift, alliances falter and true colors are revealed. This film is a mix of teenage angst, black humor and suspense that examines the underbelly of high school popularity contests.
- Released: 1999
- Directed by: Darren Stein
- 72A young woman with no strong religious beliefs, Frankie Paige (Patricia Arquette) begins having strange and violent experiences, showing signs of the wounds that Jesus received when crucified. When the Vatican gets word of Frankie's situation, a high-ranking cardinal (Jonathan Pryce) requests that the Rev. Andrew Kiernan (Gabriel Byrne) investigate her case. Soon Kiernan realizes that very sinister forces are at work, and tries to rescue Frankie from the entity that is plaguing her.
- Released: 1999
- Directed by: Rupert Wainwright
- 73A publicity stunt turns into the ultimate lopsided competition, when the world famous New York Rangers face off against the team from Mystery, Alaska -- a hockey-loving town of only 633 people. Team Mystery is a rag-tag collection of eccentric locals including the towns sheriff, its grocer, a deliveryman and a high school senior who play for the love of the game, not fame or big money.
- Released: 1999
- Directed by: Jay Roach
- 74Journalist Steve Everett (Clint Eastwood) has been sober two months, but things are still going badly. Steve's marriage to Barbara (Diane Venora) is barely holding together, and his editor (Denis Leary) hates him, since Steve has been having an affair with his wife. A chance assignment finds Everett interviewing death row inmate Frank Beachum (Isaiah Washington). When Everett uncovers evidence indicating Beachum may be innocent, he must race against time to uncover the truth.
- Released: 1999
- Directed by: Clint Eastwood
- 75Forty-year-old pitcher Billy Chapel (Kevin Costner) is practically a dinosaur by professional baseball standards, fast approaching the end of his career. But, as Chapel stands on the mound pitching the game of his life, his thoughts don't turn to his prized history in sports, but rather return again and again to his tumultuous relationship with Jane Aubrey (Kelly Preston), a single mom who has stood at his side through the good and the bad but is now on the verge of leaving him.
- Released: 1999
- Directed by: Sam Raimi
- 76When a heist goes wrong, thief Miles (Martin Lawrence) hides a diamond at a construction site before he's arrested. After serving two years, Miles returns to the location of his treasure and finds it is now a police station. Disguising himself as a recently transferred officer to infiltrate the building, Miles stops an escaping thief while trying to retrieve the jewel. Impressed by his quick action, superior Rizzo (Graham Beckel) partners him with the bumbling detective Casey (Luke Wilson).
- Released: 1999
- Directed by: Les Mayfield
- 77On the verge of bankruptcy and desperate for his big break, aspiring filmmaker Bobby Bowfinger (Steve Martin) concocts a crazy plan to make his ultimate dream movie. Rallying a ragtag team that includes a starry-eyed ingenue (Heather Graham), a has-been diva (Christine Baranski) and a film studio gofer (Jamie Kennedy), he sets out to shoot a blockbuster featuring the biggest star in Hollywood, Kit Ramsey (Eddie Murphy) -- only without letting Ramsey know he's in the picture.
- Released: 1999
- Directed by: Frank Oz
- 78An annual beauty pageant in small-town Minnesota turns ridiculously competitive and ultimately chaotic in this biting comedy. Amber Atkins (Kirsten Dunst), the daughter of hard-drinking mom Annette (Ellen Barkin), and Becky Leeman (Denise Richards), who is motivated by her former beauty-queen mother, Gladys (Kirstie Alley), are among the top contenders in the event. As Amber, Becky, and other local girls prepare for the big day, bizarre incidents occur, leading up to an ending with a bang.
- Released: 1999
- Directed by: Michael Patrick Jann
- 79This horror tale focuses on visitors to the secluded mansion of Hill House who have been called to the isolated location by Dr. David Marrow (Liam Neeson) as part of a study on insomnia. However, Marrow is really investigating fear, and he plans to scare the subjects, including the introverted Nell (Lili Taylor) and the seductive Theo (Catherine Zeta-Jones). Unfortunately for Marrow and everyone staying at Hill House, the manor is actually haunted by an evil spirit out to torment its guests.
- Released: 1999
- Directed by: Jan de Bont
- 80A millionaire with theatrical tendencies, Stephen Price (Geoffrey Rush) invites a number of people to stay in a vast creepy building that used to be an insane asylum. Stephen, accompanied by his bitter wife, Evelyn (Famke Janssen), offers a million dollars to anyone who can stay the whole night without leaving out of fear. When Stephen and Evelyn become trapped with their guests, they quickly realize that the house really is haunted -- and the spirits dwelling within are very angry.
- Released: 1999
- Directed by: William Malone
- 81This disturbing Japanese thriller follows Aoyama (Ryo Ishibashi), a widower who decides to start dating again. Aided by a film-producer friend (Miyuki Matsuda), Aoyama uses auditions for a fake production to function as a dating service. When Aoyama becomes intrigued by the withdrawn, gorgeous Asami (Eihi Shiina), they begin a relationship. However, he begins to realize that Asami isn't as reserved as she appears to be, leading to gradually increased tension and a harrowing climax.
- Released: 1999
- Directed by: Takashi Miike
- 82In a desperate attempt to boost ratings, a cable channel decides to document the life of someone on a daily basis and air the footage as a show. That lucky someone turns out to be Ed Pekurny (Matthew McConaughey), a laid-back video-store clerk. While the TV series makes Ed an overnight celebrity, it also begins to wreak havoc on his personal life, complicating his relationship with his new girlfriend, Shari (Jenna Elfman), and causing tension with his brother, Ray (Woody Harrelson).
- Released: 1999
- Directed by: Ron Howard
- 83The Limey follows Wilson (Terence Stamp), a tough English ex-con who travels to Los Angeles to avenge his daughter's death. Upon arrival, Wilson goes to task battling Valentine (Peter Fonda) and an army of L.A.'s toughest criminals, hoping to find clues and piece together what happened. After surviving a near-death beating, getting thrown from a building and being chased down a dangerous mountain road, the Englishman decides to dole out some bodily harm of his own.
- Released: 1999
- Directed by: Steven Soderbergh
- 84During her morning jog on the beach, journalist Theresa Osborne (Robin Wright Penn) discovers a bottle protruding from the sand. Inside it, she finds a heartbreaking, anonymous love letter. After her paper publishes the letter, Osborne tracks down the letter's reclusive author, world-weary widower Garret Blake (Kevin Costner), in the Carolinas. But, as Osborne finds herself falling hopelessly in love with Blake, she becomes wracked with guilt over the real impetus for her visit.
- Released: 1999
- Directed by: Luis Mandoki
- 85Upon receiving reports of missing persons at Fort Spencer, a remote Army outpost on the Western frontier, Capt. John Boyd (Guy Pearce) investigates. After arriving at his new post, Boyd and his regiment aid a wounded frontiersman, F.W. Colghoun (Robert Carlyle), who recounts a horrifying tale of a wagon train murdered by its supposed guide -- a vicious U.S. Army colonel gone rogue. Fearing the worst, the regiment heads out into the wilderness to verify Colghoun's gruesome claims.
- Released: 1999
- Directed by: Antonia Bird
- 86When astronaut Spencer Armacost (Johnny Depp) returns to Earth after a mission that nearly cost him his life, he decides to take a desk job in order to see his beautiful wife, Jillian (Charlize Theron), more often. Gradually, Jillian notices that Spencer's personality seems to have changed, but her concerns fade when she discovers that she's pregnant. As Jillian grows closer to becoming a mother, her suspicions about Spencer return. Why does it seem as if he's a different person?
- Released: 1999
- Directed by: Rand Ravich
- 87Telling their parents they're going to Hawaii, recent high school grads Alice (Claire Danes) and Darlene (Kate Beckinsale) instead travel to Thailand, thinking their money will go farther. There they meet Nick, a charming Aussie who sells them on the idea of traveling to Hong Kong with him. But things go awry at the airport when the girls are caught smuggling illegal substances in their luggage. Having been duped by Nick, the girls are sentenced to 33 years in a Thai prison.
- Released: 1999
- Directed by: Jonathan Kaplan
- 88A Greek saying states that only women who have washed their eyes with tears can see clearly. This saying does not hold true for Manuela. The night a car ran over her son Esteban, Manuela cried until her eyes ran completely dry. Far from seeing clearly, the present and the future become mixed up in darkness. She begins looking for his father who has become a transvestite.
- Released: 1999
- Directed by: Pedro Almodóvar
- 89Three old friends -- Mike (Omar Epps), Roland (Taye Diggs) and Slim (Richard T. Jones) -- recount memories of their shared childhood in Inglewood, Calif., as they prepare for Roland's wedding to his fiancée, Lisa (LisaRaye). When the groom goes missing without a word, Mike and Slim struggle to find their nervous friend and return him to his impatient bride before the wedding begins. Along the way, they continue to swap stories about lessons learned during their awkward teenage years.
- Released: 1999
- Directed by: Rick Famuyiwa
- 90In this cult-favorite documentary, Mark Borchardt, an aspiring filmmaker from a working-class Wisconsin background, is set on finishing his low-budget horror movie, despite a barrage of difficulties. Plagued by lack of cash, unreliable help and numerous personal problems, Mark wants to complete the film to raise funds for a more ambitious drama. With the assistance of his bumbling but loyal friend Mike Schank, Mark struggles to move forward, making for plenty of bittersweet moments.
- Released: 1999
- Directed by: Chris Smith
- 91Having already left three grooms at the altar, Maggie Carpenter (Julia Roberts) is branded "the runaway bride" by jaded city journalist Ike Graham (Richard Gere). But, after his facts are called into question, Ike races to Maggie's hometown to save his reputation and report on her upcoming fourth trip down the aisle -- during which he's convinced she'll run again. Though he's there on a muckraking mission, Ike can't help but fall for this breathtaking heartbreaker.
- Released: 1999
- Directed by: Garry Marshall
- 92Megan (Natasha Lyonne) considers herself a typical American girl. She excels in school and cheerleading, and she has a handsome football-playing boyfriend, even though she isn't that crazy about him. So she's stunned when her parents decide she's gay and send her to True Directions, a boot camp meant to alter her sexual orientation. While there, Megan meets a rebellious and unashamed teen lesbian, Graham (Clea DuVall). Though Megan still feels confused, she starts to have feelings for Graham.
- Released: 1999
- Directed by: Jamie Babbit
- 1Bud Cort11 Votes
- 2Mink Stole6 Votes
- 3Natasha Lyonne17 Votes
- 4Clea DuVall14 Votes
- 93A man awakens to discover a bloody shirt in his house and his boss murdered the night before. Did he do it? Why can't he remember? "The Thirteenth Floor" is a sci-fi thriller that explores the ominous possibility of computer-simulated universes, where people only believe they are real.
- Released: 1999
- Directed by: Josef Rusnak
- 94A hardworking and bright high-school senior, Leigh Ann (Katie Holmes) has her impending status as valedictorian jeopardized when her bitter history teacher, Mrs. Tingle (Helen Mirren), gives her a poor grade on a project. This antagonistic relationship quickly escalates until circumstances lead Leigh Ann and her friends Luke (Barry Watson) and Jo Lynn (Marisa Coughlan) to hold Tingle hostage in her home. As the conflict continues, it looks as if not everyone will make it out alive.
- Released: 1999
- Directed by: Kevin Williamson
- 95Anna (Jodie Foster) has been employed to educate the king's (Chow Yun-Fat) 58 children. She knows very little of King Mongkut, apart from the fact that his people revere him as a god. She brings with her an East vs. West prejudice against the king, considering him to be uncivilized. She soon realizes that her views are more than matched by the rulers own preconceptions about the West and particularly this impertinent English woman.
- Released: 1999
- Directed by: Andy Tennant
- 96All Ben Holmes (Ben Affleck) wants to do is make it from New York to Savannah, Ga., in time for his wedding. When a seagull and a hurricane ruin any chance he has of flying there, Holmes reluctantly joins the quirky Sarah Lewis (Sandra Bullock) in a rental car for a road trip back to his waiting bride-to-be, Bridget Cahill (Maura Tierney). But nature seems to conspire against his every attempt at a timely return -- and in the meantime, he finds himself growing closer to Sarah.
- Released: 1999
- Directed by: Bronwen Hughes
- 97After learning that her aunt, an elderly Mississippi widow (Patricia Neal), has taken her own life, Camille (Glenn Close) hatches an unusual postmortem plan. With her sister (Julianne Moore) in tow, Camille hides evidence that points to suicide, deciding instead to make the death look like a murder. Her scheme, fueled by vanity and greed, is not victimless, as it appears that a local handyman (Charles S. Dutton) might take the fall for a crime that never occurred.
- Released: 1999
- Directed by: Robert Altman
- 98In Wild Wild West, Captain James West (Will Smith) partners with the eccentric inventor, Artemus Gordon (Kevin Kline), on a mission to save President Ulysses S. Grant (also Kline) from a nefarious plot. The unlikely duo navigates an alternate 1869 America, populated by steampunk contraptions and unusual villains, including Dr. Arliss Loveless (Kenneth Branagh), a mad scientist bent on disuniting the States. This action-comedy amalgamation of western and science fiction genres won a Razzie for Worst Picture but remains notable for its unique premise and inventive production design.
- Released: 1999
- Directed by: Barry Sonnenfeld
- 99Years after he goes missing in the jungles of Africa, anthropologist Ethan Powell (Anthony Hopkins) resurfaces when it's discovered that he has murdered two poachers who were killing the gorillas he was studying. After spending an extended time living with the primates and without any human contact, Powell seems to be unhinged, and psychiatrist Theo Caulder (Cuba Gooding Jr.) is called in to try to get through to the withdrawn and angry man -- who may be wiser and saner than he appears.
- Released: 1999
- Directed by: Jon Turteltaub
- 100Video game designer Allegra Geller (Jennifer Jason Leigh) has created a virtual reality game called eXistenZ. After a crazed fan attempts to kill her, Allegra goes on the run with Ted (Jude Law), a young businessman who falls into the role of bodyguard. In an attempt to save her game, Allegra implants into Ted's body the video game pod that carries a damaged copy of eXistenZ. Allegra and Ted engage in a series of experiences that blur the lines between fantasy and reality.
- Released: 1999
- Directed by: David Cronenberg
- 101With the children out of the house, Henry (Steve Martin) and Nancy Clark (Goldie Hawn) head to New York City to embrace their cosmopolitan dreams. Henry has set up a job interview with an advertising firm, and Nancy hopes to add some spice to their marriage. But nothing goes according to plan for the couple, as they endure lost luggage, muggers, a diffident desk clerk (John Cleese) and a disastrous tour of the city that never sleeps -- and won't leave them alone!
- Released: 1999
- Directed by: Sam Weisman
- 102Betsy (Kirsten Dunst) and Arlene (Michelle Williams) are two 15-year-old girls in 1976. When Betsy visits Arlene at the Watergate Motel, the two accidentally stumble into the middle of the infamous Watergate robbery. In order to keep them quiet, Nixon (Dan Hedaya) appoints them as honorary dog walkers. As they travel in and out of the White House, their seemingly innocent actions start a chain of events that may eventually lead to Nixon's resignation as president of the United States.
- Released: 1999
- Directed by: Andrew Fleming
- 103The movie "Jin-Roh" is about those in society who are predators among prey. But these "beasts" never bother to change their shape; like Red Riding Hood's wolf, they merely drape themselves with human clothes that do not even disguise the eyes, teeth and claws of a killer. Society rightly fears them. In "Jin-Roh," the Capital Police are themselves hunted -- marked for elimination as a force by their own government, and by a public eager to forget the past.
- Released: 1999
- Directed by: Hiroyuki Okiura
- 104Returning from 40 years at war with the Goths, the Roman general Titus Andronicus (Anthony Hopkins) executes the eldest son of Tamora, Queen of the Goths (Jessica Lange), setting off a long chain of revenge, cruelty, and murder, aggravated when Tamora marries the new Emperor, Saturninus (Alan Cumming).
- Released: 1999
- Directed by: Julie Taymor
- 105Ringu 2 is a 1999 Japanese horror film directed by Hideo Nakata. Reiko takes Yôichi into hiding when her son begins to display frightening powers. Meanwhile, Mai Takano and the authorities begin a desperate search for them, as the mysterious Ring curse spreads.
- Released: 1999
- Directed by: Hideo Nakata
- 106Emmet Ray (Sean Penn) isn't an easy guy to be around -- among other things, he's inconsiderate and egomaniacal. He also happens to be a jazz guitarist with undeniable talent, and despite his many faults, he ends up winning the heart of Hattie (Samantha Morton), a kind young mute woman. Hattie's seemingly endless patience with Emmet is tested, however, with his incessant irresponsibility and infidelity, leading their relationship to the breaking point.
- Released: 1999
- Directed by: Woody Allen
- 107My Neighbors the Yamadas is a 1999 Japanese animated comedy film written and directed by Isao Takahata and produced by Studio Ghibli. The film stars Hayato Isobata, Masako Araki, Naomi Uno, Touru Masuoka, Yukiji Asaoka, Akiko Yano, and Kosanji Yanagiya. Unlike the other films of Studio Ghibli, the film is presented in a stylized comic strip aesthetic, a departure from the traditional anime style of the studio's other works.
- Released: 1999
- Directed by: Isao Takahata
- 108Based on the cartoon, this live-action comedy follows the adventures of Dudley Do-Right (Brendan Fraser), an enthusiastic, if somewhat dim, Canadian Mountie. When Dudley's childhood crush, Nell Fenwick (Sarah Jessica Parker), returns to their hometown in the mountains, he is eager to spend time with her, but his attempts at courting her are foiled by the villainous Snidely Whiplash (Alfred Molina), who is up to his usual schemes. Can Dudley win Nell's heart and curtail Snidely's wicked ways?
- Released: 1999
- Directed by: Hugh Wilson
- 109Postmen in the Mountains is a 1999 Chinese film directed by Huo Jianqi. It is based on the short story of the same name by Peng Jianming. Postmen in the Mountains tells the story of an old man who for years served as the postman for rural mountain communities. Retiring, he hands over his job to his son, but accompanies him on the first tour. Together, they deliver mail on a 230 li long walking route, into the rural heart of China and in the process the son learns from the mails' recipients more about the father he hardly knew. It was filmed on location in Suining County and Dao County, in southwestern and southern Hunan. A portion of the film takes place in a village of the Dong people, including an evening festival featuring a lusheng dance.
- Released: 1999
- Directed by: Huo Jianqi
- 110English art dealer Michael Felgate (Hugh Grant) is dumbfounded to learn that his girlfriend, Gina Vitale (Jeanne Tripplehorn), cannot accept his marriage proposal because her entire family is involved with the Mafia. Undeterred and in love, Michael meets Gina's father, mob boss Frank (James Caan), who immediately takes a shine to the young suitor. But before he can give his blessing, Frank has plans for Michael that may or may not end in wedding bells.
- Released: 1999
- Directed by: Kelly Makin
- 111A boy tries to stop his father from dating by programming their computerized house to be a surrogate mother.
- Released: 1999
- Directed by: LeVar Burton
- 112Ambitious television reporter Tim O'Hara (Jeff Daniels) stumbles upon a martian (Christopher Lloyd) whose spaceship has accidentally crashed on Earth. Thinking this is his ticket to a Pulitzer Prize, Tim makes plans to expose the martian, who, posing as Tim's Uncle Martin, takes human form and has plans of his own. In fact, all of Tim's efforts to divulge the truth are systematically thwarted by the resourceful alien, who ultimately recruits Tim to help him repair his ship for a return to Mars.
- Released: 1999
- Directed by: Donald Petrie
- 113In a village in the North-Western Himalayas, Tinl, a charismatic old chieftain, whose eldest son has just died, refuses to allow the young Karma to lead the yak caravan. They both end up leading on two different routes. This is the story of their rivalry in the Himalayas.
- Released: 1999
- Directed by: Eric Valli
- 114Two air traffic controllers (John Cusack, Billy Bob Thornton) who thrive on living dangerously compete to outdo each other on several levels.
- Released: 1999
- Directed by: Mike Newell
- 115Julien Donkey-Boy is a 1999 American drama film written and directed by Harmony Korine. The story concentrates on the schizophrenic Julien, played by Scottish actor Ewen Bremner, and his dysfunctional family. The film also stars Chloë Sevigny as Julien's sister, Pearl, and Werner Herzog as his father. Julien Donkey-Boy is the sixth film to be made under the self-imposed rules of the Dogme 95 manifesto, and the first non-European film to be made under the Dogme 95 "vow of chastity".
- Released: 1999
- Directed by: Harmony Korine
- 116Zenon: Girl of the 21st Century is a 1999 Disney Channel Original Movie, starring Kirsten Storms as the eponymous heroine. The film was based on the book Zenon: Girl of the 21st Century written by Marilyn Sadler and Roger Bollen. The film was originally conceived as a pilot for a potential television series, but the series never got off the ground. Nevertheless, the movie proved popular and warranted two sequels, Zenon: The Zequel and Zenon: Z3.
- Released: 1999
- Directed by: Kenneth Johnson
- 117Beau Travail is a 1999 French movie directed by Claire Denis that is loosely based on Herman Melville's 1888 novella Billy Budd. The movie is set in Djibouti, where the protagonists are soldiers in the French Foreign Legion. Parts of the soundtrack of the movie are from Benjamin Britten's opera based on the novella.
- Released: 1999
- Directed by: Claire Denis
- 118Dead or Alive, abbreviated as DOA, is a 1999 Japanese yakuza action film directed by Takashi Miike. It stars Riki Takeuchi, as the Chinese Triad boss and former yakuza Ryūichi, and Show Aikawa, as the Japanese cop Detective Jojima, and focuses on their meeting and conflict. It is the first in a three-part series, followed by Dead or Alive 2: Birds in 2000 and Dead or Alive: Final in 2002.
- Released: 1999
- Directed by: Takashi Miike
- 119James Gillespie (William Eadie) is 12 years old. The world he knew is changing. Haunted by a secret, he has become a stranger in his own family. He is drawn to the canal where he creates a world of his own. He finds an awkward tenderness with Margaret Anne (Leanne Mullen), a vulnerable 14 year old expressing a need for love in all the wrong ways, and befriends Kenny (John Miller), who possesses an unusual innocence in spite of the harsh surroundings.
- Released: 1999
- Directed by: Lynne Ramsay
- 120
Bleeder
Mads Mikkelsen, Kim Bodnia, Zlatko BuricBleeder is a 1999 Danish crime drama film written, produced, and directed by Nicolas Winding Refn. The film was a big hit in Denmark, much like Refn's previous film Pusher.- Released: 1999
- Directed by: Nicolas Winding
