The 75 Best '90s Chick Flicks, Ranked

Clueless revolutionized the '90s chick flick landscape by effortlessly blending the themes of high school drama, romance, and comedy with a modern-day adaptation of Jane Austen's Emma. The film's witty dialogue, authentic exploration of teenage angst, and memorable fashion trends offered a fresh and relatable perspective on love and friendship. Clueless smartly utilized the tropes of lavish makeovers, quirky sidekicks, and unattainable crushes, ultimately leading to the iconic, heartwarming realization that sometimes true love is right in front of us. This cult classic solidified Alicia Silverstone's status as the quintessential '90s teen queen and created a blueprint for future coming-of-age romantic comedies.

This modern retelling of Shakespeare's The Taming of the Shrew captivated audiences with its perfect blend of humor, rebellion, and sizzling chemistry between lead actors Julia Stiles and Heath Ledger. 10 Things I Hate About You expertly used the tropes of opposites attracting, hidden vulnerability, and transforming the bad boy, while still maintaining a timely and progressive feminist voice. The witty banter, memorable performances, and iconic serenade scene showcased the best of '90s teen cinema, proving that the power of love can break down even the toughest exteriors. This vibrant, clever flick has secured its place in the pantheon of beloved '90s chick flicks.

A League of Their Own is a testament to the power of sisterhood and camaraderie within the traditionally male-dominated world of sports. This historical fiction film masterfully incorporated the classic romantic comedy tropes of rivalry, growth, and self-discovery within the backdrop of an all-female baseball league during World War II. The endearing dynamics between the ensemble cast, led by Geena Davis, Tom Hanks, and Madonna, made the film both a comedic and emotional powerhouse, offering viewers an unforgettable journey of love, loss, and resilience. A League of Their Own defied genre boundaries, garnering critical acclaim and inspiring generations of women to pursue their dreams in and out of the field.

The Craft brought a supernatural twist to the '90s chick flick scene, blending elements of horror, female empowerment, and romance in a unique and captivating manner. The film centers around four young witches navigating the challenges of high school, friendship, and love, offering a fresh perspective on the age-old struggle for identity and acceptance. By combining the tropes of teenage rebellion, unrequited love, and dark magic, The Craft created a thrilling journey that resonated with audiences looking for something different in the realm of romance. This cult favorite proved that even in the darkest of circumstances, the power of love and friendship can prevail.

While You Were Sleeping offers a delightful blend of mistaken identity, humor, and unexpected romance, as Sandra Bullock's Lucy finds herself entangled in the lives of a comatose man and his brother. The film expertly plays with the tropes of serendipity, lovable deception, and the endearing chaos of family dynamics, resulting in a charming and heartwarming journey. Bullock's relatable performance and sparkling chemistry with co-star Bill Pullman ensured that audiences would fall in love with this unique and enchanting tale. While You Were Sleeping remains an iconic example of '90s romantic comedy magic, proving that love can blossom in the most unexpected of places.

Ever After reimagined the classic Cinderella tale with a refreshing and empowering twist, as Drew Barrymore's Danielle de Barbarac strived for her own version of happily ever after. The film expertly combined the tropes of the Cinderella story, forbidden romance, and the transformative power of love, while also incorporating elements of historical drama and female empowerment. Barrymore's captivating performance and chemistry with co-star Dougray Scott made Ever After an unforgettable romantic journey, proving that true love can conquer even the most daunting obstacles. This enchanting '90s favorite continues to inspire audiences with its message of resilience, self-worth, and the magic of true love.

Cruel Intentions broke the mold of traditional '90s chick flicks by delving into darker themes of manipulation, seduction, and revenge. The film's complex, morally ambiguous characters and engrossing storyline captivated audiences, while still maintaining a strong emphasis on romance and passion. Utilizing the tropes of forbidden attraction, twisted love triangles, and redemption, Cruel Intentions offered a delectable mix of drama and sensuality that has stood the test of time. This cult classic showcased the depths of human emotion and desire, proving that even the cruelest intentions can be transformed by the power of love.

Now and Then is a heartwarming ode to the bonds of female friendship and the power of shared experiences. The film expertly weaves between the past and present, showcasing the adventures and romantic escapades of four lifelong friends during a fateful summer in their youth. With its lovable ensemble cast, nostalgic atmosphere, and poignant exploration of love and loss, Now and Then employs the classic tropes of coming-of-age, first loves, and the transformative power of time. This charming '90s flick reminds audiences of the timeless connections that shape our lives and enrich our hearts.

James Cameron's Titanic took the box office by storm in the '90s, providing an epic, star-crossed love story that has become the epitome of romance for generations to come. The breathtaking chemistry between Leonardo DiCaprio's Jack and Kate Winslet's Rose, set against the tragic backdrop of the ill-fated ship's voyage, captured the hearts of millions. Titanic skillfully employed the tropes of forbidden love, social class divide, and self-sacrifice, resulting in an emotionally-charged cinematic experience. With its groundbreaking special effects, tear-jerking soundtrack, and timeless appeal, Titanic remains the ultimate romantic drama of the '90s and beyond.

She's All That flipped the classic Cinderella story on its head, introducing a relatable, down-to-earth protagonist in Rachael Leigh Cook's Laney Boggs. This '90s favorite effortlessly balanced the comedic elements of high school drama with poignant moments of vulnerability, as Freddie Prinze Jr.'s popular jock character learns to look beyond appearances. The film employed chick flick tropes such as the bet, the makeover, and the climactic prom scene, yet still managed to feel fresh and authentic thanks to the charming performances and resonant themes of self-acceptance and inner beauty. She's All That remains a beloved staple of the genre, proving that love can blossom even from the most unlikely of circumstances.

Practical Magic infused the chick flick genre with a bewitching blend of romance, sisterly love, and supernatural intrigue. Sandra Bullock and Nicole Kidman enchanted audiences with their performances as witchy sisters navigating the challenges of love and the family curse. The film expertly combined the tropes of forbidden love, magical intervention, and the power of female camaraderie, resulting in a unique and captivating tale. Practical Magic's combination of romance, whimsy, and darker elements has ensured its legacy as a cult classic, reminding audiences of the unbreakable bonds of family and the magic of true love.

Sleepless in Seattle brought together Tom Hanks and Meg Ryan once again for an enchanting tale of destiny, proving that love can conquer all obstacles. The film deftly wove together themes of grief, serendipity, and hope, using radio airwaves to create a sense of longing and connection between its two leads. Employing the classic tropes of love-at-first-sight and long-distance yearning, Sleepless in Seattle depicted a captivating and heartwarming tale of fate bringing two seemingly disparate individuals together. This poignant '90s gem showcased the power of love to heal and the magic of chance encounters that can change lives forever.

Ghost transcends the traditional bounds of the '90s chick flick genre by blending elements of romance, fantasy, and suspense. The film captivated audiences with its powerful depiction of love transcending the boundaries of life and death, as Patrick Swayze's Sam seeks justice for his murder and closure for his grieving lover, Molly, played by Demi Moore. Employing the tropes of eternal love, supernatural intervention, and the healing power of connection, Ghost offers a unique and enthralling journey full of heartache and hope. This enduring classic stands as a testament to the eternal power of love and the bonds that can never be broken.

Sense and Sensibility brought Jane Austen's beloved novel to life with a star-studded cast, breathtaking scenery, and a perfect blend of wit, romance, and drama. The film brilliantly explored the complexities of love, societal expectations, and the importance of following one's heart, employing classic tropes like forbidden romance, sibling dynamics, and the transformative power of self-discovery. With standout performances by Emma Thompson, Kate Winslet, and Hugh Grant, Sense and Sensibility captured the essence of Austen's timeless tale while enchanting '90s audiences with its irresistible charm. This elegant adaptation remains a beloved classic, showcasing the endurance of love and the importance of balancing passion with pragmatism.

Never Been Kissed offered an endearing take on second chances, as Drew Barrymore's Joséphine "Josie" Geller went undercover as a high school student, reliving her teenage years and finding love in the process. The film expertly played with the tropes of the ugly duckling transformation, unrequited love, and a dashing, sensitive leading man in Michael Vartan's character. With its comedic dialogue, heartfelt moments, and unforgettable prom scene, Never Been Kissed showcased the universal desire for self-discovery, acceptance, and the power of true love. This '90s favorite is a testament to the resilience of the human spirit and the importance of never giving up on love or oneself.

Persuasion offered a poignant and enduring love story adapted from Jane Austen’s heartfelt novel, following the life of Anne Elliot (Amanda Root) and her lost love, Captain Wentworth (Ciarán Hinds). The film masterfully explored themes of regret, second chances, and the lasting power of true love, utilizing the tropes of unrequited love, social constraints, and the passage of time to craft a captivating tale. With its understated performances, emotional depth, and beautiful period settings, Persuasion resonated with '90s audiences and remains an enduring favorite among Austen fans. This timeless tale serves as a reminder that true love, once found, can withstand the test of time and circumstance.

You've Got Mail perfected the online romance before it became a cultural phenomenon, bringing together Tom Hanks and Meg Ryan in an unforgettable pairing full of wit, charm, and heart. The film's clever use of anonymous email correspondence between rivals allowed the characters to showcase their genuine personalities, breaking down barriers and proving that sometimes opposites truly do attract. By merging modern technology with the classic trope of mistaken identity and enemies-turned-lovers, You've Got Mail offered a captivating tale of connection and love in the digital age. This romantic comedy is a standout of the '90s, with its timeless appeal and memorable performances from its captivating leads.

Pretty Woman remains the quintessential rags-to-riches love story, as Julia Roberts' enchanting performance as Vivian Ward captured hearts and solidified her status as a rom-com icon. The film expertly balanced humor and pathos, employing the tropes of the Cinderella story, opposites attracting, and the transformative power of love. Richard Gere's portrayal of Edward Lewis added depth and vulnerability to the classic Prince Charming character, resulting in a captivating, multi-dimensional romance. Pretty Woman's enduring charm and memorable moments have ensured its place as one of the best romantic comedies of the '90s and beyond.

Cry-Baby brought a distinctive blend of '50s nostalgia, star-crossed romance, and campy humor to the '90s chick flick scene. Johnny Depp's turn as the titular "Cry-Baby" Walker enchanted audiences with his bad-boy charm and tender vulnerability, proving that love can bridge even the widest social divides. The film utilized classic tropes like opposites attracting, the redemption of the rebel, and the transformative power of love to create a stylized, visually stunning journey full of memorable musical numbers and quirky characters. Cry-Baby remains an offbeat favorite within the genre, showcasing the importance of self-expression and the power of love to bring people together.

The First Wives Club challenged the status quo of '90s chick flicks by focusing on the power of female friendship and reinvention in the face of heartbreak and betrayal. With its iconic trio of leading ladies (Goldie Hawn, Bette Midler, and Diane Keaton), the film masterfully employed the tropes of revenge, growth, and rediscovered love, all while delivering laughs and memorable one-liners. The witty dialogue, glamorous costumes, and triumphant celebration of sisterhood make The First Wives Club a timeless classic that resonates with audiences of all ages. This empowering flick reminds us that true love can come in many forms, and sometimes it's our friends who help us find our way to happiness.

Notting Hill united Hugh Grant's bumbling British bookstore owner and Julia Roberts' glamorous American movie star for a delightful exploration of love and the challenges of fame. The film expertly utilized the tropes of the fish-out-of-water, Cinderella story, and the grand romantic gesture, offering viewers a rollercoaster ride of emotions. With its memorable one-liners, iconic scenes, and palpable chemistry between its leads, Notting Hill became an instant classic, striking a chord with audiences worldwide. This romantic comedy exemplifies the best of the '90s chick flick, allowing viewers to lose themselves in a world where love truly conquers all.

Jerry Maguire combined the world of sports with heartwarming romance, elevating the '90s chick flick genre with its memorable dialogue and heartfelt performances. The film follows Tom Cruise's titular character as he navigates both professional turmoil and newfound love with Renée Zellweger's Dorothy. Utilizing the tropes of opposites attracting, personal growth, and grand romantic gestures, Jerry Maguire showcases the power of vulnerability and the importance of human connection. This beloved '90s gem solidified its place in cinematic history with its iconic lines and enduring message of love and loyalty.

Girl, Interrupted offered a powerful examination of the complexities of female friendships, mental health, and self-discovery within the confines of a 1960s psychiatric facility. Led by an outstanding ensemble cast including Winona Ryder, Angelina Jolie, and Brittany Murphy, the film skillfully navigated themes of love, loss, and personal growth, while still incorporating elements of humor and compassion. Though not a traditional chick flick, Girl, Interrupted's exploration of the bonds forged in difficult circumstances and the transformative power of connection resonated deeply with audiences. This evocative '90s drama serves as a reminder that love, in all its forms, can provide the strength needed to face even the most daunting challenges.

Mansfield Park brought Jane Austen's classic novel to life with Frances O'Connor's portrayal of the spirited and independent-minded heroine Fanny Price. The film expertly balanced themes of romance, social critique, and the importance of staying true to one's convictions. Employing the tropes of unrequited love, societal expectations, and the transformative power of love, Mansfield Park provided a captivating and insightful exploration of love in the face of adversity. This '90s adaptation remains a beloved favorite among Austen aficionados, proving that true love can withstand the test of time and societal constraints.

It Could Happen to You triumphantly showcased the power of kindness and true love in the face of life's unexpected twists and turns. Nicolas Cage and Bridget Fonda captivated audiences as a New York City cop and a struggling waitress whose lives become intertwined after an unusual lottery win. The film expertly employed the tropes of chance encounters, selfless gestures, and the transformative power of love in the face of adversity. With its charming leads, relatable struggles, and heartwarming message, It Could Happen to You remains a beloved romantic comedy from the '90s. This uplifting tale reminds us that sometimes, love is the greatest fortune of all.

Stepmom delivered an emotional and poignant exploration of love, loss, and the complexities of blended families. With its powerhouse performances from Julia Roberts and Susan Sarandon, the film masterfully navigated the tropes of rivalry turned friendship, the bonds forged through adversity, and the healing power of love. By showcasing the challenges faced by both mothers and stepmothers, Stepmom provided a heartfelt, relatable journey for audiences. This moving '90s drama reminds us of the importance of family, love, and understanding in the face of life's most difficult moments.

Four Weddings and a Funeral captured the hearts of '90s audiences with its clever wit, endearing ensemble cast, and an unforgettable love story between Hugh Grant's Charles and Andie MacDowell's Carrie. The film expertly navigated the tropes of chance encounters, unrequited love, and the inevitable hurdles that arise within romantic relationships. Its exploration of love and loss within the context of friendship and celebration solidified its place as a beloved '90s classic, providing both laughter and tears for viewers. Four Weddings and a Funeral proved that love can be both exhilarating and heartbreaking, but it's a journey worth taking.

My Best Friend's Wedding is an iconic '90s rom-com that flipped the classic love triangle on its head, as Julia Roberts' character Julianne Potter found herself grappling with her newfound feelings for her best friend Michael, played by Dermot Mulroney. The film utilized the tropes of unrequited love, the fine line between friendship and romance, and the chaos of wedding preparations to create an unforgettable and heartwarming tale. With its memorable musical moments, witty banter, and a show-stealing performance by Cameron Diaz as the bubbly bride-to-be, My Best Friend's Wedding remains a beloved favorite within the genre. This charming flick reminds us that love can surprise us in the most unexpected ways.

Father of the Bride offered a heartwarming and humorous look at the trials and tribulations of planning a wedding through the eyes of an overprotective father, played by the endearing Steve Martin. The film effortlessly combined the tropes of family chaos, evolving relationships, and the inevitable passage of time, showcasing the transformative power of love on multiple levels. Martin's tender performance and chemistry with co-stars Diane Keaton and Kimberly Williams-Paisley made Father of the Bride an instant classic, highlighting the importance of embracing change and supporting our loved ones on their journeys. This '90s gem remains a beloved favorite, proving that even amidst the chaos, love brings families together.

The Joy Luck Club presented a multigenerational tale of love, sacrifice, and the unbreakable bond between mothers and daughters. Based on Amy Tan's best-selling novel, the film skillfully wove together the stories of four Chinese-American women and their immigrant mothers, exploring the complexities of cultural identity and the power of family ties. The Joy Luck Club employed the tropes of forbidden love, self-sacrifice, and the transformative power of connection, resulting in a deeply moving cinematic experience. This iconic '90s film stands as a testament to the resilience of love and the profound connections spanning generations.

Addicted to Love offered a hilariously dark take on the genre, featuring Meg Ryan and Matthew Broderick as scorned lovers plotting revenge against their exes. The film employed the tropes of unlikely alliances, misguided schemes, and the undeniable chemistry between two people who initially seem at odds. Ryan and Broderick's performances brought an edgy twist to the chick flick scene, showcasing the complexities of love, heartbreak, and sweet vengeance. Addicted to Love remains a memorable standout, proving that sometimes love can be found even in the most unconventional circumstances.

Emma brought Jane Austen's beloved heroine to life with Gwyneth Paltrow's enchanting portrayal of the well-intentioned but meddlesome matchmaker. The film expertly balanced elements of comedy, romance, and personal growth, employing the tropes of misguided matchmaking, the transformative power of self-awareness, and the enduring appeal of true love. With its charming performances, witty dialogue, and lush English countryside scenery, Emma captivated audiences and solidified its place as a beloved adaptation of Austen's classic novel. This enchanting '90s film reminds us that sometimes the path to true love takes unexpected twists and turns.

The Bachelor brought a comedic twist to the classic race-against-time trope with Chris O'Donnell's commitment-phobic leading man trying to find a bride before he loses his inheritance. Featuring a memorable performance by Renée Zellweger as the long-suffering love interest, the film cleverly navigated the tropes of reluctant romance, grandiose proposals, and the power of true love amidst chaos. The hilarious scenarios, endearing characters, and a heartwarming realization of what love truly means made The Bachelor a '90s favorite. This lighthearted jaunt offers a humorous look at the complexities of relationships, proving that sometimes love is right under our noses.

Kate & Leopold enchanted audiences with its delightful combination of time-travel, historical romance, and modern-day humor. Meg Ryan and Hugh Jackman provided captivating performances as a contemporary woman and a dashing 19th-century duke who find themselves unexpectedly united across time. The film skillfully utilized the tropes of star-crossed lovers, fish-out-of-water scenarios, and the transformative power of love, resulting in a charming and heartwarming journey. Kate & Leopold offered a whimsical escape for '90s audiences and remains a beloved favorite within the genre. This magical love story proves that love transcends time and knows no bounds.

The American President offered a charming look at love in the political spotlight, as Michael J. Fox's President Andrew Shepherd pursued a relationship with Annette Bening's environmental lobbyist Sydney Ellen Wade. The film masterfully balanced the tropes of power dynamics, personal sacrifice, and grand romantic gestures, resulting in a captivating and heartwarming journey. With its engaging dialogue, captivating performances, and exploration of love's impact on both private and public life, The American President remains a favorite amongst '90s chick flicks. This unique love story highlights the importance of remaining true to oneself and prioritizing love and happiness amidst the chaos of the world.

Sleeping with the Enemy brought a thrilling edge to the '90s chick flick scene with its gripping tale of survival and the pursuit of freedom. Julia Roberts delivered a powerful performance as an abused wife who escapes her dangerous husband and finds love and safety with a new man, played by Patrick Bergin. The film expertly balanced elements of romance, suspense, and empowerment, utilizing the tropes of love's healing power, the struggle for self-preservation, and the resilience of the human spirit. Sleeping with the Enemy offered a riveting, suspenseful journey for audiences, proving that love can shine even in the darkest of circumstances.

French Kiss whisked audiences away on a delightful romantic adventure through France as Meg Ryan's Kate pursued her straying fiance, only to find herself entangled with Kevin Kline's charming thief Luc. The film masterfully employed the tropes of mistaken identities, enemies turned lovers, and the transformative power of travel to create a heartwarming journey full of wit, charm, and passion. With its breathtaking scenery, endearing characters, and memorable moments, French Kiss proved to be an irresistible romantic comedy. This '90s favorite reminds us that sometimes the detours in life lead us to the love we're meant to find.

Jack and Sarah is a heartwarming and poignant exploration of love in the aftermath of loss. Richard E. Grant's portrayal of Jack, a widowed father struggling to care for his infant daughter, captivated audiences, while Samantha Mathis' character Sarah provided an unlikely source of support in the midst of grief. The film employed the tropes of reluctant romance, the healing power of connection, and the resilience of the human spirit, resulting in an emotional and ultimately uplifting journey. This '90s gem serves as a reminder that sometimes life's greatest challenges can lead to the most unexpected and beautiful forms of love.

How Stella Got Her Groove Back revitalized the '90s chick flick genre with its vibrant tale of rediscovered passion, featuring Angela Bassett's Stella and Taye Diggs' Winston as the magnetic lead couple. The film expertly utilized the tropes of the vacation romance, age differences, and the importance of self-discovery, resulting in an empowering and inspiring journey. With its lush Jamaican setting, captivating characters, and exploration of love's ability to transform lives, How Stella Got Her Groove Back remains an entertaining favorite within the genre. This uplifting romantic drama reminds audiences that it's never too late to embrace love and reclaim one's happiness.

Prelude to a Kiss presented a unique twist on the body-swapping genre with a poignant examination of love's ability to transcend physical appearances. Alec Baldwin and Meg Ryan shone as a newlywed couple whose lives are upended when Ryan's character unexpectedly switches bodies with an elderly man. The film expertly explored the tropes of mistaken identity, the transformative power of love, and the challenges of navigating the unknown. With its blend of humor, tenderness, and magical realism, Prelude to a Kiss offered a captivating and heartfelt journey for '90s audiences. This enchanting love story proves that when it comes to love, what's on the inside truly matters most.

Father of the Bride Part II revisited the beloved Banks family, as Steve Martin's George faced the dual challenges of becoming both a father-in-law and a father once again. The film expertly combined the tropes of chaotic family dynamics, the passage of time, and the importance of embracing change with humor and heartfelt emotion. Martin's endearing performance and chemistry with co-stars Diane Keaton and Kimberly Williams-Paisley ensured Father of the Bride Part II would be cherished by audiences. This delightful sequel reminds us that love is the driving force behind every memorable moment in life.