The Best Movies to Watch When Getting Over a Breakup

Ann Casano
Updated April 16, 2024 30.8K views 47 items
Ranked By
4.7K votes
795 voters
3 reranks

Navigating through the emotional turmoil of a breakup can be challenging, and sometimes, cinema offers an ideal escape. The silver screen features countless tales of love, loss, and healing that provide comfort and catharsis for those going through heartbreak. Following a breakup, many individuals seek solace in films about heartbreak to help alleviate their own emotions.    With a vast array of films depicting various stages of separation, viewers seek comfort in stories that resonate with their own experiences. 

Post-breakup film choices are often the ones that delve into themes of personal growth, self-discovery, or the pursuit of happiness despite the end of a relationship. Breakup movies feature relatable characters who navigate the complexities of love while expressing the universal emotions of sadness, anger, or despair. Through these films' ideologies and narratives, viewers can feel understood while witnessing others overcoming similar obstacles in their lives. 

A prime example is Forgetting Sarah Marshall, where protagonist Peter Bretter embarks on a Hawaiian vacation to forget his ex-girlfriend but runs into her with her new partner. This unexpected encounter forces him to confront his past and eventually forge new connections. The Wedding Singer, another classic breakup movie, revolves around Robbie Hart's journey from being jilt by his fiance to finding true love again as he sings at various weddings. Another film, (500) Days of Summer, portrays Tom Hansen's romantic rollercoaster ride as he recounts the highs and lows of his relationship with Summer Finn and the important life lessons he took away from it.

These compelling films are just a few examples among many about breakups that inspire introspection and offer hope amid heartache. As individuals immerse themselves in these films, they may find inspiration towards their own healing process or even rediscover their inner strength after losing love. This collection provides an unparalleled opportunity for catharsis and understanding through the magic of cinema.  

Most divisive: Anchorman: The Legend of Ron Burgundy
Over 700 Ranker voters have come together to rank this list of Movies for Your Breakup Watch List
  • Forgetting Sarah Marshall
    1

    Forgetting Sarah Marshall

    Jason Segel, Kristen Bell, Mila Kunis
    189 votes
    In the comedic romp Forgetting Sarah Marshall, Peter Bretter (Jason Segel) is a down-on-his-luck musician struggling to move on from his television star ex-girlfriend, Sarah Marshall (Kristen Bell). In an attempt to heal, he takes an impromptu trip to Hawaii, only to find himself at the same resort as Sarah and her new rockstar boyfriend, Aldous Snow (Russell Brand). Amidst the tropical backdrop, hilarity ensues as Peter navigates heartbreak, unexpected friendships with hotel staff like Rachel Jansen (Mila Kunis), and the complexities of love.
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  • The Wedding Singer
    2

    The Wedding Singer

    Adam Sandler, Drew Barrymore, Christine Taylor
    146 votes
    In the 1998 romantic comedy The Wedding Singer, Robbie Hart (Adam Sandler) is a charming, small-town wedding singer with a heart of gold. He's set to marry his longtime girlfriend, Linda (Angela Featherstone), but things take an unexpected turn when she leaves him at the altar. Enter Julia Sullivan (Drew Barrymore), a sweet and endearing waitress who's engaged to a selfish tycoon. As Robbie and Julia's paths intertwine, they find themselves drawn to each other in this light-hearted tale of love, laughter, and 80s nostalgia. With its quirky blend of humor and romance, The Wedding Singer proves that sometimes, love can hit the right note when you least expect it.
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  • Clueless
    3

    Clueless

    Alicia Silverstone, Stacey Dash, Brittany Murphy
    134 votes
    In the heart of Beverly Hills, high schooler Cher Horowitz (Alicia Silverstone) reigns as a self-proclaimed fashionista and matchmaker. Clueless, a comedy-drama flick directed by Amy Heckerling, sees Cher navigating the tricky waters of adolescence while attempting to handle love interests and maintain her social status. Alongside Cher is her best friend Dionne Davenport (Stacey Dash), who aids in her various escapades. The film, an amusing modern adaptation of Jane Austen's Emma, cleverly taps into teenage angst and the complexities of young love. Despite its light-hearted tone, it subtly addresses pertinent social issues, making it a timeless classic.
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  • Legally Blonde
    4

    Legally Blonde

    Reese Witherspoon, Luke Wilson, Selma Blair
    184 votes
    Elle Woods (Reese Witherspoon), the effervescent protagonist in Legally Blonde, is a fashion-merchandising major at UCLA, whose life takes a dramatic turn when she decides to enroll in Harvard Law School. This surprising decision comes after her boyfriend, Warner Huntington III (Matthew Davis), dumps her for someone more serious. The film traces Elle's journey through law school, defying stereotypes and proving her worth. A comedy-drama of determination and wit, this movie won the Golden Globe Award for Best Actress - Motion Picture Musical or Comedy. Elle's metamorphosis from a ditzy blonde to a respected law student forms the crux of this engaging narrative.
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  • The First Wives Club
    5

    The First Wives Club

    Goldie Hawn, Bette Midler, Diane Keaton
    124 votes
    In The First Wives Club, a comedic romp, three middle-aged friends‚ Elise (Goldie Hawn), Brenda (Bette Midler), and Annie (Diane Keaton)‚ reunite after the death of a college classmate. Shockingly, they discover they've all been dumped for younger women by their husbands. This shared misfortune ignites a pact: to exact revenge on their exes. As the trio navigate the complexities of divorce, friendship, and vengeance in New York City's high society, the movie offers a comic yet poignant exploration of love and self-worth. Notable for its star-studded cast and witty dialogue, this film is a testament to female resilience and solidarity.
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  • (500) Days of Summer
    6

    (500) Days of Summer

    Joseph Gordon-Levitt, Zooey Deschanel, Geoffrey Arend
    159 votes
    This indie rom-com follows the bittersweet relationship between Tom Hansen (Joseph Gordon-Levitt), an aspiring architect stuck in a mundane greeting card job, and Summer Finn (Zooey Deschanel), his charismatic colleague. Directed by Marc Webb, (500) Days of Summer subverts traditional narrative structure, unfolding in a non-linear fashion that mirrors Tom's emotional journey. Notably nominated for two Golden Globe awards, it explores themes of love, fate, and the nature of happiness through its protagonists' tumultuous romance and their contrasting views on relationships.
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  • He's Just Not That Into You
    7

    He's Just Not That Into You

    Ben Affleck, Jennifer Aniston, Drew Barrymore
    113 votes
    In the heart of bustling Baltimore, a group of friends navigate the complex terrain of modern relationships in He's Just Not That Into You. Gigi (Ginnifer Goodwin), a hopeful romantic, struggles to understand mixed signals from men. Her friend Janine (Jennifer Aniston) tries to save her marriage with Ben (Bradley Cooper), who's entangled with yoga instructor Anna (Scarlett Johansson). Meanwhile, Beth (Jennifer Connelly) seeks commitment from Neil (Ben Affleck), a firm non-believer in marriage. This ensemble romantic comedy explores love and heartbreak in the digital age, offering a humorous yet thoughtful look at how men and women often misunderstand each other.
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  • Eternal Sunshine of the Spotless Mind
    8

    Eternal Sunshine of the Spotless Mind

    Jim Carrey, Kate Winslet, Kirsten Dunst
    134 votes
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    In the mind-bending drama Eternal Sunshine of the Spotless Mind, Joel Barish (Jim Carrey) finds his world turned upside down when he learns his ex-girlfriend, Clementine Kruczynski (Kate Winslet), has undergone a medical procedure to erase him from her memory. Struck by despair, he decides to do the same. The movie then takes us on an intricate journey through Joel's mind as his memories with Clementine progressively vanish. Renowned for its unique narrative structure and surreal visuals, this film won the Academy Award for Best Original Screenplay in 2005. A poignant exploration of love, loss, and memory, it remains a standout in director Michel Gondry's oeuvre.
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  • John Tucker Must Die
    9

    John Tucker Must Die

    Jesse Metcalfe, Sophia Bush, Ashanti
    100 votes
    In the high school comedy John Tucker Must Die, John Tucker (Jesse Metcalfe), the charming and popular basketball captain, is at the heart of a romantic revenge plot. Discovering they're all dating the same guy, three scorned ex-girlfriends - brainy Carrie (Arielle Kebbel), cheerleader Heather (Ashanti), and vegan activist Beth (Sophia Bush) - hatch a scheme to dethrone their two-timing beau. New girl Kate (Brittany Snow) becomes the pawn in their game, transforming from wallflower to siren as part of their elaborate plan. As alliances shift and affections deepen, everyone learns that love isn't always fair play.
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  • Kill Bill Volume 1
    10

    Kill Bill Volume 1

    Uma Thurman, Lucy Liu, Vivica A. Fox
    119 votes
    In Kill Bill Volume 1, a woman known only as The Bride (Uma Thurman) awakens from a four-year coma. The child she carried in her womb is gone. Now, she must wreak vengeance on the team of assassins who betrayed her - a team she was once part of. Her journey takes her to Japan, where she battles the Tokyo yakuza and its leader, O-Ren Ishii (Lucy Liu). Directed by Quentin Tarantino, this film is a stylized homage to grindhouse cinema, filled with high-octane action and marked by its distinctive narrative structure. Despite its violent content, it won numerous awards for its innovative storytelling and direction.
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  • Old School
    11

    Old School

    Luke Wilson, Will Ferrell, Vince Vaughn
    95 votes
    In Old School, Mitch (Luke Wilson) returns home to find his girlfriend involved in an unusual affair, leading him to start anew. He moves into a house near a college campus, where his friends Frank (Will Ferrell) and Beanie (Vince Vaughn) decide to revive their glory days by starting a fraternity. The trio juggles adulthood responsibilities and fraternity antics, causing hilarity and chaos. This comedy explores the paradox of growing up while refusing to let go of youth, all within the wild framework of college life. Old School became a cult classic for its humor and quotable lines.
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  • Silver Linings Playbook
    12

    Silver Linings Playbook

    Bradley Cooper, Jennifer Lawrence, Robert De Niro
    100 votes
    Silver Linings Playbook is a captivating blend of drama and romance, presented by David O. Russell. The narrative revolves around Pat Solitano (Bradley Cooper), who finds himself back in his parents' home after a stint in a mental institution. He's determined to reconcile with his estranged wife, but destiny has other plans when he crosses paths with Tiffany Maxwell (Jennifer Lawrence). Their oddball friendship forms the heart of this movie which won Lawrence an Academy Award for Best Actress. Robert De Niro also shines as Pat's superstitious father. A tale of love, resilience, and second chances unfolds amidst the backdrop of Philadelphia's most vibrant neighborhoods.
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  • Rocky
    13

    Rocky

    Sylvester Stallone, Talia Shire, Burgess Meredith
    76 votes
    The film Rocky is a sports drama, marking the genesis of a beloved franchise. It introduces us to Rocky Balboa (Sylvester Stallone), a small-time boxer from Philadelphia with a heart of gold and fists of steel. The plot thickens when heavyweight champion Apollo Creed (Carl Weathers) offers an unprecedented opportunity - a shot at the title. Rocky's journey from obscurity to the limelight is a testament to determination and grit. This underdog tale, directed by John G. Avildsen, captivated audiences and critics alike, earning three Academy Awards including Best Picture in 1977.
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  • Notting Hill
    14

    Notting Hill

    Julia Roberts, Hugh Grant, Hugh Bonneville
    80 votes
    In the charming romantic comedy, Notting Hill, William Thacker (Hugh Grant), a humble bookstore owner in London's picturesque Notting Hill district, encounters Anna Scott (Julia Roberts), an American actress and global superstar. Their lives intertwine unexpectedly following a chance meeting in his shop, sparking a whirlwind of events that blend the mundane with the glamorous. As their worlds collide, they navigate the challenges of fame, privacy, and love. Directed by Roger Michell, this film is a delightful exploration of two contrasting lives merging in the most unexpected place.
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  • Say Anything...
    15

    Say Anything...

    John Cusack, Ione Skye, John Mahoney
    73 votes
    Say Anything... is a 1989 romantic comedy-drama directed by Cameron Crowe. The film centers on the unlikely romance between Lloyd Dobler (John Cusack), an earnest, quirky kickboxer, and Diane Court (Ione Skye), a high-achieving valedictorian. Dobler's unconventional charm and persistent pursuit of Court forms the crux of this coming-of-age tale. The movie, while encompassing themes of young love and post-high school uncertainty, also delves into familial dynamics with James Court (John Mahoney), Diane's overprotective father. Say Anything... is noted for its iconic boombox scene and was ranked by Entertainment Weekly as one of the greatest modern movie romances.
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  • High Fidelity
    16

    High Fidelity

    John Cusack, Iben Hjejle, Todd Louiso
    85 votes
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    In High Fidelity, Rob Gordon (John Cusack) navigates the tumultuous waters of romantic relationships. As a record shop owner with a deep love for music, he embarks on a self-reflective journey after his latest break-up with Laura (Iben Hjejle). This prompts him to revisit his top five past break-ups, in search of answers. Aided by his eccentric employees Barry (Jack Black) and Dick (Todd Louiso), his introspective quest takes him through an intriguing mix of humor, heartbreak, and vinyl records. A refreshing take on rom-coms, it's as much about personal growth as it is about love's high and lows.
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  • Bridget Jones's Diary
    17

    Bridget Jones's Diary

    Renée Zellweger, Colin Firth, Hugh Grant
    61 votes
    In the heart of London, Bridget Jones (Renée Zellweger) is a thirty-something woman, grappling with her love life, career and self-image. She fills the pages of her diary with humorous observations and sincere confessions, in an attempt to navigate through life's complexities. When two men, Mark Darcy (Colin Firth) and Daniel Cleaver (Hugh Grant), enter Bridget's world, they introduce a whirlwind of romantic dilemmas. Bridget Jones's Diary is a witty romantic comedy that won Renée Zellweger an Academy Award nomination for Best Actress. The film is based on Helen Fielding's best-selling novel of the same name.
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  • My Best Friend's Wedding
    18

    My Best Friend's Wedding

    Julia Roberts, Dermot Mulroney, Cameron Diaz
    77 votes
    Julianne Potter, portrayed by Julia Roberts, finds herself in a precarious romantic predicament in the romantic comedy, My Best Friend's Wedding. When her long-time friend, Michael O'Neal (Dermot Mulroney), announces his engagement to the young and vivacious Kimmy Wallace (Cameron Diaz), Julianne realizes she harbors feelings for him. As the wedding looms closer, Julianne embarks on a comedic journey of self-discovery and unrequited love. Rupert Everett steals scenes as George Downes, Julianne's confidant, adding another layer of complexity to this tale of love and friendship. Directed by P.J. Hogan, this film offers an engaging exploration of relationships from an unconventional angle.
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  • The Sweetest Thing
    19

    The Sweetest Thing

    Cameron Diaz, Christina Applegate, Selma Blair
    78 votes
    When it comes to dating, Christina Walters (Cameron Diaz) has a golden rule: avoid searching for Mr. Right and focus on Mr. Right Now. That is until one night at a club when she unexpectedly meets Peter (Thomas Jane), only to see him suddenly disappear the next day. She and her best friend Courtney (Christina Applegate) decide to break the rules and go on a road trip to find him, encountering wild and hilarious misadventures along the way.
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  • Steel Magnolias
    20

    Steel Magnolias

    Sally Field, Dolly Parton, Shirley MacLaine
    71 votes
    In Steel Magnolias, a delicate interplay of humor and heartache unfolds. This dramedy, set in a small Louisiana town, centers around a close-knit circle of friends. M'Lynn Eatenton (Sally Field), her vivacious daughter Shelby (Julia Roberts), beauty salon owner Truvy Jones (Dolly Parton), elegant widow Clairee Belcher (Olympia Dukakis), irritable Ouiser Boudreaux (Shirley MacLaine), and timid newcomer Annelle Dupuy Desoto (Daryl Hannah) form the core cast. Their lives intertwine in the comforting confines of Truvy's beauty salon, where they navigate life's ups and downs together. The film earned Julia Roberts an Oscar nomination for Best Supporting Actress.
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  • A Walk to Remember
    21

    A Walk to Remember

    Shane West, Mandy Moore, Peter Coyote
    62 votes
    In A Walk to Remember, a poignant tale of love and redemption unfolds. Landon Carter (Shane West), a rebellious teenager, finds himself unexpectedly smitten by Jamie Sullivan (Mandy Moore), the town's preacher's daughter. Set in North Carolina, this coming-of-age drama, directed by Adam Shankman, sees their worlds intertwining in ways they couldn't have imagined. Their relationship evolves against all odds, facing societal pressures and life-altering revelations. This adaptation of Nicholas Sparks's novel won the Teen Choice Award for Choice Drama Movie. The film is notable for its exploration of faith, transformation, and resilience in the face of adversity.
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  • The Notebook
    22

    The Notebook

    Ryan Gosling, Rachel McAdams, James Garner
    130 votes
    The Notebook, a romantic drama, sweeps us into the tale of Allie Hamilton (Rachel McAdams) and Noah Calhoun (Ryan Gosling). Set in the backdrop of 1940s South Carolina, it follows the couple's fervent love story from their youthful summer romance to the trials of old age. The narrative unfolds through an elderly man's recollections, Duke (James Garner), reading from his faded notebook to fellow nursing home resident, Miss Hamilton (Gena Rowlands). Directed by Nick Cassavetes and based on Nicholas Sparks's novel, The Notebook won eight Teen Choice Awards in 2005.
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  • Dumb and Dumber
    23

    Dumb and Dumber

    Jim Carrey, Jeff Daniels, Lauren Holly
    38 votes
    In the comedic masterpiece Dumb and Dumber, Harry Dunne (Jeff Daniels) and Lloyd Christmas (Jim Carrey) are two dim-witted best friends who embark on a cross-country journey to return a briefcase full of money. Unaware that it's intended as ransom for a crime boss's wife, their adventure spirals into a series of hilarious misunderstandings. This Farrelly Brothers-directed film cleverly embraces slapstick humor while showcasing the undeniable chemistry between its lead actors. Despite their characters' low intellect, both Carrey and Daniels deliver performances filled with heart, making this quintessential 90s comedy a memorable ride from start to finish.
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  • Jerry Maguire
    24

    Jerry Maguire

    Tom Cruise, Cuba Gooding, Renée Zellweger
    80 votes
    Jerry Maguire is a film steeped in the frenetic world of sports management. The eponymous character, Jerry (Tom Cruise), is an established sports agent suddenly struck by a moral crisis. This leads to a dramatic career shift, casting him down a path less travelled in his industry. His singular client, Rod Tidwell (Cuba Gooding Jr.), is an aspiring football star with big dreams and bigger personality. Their intertwined journeys form the crux of the narrative, exploring themes of ambition, loyalty, and redemption. Directed by Cameron Crowe, this dramedy won an Academy Award for Best Supporting Actor (Gooding Jr.).
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  • How Stella Got Her Groove Back
    25

    How Stella Got Her Groove Back

    Angela Bassett, Taye Diggs, Regina King
    63 votes
    In the heartwarming film How Stella Got Her Groove Back, successful stockbroker Stella Payne (Angela Bassett) finds herself in a midlife crisis. Deciding to take a much-needed vacation, she lands in sunny Jamaica where she meets the young, charming Winston Shakespeare (Taye Diggs). Despite their age difference, an unexpected romance blossoms. This romantic drama, based on Terry McMillan's novel, explores the theme of self-discovery and love beyond societal norms. It snagged Angela Bassett an NAACP Image Award for Outstanding Actress. The movie is a balance of light-hearted moments and profound life lessons, making it a watch worth its while.
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  • Birds of Prey (And the Fantabulous Emancipation of One Harley Quinn)
    26

    Birds of Prey (And the Fantabulous Emancipation of One Harley Quinn)

    Margot Robbie, Rosie Perez, Mary Elizabeth Winstead
    56 votes
    It's open season on Harley Quinn when her explosive breakup with the Joker puts a big fat target on her back. Unprotected and on the run, Quinn faces the wrath of narcissistic crime boss Black Mask, his right-hand man, Victor Zsasz, and every other thug in the city. But things soon even out for Harley when she becomes unexpected allies with three deadly women -- Huntress, Black Canary and Renee Montoya.
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  • The Break-Up
    27

    The Break-Up

    Vince Vaughn, Jennifer Aniston, Joey Lauren Adams
    42 votes
    In the heart of Chicago, Gary Grobowski (Vince Vaughn) and Brooke Meyers (Jennifer Aniston) find their romance spiraling into a tumultuous break-up in this rom-com drama. The pair, once hopelessly in love, now battle over their shared condo as their relationship deteriorates. The Break-Up is a stark portrayal of love's demise, peppered with comedic interludes that provide relief from the tension. This film intertwines humor and heartbreak, creating an engaging narrative that explores the complexities of relationships and break-ups.
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  • P.S. I Love You
    28

    P.S. I Love You

    Hilary Swank, Gerard Butler, Lisa Kudrow
    25 votes
    In P.S. I Love You, a romance-meets-drama film, Holly Kennedy (Hilary Swank) finds herself navigating the choppy waters of widowhood after her husband Gerry's (Gerard Butler) untimely death. But Gerry, in his love and foresight, has left Holly a series of letters designed to ease her grief and guide her towards reclaiming life. The movie weaves through these poignant moments as Holly discovers each letter. Directed by Richard LaGravenese, this film is an exploration of love, loss, and self-discovery set against the backdrop of Ireland's awe-inspiring landscapes.
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  • Anchorman: The Legend of Ron Burgundy
    29

    Anchorman: The Legend of Ron Burgundy

    Will Ferrell, Christina Applegate, Paul Rudd
    75 votes
    Anchorman: The Legend of Ron Burgundy, a comedy set in the 1970s, features Will Ferrell as egotistical news anchor, Ron Burgundy. This San Diego star is thrown off his throne when ambitious reporter Veronica Corningstone (Christina Applegate) challenges the male-dominated industry. Directed by Adam McKay, this laugh-out-loud film showcases an ensemble cast including Paul Rudd and Steve Carell. It's a comedic exploration of gender dynamics in the workplace, wrapped up in absurd humor and vintage fashion. The film was nominated for two MTV Movie Awards, further cementing its cult status.
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  • City Slickers
    30

    City Slickers

    Billy Crystal, Daniel Stern, Bruno Kirby
    31 votes
    City Slickers, a comedy-western film, follows the life of Mitch Robbins (Billy Crystal), a radio ad salesman. On his 39th birthday, he and his two friends, Phil Berquist (Daniel Stern) and Ed Furillo (Bruno Kirby), embark on a two-week cattle drive from New Mexico to Colorado. This adventure is designed to help them escape their city lives. Along the way, they encounter Curly Washburn (Jack Palance), an intimidating cowboy who won an Academy Award for this role. The combination of humor, friendship, and self-discovery makes this movie a must-watch.
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