The 30 Best Romantic Comedies of All Time, Ranked

Hollywood has produced many amazing romantic comedies throughout the years. The greatest of these game-changing, grin-generating romances rank among the best and most memorable pictures in American cinema, whether because of their heartwarming storylines, unforgettable quotes, electrifying chemistry between their leads, or a combination of all these factors. Acclaimed by fans and critics, the following rom-coms (Hollywood and international) are the best the genre has to offer, among them outright legends in pop culture and milestones in the entertainment industry.

30 ‘How to Lose a Guy in 10 Days’ (2003)

Modern rom-com queen Kate Hudson joins Matthew McConaughey in 2003’s How to Lose a Guy in 10 Days. The plot centers on Andy Anderson and Benjamin Barry, a couple who go into a whirlwind romance. Unbeknownst to one another, they each have their own agendas: he bet he could make her fall in love in one week while she is on a work assignment to drive him away in 10 days.

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How to Lose a Guy in 10 Daysfeatures the most rom-com plot ever in that it’s wholly unbelievable but weirdly irresistible. Hudson and McConaughey are outstanding together, bringing equal amounts of humor and romance to a film as funny as it’s charming. How to Lose a Guy in 10 Days is a modern rom-com classic, proving that the genre can sell the most ludicrous plots as long as the central couple is engaging, beautiful, and endearing.

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29 ‘Silver Linings Playbook’ (2012)

Silver Linings Playbook stars Bradley Cooper and Jennifer Lawrence in their first collaboration. The film tells the story of Patrick “Pat” Solatano, a bipolar man who forms an unexpected connection with the young Tiffany Maxwell, a young and emotionally unstable widow while training for an upcoming dance competition,

The romantic comedy seldom attracts acclaim from critics. However, Silver Linings Playbook is the rare rom-com that ruled the Oscars, thanks to its unique approach to love, loss, and romance. Cooper and an Oscar-winning Lawrence are electrifying together, crafting a unique cinematic relationship with emotional heft. However, they never sacrifice the feels, finding gentleness in the most unexpected sides of romance.

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28 ‘Trouble in Paradise’ (1932)

The pre-Code romantic comedy Trouble in Paradise is among the genre’s most underappreciated efforts. Directed by Ernst Lubitsch, the film stars Miriam Hopkins, Kay Francis, and Herbert Marshall and follows a con artist and a pickpocket who team to scam a wealthy woman.

An essential entry for Lubitsch aficionados, Trouble in Paradise is one of the earliest romantic comedies to feel like one. A passionate and surprisingly frank love triangle with effervescent performances from its three well-matched leads, Trouble in Paradise juggles ideas of its era with a distinctively progressive approach. The result is a singular romantic comedy that deserves far more attention from modern audiences.

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27 ‘Notting Hill’ (1998)

The undisputed rom-com queen of the 90s, Julia Roberts, joins the undisputed rom-com king of the 90s, Hugh Grant, in a once-in-a-lifetime pairing for fans of the beloved genre. Notting Hill sees Grant as a meek bookshop owner, William Thacker, who falls in love with world-famous actress Anna Scott, leading to a complicated romance.

Notting Hill lives and dies with its two powerful and never-better stars. Roberts and Grant are utterly winning with their clumsy, awkward, enchanting chemistry; they might possibly be the ultimate rom-com couple of the decade. Few times have two actors been more well-suited, playing off each other’s strengths in a delicate balancing act. Notting Hill is among Roberts’ and Grant’s all-time best movies, solidifying their legacies as titans of the rom-com.

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26 ‘Pillow Talk’ (1959)

Rock Hudson and Doris Day are one of the all-time great cinematic pairings. Their three films together have become synonymous with romance and passion, turning them into icons of the romantic comedy genre and legends of American cinema. All three movies are classics of 50s cinema, but their first collaboration, 1959’s Pillow Talk, reigns supreme atop the mountain of their success.

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Pillow Talk is very much a film from 1959, meaning it has some themes, scenes, and dialogues that might seem outdated to modern audiences. However, Hudson and Day are explosive together, crafting a unique dynamic many have tried to imitate, but none have succeeded in replicating. Pillow Talk is fun, funny, witty, seductive, and absurdly romantic; everything a great rom-com should be.

25 ‘Bridget Jones’s Diary’ (2001)

Renée Zellweger received her first Oscar nomination for her star-making performance in the 2001 adaptation of Helen Fielding‘s 1996 novel. Bridget Jones’s Diary follows the romantic misadventures of the titular character, a thirty-something living in London who finds herself deciding between two romantic interests. The film, a modern adaptation of Jane Austen‘s Pride and Prejudice, co-stars Hugh Grant and Colin Firth.

Bridget Jones’s Diary is a modern triumph and further proof of the universality of Austen’s stories. Powered by a spectacular, vulnerable, and self-deprecating performance from Zellweger, Bridget Jones’s Diary is an ode to the modern woman – or at least, the idea of the modern woman from the late 90s. Further elevated by Grant and Firth – two of the defining leading men in modern rom-coms – Bridget Jones’s Diary is a classic story of romantic deceit and confusion, with a memorable ending that will leave audiences cheering at Zellweger’s clumsy heroine’s happy ending.

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24 ‘While You Were Sleeping’ (1995)

Sandra Bullock is one of modern cinema’s ultimate rom-com queens, thanks to her generous contributions to the genre. 1995’s holiday rom-com While You Were Sleeping sees her starring opposite Bill Pullman and Peter Gallagher in the story about Lucy, a woman who saves Peter, her longtime crush, from an oncoming train. Mistaking her for his finacée, his family takes her in, but things get complicated when she develops feelings for Peter’s brother.

Although the plot is admittedly silly – perhaps a tad questionable under the modern gaze –While You Were Sleeping soars thanks to Bullock’s endearing portrayal of loneliness and longing. The film finds Bullock at her warmest and most sympathetic, almost single-handedly elevating the formulaic premise and turning it into a feel-good classic.

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23 ‘Fire Island’ (2022)

Jane Austen’s Pride and Prejudice stands as one of the most adapted books. However, few adaptations feel as fresh or topical as 2022’s Fire Island, a gender-bent, LGBTQ+ take on Austen’s most famous romance. The plot centers on a group of gay friends on holiday at Fire Island, finding love but facing challenges that might risk their bond.

Fire Island feels like a genuinely interesting take on Austen’s novel. The film keeps the story’s main themes but reframes them under the queer perspective, delivering a satisfying tale of romance, identity, social expectations, and class. Thanks to a winning cast, a clever screenplay, and an earnest, empathetic portrayal of LGBTQ+ sexuality and romance, Fire Island is among the best modern rom-coms.

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22 ‘(500) Days of Summer’ (2009)

The antidote to the classic romantic comedy, Marc Webb‘s often misinterpreted classic (500) Days of Summer stars Joseph Gordon-Levitt and Zooey Deschanel. The plot centers on the complicated relationship between Tom, a hopeless romantic, and Summer, a cynical woman unwilling to commit to him.

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(500) Days of Summer features one of the most intriguing plots in any modern rom-com. Challenging audiences’ notions about love and romance, the film presents a narrative that subverts familiar tropes, offering a more nuanced and realistic approach to the boy-meets-girl tale. (500) Days of Summer is bittersweet and almost tragic, but it’s an undeniably satisfying alternative to the saccharine offerings that dominate the rom-com genre.

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21 ‘The Shop Around the Corner’ (1940)

James Stewart and Margaret Sullivan star in Ernst Lubitsch‘s romantic comedy The Shop Around the Corner. The plot centers on two employees at a Budapest store who can’t stand each other. Unbeknownst to them, they are falling in love by anonymously exchanging letters with each other.

The Shop Around the Corner features a classic rom-com premise of mistaken identity and unexpected love. More interestingly, it subverts classic notions about this notoriously elusive and ever-changing feeling, challenging classic perceptions about what it truly feels like to fall in love. Aided by the chaotic chemistry between Stewart and Sullivan, the film delivers an acidic take on relationships and love perfect for cynics and hopeless romantics.

20 ’10 Things I Hate About You’ (1999)

The late Heath Ledger stars opposite 90s icon Julia Stiles in the 1999 teen rom-com 10 Things I Hate About You. A modern retelling of William Shakespeare‘s The Taming of the Shrew, the plot centers on rebellious student Patrick Verona, paid by meek classmate Cameron James to seduce the abrasive Kat James so that Cameron can date her sister, popular pretty girl Bianca.

10 Things I Hate About You is a certified 90s classic. Strengthened by the fiery chemistry between Ledger and Stiles, the film is a clever updating of one of Shakesperare’s naughtiest and most playful works. It doesn’t always rise above tropes typical of the teen genre, but 10 Things I Hate About You still stands out as a smart and funny rom-com whose reputation seemingly improves every new year.

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19 ‘Crazy Rich Asians’ (2018)

2018’s Crazy Rich Asians was a groundbreaking commercial and critical success, proving that the rom-com was far from dead. The film stars Constance Wu as Rachel Chu, who travels to Singapore with her longtime boyfriend only to discover he belongs to one of the country’s wealthiest families. Dealing with far more than she had anticipated, Rachel’s relationship is put to the test.

Based on the eponymous 2013 novel, Crazy Rich Asians was a milestone achievement for Asian representation. The film is a triumph of the classic rom-com formula, updating but respecting it and delivering a visual and romantic spectacle that enchanted critics and audiences. With a terrific cast, including a scene-stealing turn from the ever-reliable Michelle Yeoh, Crazy Rich Asians is among the 2010s’ best rom-coms.

18 ‘Jerry Maguire’ (1996)

Cameron Crowe directed Tom Cruise to his second Oscar nomination with his 1996 romantic sports comedy Jerry Maguire. The plot revolves around the titular character, a sports agent who starts his own management firm alongside a single mother, Dorothy Boyd, played by Renée Zellweger in her breakthrough role.

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Jerry Maguire is among the best films of 1996, the perfect marriage between a sports dramedy and a rom-com, with Cruise delivering arguably his best performance as the passionate but struggling Jerry Maguire. Thanks to Crowe’s intelligent, tender, and impossibly quotable screenplay, and with Cruise and Zellweger’s charming chemistry as the fiery fuel to keep it going, Jerry Maguire is a smashing success, proving that there’s more to the rom-com than tears and laughter.

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17 ‘Love Actually’ (2003)

Richard Curtis‘ Christmas rom-com Love Actually stars an epic ensemble of British talent, including Hugh Grant, Colin Firth, Liam Neeson, Emma Thompson, Bill Nighy, Keira Knightley, Laura Linney, and the late Alan Rickman. Set throughout the five weeks before Christmas, the film features several loosely connected storylines about love, friendship, longing, and loss.

Love Actually marks Curtis’ directorial debut, with the film juggling many of the famous trademarks that made him a household name in the rom-com genre. It might not be particularly polished, but Love Actually thrives on the strength of a stellar ensemble that brings a refreshingly honest and vulnerable approach to the crowded screenplay. Touching, funny, and outright unforgettable, Love Actually is a modern Christmas classic as joyful and irresistible as the season it revolves around.

16 ‘Clueless’ (1995)

The Jane Austen adaptations strike again; this time, it’s Austen’s most confident, brattiest and, in many ways, modern heroine, Emma Woodhouse, who receives an updating courtesy of Amy Herckerling. Clueless stars Alicia Silverstone as Cher Horowitz, a handsome, clever, and rich high school student living in Beverly Hills and using her charm and beauty to get her way.

It wouldn’t be an overstatement to call Clueless the best of the many Austen updates. Herckerling’s adaptation is clever and timely, seamlessly updating the main themes in Austen’s seminal novel and transitioning them to 90s Beverly Hills. For her part, Silverstone delivers a charismatic, star-making performance as the assured and vain yet sympathetic and inspiring Cher, whose romance with Josh, her step-brother of only a few weeks, makes for an unexpectedly winsome love story. Funny, endearing, and endlessly quotable, Clueless is a pop culture masterpiece.

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15 ‘Breakfast at Tiffany’s’ (1961)

Audrey Hepburn cemented her place as a screen icon with her now-iconic portrayal of Holly Golightly in Blake Edwards‘ 1961 rom-com Breakfast at Tiffany’s. The plot centers on Paul Varjak, a struggling writer who falls for Holly, a free-spirited and erratic café society girl.

Breakfast at Tiffany’s has little in common with Truman Capote’s original novella. It changes the themes and plot, sacrificing Capote’s dramatic cautionary tale in favor of a lighter romantic plot. However, the film excels as a romantic comedy, thanks to Hepburn’s charming performance and her chemistry with George Peppard. Hepburn’s Holly is a bona fide cinematic legend, a fashion goddess whose effortless glamour and unassuming allure have turned her into a near-perfect embodiment of the romantic comedy genre.

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14 ‘The Big Sick’ (2017)

Based on his real-life story with wife Emily V. Gordon, who co-wrote the screenplay, The Big Sick stars Kumail Nanjiani opposite Zoe Kazan, Ray Romano, and Holly Hunter. The plot revolves around an interracial couple who must deal with their inherent differences after she becomes ill.

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The Big Sick is the rare rom-com that is truly and ridiculously hilarious. Filled with natural, laugh-out-loud moments that perfectly dissect the nature of the couple’s chaotic yet loving relationship, The Big Sick is a thoughtful, clever, and affecting exploration of culture, tradition, love, and faithfulness. Funny, wise, and heartbreaking, The Big Sick is arguably the best rom-com from the 2010s.

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13 ‘My Best Friend’s Wedding’ (1997)

Julia Roberts stars opposite Dermot Mulroney and Cameron Diaz in P. J. Hogan‘s subversive 1997 rom-com My Best Friend’s Wedding. The film follows Julianne Potter, a 28-year-old food critic who receives news that her lifelong best friend is marrying Kimberly Wallace, a beautiful young heiress. Realizing she is in love with him, Julianne agrees to be maid of honor to disrupt the wedding from within.

Many might say Pretty Womanis Roberts’ best 90s rom-com; however, the film has aged poorly, unlike My Best Friend’s Wedding, which still feels fresh 25 years later. The film was a return to form for Roberts after a string of commercial and critical failures. More importantly, My Best Friend’s Wedding proves that Roberts is one of the genre’s undisputed queens, unafraid of disrupting the classic formula to tell an original and bittersweet story about lost love. Roberts delivers a tricky performance that can easily be unlikable; however, one flash of her winning smile is enough to make audiences empathize with Julianne, even when she is objectively wrong.

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12 ‘The Worst Person in the World’ (2021)

Joachim Trier created a certified classic of the 21st century with his acidic 2021 romantic comedy, The Worst Person in the World. Renate Reinsve stars as Julie, a young Norwegian woman struggling to find her path and purpose while dealing with a complicated love life involving two men.

Few romantic comedies are as richly affecting as The Worst Person in the World. Reinsve is an instant icon of the millennial generation: messy, lost, self-sabotaging, and aimless, an imperfect figure that might as well become a new cinematic archetype. Insightful and thought-provoking, The Worst Person in the World is a profound exploration of purpose and meaning, a layered character study and a bittersweet love letter to the wild and chaotic feeling of restlessness that haunts and defines those crucial formative years.

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11 ‘The Lady Eve’ (1941)

Henry Fonda and Barbara Stanwyck star in Preston Sturges‘ 1941 rom-com The Lady Eve. The plot centers on a beautiful con artist posing as an English aristocrat to get back at the hapless man who scorned her upon discovering her gold-digging intentions.

The Lady Eve benefits greatly from Fonda and Stanwyck’s against-type performances in service of a classic romance story that cleverly subverts gender roles. Stanwyck plays up the vamp persona, imbuing the character with charming ruthlessness, making her irresistible to Fonda and audiences alike. Wickedly funny and with a rather dark sense of humor, The Lady Eve is a romantic comedy unafraid to bear its sharp and honey-laced teeth.