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The 20 Best Romantic Comedies of All Time, Ranked

As the holidays approach and temperatures plummet, what better time is there to get lost in a classic romantic comedy? When it’s too cold to go outside, movie lovers can bring a bit of warmth into their home with a timeless tale of love and devotion, though romantic comedies have much more to offer than the satisfaction of a meet-cute blossoming into a lifelong bond. The feel-good nature of these films is sure to entertain and engage on a calm night in, with many films in the genre exploring a range of themes that can be greatly moving and introspective.

This is important to note given the reputation that romantic comedies once had, seen as a shallow and predictable favorite of the Hollywood production machine. Romantic comedies have evidently fallen into a significant slump in the past decade, but the genre seems to be slowly but surely rising up again. The popularity of holiday rom-coms in particular would seem to signal a new age of romantic comedies, the possibilities for which are endless in an era of filmmaking that embraces raw, diverse stories more than ever before. As we eagerly await what the future of the genre holds, here are the best rom-coms of all time, ranked.


20/20 The Proposal (2009)

Touchstone Pictures

Sandra Bullock and Ryan Reynolds star in this unique romantic comedy in which a rather frigid and ambition-driven woman, Margaret (Bullock), and her stark contrast of an easy-going assistant, Andrew, (Reynolds) agree to marry in order to prevent Margaret’s deportation to Canada. Along the way, the two characters reluctantly fall in love, of course. The movie explores Margaret’s transformation from someone utterly closed off to vulnerability into someone ready to open her heart, without stripping the character of the independent spirit and self-driven ambition that makes her who she is. The film also features a wonderfully lighthearted performance from the late Betty White.

19/20 Clueless (1995)

Clueless 1995
Paramount Pictures

This iconic film was a cultural reset in the world of teen rom-coms. Cher Horowitz (Alicia Silverstone) is an unapologetically glamorous young lady, albeit with shallow tendencies. Nevertheless, the queen bee of her local high school sets her sights on a new project: turning the clueless new student, Tai (Brittany Murphy), into an it-girl like herself. Cher ends up finding this effort to be erroneous as Tai overtakes her as the most popular girl in school, the reality check of which prompts character development and her subsequently falling for her former step-brother, Josh (Paul Rudd). Could this movie be made today? On account of the romance between former step-siblings, probably not. Despite the ending getting maybe a bit weird, this teen classic still hits all the major tropes for a rom-com success, with unforgettable trendsetting fashion to boot.

18/20 He’s Just Not That Into You (2009)

He's Just Not That Into You
Warner Bros. Pictures

It seems that 2009 was a monumental year for pop culture. Lady Gaga’s 2009 VMAs performance of “Paparazzi”, The Proposal, Avatar, Kanye stealing the mic from Taylor Swift, and last but not least, the release of He’s Just Not That Into You. For a hopeless romantic, that title alone is a big ouch. That’s the beauty of the film, as it explores multiple facets of dating— the good, the bad, and the ugly. Just as the viewer may feel pessimistic about love upon witnessing the betrayal of Janine (Jennifer Connelly) by her husband Ben (Bradley Cooper), our spirits are lifted by the triumph of Gigi and Alex (Ginnifer Goodwin and Alex Long). The film also follows a range of other characters, showing multiple sides to what love actually means.

17/20 Life As We Know It (2010)

Untitled (1200 × 630 px)-39
Warner Bros. Pictures

This touching but funny movie tells the story of a pair who face a life-changing tragedy that later leads to a beautiful life together. Holly (Katherine Heigl) and Messer (Josh Duhamel) are unsuccessfully set up on a date by mutual friends. The date is a disaster and fails before it even really begins, but the pair remain reluctant acquaintances on account of the couple they are both friends with. When that couple tragically passes away and leaves behind and infant daughter, they are shocked to learn that the two of them have been named as the child’s joint guardians. The film follows Holly and Messer as they navigate the difficulties of sudden and unexpected parenthood, the journey of which ultimately leads them to fall in love with each other.

16/20 Bridget Jones’s Diary (2001)

A scene from Bridget Jones's Diary
Miramax Films/Universal Pictures

Renée Zellweger stars as the titular character as she embarks on a journey of self-discovery and exploration on New Year’s. Bridget Jones vows to make this next year exciting and memorable, and she documents all the adventures that her newfound confidence takes her on in her bedside journal. The leading lady shares a special journey with the audience, redefining her relationships with romance, food, friendship, work, and most importantly, herself.

15/20 Amélie (2001)

Audrey Tatou in Amelie
Claudie Ossard Productions

For the lover of both romantic and foreign films, Amélie is a delightful and whimsical tale of a shy young waitress whose life is changed by a simple and unexpected discovery. Amélie is a refreshingly positive character, but it is not lost on the viewer just how lost and lonely the friendliest of people can be. As we follow Amélie around Paris, with the beauty and rich culture of the city being a quiet character of its own, we watch her find herself as she devotes herself to others.

14/20 Love & Other Drugs (2010)

Untitled (1200 × 630 px)-38
20th Century Studios

Anne Hathaway and Jake Gyllenhaal star as Maggie and Jamie, a woman suffering from Parkinson’s disease and a man working for pharmaceutical giant Pfizer, respectively. The film does a fantastic job of marrying a raw, imperfect romantic storyline with the realities of greater social issues such as healthcare policies and the realities of disability. Both actors give moving performances in a film that completely subverts the lighthearted expectations one may have for a romantic comedy.

13/20 Crazy Rich Asians (2018)

crazy rich asians
Warner Bros.

Crazy Rich Asians is a great example of the sort of film heralding in a new era of romantic comedies. Newer projects are placing a greater emphasis on diversity, with this particular film highlighting Asian culture and identities within the context of a classic romantic comedy. Constance Wu plays Rachel Chu, a second generation Asian American young woman and mahjong prodigy who teaches at New York University. She has an unassuming but happy romance with Nick Young (Henry Golding), blissfully unaware that he is in fact from one of the wealthiest families in all of Asia. She discovers the truth when she accompanies him on a trip home to Singapore, where she finds herself to be met coldly by her boyfriend’s family, who do not find her worthy for the highly desired young heir.

Luckily, Rachel finds an ally in Nick’s cousin, the perennially elegant Astrid. Despite being a woman of great beauty and grace, she discovers her husband is cheating on her. Though she is facing her own personal heartbreak, Astrid defends Rachel as the women of the Young family lead an onslaught on her meant to send her packing. Love ultimately prevails, and along the way we see stunning displays of magnanimous wealth; rich cultural traditions; gorgeous costuming and vivid set design, and strong performances from the whole cast.

Related: Crazy Rich Asians Spinoff: Plot, Cast, and Everything Else We Know

12/20 How To Lose a Guy in Ten Days (2003)

How To Lose a Guy in 10 Days-2
Lynda Obst Productions

As per the title of the film, the character of Andie (Kate Hudson) fervently attempts to drive a guy to the edge of insanity, and far away from her, within ten days of dating. Unbeknownst to her, her chosen victim of Ben (Matthew McConaughey) has a quest of his own to fulfill. While she seeks to drive him away within ten days, he is looking to get her to fall in love within the same time frame. Since their motivations for one another are stark opposites, both of their schemes come to a frustrating stalemate. Motivated by career advancement, both characters lose themselves in this charade, until it is no longer a game. When real feelings develop, the characters must confront their truth and reassess what is important to them.

11/20 Pretty Woman (1990)

Pretty Woman Richard Gere and Julia Roberts as the Main Love Interests
Touchstone Pictures

With Julia Roberts, the queen of romantic comedies herself, as leading lady Vivian, Pretty Woman was bound to be yet another rom-com classic. Alongside a dashing Richard Gere as Edward, the story revolves around Vivian, a sex worker who Edward hires to play his girlfriend for the week. Considering that the 1990s were not as openly accepting as gen-z viewers may erroneously assume, this sort of media was entirely pushing the envelope of what a proper love story could be. The film begins with Edward unapologetically soliciting sex work without being portrayed as a sleazy or shady individual, and Vivian is likewise portrayed largely as a typical worker just doing her job in an environment that has her a bit out of her depths.

Despite the taboo nature of Vivian’s occupation and the circumstances of her meeting with Edward, the pair are given a healthy and well-rounded romantic story. One of the best features of the movie is that it portrays the transformation of Vivian’s character without belittling her or chastising her for her lifestyle (in fact, the film condemns its leading man when he does so). Overall, the film is a refreshing project for its time, and an enduringly enjoyable movie.

10/20 But I’m a Cheerleader (1999)

But Im a Cheerleader
 Ignite Entertainment

This film is important to note, and earns its spot among the top ten, as a groundbreaking project that helped to pioneer openly queer storylines in Hollywood. In fact, the movie touches on a number of incredibly touchy topics in American politics, including conversion therapy, religion, and gay rights. While enjoying no sort of massive acclaim, the film gathered a loyal cult following, likely on account of the subject matter that means so much to a marginalized community. So many queer young people got to watch a happy and successful gay love story at a time when this was not a popular story to produce.

The film playfully pokes fun at baseless and superficial stereotypes surrounding queer identities, such as when the leading character of Megan (Natasha Lyonne) is suspected of being a lesbian, when she decides to go vegetarian. The film begins to take a bit of a darker tone as two young boys are punished for homosexual relations, really just for an innocent kiss. Witnessing the treatment of this couple leads Megan into a radical realization and acceptance of her sexuality, shirking the shame imposed by her ultra religious background. Opening to mediocre reviews upon its release, the film is aging better with time as more accepting audiences discover this gem.

9/20 Sleepless in Seattle (1993)

Untitled (1200 × 630 px)-37
TriStar Pictures

One of many Meg Ryan classics, Sleepless in Seattle follows Meg Ryan’s direct and driven Annie as she falls for Sam (Tom Hanks), a widower who opens up about his feelings on a national radio program. Despite living on opposite coasts, Annie challenges Sam to meet her at the top of the Empire State Building for Valentine’s Day. The film captures the essence of a complicated love story where the characters have to make real sacrifices and consequential choices in order to follow their hearts. Ryan’s character of Annie is actually already engaged when she falls for Sam, a man whose face she has not yet seen. Sam, on the other hand, struggles with opening himself up to real love once more. Both characters take incredible leaps of faith for love in a storyline that allows viewers to indulge in the sort of reckless whirlwind that would culminate with a kiss upon the iconic Empire State Building.

8/20 Notting Hill (1999)

PolyGram Films

This fun is particularly fun because it subverts the role played by the male and female characters of a previous Julia Roberts film, Pretty Woman. In this movie, Roberts finds herself leading the life of luxury as Hollywood star Anna Scott. She meets humble bookshop owner Will (Hugh Grant), diving head-first into a romance. Anna proves to be a rather flawed leading lady, as Will discovers she is actually cheating on her current boyfriend with him. She leaves him, leaving Will dejected. The pair reunite once again, only for Anna to once again leave as she blames Will for some unfortunate paparazzi photos.

Despite having been burned twice now by this woman, the lovelorn Will continues to chase after Anna until they get their happily ever after. Will is objectively a bit of a pushover and maybe deserves better than some of Ana’s worst traits, but he isn’t necessarily the ideal catch himself. He is kind, but his personal life is a mess compared to Anna’s success. Nevertheless, the film explores these flawed characters with fairness and compassion. The film has also produced iconic lines, such as “I’m just a girl, standing in front of a boy, asking him to love her”.

7/20 10 Things I Hate About You (1999)

A scene from 10 Things I Hate About You
Buena Vista Pictures

This romantic comedy can confidently avoid the derision that many teenage films face because the subject matter comes from the imagination of none other than William Shakespeare. A modern reimagining of The Taming of the Shrew, 10 Things I Hate About You follows the Stratford sisters, as the popular youngest sister, Bianca (Larisa Oleynik) is banned from dating until her antisocial older sister, Kat (Julia Stiles) does. Bianca’s suitors bribe the infamous school bad boy, Patrick (Heath Ledger) into winning over the hostile Stratford sister and thus opening the doors for them to pursue Bianca. The film is witty, well-paced, and well cemented in its place as one of the best rom-coms of all time.

6/20 Roman Holiday (1953)

Gregory Peck and Audrey Hepburn in Edith Head's costumes for Roman Holiday
Paramount Pictures

For this film, we’re throwing it back all the way to 1953 as Audrey Hepburn’s character of Princess Ann finds love on the streets of Rome. She is here strictly for business, performing her royal duties for the vague kingdom from which she hails. Weary from her travels, she serendipitously stumbles upon Joe (Gregory Peck), an American journalist and expat. The pair share a romantic grand tour of Rome as Joe seeks to capture photos of her to sell at work, only to find himself falling for the young royal. In the end they go their separate directions, with the film showcasing the bittersweet experience of finding love on holiday.

5/20 Me Before You (2016)

Warner Bros. Pictures

Game of Thrones star Emilia Clarke and Hunger Games star Sam Claflin star as the star-crossed lovers of this unconventional love story. As Louisa and Will, the characters grow from a barely polite working relationship to a deep and intimate connection despite Will’s physical limitations. Me Before You allows two people to simply fall in love despite the obstacles at hand, while still remaining realistic about those obstacles. The film portrays Louisa as a genuinely kind and un-shallow woman, without belittling disabled individuals by making her into a hero for choosing to love him. It likewise preserves the dignity and autonomy of Will, who ultimately makes an important medical decision on account of what is best for him rather than his newfound romance.

4/20 Gentlemen Prefer Blondes (1953)

Untitled (1200 × 630 px)-36
20th Century Fox

Released in the same year as Roman Holiday, Gentlemen Prefer Blondes stars Marilyn Monroe and Jane Russell as polar opposite showgirls and best friends. Marilyn’s Monroe’s Lorelei is an effervescent and shamelessly gold-digging yet genuinely charming young lady, while Russell’s Dorothy remains more conservative in her simple standards of good looks. The film established Marilyn Monroe as a leading lady and box office draw, producing the iconic performance of “Diamonds Are a Girl’s Best Friend”.

Related: Blonde: Sorting Through the Facts and Fiction of the Marilyn Monroe Movie

3/20 500 Days of Summer (2009)

500 Days of Summer (2)-1
Fox Searchlight Pictures

This film earned its spot in the top three in that it provokes a good deal of thought and analysis on what presents as a relatively straightforward and relatable story of being unlucky in love. Joseph Gordon-Levitt’s Tom falls madly in love with Zooey Deschanel’s noncommittal and aloof Summer, entrapping himself in a self-imposed cycle of unrequited affections. The interesting thing is that Summer is entirely up front about her intentions from the beginning, so the viewer has to reconcile the image of her they see from Tom’s biased point of view versus who she really is as an actual human being with more to offer than dating Tom. The film invites the viewer to sympathize with Tom while also recognizing the pitfalls of his unhealthy dating habits and attachment style.

2/20 When Harry Met Sally (1989)

When-Harry-Met-Sally-1989 (1)
Columbia Pictures

What makes When Harry Met Sally so special is that it feels so real. As the titular characters, Meg Ryan and Billy Crystal feel like real people who take the scenic route to happily ever after. Their story feels like it could be that of the next door neighbors who find love where they least expect it. When Harry Met Sally is ranked as the second best rom-com of all time because its just romantic and funny, and manages to tell a great story while sticking to just those tenants without fanciful bells and whistles for plot enhancement.

1/20 About Time (2013)

Untitled (1200 × 630 px)-35
Universal Pictures

Coming in at number one is About Time, starring Dohmnall Gleeson and Rachael McAdams as Tim and Mary. Like When Harry Met Sally, this movie tells us the story of regular people. The film preserves this ordinary quality about Tim despite his extraordinary ability to travel back in time to moments within his own life. The heart of the film lies in watching the awkward main man use his incredible powers for something as simple as love. The story is about more than just romantic love, however, with it being a touching story on familial love as well, especially that between father and son. The film is ultimately about time itself, as the title tells us. It is about learning to find joy in the simple moments of everyday life and finding the beauty in the ordinary and unassuming things we take for granted.

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