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The 50 Best Romantic Comedies of All Time

The 50 Best Romantic Comedies of All Time

Welcome to our epic list of the best romantic comedies of all time… 50 of them.

50. Moonrise Kingdom (2012)

Most of Wes Anderson’s films could be described as romantic comedies, but his 2012 effort stands out, as its central story focuses on young love and the need to find acceptance. In Anderson’s world, while quirks abound, true connections between characters are commonplace. With Moonrise Kingdom, Anderson chose two child actors to lead his film, Jared Gilman and Kara Hayward, as they run away together through an Anderson-esque version of New England. While the film adds a bevy of Anderson regulars (Bill Murray, Jason Schwartzman) and new additions (Tilda Swinton, Edward Norton) to the universe, his ever-present focus on these two youths is what makes the film a testament to storytelling. There isn’t a second of the relationship between Sam and Suzy that doesn’t feel genuine, in its own outlandish, pastel way.

49. That Obscure Object of Desire (1977)

Director Luis Buñuel made a career of creating absurdist cinema. From his famed collaboration with Salvador Dali, Un Chien Andalou on, Buñuel consistently criticized the class system through his adventures in filmmaking insanity. For his final film, Buñuel turnd his camera onto the absurdity of romantic obsession with Cet obscur objet du désir (That Obscure Object of Desire). Centering around an aging Frenchman Mathieu (Fernando Rey) and a beautiful Spanish dancer named Conchita, it is told almost entirely in flashback, as we see how Mathieu has been brought to wit’s end by Conchita and his obsession with her. While it sounds, on the surface, like a typical rom-com, Buñuel refuses to be underestimated, casting two separate women (Carole Bouquet and Angela Molina) as Conchita, who look and act nothing alike. They never appear in a scene together, but play Conchita in various pieces of the story. Buñuel’s probably right – we fall madly in love, but can’t remember the exact person who brought us to our knees.

48. The Wedding Singer (1998)

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Romantic comedies have a habit of putting the same story in different time periods, then juicing up the meta humor to say “Look how different things were. Isn’t it funny?” None may have done it better than The Wedding Singer,  the first film to give Adam Sandler a role that showed the mild range he would later realize in Punch Drunk Love. Sandler plays the title singer, Robbie, a idealistic musician who can’t seem to catch a break. Enter Julia (Drew Barrymore), a new waitress who Robbie quickly falls for as she plans her own wedding. One-dimensional characters abound and topical 80’s humor overshadows most of the film’s aspects, but the first pairing of Sandler and Barrymore reveals a chemistry they would try to duplicate multiple times going forward, for diminishing results. Here, they do it right, despite the overly sappy elements of the film. Besides, Billy Idol is in it.

47. Silver Linings Playbook (2012)

Detractors  be damned: David O. Russell’s 2012 foray into rom-coms worked on enough levels to escape from the “crazy characters fall in love” trash heap. Headlined by Bradley Cooper and Jennifer Lawrence in her Oscar-winning role, Silver Linings Playbook details Pat Solitano’s (Cooper) return home after a stint in a mental ward, determined to get well simply by eating right and exercising. Through extenuating circumstances, he ends up striking a deal with Tiffany (Lawrence), agreeing to help her in an upcoming dance competition if she helps him try to reconcile with his wife. The film goes where you expect it to go, but Cooper and Lawrence give phenomenal lead performances, along with fine supporting turns from Robert De Niro and Jacki Weaver. It’s not a prestige film by any means, but an example of what a rom-com can be if it’s written and directed well and the actors go for broke.

46. The Shop Around the Corner (1940)

Long before Meg Ryan had to close her bookstore thanks to money-hungry Tom Hanks and you could have a romance over instant messenger, Ernst Lubitsch produced and directed this adaptation of the Hungarian play Parfumerie by Miklós László. The Shop Around the Corner stars James Stewart as Alfred, the top salesman at a local gift shop, who argues with his boss over the sale of a cigarette box. After their disagreement, Klara (Margaret Sullivan) enters the shop, looking for a job. After she successfully sells one of the boxes, she is hired and a rivalry forms between Alfred and Klara. Simultaneously, Alfred tells his friend that he has been anonymously exchanging letters with a woman he found in the newspaper. As you can guess, Klara is this mysterious woman. It seems old hat now, but in 1940, the secret-admirer romantic comedy had yet to get its day in the sun, until this little gem hit the screens. It was remade by Nora Ephron in 1998 as You’ve Got Mail – a good movie in its own right. But it’ll never touch the original.

45. High Fidelity (2000)

The first of writer Nick Hornby’s novels to come to the screen, High Fidelity stars John Cusack as Rob Gordon, a recently dumped record store owner recounting all his failed relationships in an attempt to figure out what he’s doing wrong. Paired with his contempt for popular music and his “musical moron twins” (Jack Black & Todd Louiso), he spends his time making music-themed lists and ridiculing customers who don’t share their tastes. Eventually, he sets his sights on reconciling with his most recent ex Laura (Iben Hjejle), trying to figure out ways to win her back. Directed by Stephen Frears, High Fidelity finds a wonderful balance between the two sides of Rob – a self-indulgent snob and a needy man-child. As always, Cusack walks a fine line between likable and unlikable, but manages to get the audience on his side as he tries to piece together a life full of loves lost and lack of self-realization. Few films can embed a soundtrack into a rom-com, but refuse to let it overshadow the story the way this one does.

44. Clueless (1995)

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If Jane Austen moved to Los Angeles, the result would be this Amy Heckerling romantic comedy. Clueless, based on the Austen novel Emma, takes us into the life of Cher (Alicia Silverstone) as she navigates Beverly Hills in her designer clothes and good looks. Standing at the top of her popularity empire, Cher plays matchmaker for the new girl Tai (Brittany Murphy), only to find her schemes unsuccessful. All the while, she bickers with her ex-stepbrother Josh (Paul Rudd), setting the stage for the slow burn that becomes their “courtship.” Let’s not split hairs – Clueless is lightweight, sometimes stupid, and a little full of itself. But it’s also supremely entertaining and gave birth to a laundry list of terminology that made itself into the American lexicon in the mid-1990’s. It may only be loosely inspired by Austen’s work, but don’t ignore the fact that love and friendship haven’t changed all that much since the 1800’s.

43. As Good As It Gets (1997)

James L. Brooks made a career writing brilliant screenplays for both movies and television, but has only sporadically stepped behind the camera as a director. In 1983, his film Terms of Endearment swept the Oscars with Brooks taking home Best Director and Adapted Screenplay. But it wasn’t until 1997 that he would make another Oscar-winning film, with As Good As It Gets. The strange pairing of Jack Nicholson and Helen Hunt certainly made for interesting conversation, but at the center of it all was Nicholson’s performance as Melvin, an author with a serious case of OCD, who hates almost everyone. Melvin becomes a fully conceived character thanks to his involvement with Hunt’s Carol, his gay neighbor Simon (a career high for Greg Kinnear), and, of all things, Simon’s dog. A strong script, meticulous direction, and plenty of funny lines of dialogue make this romantic comedy a necessary venture.

42. Shakespeare in Love (1998)

So, what does it take to beat a Steven Spielberg-directed, Tom Hanks-starring film about World War II? A British romantic comedy/drama about William Shakespeare (Joseph Fiennes) and his love affair while writing Romeo and Juliet. This Best Picture winner, directed by John Madden, tells a fictionalized story of Shakespeare, as he rises from a poor playwright to a literary legend, thanks, in part, to his falling in love with, ironically, a woman who auditioned for the role of Romeo in another play. Viola (Gwenyth Paltrow) inspires him to completely rewrite the play, eventually becoming his most famous work. Shakespeare in Love will long be remembered as the film that beat Saving Private Ryan, but look again: this is a well-written, well- acted story that deserves a better reception that it has historically received in critic circles.

41. Amélie (2001)

The full French title is Le Fabuleux Destin d’Amélie Poulain, but English-speaking audiences know it as Amélie. Starring Audrey Tautou in her star-making role, Amélie follows the title character as she navigates a world of wonder, thanks to her incredible imagination. Having been raised by eccentric parents who sheltered her from other children, she goes on a quest of discovery after she finds a metal box of memorabilia left by a previous tenant. She decides to track him down to return the box. What results is a strangely episodic, wondrous film that moves from character to character, with Amélie being our eyes and ears. While the film does not really begin as a love story, exactly, we slowly see Amélie evolve as she meets more and more people and finds more and more beauty in the world outside of her imagination. We all may end up in love with someone else, but we must first love our world as it stands on its own.

40. Groundhog Day (1993)

Bill Murray was nominated for an Oscar after his dramatic turn in Sofia Coppola’s Lost in Translation. He has shown great promise in Wes Anderson’s films. But his best performance to date came in this Harold Ramis comedy about a man who can’t escape February 2nd in Punxsutawney, Pennsylvania. Starring as Phil, a weatherman in Pittsburgh sent to cover the Groundhog Day festivities in the tiny Western Pennsylvania town, Murray shows a range beyond any of the screwball or deadly serious work he’s done. As Phil gets trapped in a time warp that repeats the same day over and over, we see a man go through all the stages of grief – denial, anger, bargaining, depression, and acceptance. It isn’t until Phil realizes that being a good person isn’t about what it does for you that he sees his tomorrow with Andie MacDowell’s Rita. An existential love story if ever there was one, Ramis and Danny Rubin’s screenplay is still one of the best ever.

39. Knocked Up (2007)

Judd Apatow was building his empire of stoner comedy and gross out humor when one of his better efforts premiered in 2007. Knocked Up stars Seth Rogen as a slacker named Ben who manages to land a one-night stand with rising E! journalist Allison, played by Katherine Heigl. The resulting pregnancy and forced courtship is hilarious, despite the criticism of the film and the accusations of it being sexist (including plenty from the leading lady). It’s not a mystery – this is a movie about a pregnancy that doesn’t focus on the woman. Not only that, she is without a doubt the least interesting character in the film. Regardless, Apatow’s film boasts a funny script, solid performances, and has stood up as one of the better films of his catalog.

38. Adam’s Rib (1949)

In 1949, George Cukor directed two screen legends, Katharine Hepburn and Spencer Tracy, in Adam’s Rib, a story of two married lawyers representing either side of a court case involving a woman shooting her husband after catching him cheating on her. Obviously, in this scenario, Adam (Tracy) sides with the man, while Amanda (Hepburn) sides with the woman. What ensues is a screwball battle of the sexes, involving fiendish pranks and various attempts at litigation and gaining the upper hand on the other. Eventually, the case takes its toll on their relationship. Tracy and Hepburn were never married in real life, but had a private affair that lasted 26 years, leading to them being paired up in numerous films. Adam’s Rib was just another example of two of the greatest actors in film history and how much easier it looks when the two leads have a real, honest connection. It’s tough to fake real love.

37. Harold and Maude (1978)

Director Hal Ashby’s second film, Harold and Maude, was more black comedy than romantic comedy. Despite that, the story of a surprising pair of companions elevates beyond the typical romantic comedy tropes. Starring Bud Cort as Harold, a young man obsessed with death, the film sees him drifting away from his life and into a relationship with a 79-year-old woman names Maude, played by Ruth Gordon (oddly enough, Gordon was a screenwriter for Adam’s Rib). Ruth teaches Harold about the need to embrace life and live it to the fullest, something he has never felt the need to do. Somehow, their relationship blossoms into a romantic one, despite their incredible age difference. It’s a one-of-a-kind romance that works thanks to the performances of Cort and Gordon. Hey, the heart wants what the heart wants.

36. Chasing Amy (1997)

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From age difference to sexual orientation difference, Kevin Smith’s third film remains his most interesting and effective, centering around a comic book artist named Holden (Ben Affleck) and his relationship with another comic book artist named Alyssa (Joey Lauren Adams). After Holden and Alyssa become good friends, he slowly realizes that he’s falling for her. Unfortunately for him, she’s a lesbian. Where the film goes from there is previously unmarked territory, as it explores sexuality and love in a way not really seen in many mainstream films before then. But while the relationship blossoms, we see Holden’s business partner Banky (Jason Lee in his best performance) slowly begin to lose touch with his friend, turning that anger toward Alyssa, adding another layer to the complicated relationship. Extremely crude and straight-forward about sex, Chasing Amy found a niche by exploring how important history is to relationships and how it defines you as a person.

35. Moonstruck (1987)

Before he became wildly unpredictable, Nicolas Cage laid the groundwork to be a pretty successful comedic actor, with work in Valley Girl and Raising Arizona. In 1987, Cage turned in his first performance to get him on the Oscar radar in Moonstruck. The Norman Jewison-directed film centers around Loretta (Cher in her Oscar-winning role) as she falls in love with the brother (Cage) of a man she had agreed to marry (Danny Aiello). In essence, it’s a simple love triangle, but with a cartoonish Italian spin.  The film grabbed six Oscar nominations, four of them for acting. The screenplay grabbed an Oscar victory for John Patrick  Shanley, who wouldn’t get nominated again until 2009, with Doubt. For years to come, the film (and Cher’s movie career) will always be summed up by one line: “Snap out of it!” Sums up Cage’s career lately, too.

34. Sense and Sensibility (1995)

Long before Ang Lee caught the American public off-guard with Brokeback Mountain, he directed the best theatrical adaptation of a Jane Austen novel, 1995’s Sense and Sensibility. Starring (and written for the screen by) Emma Thompson, the film took Austen’s prose and, while not staying completely faithful, translated it into a beautifully shot, whimsical story of love in the life of two polar opposite sisters. Also starring a pre-Titanic Kate Winslet, Alan Rickman, and Hugh Grant at his most charming, Sense and Sensibility may be best described as an exercise in delight – by the end of the film, if you aren’t smiling, you probably have no soul.

33. Manhattan (1979)

Woody Allen is Woody Allen. His films are idiosyncratic and his stories are microcosms of an overwhelming sense of self-loathing. At the same time, he really knows how to create characters. Probably the best job he did as a director came in 1979 with Manhattan, the story of a divorced New York man (Allen) dating a high schooler (Oscar-nominated Mariel Hemingway), but slowly falling for his friend’s mistress (Diane Keaton). Filmed in black and white, Manhattan lays Allen’s typical neurosis over a beautifully shot New York City better than any of his other films have done since. It’s a funny film, but it’s also one of Allen’s most realistic portrayals of life and love in the big city. The acting feels more natural than many of his other efforts and the connection formed between Allen and Keaton on screen is as genuine as ever. But, first and foremost, this film is in love with the Big Apple.

32. Splash (1984)

After Tom Hanks gained semi-fame in TV’s Bosom Buddies, he made his first big splash (pun very much intended) in this 1984 fantasy romantic comedy about a man who reunites with the mermaid who saved his life when he was a child. Directed by Ron Howard, Splash spotlighted Hanks’ comic timing and Everyman likability, while also proving he could carry a film. It didn’t hurt to throw in great supporting performances from John Candy and Eugene Levy, a supermodel (Daryl Hannah) to play the mermaid, and an Oscar-nominated screenplay. As a bonus, it was the first film released by Disney under their offshoot production company Touchstone Pictures, essentially becoming the first film Disney produced that wasn’t specifically geared toward children.

31. Four Weddings and a Funeral (1994)

A year before Hugh Grant stole hearts as Edward Ferrars in Sense and Sensibility, he won his first (and only) Golden Globe for his performance in Four Weddings and a Funeral, a Mike Newell-directed, Richard Curtis-written episodic romp through wedding after wedding, following Grant’s Charles, as he keeps running into an American woman named Carrie (Andie MacDowell) at each event. As he always does, Grant puts on his “bachelor lifestyle” face and eventually gets broken down, always putting on the charms he needs to, despite how confused and awkward he seems to be. In any case, the sharp British wit stands out as the star of the film, another indication that Curtis knows how to write a romantic comedy well, especially for British audiences. Nominated for Best Picture in one of the best years for movies ever (Pulp Fiction, The Shawshank Redemption, and more), it still manages to stand out on its own.

30. Bull Durham (1988)

Baseball movies had worn out their welcome a bit in the mid-80s and audiences weren’t clamoring for a romantic comedy based around the national pastime. Enter writer/director Ron Shelton, who decided to write a film based on his experiences in the minor leagues. The movie was Bull Durham, the story of a baseball groupie named Annie (Susan Sarandon) and her yearly goal to seduce one of the players on her local team, the Durham Bulls. As she romances stud pitcher Nuke LaLoosh (Tim Robbins), she slowly starts to fall for veteran catcher Crash Davis (Kevin Costner), brought in to teach LaLoosh the art of the game. After the dust settled, Bull Durham offered up more laughs than any other baseball movie and provided a solid love story behind it, thanks to the chemistry between Sarandon and her two leads. It will always stand up as a great film for fans of baseball, love stories, and anyone who believes in long, slow, deep, soft, wet kisses that last 3 days.

29. Eternal Sunshine of the Spotless Mind (2004)

It’s not the funniest romantic comedy, but this film is funny enough to fall into that shaky category. It’s one of the most original, that’s for sure. When Joel (Jim Carrey) finds out his ex-girlfriend Clementine (Kate Winslet) had him erased from her memory, he decides to do the same to her, slowly traveling through his memory of their courtship and learning why, despite the bitter end, its existence should be sustained. Teaming director Michel Gondry with screenwriter Charlie Kaufman will always produce fascinating results, and Eternal Sunshine is one of the most critically loved films of the past 20 years, thanks to the imaginative writing, daring direction, and brilliant lead performances from Winslet and Carrey, at his career best. It doesn’t hurt to have a supporting cast including Tom Wilkinson, Kirsten Dunst, Mark Ruffalo, Elijah Wood, and David Cross, either.

28. There’s Something About Mary (1998)

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Let’s get dirty for a moment. For years, the “romantic comedy” sat in the realm of PG and PG-13, never really fraying from that rating. That is, until the Farrelly brothers decided to put a grossout spin on it. It had been raunchy before, but never this raunchy. There’s Something about Mary took budding star Cameron Diaz and made her a household name, as the object of desire for a bounty of men, namely Ben Stiller’s Ted and Matt Dillon’s Healy. Ted finally gets to date Mary years later, after a disastrous high school experience with her involving a stray zipper. He hired Healy to track her down, only to see him also fall for Mary. The movie takes ridiculous twists and turns, as more and more possible suitors for Mary reveal themselves, including NFL star Brett Favre. The Farrellys managed to take the old trope of an old flame reemerging and spun it on its head, adding plenty of fart jokes and f-bombs along the way.  Most importantly, we’ll never look at hair spray the same again.

27. The Seven Year Itch (1955)

Billy Wilder (who appears plenty more on this list) made a career out of the clever romantic comedy. In 1955, he worked with the world’s favorite pinup girl Marilyn Monroe, for The Seven Year Itch, a silly rom-com about a man’s mid-life crisis. Richard (Tom Ewell) is a publishing executive who meets an actress who rents an apartment upstairs from him. His psychiatrist had informed him of the concept that a large percentage of men tend to have affairs in the seventh year of marriage, so he sees this as “normal.” A good portion of the film involves Richard’s fantasy conversations with his wife and his strange, imagined irresistible nature. Wilder had to be discrete – according to production codes, he couldn’t actually show a man committing adultery. Of course, Richard eventually comes to his senses, but not before this well-received rom-com gave us one of cinema’s most memorable images, with Monroe standing over a subway grate. For that image alone, it belongs on the list.

26. The 40-Year-Old Virgin (2005)

Eight years after the Farrelly brothers brought off-kilter humor to the romantic comedy and the mainstream, Judd Apatow emerged from years of critically acclaimed, yet commercially ignored work to co-write, produce, and direct The 40-Year-Old-Virgin. Starring Steve Carell, the film shows the life of Andy, a friendly, but socially ignorant middle-aged man who has yet to experience one of life’s greatest pleasures. What makes this film a success is the funny, yet honest portrayal of the dual importance/unimportance of sex in a relationship and how missing out can make you both a warped and well-rounded individual. Andy’s romance with Trish (Catherine Keener) is touching and believable, but what sets the film apart is how Andy’s “friends” are the ones who eventually go through as much growth as the lead couple. Plenty of throwaway jokes abound (as in all Apatow films), but the emotional core is what makes this one his most affecting.

25. About a Boy (2002)

A surprisingly nice double feature with The-40-Year-Old-Virgin, About a Boy stars the ever-charming Hugh Grant as Will, an immature man nearing middle-age who finally grows up, thanks to a little boy named Marcus (Nicholas Hoult). Based on a best-selling novel by Nick Hornby, About a Boy follows Will as he tries to serve as a “plaything” for single mothers, only to meet Marcus and have his world turned upside-down. He eventually finds himself serving as a surrogate father to this pre-teen, who spends his time trying to cheer up his emotionally disturbed and chronically depressed mother (Toni Collette). Enter Rachel (Rachel Weisz), a single mother who Will can’t help but fall for, despite the dishonest manner in which they met. Grant gives one of his better, more layered performances here, as he shifts between a man who feels image is of utmost importance to one who begins to care deeply about others, even if those others feel like a burden. Hornby’s novels tend to make good films if in the right hands – About a Boy is no exception, with an Oscar-nominated screenplay.

24. (500) Days of Summer (2009)

It literally begins with “This is a story of boy meets girl, but you should know upfront, this is not a love story.” So begins the nonlinear narrative story of Tom (Joseph Gordon-Levitt) and Summer (Zooey Deschanel). Summer begins working at the greeting card writing company at which Tom is employed, though he dreams of being an architect. The story focuses on Tom’s unwavering belief that Summer is the “one,” despite her constant statements that she doesn’t want anything serious and may not even believe true love exists. What results is an imaginative jump between happy days and sad days, re-imagining memories Tom believed were positive, but were simply clouded by his vision of love. Few romantic comedies can boast an ending that isn’t quite a happy one, but can still make the audience smile. (500) Days of Summer manages to do that, with the help of a fine “indie” soundtrack. Also: look for an early performance from Chloe Grace-Moretz as Tom’s younger sister, who steals every scene she’s in.

23. Roman Holiday (1953)

Audrey Hepburn has seen her fair share of criticism, but behind that gorgeous facade, there was a pretty solid actress, if given the right part. She earned her only Oscar win in 1953 for Roman Holiday, the story of a princess getting away from her royal lifestyle. While away from her caretakers, she meets and falls in love with an American journalist, played by Gregory Peck. The story sounds old hat at this point, being redone in the forms of movies like Chasing Liberty and, in a twisted way, Eddie Murphy’s Coming to America. But the chemistry between Hepburn and Peck (not to mention the beautiful shooting locations) is enough to win over even the coldest of hearts. Delineating from the norm and avoiding a perfectly happy ending, Roman Holiday is exactly what it sounds like: a nice vacation away from typical rom-coms, breathing just enough charm and whimsy to make for a joyous experience.

22. Bridget Jones’ Diary (2001)

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Helen Fielding’s 1996 novel was a book for the modern insecure woman: a story told from the point of view of a thirty-something British woman who obsesses about her love life, drinks a bit too much, and documents all of it in a diary (how the book is delivered). Inspired in part by Jane Austen’s Pride and Prejudice, Fielding’s work was adapted for the screen in 2001 by Fielding, with help from Andrew Davies and, you guessed it, Richard Curtis. The movie starred Renée Zellweger as Bridget; at the time, this seemed like an odd choice, given she wasn’t British, in a film based on an award-winning British novel. But it turned out to be perfect casting, as Zellweger gave what may be her best (or, at least, most memorable) performance, earning an Oscar nomination while showing excellent comic timing and going toe to toe with England’s most recognizable talents at the time, Colin Firth and Hugh Grant. The film follows Bridget through a series of misadventures with the men in her life, her job, and her family, all while documenting  her experiences in an attempt at self-preservation. If anything, Bridget Jones’ Diary managed to bridge a gap between British and American romantic comedies, proving they aren’t that different. We all have the same problems, right?

21. Say Anything… (1989)

Lloyd Dobler (John Cusack) screwed up hundreds of high school boys with that stupid boombox, didn’t he? Cameron Crowe’s directorial debut told the story of Lloyd as he sets his sights on Diane Court (Ione Skye), the class valedictorian, in the summer after graduation. Lloyd is average at best, setting his goals on very different things than Diane, first and foremost his dream to be a professional kickboxer. But, even as Diane skirts his attempts at her heart, his persistence and unending pursuit eventually wins her over, eventually being her support when her father (John Mahoney) falls into trouble with the IRS. What Say Anything… does better than any other rom-com is making that “never give up” mantra seem like a realistic pattern of behavior. Sometimes the normal guy wins out, yes. But not like this. Cameron Crowe’s screenplay is what makes Lloyd such a lovable character and makes Diane such an unattainable end game. But that boombox. Rarely is a song used as a plot device so clearly (in a non-musical, mind you) than here, as Peter Gabriel’s “In Your Eyes” became the love song to end all love songs. Briefly.

20. Sleepless in Seattle (1993)

Tom Hanks had been the leading man in romantic comedies before (e.g. Splash). But the same year he took home his first Oscar (Philadelphia), he also starred opposite Meg Ryan in this Best Original Screenplay Oscar nominee about a widower and his son, who takes it upon himself to call a radio show, trying to find his father a partner. When Jonah (Ross Malinger) calls the station, it prompts Sam (Hanks) to pour his heart out about his lost wife and his subsequent loneliness. Among the women who fall head over heels for this man sight unseen is Annie (Ryan), an engaged Baltimore writer who can’t shake her obsession with the possibility of a fairy tale ending. It’s incredibly unrealistic and insanely wrought, but somehow the film found a huge audience in the early 90’s who were dying for this kind of story. Hanks was on his way to becoming the greatest actor of his generation. Meg Ryan was in the midst of her short run of quality performances. And so it became a love story that birthed dozens of imitators in the 90’s and found its place as a universally adored little story. If you haven’t seen it for a while, you might be surprised. Sleepless in Seattle is better remembered as the fairy tale it tries to be, rather than an easy target to lob critical hatred. But, maybe that’s what a rom-com should do.

19. Jerry Maguire (1996)

Cameron Crowe had already proved his ability to write and direct a solid romantic comedy (Say Anything…). Renée Zellweger was a near-unknown young actress trying to break into the industry. Tom Cruise was Tom Cruise. These people converged in 1996 to deliver an Oscar-friendly love story surrounding the world of a sports agent and his sudden morality complex. When Jerry (Cruise) is fired for taking an ethical stand, he goes out on his own with only one athlete to represent: the outspoken Rod Tidwell (Oscar-winner Cuba Gooding, Jr.). In addition, a 26-year-old single mom named Dorothy (Zellweger) quits her job at the company to follow him. What results is an expected story of struggle and awakening, both professionally and personally, as Jerry is sent away by his fiancee, eventually spending more time with Dorothy and her son (Jonathan Lipnicki). The love story goes back and forth and, a handful of famous quotes later, they end up together. Filled with decent performances and a witty screenplay, Jerry Maguire provided a jumping off point for Zellweger, the only Oscar for Gooding’s disappointing career, and one of Cruise’s finer performances. Plus, more memorable quotes than probably any film of the 90’s.

18. The African Queen (1951)

Katharine Hepburn has gone down in history as one of the greatest actresses we’ve ever seen. However, among all those dramatic performances, she has quite a bit of romantic-comedy blood in her (as you’ll see later on this list). One of her Oscar-nominated turns in a rom-com came in 1951’s The African Queen, a silly little story of a riverboat owner who is convinced to take an uptight missionary to attack an enemy boat. Hepburn plays the missionary, named Rose, while the riverboat owner Charlie is played by the great Humphrey Bogart, in his only Oscar-winning role. After the death of her brother at the hands of the enemy, Rose is convinced that she must do her part for the war effort, forcing Charlie to oblige. What results is a mismatched trip up the Ulana River, where the upper-class Rose clashes constantly with the grumpy, lower-class Charlie. Bogart departs from his typical film noir style to play Charlie fast and loose, pairing up perfectly with Hepburn’s anal retentive Rose. Opposites attract on screen, especially when you’re stuck in close quarters for extended periods of time. The African Queen is no exception.

17. Love Actually (2003)

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Christmas + a dozen storylines + every talented British screen actor + Richard Curtis = Love Actually, a surprisingly endearing, yet overstuffed holiday film. Written by Curtis, it was also the first film he stepped behind the camera for, earning his first directing credit. The result is a lovesick mess that has plotlines all over the place: a man who loves his best friend’s new wife, a writer who falls in love with his Portuguese housekeeper despite a language barrier, a man who considers cheating on his wife, the prime minister’s eye on an assistant, a tween who pursues his first love with the help of his stepfather, a woman who cannot risk leaving her sick brother unattended, and a twenty-something Brit who flies to America believing that American girls are easier. And there are a few more. But, look closely – surprisingly few of these stories end happily. Somehow, stuffed with oodles of talent, Curtis made this saccharine motion picture work enough to spurn plenty of terrible imitators since.

16. Sixteen Candles (1984)/Pretty in Pink (1986)

How could we split these up? They vary in storylines, but are basically the same film. Both feature the 80’s high school rom-com queen, Molly Ringwald. Candles tells the story of Samantha’s (Ringwald) upcoming 16th birthday, while everything terrible that could happen to her, in fact, does. Pink focuses on Andie (Ringwald) as she crushes on one of the rich popular guys, Blane (Andrew McCarthy). Both films deal with high school love and relationships. Both films feature a geeky kid who has eyes on the protagonist (Anthony Michael Hall in Candles; Jon Cryer in Pink). Both films were written by John Hughes. Only Sixteen Candles was directed by Hughes, though he produced both. Between these films, Molly Ringwald cemented her place as the face of teenage love and misery in the 80’s, serving as Hughes’ muse in every facet. Despite the cartoonish qualities of both films, what they manage to say about high school life and how it dominates every aspect of our personalities while we’re there is brutally honest. Still: Duckie is the man.

15. Breakfast at Tiffany’s (1961)

It’s a featherweight film based on a Truman Capote novella that, in retrospect, has one of the most insanely racist characters ever put on film (Mickey Rooney as Mr. Yunioshi). But it’s in the National Film Registry of the U.S. Library of Congress. And, it has Audrey Hepburn’s career-defining role, which brought her a fourth Oscar nomination, as Holly Golightly, in the Blake Edwards directed Breakfast at Tiffany’s. The film centers around Holly, a socialite in New York City who begins to fall for a new neighbor in her apartment building. It doesn’t really go anywhere, but the interplay between Hepburn and her co-star George Peppard drives the entire film, as Hepburn switches between confident party-goer and nervous wreck between her two worlds: the public one and the private one. But somewhere, in all this silliness, Hepburn gives the world one beautifully memorable scene, strumming her guitar and singing “Moon River,” a song written specifically for her vocal range. Regardless of the rom-com traps and the insensitive nature of some of the film, that scene alone and the endearing image of Hepburn, cigarette holder in hand, makes this iconic film a keeper.

14. Tootsie (1982)

Dustin Hoffman had already built up a stellar career by 1982, nominated for four Oscars, winning one (Kramer vs. Kramer). But he had yet to perform in a film clearly branded as a comedy. The best way to be funny – dress in drag, right? In Tootsie, Hoffman stars as Michael Dorsey – a notoriously difficult actor who can’t get another job. When told he has no chance of being hired again, he decides to go to the extreme:  disguise himself as a woman and audition for a soap opera. Now Dorothy Michaels, he not only wins the part, but finds a way to grow as a man, ironically while being a woman. As Dorothy, Hoffman gets caught up in a twisted love triangle (almost rectangle), where he falls in love with co-star (played by Jessica Lange), her father begins to pursue him/her, another co-star falls in love with him/her, and so on. All the while, Hoffman’s roommate is played by a young, snarky Bill Murray, serving as the audience’s eyes and ears through this ridiculous premise. Above all the crazy twists, Tootsie exposes the inherent sexism found in the system and the extremes it might take for some of our stupidest men to understand how to treat women and, in turn, be worthy of them.

13. The Princess Bride (1987)

The original romantic comedies were probably the fairy tales we all know and love. Well, the PG versions of them, anyway. In 1987, director Rob Reiner collaborated with author/screenwriter William Goldman to present The Princess Bride to the world. A fantasy/adventure/romantic comedy, the film stars Robin Wright as the title character Buttercup, with Cary Elwes playing her lost love Westley. Similar to Robin Hood in many ways, The Princess Bride centers around the princess’ love for Westley, despite his social status, only to see him banished from the kingdom. What results is Westley’s undying attempts to return to her, defeating a Sicillian (Wallace Shawn), joining forces with a pair of outlaws (Mandy Patinkin and Andre the Giant), and crossing paths with other fascinating characters. Delivered as a bedtime story a grandfather (Peter Falk) tells to his son (Fred Savage), The Princess Bride has the kind of slick humor and movie magic that has made it a cult favorite since its original release.

12. His Girl Friday (1940)

Romantic comedies don’t talk much faster than this one, that’s for sure. Based on the play The Front Page, written by Ben Hecht and Charles MacArthur, His Girl Friday follows newspaper editor Walter Burns (Cary Grant) as he does everything in his power to keep his best reporter from getting married and leaving the paper. The catch: the reporter is Hildy Johnson (Rosalind Russell), his ex-wife. This screwball comedy has plenty of twists and turns, some of which involving her future husband Bruce (Ralph Bellamy), Bruce’s mother, and the city mayor. Directed by Howard Hawks – the king of screwball comedy in the 30’s and 40’s – His Girl Friday set the standard for future offerings in the genre, as its quick-talking dialogue and clever screenplay managed to run circles around the competition. Every characters is quick-witted, interesting, and funny, while the story leads to the obvious, yet still satisfying ending.

11. My Big Fat Greek Wedding (2002)

Pop quiz: what’s the highest-grossing film never to reach #1 at the box office? This little independent gem, produced by Tom Hanks and Rita Wilson. My Big Fat Greek Wedding stars (and is written by) Nia Vardalos as Toula, a middle-aged woman who lives in Chicago and can’t escape her very loud and very Greek family. Enter Ian (John Corbett), a non-Greek who she finds herself falling in love with behind her family’s back. In a world of over-the-top comedies where someone’s family is standing in the way of happiness, this one manages to find a way to deliver tons of heart, while shaping all the relatives individually into interesting characters. All our families are crazy. Toula’s may be the craziest, but it’s all out of love: love for her, love for the family, love for their culture, and love for what the ones who came before them have done to make the lives they have now. Love is an international language, after all.

10. Some Like It Hot (1959)

What’s funnier than men dressing in drag? Depends on who you ask. It’s Billy Wilder again with a fictional story of two musicians – Joe (Tony Curtis) and Jerry (Jack Lemmon) – who witness the St. Valentine’s Day massacre in Chicago and leave town. But, since the mob has ties everywhere, they need to disguise themselves as best they can: as women in an all-girl band on their way to Florida. Now Josephine (Curtis) and Daphne (Lemmon), the two find themselves enjoying their time with the women, especially with Sugar Kane Kowalczyk (Marilyn Monroe), who Joe tries to win over while disguising himself as another man. Meanwhile, Daphne/Jerry finds himself being pursued by a millionaire (Joe E. Brown) who won’t take no for an answer. As you can see, this leads to plenty of ridiculous situations that play themselves out well, thanks to Lemmon and Curtis and their go-for-broke performances. Surprisingly, while the Sugar Kane-Joe pairing gathers more steam (literally and figuratively), the Osgood (Brown)-Daphne pairing is the more interesting couple, especially at the film’s conclusion. It’s not as romantic as the other films on this list, but its certainly as funny. Besides, nobody’s perfect.

9. Pretty Woman (1990)

Posters USA Richard Gere Pretty Woman Movie Poster GLOSSY FINISH - FIL135 (24" x 36" (61cm x 91.5cm))

It’s become a go-to trope in the romantic comedy genre (or, at least, variations on it), but Pretty Woman pretty much created the “hooker with a heart of gold” motif. It won Julia Roberts a Golden Globe and grabbed her an Oscar nomination, blowing up her popularity to an unseemly level. Roberts had been around for a few years, but putting her opposite Richard Gere and in streetwalker wardrobe worked. Directed by Garry Marshall (when he still made decent films), Pretty Woman became a cultural landmark in the early 90s, thanks to the lead performances and a number of stand-alone moments that stuck in moviegoers’ collective psyche: the red dress, the polo match, the game of necklace keep-away. Roberts would slowly find her roles as a serious actress, but in 1990, it was tough to find a better leading lady for a rom-com.

8. Bringing Up Baby (1938)

You know what really helps people fall in love? Jungle cats. In 1938, after being fired by RKO when his adaptation of Gunga Din was going poorly, Howard Hawks jumped on board Bringing Up Baby, a screwball comedy starring Cary Grant and Katharine Hepburn. The film was written specifically with Hepburn in mind, meant to fit her personality as Susan, a free-spirited woman who meets a paleontologist named David (Grant) the day before he is meant to marry a fellow scientist. Unbeknownst to David, Susan is the niece of a probable donor to his museum. She also owns a leopard named Baby and tries everything she can to get him to accompany her to Connecticut to see Baby, while trying to keep him from going through with his marriage. Antics ensue, of course, while Hepburn gets her feel for the type of comedy needed for the film. The film was a flop upon its initial release, but slowly became an incredibly popular landmark of the studio system era. It also contains what is suspected to be the very first use of the word “gay” as a term for homosexuality in major media, from a line improvised by Grant on the spot. Regardless: Cary Grant as a nerdy scientist (at least, trying to be one) is a fun departure from his typical big screen persona.

7. The Graduate (1967)

A year after his directorial debut with Who’s Afraid of Virginia Woolf?, Mike Nichols softened his camera a bit with a look at love, success, and loneliness in 1967’s The Graduate, based on the novel by Charles Webb. Starring Dustin Hoffman as recent college graduate Benjamin Braddock, it grabbed seven Oscar nominations, winning one (Director). Now that Benjamin is done with school, he finds himself struggling with his “next step,” only to be drawn into an illicit affair with the wife of his father’s business partner, Mrs. Robinson (Anne Bancroft).  Shortly thereafter, Benjamin finds himself falling for Mrs. Robinson’s daughter Elaine (Katharine Ross), all while trying to hide everything at once. The Graduate found a way to capitalize on Hoffman’s ability to play awkward, easily succumbing to the appeal of Bancroft’s Robinson. Benjamin is rumbled out of his funk by her friendly hand (and more), but has to find a way to escape the rabbit hole he’s pulled into with this affair. While the famous ending can be viewed as a “happy” one, it says more about the nature of youth and acting on impulse. That grand gesture may feel right at the time, but when all is said and done and you get what you want, what then? Where do you go from there?

6. The Apartment (1960)

Apparently, there was a time in history when your best chance for professional advancement was to let people have sex at your house. True story. Billy Wilder’s The Apartment stars Jack Lemmon as C.C. Baxter, an insurance salesman who tries to rise within his organization by allowing executives to borrow his place for extramarital affairs. Unfortunately, when his married boss Sheldrake  (Fred MacMurray) gets added to his rotating list of “borrowers,” Baxter falls for the woman he is cheating on his wife with, an elevator girl named Fran (Shirley McLaine). Of course, Fran has no idea that she is the latest in a string of affairs Sheldrake has engaged in, no idea that Baxter is fond of her, and believes Sheldrake will leave his wife. The three lead performances are outstanding, only furthered by the always excellent hand of Billy Wilder. Wilder relationships are better than real ones, which means the conflict is always more interesting and, most of the time, funnier. The Apartment melds the romantic comedy with the office comedy in a way that adds flavor to both sub-genres and helps it stand out as one of the best written and funniest of Wilder’s impressive filmography.

5.  City Lights (1931)

If you had to start somewhere, why not start with one of film’s greatest icons? Charlie Chaplin’s Tramp character had been in numerous shorts, but found his big-screen bearings in what is one of the most romantic films of all time. City Lights features the Tramp falling in love with a destitute blind girl (Virginia Cherrill), when she mistakes him for a wealthy duke. When he learns that she can have an operation which may restore her sight, the Tramp goes on a series of adventures to earn money, using a relationship he has with a wealthy man to slowly build up income. The Tramp does all this, all while knowing that, when she can see, she will see he is not the rich man he has pretended to be. Chaplin’s physical humor always brings his silent films to life and City Lights is no different. However, unlike his other comedies, this one is injected with more emotion. His films always contains strings of satire, but not the undercurrent of romantic love like City Lights does. Still packed with plenty of laughs, City Lights stands out as the true gem of Chaplin’s career for saying more about love in silence than the vast majority of other films can say with oodles of dialogue.

4. When Harry Met Sally… (1989)

If this was a list of just modern romantic comedies, this film would probably be #1. But, alas, there were some that did it long before Rob Reiner did. All that in mind, When Harry Met Sally… is still the gold standard for romantic comedies made in the last 30 years. Starring Billy Crystal and Meg Ryan, the film documents their relationship as two people  going through their own romances, always bumping into each other and eventually turning to each other for support and guidance. But the question always remains: can a man and woman have a friendship that strong without always wanting sex? The film as a whole revolves around that question, providing a template for every “will they, won’t they” scenario possible as they move through their lives separately. The movie spans over a decade; Reiner intercuts the narrative with interviews with real-life couples, explaining their relationships and how, despite all our differences, we all generally go through similar things. Crystal and Ryan give two of their best performances and, despite both having taken a bit of a dive in terms of movie roles as of late, they will always have this shiny little glimmer of hope that, if you write a good script, get a good director, and get two leads together with strong chemistry, it’s possible to tell a charming, relatable story about love on screen.

3. Annie Hall (1977)

Whether or not the female characters Woody Allen writes are accurate or not is beside the point. The majority of them are extremely memorable. For his entire career, he has basically written/directed one movie annually, but grabbed his only Best Picture Oscar with his seventh feature film, Annie Hall (beating Star Wars). The film is the story of a relationship between Alvy (Allen) and the title character (Diane Keaton) and how it evolves over time. Alvy is a pessimistic neurotic, while Annie is fun and fancy free, while a bit ditzy. They follow a normal trajectory: meet cute, fall in love, things are great, things get sour, things fall apart. What Annie Hall does differently is subvert that process. We see behind the curtain and see what happens when two very different people find something special, only to watch the ship sail from both sides. Both Keaton and Allen are marvelous as the leads, as they navigate a relationship that, for lack of a better term, needs to happen. Unlike most rom-coms that have you believe happy endings only exist when couples end up together, Annie Hall acknowledges that, sometimes, it may not work out. But, the time together is necessary for growth and maturity. But, until that hole is filled by someone or something, misery can be expected. Allen never shies away from that and, with such well defined characters, it becomes all the more real.

2. It Happened One Night (1934)

Frank Capra’s It Happened One Night was the first movie to win all five major Oscar categories (Picture, Director, Actor, Actress, Screenplay), a feat that wouldn’t be matched until 1975 (One Flew Over the Cuckoo’s Nest), and for good reason. Ellie (Claudette Colbert) is the heiress to a wealthy father who, upon learning she had a secret wedding to a fortune-hunter, wants to annul the marriage. Ellie runs away and boards a train in the hopes to meet up with her secret husband. There, she meets a newspaper reporter named Peter (Clark Gable), who says he will help her if he gets the rights to her story. Otherwise, he turns her in and collects the prize money. They begin to rely heavily on each other as they travel together – Peter explains how a man should get dressed; Ellie outdoes Peter by flagging down cars to hitchhike in her own way. But, through it all, they slowly fall in love with each other, despite the many reasons they keep telling themselves they shouldn’t. Colbert and Gable were not the first choices – Gable is rumored to have been “lent” to the studio to make the film; Colbert’s last film was directed by Capra and, after its failure, swore to never work with him again. But the stars aligned, as they say. What results is one of the greatest romantic comedies of all time, one of the greatest road trip movies of all time, and a template for how a rom-com should be made. It’s not about triangles, affairs, or stupid jokes; it’s about love and love alone.

1. The Philadelphia Story (1940)

The Philadelphia Story Poster Movie (22 x 28 Inches - 56cm x 72cm) (1940) (Half Sheet Style A)

And so it comes to this. What’s the recipe for the perfect romantic comedy? Hire a good director (George Cukor). Find good source material (play by Philip Barry). Cast the most handsome man you can find (Cary Grant). Cast the most identifiable Everyman you can find (Jimmy Stewart). And, for fun, why not cast the greatest actress alive (Katharine Hepburn)? Mix it up and you have The Philadelphia Story, the definitive romantic comedy. Just before wealthy Tracy Lord (Hepburn) is to be married, her ex-husband C.K. Dexter Haven (Grant) shows up with a tabloid reporter named Macaulay Connor (Stewart), throwing wrenches into the ceremony. From there, we have something of a love quadrilateral, as Dexter is bent on causing trouble, not expecting Macaulay to fall for Tracy, too.  In all the hustle and bustle of wedding planning, drinking too much, covering up intentions, and all-purpose mischievousness, all the characters begin to see exactly who they are. Tracy sees her domineering nature, Dexter sees his playboy persona, and Macaulay…well, he sees something he never expected to see right in front of him. The Philadelphia Story is a whirlwind of romance and comedy, with a semi-unexpected ending where everybody seems to be happy. But, among all the happy endings romantic comedies give us, there’s something about how this little parable ends that can’t help but be enjoyed.

So, there you have it: 50 definitive romantic comedies. There are obviously going to be some disagreements about them and, while the order of the top 10 may not be what everyone envisions, it can’t be denied that they belong here. Thanks for reading–and now, the floor’s open for discussion and debate.