So, we’ve arrived at the top 20, slowly creeping toward those films that are exactly what a romantic comedy should be. We’ve seen films that fall into the category, but lean more toward other genres. We’ve seen romantic films that are funny enough to be comedies, but don’t entirely represent the spirit of the rom-com, despite being brilliant films. Now, we form a clearer picture of what a romantic comedy is. Not all of the films in this section are necessarily “good,” but they’re all iconic, definitive romantic comedies (hence their inclusion). Memorability does not necessarily come partnered with quality. It means right place, right time.
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)
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.
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.
Only 10 to go. Ten movies that, if you’re in a happy relationship, melt your heart. Ten movies that, if you’re alone and miserable, are the stupidest thing you’ve ever seen.
— Joshua Gaul