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The 55 Best Romantic Comedies of All Time
There is no “best” romantic comedy. Something is funny when someone laughs, or romantic when their heart swells, for better or for worse, and we have no right to say why one of these should top another. Your uncle, or cube-mate might say, “That’s stupid. Breakfast at Tiffany’s is obviously the best rom-com of all time.” And they may not be wrong. But maybe you have some reservations about the horrifyingly racist overtones in some of that movie’s scenes, even though you can’t help loving Audrey Hepburn. Maybe it’s the best for a certain time period. It’s tough. Comedy is subjective. So is romance.
It’s for this reason that we had such a good time making this list, at least initially. And lots of help. People keep a special place in their heart for romantic comedies. They talk about them differently than other movies, and they like to talk about them a lot. When the call went out, we heard from writers, editors, friends, moms, therapists, bartenders, people we hadn’t talked to since high school; the list goes on. The initial gathering of candidates was great fun; the subsequent reaping less so.
First, we had to limit the category. We love Dazed and Confused and it contains plenty of romance, and comedy, but we can’t be sure it’s a romantic comedy per se. Same with Secretary, McCabe & Mrs. Miller, My Girl, Hedwig and the Angry Inch, and about 500 other films. We don’t have enough space here to get into exactly what makes a romantic comedy, but let’s agree that the fact it is not a tragedy or a history is not enough. Somewhere we have to draw the line between the actual rom-coms and the coming of age movies, or mysteries, or adventures.
It’s for this reason we need to apologize in advance: A number of your favorite romantic comedies will not be on this list. Some of them didn’t fit the mold. Others—and this part got a little heated—we just couldn’t get on board with. Decisions had to be made. Hopefully, as a benefit to any disappointment of missing favorites, you’ll find some new ones you didn’t yet know you liked. After all, that’s the message from Pretty Woman, right? It’s important to keep an open mind. Otherwise, you could be making a big mistake, big, huge.
These are the best 55 rom-coms for every situation. We hope you love them.
. . . to put your one-night stand in perspective:
Photo: Everett Collection
The hardest you’ll ever laugh about abortion. That’s right, abortion. Talk about playing with fire, but this tender, deeply human comedy from director Gillian Robespierre finds entirely new ways into the story of losing Mr. Wrong, then Finding Mr. Right (by having our hero, a struggling comedian—played by the irrepressibly honest and infinitely endearing Jenny Slate—get drunk with Mr. Right, sleep with Mr. Right, get pregnant by Mr. Right, and then deal with the consequences). While riotously funny, Obvious Child set a new standard for intimacy, and Robespierre’s ribbed, tone-perfect writing and Slate’s raw but intelligent performance managed to shape a millennial mirror more reflective than anything Girls could put forward in six seasons. And give us the abortion comedy we didn’t know we needed.
. . . to deal with your workplace crush(es):
Photo: Everett Collection
In the mid to late ’80s, there was nothing bigger than TV news and James L. Brooks, and Broadcast News was their meeting ground. After the slaphappy, very silly, and very male comedies of the late ’70s and early ’80s (think Animal House, Porky’s, and Revenge of the Nerds), and alongside the epic big-budget projects like Ghostbusters and the original Indiana Jones, James L. Brooks continued to redefine what rom-coms could be with this sprawling, occasionally dramatic but never self-serious, workplace comedy. We root for Albert Brooks’s Aaron Altman, the brainy, nervous, serious journalist who competes for the affections of neurotic producer Jane Craig (Holly Hunter) against the impossibly polished (and intellectually inferior) Tom Grunick (William Hurt). Brooks is the producer behind films like Bottle Rocket, Say Anything . . ., and Big, and TV series like Mary Tyler Moore, Taxi, and The Simpsons. No one knows how to get at our hearts—thoughtfully, gracefully, and with humor—like James L. Brooks. And this is him at his peak.
. . . to see past a gruff exterior:
Beauty and the Beast (1991)
©Buena Vista Pictures/Courtesy Everett Collection
“Tale as old as time . . .” It really is. Lonely, powerful dudes have been making off with damsels and then hiding them away since at least Greek mythology and probably before. Where Disney scored with its animated musical was in—pardon the pun—reanimating that classic story line in a way that was appealing to our eyes and ears, and that of our kids’, while maintaining some real danger in the narrative. It’s a triumph they repeated with Aladdin and The Lion King, but is especially notable with a romance—making the stakes high enough—and real, even when accompanied by singing teapot—that we root for these characters to end up together.
..for when you’re in the mood for first love, Wes Anderson-style.
“I will meet you in the meadow,” writes bespectacled Sam (Jared Gilman) to serious Suzy (Kara Heyward) as they prepare to run away together. Wes Anderson’s Moonrise Kingdom, a whimsical tale of a romance betwixt a pair of wise-beyond-their-years 12-year-olds (beautifully art-directed and accessorized as always), is a tonic to the jaded palate. The children, with their barely sexual, pure-hearted affection for each other, could teach the misbehaving adults around them a thing or two about love. Who wouldn’t want to dance on the beach in their underwear to Françoise Hardy?
. . . to get you over getting over your ex:
The Philadelphia Story (1940)
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The credits of The Philadelphia Story read like something out of a dream: Cary Grant and Jimmy Stewart vying for the love of Katharine Hepburn. It’s produced by Joseph L. Mankiewicz (writer of All About Eve and Cleopatra), and directed by George Cukor (who made 1954’s A Star Is Born, Justine, and My Fair Lady, and once told Marilyn Monroe, “That will be just fine, darling” when, about to film a skinny-dipping scene for Something’s Got To Give, she expressed her concern that she only knew how to dog-paddle). The Philadelphia Story relies on some dependable tropes—lovers who’ve fallen out; will-they-or-won’t-they-get-back-together—that have provided romantic tension from A Midsummer Night’s Dream to Crazy, Stupid, Love. But it’s Hepburn, aiming for a comeback following some serious bombs, and her witty repartee with her two love interests, Grant (her yacht-designing reformed bad boy of an ex-husband) and Stewart (a tabloid reporter), that is the movie’s bread and butter. The Main Line has never been so well represented.
Lost in Translation (2003)
©Focus Films/Courtesy Everett Collection
There was never any doubt that Scarlett Johansson was going to be a mega star, but Sofia Coppola’s movie—about the lonely wife of a photographer who befriends an over-the-hill movie star (Bill Murray) while visiting Tokyo—is what made the world stand up and realize we were dealing with a serious actor. Like many of the films on this list, Lost in Translation takes place in a bourgeois universe, where the greatest thing at risk is someone’s heart, or future emotional happiness, but few films have so effectively crystalized the alienation of both travel and marriage, as well as the difficulties of postcollegiate, and then midlife, malaise. The older man and the younger woman don’t so much meet-cute as crash into each other, picking up each other’s pieces, redeeming each other’s lives as they navigate their surreal setting. It’s a match made in heaven—and without spoiling anything, their goodbye scene is among the best in Hollywood history.
. . . to reevaluate your checklist:
©Paramount/Courtesy Everett Collection
The motherless daughter, caring for her father and looking for her prince, is a trope that goes back to the fairy tales, but how Alicia Silverstone (who plays our hero, Cher) and writer-director Amy Heckerling contemporized that narrative is what made what could have been a silly teen flick into an instant classic. They imported a Jane Austen story line of a meddling would-be matchmaker (Emma) into a bright pink, plastic, kids-are-adults world of Beverly Hills privilege populated by overly dramatic in-talk (“Whatever!”; “As if!”), lunatic high fashion, and decidedly un-relatable problems. At the same time, they maintained a storybook sensibility, and somehow kept our sympathies with the lovelorn Cher, whose insipidness is overshadowed by her charity, loyalty, and genuine goodwill. We believe she deserves love, and if she gets smart enough to stop looking for it in the “right” places, we want her to find it.
. . . to help you sort out what to do with the rest of your life:
Courtesy Everett Collection
This is the film on this list that is least certainly a rom-com; it caused a bit of a row, in fact. Some of us believe that this movie is ultimately too sad to give the viewer the warm fuzzies they depend on this genre for. Others argue that this line of thinking may confuse what’s depressing with what’s complicated. The story of the listless Benjamin Braddock, recent graduate of Williams College, who begins an affair with his father’s partner’s wife, and ends up falling for her daughter, did more to advance the critical value of comedy than perhaps any other film. (Not to mention the sexual viability of Williams grads.) There may be no more iconic line than Dustin Hoffman’s “Mrs. Robinson, you’re trying to seduce” but this movie is so much more than dialogue. (Note: Hoffman might have been playing 21 when he said this line, but the actor was 29; Anne Bancroft, the supposedly senior Mrs. Robinson, was all of 35.) Oft-quoted, ripped off, referenced, and discussed, Mike Nichols’s 1967 romp through Braddock’s postcollegiate uncertainties was released a few months after the Summer of Love, as the counterculture had peaked and what Hunter S. Thompson called the “high and beautiful wave” was getting ready to roll back. Young America was, and to some extent still is, Benjamin Braddock, which reveals the power of this film.
. . . to ask for assistance in the ol’ love department:
Sleepless in Seattle (1993)
©TriStar Pictures/Courtesy Everett Collection
Tom Hanks had been responsible for some ’80s hits—Splash and Big—but with Nora Ephron’s 1993 film about a widower whose son calls in to a radio show in an attempt to find him a new wife, he cemented himself as America’s favorite, well, person. Meg Ryan, his competition for that title (at least in the ’90s), plays an unhappily engaged Baltimore Sun reporter who writes Hanks’s character on a whim, asking him to meet her at the top of the Empire State Building (cue: An Affair to Remember) on Valentine’s Day. Utterly contrived, but utterly charming, this quick, silly, funny film is pabulum superfood for anyone who believes in second chances and true love.
. . . to leave the past behind you:
Breakfast at Tiffany’s (1961)
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No one has stolen more hearts than Holly Golightly (Audrey Hepburn). Based on Truman Capote’s 1958 (harsher) novella of the same name, Breakfast at Tiffany’s—the story of a friendship struck between a rarely employed writer, Paul Varjak, and his neighbor, the naïvely beautiful Golightly, a freewheeling party girl whose lifestyle is paid for by the rich suitors who surround her—is a building block of our Hollywood romantic fantasies. It has the unclassifiable, magnetic object of affection, the reliable underdog who pursues her, expectations dashed, new friendships formed, true selves discovered, and an undeniably racist portrayal of an Asian landlord (by Mickey Rooney). Yes, it was a different era, but this detail can be difficult to ignore. That said, there are generations of viewers who consider this the greatest rom-com of all time.
. . . to get past that one little (or gigantic) flaw:
©MGM/Courtesy Everett Collection
Cher plays a widowed bookkeeper in Brooklyn Heights confronting her parents’ infidelity (and fallibility) who—whoops!—falls for her fiancé’s younger brother (Nicolas Cage), who sports a prosthetic wooden hand after an accident with a bread slicer. Their first night together produces one of the great moments in the annals of rom-coms: When Cage tells Cher he loves her, she slaps him, saying “Snap out of it!” The film portrays a New York that doesn’t really exist anymore—for one thing, Brooklyn Heights is full of bankers now. It’s a window to another time, when marriage meant something different in male-dominated second-generation immigrant families and the challenges Cher’s character places against the social order are both important and revelatory (she won an Oscar for her efforts). You end up cheering not just for her romance, but also for an entire insurgency.
. . . to put the fuckboys behind you:
Bridget Jones’s Diary (2001)
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Hollywood does this silly, shitty thing when they want to make it clear that a woman is “funny”: They make her clumsy. “Did you see that? She fell down in front of the boss she has a crush on while carrying many things! What a wit!” Thankfully, this film is actually funny, and so is Renée Zellweger, the titular Bridget Jones, who is 32 and a bit clumsy, and believes herself to be both a tad overweight and running short of romantic options. She confesses to her diary her feelings about the men in her life: her caddish colleague, Daniel (Hugh Grant), and her pill of a childhood friend, Mark Darcy (if that surname sounds familiar from one of your favorite literary comedies, that’s not by coincidence), who begin vying for her hesitant affections in their respectively charmless ways. Who will win—the nice guy or the jerk? The clumsy, funny, openhearted girl, of course! The story has a classic but important lesson to share: First impressions aren’t everything (and a fashion-related takeaway—never judge a man by his Christmas sweater).
. . . to make you even more neurotic about your love life:
Courtesy Everett Collection
Like Breakfast at Tiffany’s, this is one of those movies that any list of top rom-coms would be remiss without. Yes, Alvy Singer’s (Woody Allen) story about how he met, and then lost, and then maybe regained, the love of his life, Annie Hall (Diane Keaton), is a wonderfully funny underdog-meets-girl story. But Allen’s uniquely observational humor also introduced some pioneering tropes and storytelling devices to the annals of rom-coms. The moment his grade school classmates stand up and give short peaks into their future (“I used to be a heroin addict; now I’m a methadone addict”). Or when Alvy interrupts a pedantic professor in a movie line—lecturing his date on Marshall McLuhan—by bringing the actual Marshall McLuhan out from behind a sign to set the man straight. These established entirely new directions for comedy. Moreover, Allen’s confessional style and the monologue with which he begins telling his warts-and-all fictional tale established a new paradigm for romantic storytelling, one that continues to influence rom-coms today (same for Diane Keaton’s outfits, but that’s a topic for another list).
. . . to get you pumped up:
©Universal/Courtesy Everett Collection
This is the pregame of romantic comedies. It’s a love story—between millennial hotties Kirsten Dunst and Jesse Bradford—packed into 98 minutes of jokes, rivalries, teen romance, and ridiculous cheers. (“Hate us ’cause we’re beautiful—well, we don’t like you either. We’re cheerleaders. We. Are. Cheerleaders!”) Some of us have defended this movie since it bowed (and then cartwheeled into an aerial walkover) in 2000 as a sharp appreciation of teen culture and teen cinema, both devoid of cynicism and long on wordplay. If you agree, welcome to the squad. If not, please keep in mind, “This is not a democracy; it’s a cheer-ocracy.”
. . . to take an break from yourself:
Courtesy Everett Collection
There’s a wonderful moment in Roman Holiday—the story of a European princess, played by Audrey Hepburn, who tires of her duties and runs away from her handlers while visiting Rome—when Joe (Gregory Peck), a reporter showing her the city, puts his arm in the Mouth of Truth (a statue that supposedly bites off the hand of liars) and removes it with his hand missing. The princess screams—Hepburn was apparently not acting here—and then recovers. It’s a metaphoric yawp for all that a romantic comedy should be. It’s being taken by surprise, taken by a stranger, the discovery a new side of oneself while falling for someone else. And that’s just one moment!
. . . to get him into rom-coms:
The Princess Bride (1987)
©20thCentFox/Courtesy Everett Collection
“Is this a kissing book?” Fred Savage’s little boy asks his grandfather, at his bedside to read him The Princess Bride when he’s home sick from school. Sure is, but it’s also a tale of swashbuckling, cruel kings, giants, swordsmen, poison, monsters, rebels, and knights—without a dull or unfunny moment. The kid, and the viewer, is quickly on board. More than anything, it’s a tale of true love, and fantastic as it might be, the adventure that leads the stable boy, Westley, back to his mistress, Buttercup (played by an impossibly beautiful Robin Wright), has left few hearts unmoved, and few faces without with smiles.
. . . to consider what you could have done differently:
©Columbia Pictures/Courtesy Everett Collection
One of the few rom-coms that comes with both a stamp of approval from your philosophy professor and the Tony reaches of Broadway. A cynical Pittsburgh weatherman (Bill Murray) is sent to Punxsutawney, Pennsylvania, with his producer, Rita (Andie MacDowell) on a dead-end assignment: to cover Groundhog Day. And boy, is it a dead end. Murray gets stuck there, not just in a snowstorm, mind you, but in a continuous loop where no matter what he does—including suicide—he wakes up in the same hotel, on the same day. At first, the weatherman is predictably bummed, but eventually he uses all the information he’s picked up living the same day over and over to better himself and the lives of those around him, eventually impressing Rita with his change of personality. Watching Bill Murray is fun, watching Bill Murray struggle is really fun, and watching Bill Murray caught in a space-time logjam, wrestling with moral philosophy while pursuing Andie MacDowell is the most fun.
. . . to find “our song”:
Nick and Norah’s Infinite Playlist (2008)
Entertainment Pictures / Alamy Stock Photo
There’s something almost quaint about Norah’s search for her orgasm. The high schooler, played by Kat Dennings, is demeaned by her fellow classmates for having yet to experience the big O. It may sound tawdry, yet this plot point harkens back to a sweeter, John Hughes–era teen comedy (with a few switches flipped) wherein the search for a simple sex act was enough motivation for a number of scenes, if not an entire film. Norah’s lack of fulfillment isn’t what moves the action here; instead we’re on a search for her best friend and an oh-so-cool band’s secret show, with Nick’s (Michael Cera) hapless band, in his hapless car (a Yugo), through downtown New York City’s music scene. It’s a good-time flick, with cheerful performances and the kind of supporting cast (Ari Graynor as the beyond-drunk best friend) that make 90 minutes seem like a brisk 30. One of these is Alexis Dziena, who plays Nick’s very recent ex-girlfriend: She toyed with him and never appreciated the music mixes he made for her (spoiler: Norah loves them). Her “sexy” dance, in the glaring light of Nick’s high beams, to Hot Chocolate’s “You Sexy Thing” is one of the great falls from grace, and worth the price of admission.
. . . to inspire some big changes:
©Buena Vista Pictures/Courtesy Everett Collection
Is there a rom-com list that doesn’t include this movie? What’s left to say about the 1990 tale of the beautiful, charming prostitute and the Wall Street corporate raider who meet and fall in love? Here’s director Garry Marshall’s (and Julia Roberts and Richard Gere’s) genius with this film: They make us forget about the various horrors of sex work and instead convince us the whole thing is kind of a lark. This film takes place in the late 1980s; a high-water mark in terms of the HIV crisis. Those things aren’t on our minds when we watch this movie (barring an early scene discussing methods of birth control); we think about stomping divots and Richard Gere conquering his fear of heights. So what? The Great Escape doesn’t exactly feature the horrors of World War II. That’s not the story they’re telling. Exactly our point. That’s how delightful this movie is.
. . . to make your arguments a little sweeter:
Courtesy Everett Collection
Here’s how cute rom-coms were in the 1930s: The entire plot rests on a dog burying a bone of a brontosaurus. Katharine Hepburn, whom the movie was written for, plays a whimsical, adorable socialite who has become besotted with an otherwise engaged (literally and figuratively) paleontologist, played by Cary Grant, and is trying to keep him around so he won’t go marry some pill. Her strategy for doing this is to invite him to her house so that he can help her bring a baby leopard to the city. (Later, the dog and the leopard wrestle.) This is what we call a screwball comedy. It’s also priceless, with Hepburn peppering Grant in her sweet, Gatling gun style, and Grant, playing stiff, as if any man, never mind a mild-mannered paleontologist, could ever resist such wiles.
. . . to make it a girls night:
10 Things I Hate About You (1999)
©Buena Vista Pictures/Courtesy Everett Collection
Why is there no actual Shakespeare on this list? Because often a three-hour production: (1) is rarely funny, and (2) doesn’t really fit into a modern romantic comedy structure. Instead, we have movies that are actually fun to watch, like Shakespeare in Love, and this one, a teen-ready take on The Taming of the Shrew. There are some cute turns from youngsters Joseph Gordon-Levitt, Julia Stiles, and Larisa Oleynik, but ask most women and the performance that sticks out is Heath Ledger’s, whose thuggish Patrick Verona made many of us weak in the knees. Like Bring It On, and unlike most films, especially teen films, this one is female focused. They’re the moral centers. The heroes we cheer for. And they are active in as much as the narrative as they are subject to it (rare!).
. . . to better understand your parents:
©Focus Features/Courtesy Everett Collection
“The History of Sadness” is a sketchbook drawn by Ewan McGregor’s Oliver, a graphic designer who is dealing with the recent coming out of his septuagenarian father, Hal (Christopher Plummer—who won an Oscar for his performance). Hal’s new openness about his own life inspires Oliver to reevaluate his own sadness and pursue a lovely French actress, Anna. It’s an incredibly touching, difficult story, told mostly in flashback, that involves Oliver coming to grips with his father’s past, his parents’ relationship, his own choices, and his art. But it’s ultimately a love story. A story about how our parents love us, and each other—despite the difficulties imposed society, time, and work—and how in turn, we learn to love, or not. We’re all beginners, in all our loves, and to think otherwise is foolhardy.
. . . to freeze some already cold feet:
The Wedding Singer (1998)
©New Line Cinema/Courtesy Everett Collection
Millennials might not realize from Adam Sandler’s recent descent into perennial schlock (some of it racist and sexist)—like The Ridiculous 6, Blended, Jack and Jill, and Grown Ups—that his movies were, at one point, very funny. Billy Madisonand Happy Gilmore are ’90s classics, and The Wedding Singer, his only rom-com from that era (there’s some debate over whether P. T. Anderson’s Punch-Drunk Love, released in 2002, qualifies as such), is a hilarious, touching ode to traditional values. Set in the ’80s, Sandler’s Robbie Hart is a wedding singer (and hopeless romantic) recently left at the altar who helps Drew Barrymore’s Julia plan her wedding to the wrong man. Sandler and Barrymore’s chemistry is off the charts, and this film—not Mad Love, sorry—established the actress as rom-com gold (see Never Been Kissed, 50 First Dates, and Fever Pitch). The romance is great, the jokes are great, the costumes are great, and not to ruin anything, but Billy Idol is pretty great too.
. . . to get you singing and dancing (and maybe moving to L.A.):
©Lions Gate/Courtesy Everett Collection
The highway scene. Ryan Gosling hunkered over the piano. Emma Stone embodying “irrepressible.” His dance on the boardwalk. Her spins. The way she pulls at her dress. The way he grins while he smolders. Their love. It’s a panacea for the reasons we go to the movies. At no point do we believe they won’t end up together, but we stay transfixed, in fact we tap along. For younger viewers—those of us who might not have drank down the moving magic of Singin’ in the Rain, West Side Story, or Gigi—Damien Chazelle’s La La Land forgives those lapses. It embraces their greatness as it embraces us in its giant, vibrant arms. We lean closer to the screen, not to learn but to feel for the whole experience of youth and performance: all that hope, drive, sweat, and love. Can’t forget love.
. . . to kick-start your career goals:
Singin’ in the Rain (1952)
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Here’s the thing: You’re not really allowed to like La La Land if you don’t like Singin’ in the Rain. Or, you at least have to watch it; it’s the original musical about making it in Hollywood. The story of a sellout leading man (Gene Kelly) who falls for the chorus girl (Debbie Reynolds) who might just change his life (and he hers), this 1950s romp through 1920s Hollywood really has it all: singing, dancing, and bedrock songs like “Make ’Em Laugh,” “Good Morning,” and of course, “Singin’ in the Rain.” It’s cute as hell and tap-happy to the extreme.
. . . to unplug from the office (and get your due):
How Stella Got Her Groove Back (1998)
©20thCentFox/Courtesy Everett Collection
The movie that inspired 90 percent of vacation hookup jokes since 1998 (but seriously, we need to talk about Taye Diggs in a puka shell necklace; the man can make anything look good). Workaholic executive and single mom Stella (Angela Bassett) finds more than she bargains for when her best friend, played by Whoopi Goldberg, convinces her to take a much-deserved Caribbean vacation. Cheeky, subversive, and sexy as hell, this movie turned the tables on so many male-dominated rom-coms (courtesy of one very hot and heavy matchup between Bassett and Diggs, playing some 20 years her junior)—and passes the Bechdel test with flying colors. One of the very few rom-coms to do so.
. . . to get dressed up for:
©Columbia Pictures/Courtesy Everett Collection
Michael Dorsey (Dustin Hoffman) is a New York actor who is such a perfectionist, no one wants to work with him. So he does what any rational man would do: He dresses as an entirely different person—an older woman who goes by then name of Tootsie—and lands a role on a soap opera where he becomes a sensation. Problems arise when he falls in love with his costar (Jessica Lange) and a fellow castmate, an older man, falls in love with him. It’s madcap and zany but also profoundly funny, with insights aplenty—it sends up television, sexism, and New York society—and performances that were Oscar-worthy (Lange’s in particular—of Tootsie’s 10 Oscar nominations, she’s the only one who walked away with a statue).
. . . to reevaluate the nice guy (and the bad boy):
©Orion Pictures Corp/Courtesy Everett Collection
Before Johnathan Demme decided to win an Oscar and scare the pants off an entire generation with The Silence of the Lambs, he was an ’80s funnyman. And this is his best work. It’s the story of a mild-mannered exec (played by Jeff Daniels), whose sedentary life is turned upside down by the wildly adventurous, somewhat grifting Lulu (Melanie Griffith)—whose checkered past includes a roustabout, criminal ex-boyfriend played by Ray Liotta. The idea of a “crazy” girl coming in and turning a straight man’s existence topsy-turvy is repeated countless times in this genre, from Bringing Up Baby to The Girl Next Door. Demme’s alchemy here is to infuse the trope with unpredictability. The comedy keeps us on the edge of our seats by compounding the will-they-won’t-they question with sudden breaks into violence, threats, or chase. Rom-coms don’t get more exciting than this.
Sony Pictures Classics/courtesy Everett Collection
The love story here is as much between writer-flaneur Gil Pender and Paris as it is between Gil and any of the women in this film. While visiting the French capital with his uptight fiancée, Inez (a sublime Rachel McAdams), and her parents, each night Gil goes walking and finds himself in the City of Light of the 1920s, complete with Hemingway, Gertrude Stein, the Fitzgeralds, Man Ray, Josephine Baker, Cole Porter . . . and a beautiful woman named Adriana (Marion Cotillard). It’s a writer’s fantasy made real (Stein volunteers to read his novel), but it’s also Woody Allen at his most effective: taking the vicissitudes of relationships and turning them into a mirthful, if neurotic, journey. This one just happens to also navigate through another time and place as well. And a beautiful one, at that. There’s a reason this is Allen’s highest-grossing film of all time.
. . . to escape the friend zone:
When Harry Met Sally. . . (1989)
©Columbia Pictures/Courtesy Everett Collection
If this list were a top 20 instead, this film would still be on it. Same with top 10—and five. It’s in the running for the best rom-com of all time because it is sassy, sultry, snappy, cinematic perfection, thanks to words from Nora Ephron and direction from Rob Reiner. It’s something of an epic of the genre, spanning over 10 years of the kind of friendship (between Meg Ryan and Billy Crystal’s characters) where no one can help but ask, “Why aren’t those two together?” Should friends ever sleep together? If they do, what happens next? This movie should be watched by every college student on the planet. Bonus: Watch this movie with a boyfriend, and pay attention to what happens to his face during Meg Ryan’s most famous scene, in which she illustrates just how easy it is for a woman to fake an orgasm.
. . . to unite with your crew:
©Universal/Courtesy Everett Collection
Who ever thought getting food poisoning in a wedding dress could be so funny? Bridesmaids is as much a buddy comedy (think Old School or Twins) as it is a rom-com, proving that female actors can be just as bawdy and into gross-out humor as their male counterparts in The Hangover. This is about the love between friends, yes, and the agony that comes with maturing at different paces, but what ultimately drives the film is the desire of Annie (Kristen Wiig, who also wrote the script, with Annie Mumolo) to catch up. This movie isn’t as much about what we have as about what we’re missing, and how a wedding can bring that to the fore. Along with nonstop laughs, we get a powerhouse performance from Wiig—even as Melissa McCarthy steals the show.
. . . to remind you that guys will try anything:
There’s Something About Mary (1998)
©20thCentFox/Courtesy Everett Collection
Before we had a president who bragged openly about grabbing women “by the pussy”, this is what qualified as a gross-out film. Amid scenes of semen being used as hair gel and testicles jammed in zippers, the Farrelly Brothers managed to concoct an amiable story about a nerdy Ted (Ben Stiller) hiring a private detective to find Mary (Cameron Diaz), the object of his unrequited love in high school. Despite the over-the-top locker-room gags, the movie has virtually no sex, and manages to emerge as hilarious, sweet, and satisfying.
. . . to make up your mind, dammit:
©United Artists/Courtesy Everett Collection
Elephant in the room: Yes, this is Woody Allen pursuing a high school student (a luminous Mariel Hemingway). It was also made in 1979, and that didn’t carry quite the same connotations as it does now. The year is important, because as the film’s title suggests, this movie is as much about New York as it is about the lovers who collide inside of it (Allen’s character, Isaac, begins the film dating the high schooler, but leaves her for his friend’s mistress, played by Diane Keaton). In the mid-to-late 1970s, New York was a bit of a cesspool: Crime was out of control, repeated requests for federal aid were denied, and the city was on the edge of bankruptcy. It’s in the wake of this tumult that Allen pens his black-and-white love note to his fair city. The film opens with a montage of New York’s skyline and street scenes, revealed to “Rhapsody in Blue,” and Allen’s voice-over as Isaac, writing about his romantic love for the city. That’s where he gets us with this film; Allen crystalizes the outsize feelings that can swell with romance, despite any and all evidence that should temper them. It’s a movie about indecision, bad choices, and falling for the wrong people, but it celebrates the impetus for all of these. We love the things we shouldn’t. That’s life. That’s Manhattan.
. . . to know if he’s worth the trouble:
Photo: Courtesy of © 20th Century Fox Film Corp./Everett Collection
If for no other reason, you need to see this movie so you’ll understand what it means when someone holds a ghetto blaster over his head outside the window of the woman he loves. Like most of the teen romance flicks on this list, Say Anything. . . doesn’t end at the Big Dance. This movie, from director Cameron Crowe (and produced by James L. Brooks) is far too sophisticated for such a middling finale. It’s too busy diving into the angsty, all-consuming, awkward challenge that is young love, as embodied by consummate underdog Lloyd Dobler and his attempts to woo the beautiful valedictorian Diane Court.
Crazy, Stupid, Love. (2011)
©Warner Bros/Courtesy Everett Collection
If The 40-Year-Old Virgin was evidence that Steve Carell could be a romantic lead, this was the proof. Alongside Julianne Moore, as the cheating wife he wants to win back, and with Ryan Gosling, who plays his cad coach, as well with a terrific performance from a teenage son who loves his babysitter, who in turn loves his nice-guy dad, Carell is well matched. Throw in Kevin Bacon as a romantic rival and Emma Stone as a law student just out of Gosling’s reach, and we’re ready to go. It’s a comedy that’s as much about accepting the facts of life—be they middle age, the people we can’t have, or the people we don’t want others involved with—as much as it is about a pursuit, or any one relationship. It’s about how love really is, sometimes, which can be romantic in its own right.
. . . to fall in love with literature:
Shakespeare in Love (1998)
©Miramax/Courtesy Everett Collection
People forget about the competition Shakespeare faced, and we don’t mean the other plays. In the late 1500s, one could go to the theater, or one could go watch some people be executed or a bear be torn apart by dogs. That’s how entertaining Shakespeare’s work had to be! In 1998, this film competed with Saving Private Ryan, Elizabeth, and Life Is Beautiful for Best Picture and managed to come out with the Oscar. What drew the academy to the fast-paced mash-up of Romeo and Juliet with a very loosely interpreted history of William Shakespeare’s life was the film’s ability to capture exactly what Shakespeare did back in his day: the urgency of love and the power of its expression—its ability to consume us and change lives.
. . . to tell your real friends from the sham ones:
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Muriel (Toni Collette), a daydreamer and the target of the bitchy girls she considers her friends, wants nothing more than to get out of her small town and away from her awful father, move to Sydney, and get married. When she makes off with her parents’ savings, reunites with a fellow outcast from her town, and is offered the chance to marry a gorgeous South African swimmer who needs a visa, she can make her dreams come true. As much of a coming-of-age story as a rom-com (Muriel may be in her 20s, but she has much growing up to do), this film does a brilliant job of cutting the legs out from underneath our expectations by giving us exactly what we’ve always wanted, and tying us up in the strings attached.
. . . to relive high school (or what you wish high school was like):
To All the Boys I’ve Loved Before (2018)
Netflix’s most popular entry into the rom-com genre (based on the novel by Jenny Han) was for many an instant classic—not least for blessing the world with Peter Kavinsky (Noah Centineo), the Jake Ryan of the Internet era. Lana Condor stars as Lara Jean, a quiet high school kid who relieves her romantic pressures by writing never-to-be-mailed love letters to the objects of her affection—including her older sister’s ex-boyfriend. Until, of course, one night they get sent out. Hijinks—and a fake turned not-so-fake relationship—ensue.
. . . to remind you how much better it gets after high school:
©Universal/Courtesy Everett Collection
A teen sex comedy with a heart of gold, this story of four high school friends determined to have sex before they graduate was the surprise hit of 1999. But underneath all the masturbating with pastry and accidentally ingested semen cocktails, there’s real sentiment to the adolescent boys trying to find their way with women, and vice versa. The reason we can safely call this a rom-com is that, while it doesn’t exactly pass the Bechdel test with flying colors, the objects of the guys’ affections are far from just objects. They have goals of their own we’re brought on board with. The girls aren’t just out for the boys, they’re out for themselves—as disappointingly rare in a rom-com as it is in a teen comedy, and the reason we love this one.
. . . to learn how far to take it:
©Buena Vista Pictures/Courtesy Everett Collection
This is Wes Anderson’s most completely stylish movie, and perhaps his best, made before stylized fuckery got in the way of things like writing (like all his best work, this was cowritten with Owen Wilson). Max Fischer (Jason Schwartzman) is a scholarship student at a private school. His academics are dismal, but he’s game for any and all extracurriculars, especially the over-the-top plays he produces and directs. He gets into a contest for the affections of a widowed first grade teacher with local industrialist, and his newfound mentor, Herman Blume (Bill Murray). Several phenomenal executions come together in this film, including the ensemble cast, the just-on-this-side of believable production design, and an absolutely killer classic rock soundtrack. But what pushes it above the rest is the utter drive of both Max and Herman, as love and competition gains primacy over every aspect of their lives. They’re both willing to burn the village to save it, which is simultaneously hilarious to watch and cathartic to anyone who’s ever had a crush.
. . . to locate your other half:
©TriStar Pictures/Courtesy Everett Collection
Cameron Crowe has a couple of films on this list (Almost Famous was close, but ultimately more coming-of-age than comedy) with good reason: He understands people and how they tick. Despite its memorably demonstrative, over-the-top lines, like “You complete me,” and “Show me the money,” this is ultimately a movie about how people really fall in love. Sure, Renée Zellweger loves Tom Cruise from the beginning—it’s a movie after all, and he is Tom Cruise—but what Jerry Maguire gets to is what happens after that first kiss, after the honeymoon period, when we have to learn about the other person as a person, and not just see them and their adorable puppy (or in this case, an adorable son, played by Jonathan Lipnicki) as an escape or alternative from our own lives.
. . . for a dose of realism (and Paris!)
For sheer hilarious, messy, complicated realism, Two Days in Paris takes the prize. The brilliant and surprising Julie Delpy writes, directs, and stars as Marion, a young Frenchwoman who has brought her American boyfriend Jack (Adam Goldberg) to her hometown en route from a trip to Venice. They struggle through misunderstandings, language barriers, cultural clashes, encounters with Marion’s many ex-boyfriends, and her unruly parents (played by Delpy’s real-life mother and father, actors Marie Pillet and Albert Delpy,) and barely come out the other side. The moral, as Marion paraphrases Jack: “It’s not easy being in a relationship, much less to truly know the other one and accept them as they are with all their flaws and baggage.” It may not be easy, but it’s highly entertaining to watch them try.
. . . to get you through the holidays:
©Universal/Courtesy Everett Collection
Is this? Not really. But that’s not why we go to the movies. Love Actually is, actually, a rather clichéd Christmas rom-com, but jeez, we love it anyway. How can we not, with this ensemble cast of British romance all-stars (Hugh Grant, Emma Thompson, Liam Neeson, Colin Firth, and Keira Knightley, among others)? The prime minister (Grant) falling for a junior staff member? A quiet suitor in love with the new bride (Knightley) of his best bud (Chiwetel Ejiofor), who is apparently one of three people of color in London? A cuckolded boyfriend (Firth) rebuilding his shattered life with the help of his shy housekeeper? Balderdash. All of it. But it’s irresistible. Come on, what are you, made of stone?
. . . to fall for his funny bone:
©Paramount/Courtesy Everett Collection
Think of it as Before Sunset meets Funny People, with New York taking the place of Paris. If that notion produces a little eye roll, get those peepers back down, and then on to the screen before you miss some laughs. Rosario Dawson plays a New York Times journalist tasked with interviewing a hugely famous comedian, played by Chris Rock, who is attempting to take his career in a new direction (courtesy of an ill-advised serious film about a Haitian revolutionary). Like Roman Holidaybefore it, this is a film rooted in our society’s placement of, and expectations for, certain figures (a celebrity and a princess, respectively). In both cases, the journalist finds the human being inside of their famous subject, falling for them while trying not to fall for their shtick, or what they represent. As the pair make their way through Manhattan—with visits from Jerry Seinfeld, radio hosts Opie and Anthony, Whoopi Goldberg, and a fantastic supporting job from the ageless Gabrielle Union, playing a reality TV starlet—we can’t help but get on board with their journey.
. . . to look past his neurotic, potentially mentally ill exterior:
As Good as It Gets (1997)
©Sony Pictures/Courtesy Everett Collection
There are few actors who can go toe-to-toe with Jack Nicholson. Director James L. Brooks found a suitable sparring partner with Shirley MacLaine in Terms of Endearment and struck gold again nearly 15 years later with Helen Hunt. Hunt plays a waitress with a sick child for whom Nicholson—a mean, racist, homophobic, obsessive-compulsive writer and her regular customer in the restaurant where she waits tables—has some affection. Bring in Nicholson’s neighbor, a gay artist (played by Greg Kinnear) who has to lean on the Nicholson’s character for help (beginning with care for his adorable dog), add a road trip, and you’ve got yourself one of the most delightful, well-thought-out comedies of the ’90s. The movie takes it time, but it’s to our benefit—Brooks allows us to get to know each of these people, and them each other, intimately, which means when the jokes, and the romance, land, they land hard, and then stay around. (Plus, who among us could resist Nicholson growling, “You make me wanna be a better man”?)
. . . to confirm that, yeah, he’s probably cheating:
Courtesy Everett Collection
There’s a lot going on in Shampoo—the story of an L.A. hairdresser (Warren Beatty) who is sleeping with, well, everyone (including Julie Christie, who plays a prime target of his affections)—which, at first glance, could just be another ’70s sex comedy. Keep in mind, it’s directed by Hal Ashby, the king of thoughtful, offbeat romances, and was both written by and featured, Warren Beatty, a major voice of the Hollywood Left in the 1970s. The film, released a year after Nixon’s downfall, takes place during on the eve of Nixon’s election in 1968, so there’s a good deal of interplay between the politics and the sexual politics that were in the air as the counterculture died, the pill became mainstream, and the country saw itself in a whole new, darker light. That said, Beatty’s portrayal of the harried, discursive, libidinous George is irresistible even without context, as is the performance given by a young Goldie Hawn, who illuminates every frame—and perfectly counteracts Beatty—with blonde California light, and a heart-melting, downy innocence.
. . . to get you on board with AI:
©Walt Disney Co./Courtesy Everett Collection
There are more epic Disney romances (one of them is on this list), but none more thoughtful. What we love about this futuristic tale of a little trash compactor, WALL-E, who falls in love with his technological better, EVE, is the considered environmental, anti-consumerist message that suffuses the dystopian love story. With barely a word, only whirrs, between them, EVE and WALL-E convincingly fall in love. His efforts to save her, once the megacorporation Buy-n-Large (their maker) comes for her, is as authentic as Hawkeye’s return for Cora, or Jack’s sacrifice for Rose. Forget Finding Nemo, this is writer-director Andrew Stanton’s Pixar masterpiece.
. . . to justify your May-December romance:
Courtesy Everett Collection
There’s a question that lingers throughout most of Harold and Maude—the story of a death-obsessed young man (he enjoys driving a hearse, attending funerals, and faking his suicide) who falls for a much, much older woman—are these two going to get it on? It sounds sophomoric, but it’s actually essential. Harold and Maude are separated by approximately 60 years; for the movie to hit home, for us to believe that love is truly about what we share, not what we look like or other aesthetic values, we have to believe a genuine attraction has formed. No one prodded existentialism (especially in films deemed “romantic”) like director Hal Ashby, and Harold and Maude is no exception. The darkly funny tale will leave you questioning just what is important to you in your own conception of love—and, moreover, in your life.
. . . to give comic books their due:
©Miramax/Courtesy Everett Collection
A comic book artist (Ben Affleck) with an inseparable best friend (Jason Lee) falls for a beautiful gay girl (Joey Lauren Adams)—who then falls for him—only to discover he can’t handle it. Comic books? Lesbian conversion? Best buds? Sounds like a romantic comedy made by men, for men. And it is! But Kevin Smith also managed a somewhat nuanced exploration of friendship and art, as well as of contemporary romantic standards in his rejiggering of the love triangle. Simultaneously, at a time when every other joke on Friends involved gay panic, he was portraying three-dimensional concepts of lesbian identity. What could be identified as a typical male-driven fantasy could also be seen as a ’90s Torrents of Spring.
. . . to make you fall in love with your friends:
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In what was then a cult hit and is now a piece of ’90s nostalgia catnip, a post–Edward Scissorhands (and post–Johnny Depp) Winona Ryder plays Lelaina, an aspiring documentarian assisting an obnoxious TV host in Houston. She and grungy, Generation X friends—played by Steve Zahn, Janeane Garofolo, and a simmering Ethan Hawke (who may be more than just a friend)—are just trying to figure out who they are, and what they want in life. In Ben Stiller’s feature directorial debut, he also plays a TV executive whose budding romance with Lelaina and interest in her work brings the real world crashing into their postcollegiate hipster existence. Aside from a nonstop ’90s fashion buffet that is Winona’s wardrobe (mom jeans, crop tops, baby doll dresses, cardigans, men’s shirts, blazers), there’s also love and heartbreak, sex, betrayal, Lisa Loeb, Dickies, pizza, and lines like “He’s so cheesy, I can’t watch him without crackers.” What else do we want, really?
. . . to dance your troubles away:
©Paramount/Courtesy Everett Collection
The ’50s nostalgia of the 1970s culminated with this unreal musical about the return to high school for summer lovers Danny Zuko (John Travolta) and Sandy Olsson (Olivia Newton-John). It’s hard for current viewers to understand just how big John Travolta was at the time; the year this film bowed, 1978, the two top-selling albums were the soundtracks to Saturday Night Fever (another Travolta film) and this one. And that was in a year when the Rolling Stones released Some Girls and Bruce Springsteen dropped Darkness on the Edge of Town. In this irresistibly playful film, Travolta embodies the bursting sexuality of the newly emerged teen culture, but at the same time, he’s a tampered-down throwback—we buy him drag racing cars and singing with his gang, the T-Birds, whose rivals are the Scorpions, and making clumsy moves at the drive-in. Similarly, the Pink Ladies, a popular clique headed by Rizzo (Stockard Channing), deliver their wiseacre lines with a fair dose of irony. These skirts know what’s up, and that’s what makes us interested, and invested, in their outcomes. We’re locked in from the first frame: There may be better musicals, but none more fun.
. . . to get you through wedding season:
Four Weddings and a Funeral (1994)
©GramercyPictures/Courtesy Everett Collection
For anyone who’s ever been encumbered by the beautiful, annoying, expensive ordeal that is a wedding, how can we not love a wedding movie whose first pages of dialogue are just the word Fuck? As much as we commiserate, this is ultimately Hugh Grant’s movie. And a little Andie MacDowell’s movie. But mostly Hugh Grant’s. It’s the film that introduced us to his stumbling, bumbling, yet confident Etonian charms and wit, which we’d witness again and again in Nine Months, Notting Hill, Music and Lyrics, About a Boy, and more). The story of Grant and his friends attending their friends’ weddings—and one funeral—perfectly captured the romance of nuptials as well as all the stress, commitment, and emotional . . . what do the British call it? . . . oh yes, bother that comes with that period in your life where your friends are tying the knot. The question this rom-com dares ask is this: In all this wedding madness, can you be the odd man out and still be happy?
. . . to find your prince:
©Paramount/Courtesy Everett Collection
It’s unfair that Eddie Murphy only has one entry on this list. The guy ruled the ’80s and made some of the era’s great comedies—Trading Places, Beverly Hills Cop, 48 Hrs.—but this is really the only one where the romance narrative rules supreme. In short: Murphy plays the prince of a fictional African nation who is unsure about his arranged marriage, and so heads to what he suspects will be greener pastures in search of his queen. So where better to start that Queens, New York? Essentially slumming it with his best friend (a terrific Arsenio Hall), Murphy’s character finds work at a McDonald’s-type restaurant where he falls in love with the owner’s daughter, a woman who just might fit the bill. It’s a super simple story that elicits big laughs in every scene, but it’s also a clever send-up of class and race that simultaneously owns itself as perhaps the ultimate Reaganite comedy: If you are rich and follow your heart, you can be even richer!
…remind you that life doesn’t always go as planned, but sometimes that’s okay.
Life’s not perfect, but it can be most endearing— that’s the takeaway, anyway, from Jason Reitman’s nuanced teen comedy, Juno. Ellen Page gives her breakout performance as the titular pregnant-by-accident teen who soldiers on through high school while preparing to give her baby up for adoption to a painfully needy rich couple (or “baby-starved wingnuts,” as her father calls them.) Juno’s honesty and her backward love story with the adorably nerdy Paulie (Micheal Cera) reminds us of the true meaning of being cool, and that heartache can resolve itself into a tender, resilient future.
. . . to get your boss’s job:
©20thCentFox/Courtesy Everett Collection
First, consider the cast: Melanie Griffith, Harrison Ford—who owned the ’80s in Hollywood and made this his only rom-com—Sigourney Weaver, Joan Cusack, Oliver Platt, Alec Baldwin (at his douchiest), and Kevin Spacey. Next, look at the director: Mike Nichols—if there is a pantheon for romantic films, he probably has Zeus’s seat. Finally, the shoulder pads; my god, the shoulder pads. Were doorways made wider in the 1980s? Adventures in Babysitting aside, this movie is really as feminist as mainstream movies got in the ’80s. Melanie Griffith plays Tess McGill, a wily business school graduate working as a secretary at an investment bank with such memorable one-liners as “I have a head for business and a bod for sin.” When her boss (Weaver) steals her idea for a merger and then ends up out of commission (temporarily bedridden after a ski accident), Tess rises to the occasion: scheming with the support of her friends and maybe-lover (Ford), conniving, flirting, and using some good old-fashioned elbow grease to outwit her superiors, beat the boys, and claim the position she’s rightfully earned. Griffith is miraculous (one critic compared her to Marilyn Monroe; younger viewers might see a mold for Alicia Silverstone’s Cher), taking a role that could have just been “cute” and elevating it to nuanced and beguiling. That’s what this film is—so much so, we’ll forgive you if, after watching it, you suddenly have a soft spot for shoulder pads.
