The Best Sex Comedies of All Time, from ‘The Seven Year-Itch’ to ‘Magic Mike XXL’ to ‘Bottoms’

“The Seven-Year Itch” (1955)

“The Seven-Year Itch” is far less famous as a movie than it is as a vessel for one of pop culture’s all-time most famous images: Marilyn Monroe standing on a subway grate, struggling to hold down her billowing white dress as a train passes by. The actual film is a lot weirder and spikier than that iconic scene might suggest. Monroe plays an unnamed girl who meets Richard (Tom Sewell), a middle-aged publishing executive in a somewhat stale marriage. While Richard’s wife and son are away for Maine in the summer, Richard entertains a flirtation with Monroe’s bombshell, and struggles with his guilt and lust through increasingly bizarre dream sequences. A sympathetic protagonist Richard is not, but the film realizes it, and mines his neurotic obsession for utter cringe comedy. And Monroe is as wonderful as she always is, playing with unwinking sweetness a ditzy blonde with a heart of pure gold. —WC

“Pillow Talk” (1959)

The first of three comedies starring Rock Hudson and Doris Day, “Pillow Talk” remains the most famous of them six decades later. Michael Gordon’s phone call comedy revolves around Jan (Day) and Brad (Hudson), two strangers who share a telephone line. When Jan files a complaint against the womanizing Brad for constantly using the line to pick up women, he decides to pick her up by faking his identity as a Texan racher, only to fall in love with her in the process. Although the plot definitely doesn’t hold up perfectly as a shiny example of consent through a modern lens, Day and Hudson’s wonderful chemistry still makes it a fizzy, delightful treat. Also, there’s a scene where the then-closeted Hudson plays a straight man pretending to be gay, which is both hilarious and oddly touching. —WC

“Animal House” (1978)

One of the most influential comedy films ever, “Animal House” has been endlessly parodied and imitated in the years since its release, and its success helped pave the way for many not very good sex comedies to come. And the movie hasn’t aged one hundred percent gracefully, with several scenes of questionable consent that are downright difficult to watch now. But the parts of John Landis’ film that hold up are still uproariously funny, thanks to the talented comedic cast playing the slacker Delta House that causes mischief at the fictional Faber College. Led by John Belushi as the animalistic Bluto, the Delta House engages in all sorts of wild partying and poor behavior that makes for a loose, silly film, and still the first title that comes to mind when people think of a classic college movie. —WC

“Fast Times at Ridgemont High” (1982)

Sex comedy is a genre largely shaped by the voices of men, with teen boys’ sexual desires being placed at the forefront over their female counterparts. “Fast Times at Ridgemont High” isn’t necessarily a full rejection of that; the movie was written by Cameron Crowe, and the scene that everyone remembers is Phoebe Cates taking her bikini off to the sound of  “Moving in Stereo” by The Cars. But the ensemble film is the rare sex comedy from a female filmmaker in director Amy Heckerling, and that’s perhaps why it shows refreshingly equal investment between its male and female characters.

Focusing on six teenagers at the titular Ridgemont High, “Fast Times” follows several loosely linked plotlines as the high schoolers pursue their first experiences with sex. The closest thing to a main figure holding it together is Jennifer Jason Leigh in her breakthrough role as virgin freshman Stacy, whose attempts to find love end in disaster and an abortion, boldly portrayed in a relatively matter-of-fact manner by the film. Leigh’s brilliant performance is supported by an incredibly stacked cast of future stars, including Sean Penn, Phoebe Cates, and Judge Reinhold, with Forest Whitaker and Nicolas Cage in minor roles, and by a smart, sensitive script that’s plenty sexy while still being frank and real about the realities of growing up. —WC

“Risky Business” (1983)

There are few star is born moments more iconic, or more fun, than Tom Cruise shimmying in his undies to “Old Time Rock and Roll” during the opening minutes of “Risky Business.” The scene is so famous that it overshadows the rest of the film from director Paul Brickman about do-gooder high schooler Joel’s efforts to loosen up and have some fun when his parents leave him alone at home for a few days. One of his efforts include hiring a prostitute Lana (Rebecca De Mornay), which quickly spirals into him turning his home into a makeshift brothel for a wild teen party. The film plays most of the conventions of sex comedies fairly straight, but it’s heightened by a sharp script that gently satirizes ‘80s consumerism and strong, moody direction by Brickman. And after years of Cruise playing stoic, unflappable action heroes, it’s a shock to go back and see how electrifying he is in “Risky Business,” as loose and charming as any teen protagonist has ever been onscreen. —WC  

“There’s Something About Mary” (1998)

One of the best comedic actresses of her generation, Cameron Diaz had successful roles before “There’s Something About Mary,” but her leading turn in the raunchy film is what cemented her as a star. Diaz’s Mary is a gorgeous, kind-hearted surgeon whose beauty attracts a lot of male attention. So much so that she gets numerous stalkers over the course of the film, played by the likes of Ben Stiller, Matt Dillon, Chris Elliot, and Lee Evans, who all compete to get her for themselves. Peter and Bobby Farrelly’s film is ridiculously puerile, as the men get themselves into disgusting sexual situations in their chase of Mary. And the film lets Mary engage in some hijinks of her own, and Diaz absolutely smashes them — especially in the infamous “semen hair gel” scene, one of the funniest gags of any ’90s comedies. —WC

“Along Came Polly” (2004)

Jennifer Aniston and Ben Stiller lead this criminally underrated 2004 romantic comedy from writer/director John Hamburg. When a nervous insurance adjuster (who just found out his soon-to-be-ex cheated during their honeymoon) meets a free-spirited cater waiter, the unlikely duo embark on a rocky, but easy to root for dating journey as uproariously funny as it is sincere and sweet. There’s a bubbling chemistry between one Polly Prince and Reuben Feffer, and “Along Came Polly” supports that oddly intoxicating awkwardness with a world just as rich, entertaining, and unusual. Claude the scuba instructor! Reuben’s bizarre parents! Rodolfo the (blind) ferret! Not to mention, the late Philip Seymour Hoffman’s unforgettable performance as Reuben’s best friend Sandy Lyle: one of the actor’s funniest and sharpest roles.

“Along Came Polly” wasn’t especially popular upon release, and the movie remains divisive among typical rom-com lovers for its gross-out humor. And yet, the film’s hapless horniness makes director John Hamburg’s flick the perfect sex comedy. To reduce this complex and original romp to its most lowbrow moments (true, the basketball scene is horrifying) is to miss out on its oceans of brilliant writing, mid-aughts charm, and clever perspective on getting under someone to get over someone. Conversely, to appreciate it for what it is — an out-of-the-box romance that gave us Ben Stiller salsa dancing and Jennifer Aniston playing an even more hapless Rachel Greene-type, now with a newfound sense of cool — is to be truly happy. “Happy as a hippo.” —AF

“The 40-Year-Old Virgin” (2005)

Judd Apatow makes his directorial debut with Steve Carell as his titular “40-Year-Old Virgin” in this heavyweight rom-com. When timid but sweet tech salesman Andy (Carell) tells his co-workers (Paul Rudd, Romany Malco, Seth Rogen) that he’s never had sex, the moronic pack of misogynists embarks on a quest to get him laid as soon as possible. Leslie Mann and Elizabeth Banks are painfully funny standouts in a rotating cast of potential hookups for Andy (“Let’s get some fuckin’ French toast!”), but it’s Catherine Keener as the film’s main love interest, Trish, who really gives the movie its heart and makes this sexist hero’s journey into a melancholy look at being unlucky in love.

“The Office” fans will find particularly perverse joy in seeing the Michael Scott actor, and famed big sweetie, get put through the ringer of raunchy aughts comedies (the condom scene never gets less painful to watch!) and come out the other side as likable as ever. You know, even if Carell’s chest hair can’t have been the same after cinema’s most infamous practical waxing. —AF

“John Tucker Must Die” (2006)

A teen boy’s scheme to juggle three chicks comes to a screeching halt in the hilariously named “John Tucker Must Die”: the under appreciated aughts classic that made official the arrival of star Brittany Snow — and resulted in one of lesbian cinema’s all-time great teen kisses.

Jesse Metcalfe appears as the titular womanizer, John, opposite Arielle Kebbel as Carrie, an overly organized school newscaster; Sophia Bush as Beth, a tree-hugging student activist with a promiscuous streak; and singer-songwriter Ashanti as Heather, the intimidating head cheerleader. When new girl Kate (Snow) finds herself at the center of the group’s messy relationship drama, her mom’s complicated dating past compels her to go undercover and take John down. (Well, maybe more like, up? They did make him scale that building.) —AF

“Superbad” (2007)

A lunchbox of dick jokes wrapped in low-rise, period-stained jeans, “Superbad” may very well be one of the greatest friendship epics of the 21st century. Written by real-life buddies Seth Rogen and Evan Goldberg, who would further canonize their friendship in 2013’s “This Is the End,” this full-on capital “c” CLASSIC from 2007 charts the last high school days of two teen heroes terrified to grow apart. They’re also horny as hell and dead-set on getting laid before college. Enter a series of spectacularly unlucky women, two truly baffling police officers, and a career-creepiest Kevin Corrigan. 

Jonah Hill and Michael Cera star in their breakout roles, opposite a baby-faced Emma Stone, Bill Hader at his funniest, and countless other recognizable faces in the comedy scene to come. Christopher Mintz-Plasse steals the show as Fogel (aka “McLovin”): an endearing outcast who leverages a liquor story robbery into a single night of cool kid status and one of teen cinema’s most relatable character arcs. —AF

“Forgetting Sarah Marshall” (2008)

“Forgetting Sarah Marshall” doesn’t just have a stellar ensemble cast — Jason Segel, Kristen Bell, Mila Kunis, Paul Rudd, Jonah Hill, Russell Brand, and Bill Hader — but the comedy hits the perfect tone between WTF wallowing in heartbreak, sad-sack sickness, and elated new romance feels. The 2008 comedy stars Segel (who also wrote the screenplay) as Peter Bretter, a TV music supervisor who tries to do the impossible: get over his actress ex-girlfriend Sarah (Bell) by traveling to Hawaii. Turns out, Sarah is also staying at the same resort with her new rockstar love (Brand). Cue up a series of cringe run-ins as Peter attempts to forget Sarah at all costs and a concierge (Kunis) helps him get his groove back. “Forgetting Sarah Marshall” is undoubtedly a classic — what other film ends with a vampire puppet musical? — and a serious no-brainer for our best comedy list. —SB

Read IndieWire’s complete list of The Best Comedies of the 21st Century.

“Easy A” (2010)

The tale of a funny and kind teenager wrongly maligned as the school slut, “Easy A” could’ve been played straight. To quote Patricia Clarkson’s character, even “a little too straight… if you know what I mean, girlfriend.” But director Will Gluck’s endearing 2010 spin on “The Scarlet Letter” is packed with jokes and wastes no time denying the innate stardom of its supremely likable star, Emma Stone. 

Coming off brilliant comedic turns in “Superbad” and “The House Bunny,” the eventual Oscar winner luxuriates in every minute as Olive Penderghast: an instantly iconic avatar for seemingly ill-behaved women (the black corset and Ray-Ban look is legendary!) and one of the most richly imagined high school girls ever written.

When Olive foolishly lies about having lost her virginity, her best friend Rhiannon (a fabulously feisty Aly Michalka) and her nemesis Marianne (a ludicrously phenomenal Amanda Bynes) fuel a rumor that rapidly grows too big to extinguish. Penn Badgley also appears as Woodchuck Todd: the second most confusing hearthrob of his career, behind Joe Goldberg in “You.” And Stanley Tucci is just stupidly funny as Olive’s dad. (“Where are you from originally?”) —AF

“Friends with Benefits” (2011)

The “just sex” set-up pretty much never works out for couples in romantic comedies, but 2011 marked a particularly spicy year for so-called “casual” hookups on screen. Eventual real-life spouses Ashton Kutcher and Mila Kunis went head to head in the competing films “No Strings Attached” and “Friends with Benefits,” with Natalie Portman and Justin Timberlake as their respective co-leads.

Reader, the fight wasn’t even close. Yes, Ivan Reitman is one of the great directors. And sure, seeing 5′ 3″ Portman cuddling up to 6′ 2″ Kutcher in a button-up shirt was inarguably… cute. But Will Gluck’s bicoastal rom-com starring Kunis and Timberlake not only has a fuller story, sharper writing, and gay Woody Harrelson (“I ain’t taking no ferry…unless it’s out to dinner and a show!”), but it also boasts a sparky, gently teasing, cynical chemistry that makes even the tired New York-versus-Los Angeles debate feel fun. In this fizzy delight — also featuring Patricia Clarkson, Richard Jenkins, and Shaun White as himself in a bit part that has aged very poorly for the pro-athlete! — head hunter Jamie is tasked with finding a new ad man for GQ. Of corse, creative director Dylan is perfect for the job… wink! —AF

“Magic Mike XXL” (2015)

The first “Magic Mike” was plenty sexy, but not exactly a comedy. Steven Soderbergh’s male stripper film was a drama first and foremost about Channing Tatum’s title character’s broken dreams. The 2015 sequel, this time with Gregory Jacobs’ in the director’s chair, mostly abandons the sadness of the original in favor of sexier, wackier hijinks, as Mike and his stripper friends go on a road trip to a Myrtle Beach stripping convention. It’s bawdy, ridiculous, sexy, and a lot of fun. And it features one of the greatest film scenes of the 21st century, when Joe Manganiello’s Big Dick Richie does a legendary supermarket striptease to a disinterested cashier. —WC 

“Yes, God, Yes” (2019)

Set in the heyday of naughty AOL chatrooms, “Yes, God, Yes” stars Natalia Dyer as Alice: a curious high school junior whose burgeoning sexuality soon bumps against the strict abstinence-only stance of her Catholic community. Writer/director Karen Maine’s coming-of-age comedy merits inclusion here not because that many sexy things happen in it (seriously, these characters use the phrase “tossing salad” far too often to find them truly sexy), but because it brilliantly captures the zippy adolescent inquisitiveness that is first learning about intimacy. Dyer delivers a wide-eyed performance that’s not only profoundly endearing, but evokes the sort of radical sexiness you can only really experience when you’re profoundly sheltered. —AF

“Bottoms” (2023)

A watershed moment of representation for ugly, untalented gays, Emma Seligman’s “Bottoms” feels like a miracle in 2023: an honest to god mainstream teen sex comedy, centering on lesbians, with the boldness and confidence to make those lesbians terrible people. Ayo Edebiri and Rachel Sennott star as Josie and PJ, two unpopular high school seniors who desperately lust after unattainable cheerleader hotties Isabel (Havana Rose Liu) and Brittany (Kaia Gerber). After a misunderstanding causes the entire school to think the two spent the summer fighting other girls to the death in juvie, the pair parlay their sudden notoriety into starting a “female self-defense class” (glorified fight club) in the hopes of getting closer to the objects of their desire. 

The film’s wild premise fits perfectly in the almost surrealist teen comedy world it creates, where classes end after one minute and the rival football team literally attempts to murder the star quarterback, and Sennott and Edebiri’s incredible comedic chops ensures the joke-a-millisecond script is in good hands. It’s an incredibly queer take on sex comedies, but isn’t precious or cloying about representation — letting its leads fit comfortably in the dirtbag sex comedy protagonist hall of fame. —WC