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The 20 Best R-Rated Comedies of the Last 20 Years

What's the funniest, raunchiest comedy of the last 20 years? We've got some ideas.

Wet Hot American Summer


A number of the biggest comedies from recent years have been pieced together, at least in part, from some of the best improv performances in the business. But David Wain’s cult hit is the closest any movie has come to capturing the rapturous feel of a live improv show in scripted form. Janeane Garofalo frantically yelling while she and Joe Lo Truglio systematically destroy a hotel room, a motivational speech from a can of vegetables and a Kenny Loggins singalong gone awry all feel like the kind of moments that come from bizarre, on-stage inspiration. “Wanderlust,” “They Came Together” and the vastly underrated “The Ten” all have these components in flashes, but “Wet Hot” will always be the purest, most consistent effort from this team. Despite the summer camp wackiness, the complete level of commitment to the simplest of jokes (this will always be Christopher Meloni’s career-defining work) makes this an expertly tuned treasure that’s as watchable as it is quotable. — SG

Kiss Kiss Bang Bang


Shane Black’s wonderfully self-reflexive black comedy gleefully blends genres — part hardboiled detective story, part love story, all hilarious — to deliver perhaps the most pure vision of what the filmmaker can do. Starring Robert Downey Jr. and Val Kilmer as a delightfully mismatched set of seekers attempting to unravel a good, old-fashioned Hollywood murder mystery, the film skewers expectations at every turn. Michelle Monaghan joins the fun as Downey’s longtime love interest, contributing both femme fatale allure and “girl next door” charm in equal measure. The film doesn’t balk at the kind of stuff that earned it an R — dead bodies, gruesome accidents, foul-mouthed bad guys and good guys — but what sets it a cut above the rest is the way it manages to blend that sort of stuff with a genuinely smart take on the world around its characters, heightened and wacky as it may be. — Kate Erbland

The 40-Year Old Virgin


If any one film defined the R-rated modern comedy, it’s Judd Apatow’s debut feature film, “The 40-Year-Old Virgin.” The best of Apatow’s directorial efforts and arguably the most complete work of his producing and writing careers, the raunchy, star-studded adventure in sexual education, experimentation and maturity has held up over the past decade because of its core values. Andy, Steve Carell’s pure-hearted romantic, keeps the narrative focused on making love instead of having sex, while his cobbled-together crowd of co-workers push the boundaries of sexuality on their own. When you bring all the elements together, you’ve got a comedy that will be as jocular as it is insightful for at least the next 40 years. — BT

Hot Fuzz


For the second Edgar Wright and Simon Pegg film in their comedic Three Flavours Cornetto trilogy, they spoof the buddy cop genre brilliantly. All of the hallmarks — the too-serious detective, the “Odd Couple” chemistry, chase scenes, colorful perps — have the piss taken out of them in the most impish, brilliant way, and there’s actually quite a bit of legitimate action as well. A series of killings makes up the central mystery, which isn’t quite as compelling as it is an opportunity for some over-the-top gore and explicit homages to its action movie predecessors, satisfying “Shaun of the Dead” fans and Wright/Pegg newcomers alike. — HN

Step Brothers


The “Citizen Kane” of movies, “Step Brothers” is the best thing that Will Ferrell has ever made — in fact, it might be the best thing that anyone has ever made. The story of two overgrown man-children who become the fiercest of enemies (and then the closest friends) after their parents get married, the endlessly quotable 2008 comedy takes the tropes of a Judd Apatow movie and drives them towards uncharted realms of magical idiocy. The cast is brilliant from top to bottom (Adam Scott is a legendary asshole), the chemistry between Ferrell and John C. Reilly puts anything Marie Curie ever did to shame, and the movie is so funny that its deleted scenes tower over almost everything else from the last 20 years. Dale Doback declared that he and Brennan were “Here to fuck shit up!,” and they were. They really were. — DE

Up next: Pitch-perfect parodies and more contemplative comedy

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