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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.

Let’s acknowledge it up front: Rating films for their content is a dubious process at best and a dangerous one at worst. Trying to place disparate, diverse films into a handful of age-based categories has rarely come without controversy, especially when the MPAA ratings board deems a hint of language and nudity untenable while excusing wide swaths of violence for lower classifications. Yet, there’s a way that a “R” rating has become shorthand for a specific type of comedy. Geared toward older viewers (or those on the precipice of adulthood), these are the laugh-based moviegoing experiences so confident in their own ability to attract an audience that they’re willing to accept what some might see as a theatrical release stigma.

These are films that luxuriate in moving swiftly past their allotment of one, non-sexual use of everyone’s favorite four-letter “f word,” further flaunting their disregard for the ratings powers-that-be by giving their villains a last name like “Dieter von Cunth.” But most importantly, they are testaments to the idea that comedies can be commercial and artistic successes, even without being sanitized to fit under a more box-office-friendly designation.

Not all of them are filled with wall-to-wall laughter (not every modern classic has a Catalina Wine Mixer). But they all manage to encompass the ways we turn to comedy as a soothing antidote in times of need. These are laughs tinged with sadness, nostalgia, loss….but also a few poop jokes, winking industry references and funny people swearing along the way. So below, in chronological order, here are some of the best comedies to hit theaters with a “R” rating since IndieWire’s been around.

Shakespeare in Love

 

Are you ready for some real talk? “Shakespeare in Love” deserved to win Best Picture in 1998. Which isn’t necessarily to say that it’s a better film than “Saving Private Ryan,” or that it had even a fraction of the same influence on the cinematic landscape, but rather to convey a truth that’s easily lost in the awards season hubbub: John Madden’s sumptuous comic riff on the greatest romance ever told is a masterpiece, one that resonates with — and slyly undercuts — the immortal story that inspired it. But it’s not on this list because it’s great, it makes the cut because it’s bawdy as hell, earning that R rating by embracing all the lewd and lusty business that the Bard’s audience would have expected in his own time. In the words of Ned Alleyn: “Pay attention and you will see how genius creates a legend.”  — David Ehrlich

Rushmore

 

One of the most deadpan movies ever made, “Rushmore” barely qualifies as an R-rated film (it earned the rating for profanity and brief nudity), but a more PG-13-friendly cut would neuter one of the greatest high school movies ever made. The film that established Wes Anderson as a filmmaker to whom attention must be paid, aided and abetted by Owen Wilson as co-writer, was packed with hilarious theatrical recreations of classic films and some of Bill Murray’s best work ever. It’s a film that screams “unique voice,” even as it drops a few F-bombs. — Liz Shannon Miller

The Big Lebowski

 

Filled with heavy drug use, coarse language, sexual innuendos and nudity, “The Big Lebowski” certainly earns its R-rating. But there’s an innocence about the Coen brothers’ cult favorite comedy — embodied by its lead character’s attitude and his ultimate quest — that makes the film feel unique to other “adult” genre entries of the last 20 years. The Dude just wants to replace his rug. It’s not his fault that his name coincidentally links him to a wild cast of characters explicitly connected to kidnapping, murder and other ugly activities. His life would be a simple one if he had his way, making his easy-going attitude the perfect foil to the film surrounding him. — Ben Travers

But I’m a Cheerleader

 

From its high-flying opening credits, there’s an unmistakable energy to Jamie Babbit’s feature debut. A late-90s Sundance favorite, “But I’m a Cheerleader” gave pivotal roles to a group of women (Natasha Lyonne, Clea DuVall, Melanie Lynskey, Michelle Williams) that still populate the indie film scene (keep an eye out for the unofficial cast reunion in DuVall’s hilarious “The Intervention”). That this was originally rated NC-17 is one of the MPAA’s most egregious decisions. It’s a romantic comedy/summer camp romp wrapped up in a 90-minute takedown of gender stereotypes and traditional conceptions of teen sexuality. Amidst the heavy pastels and identity-ignorant parents, there’s a sweet, tender high-school love story at its core, paced blissfully through its five chapters. Legions of millennials know the script of “Mean Girls” as if it were scripture — it’s hard not to imagine this as a spiritual ancestor. — Steve Greene

Office Space

 

At the time, it didn’t seem entirely logical for Mike Judge to make the leap into live action after being primarily known for “Beavis and Butt-Head.” But his “Milton” cartoon shorts, about a morose pencil-pusher working in his office’s basement, inspired the ultimate white-collar comedy. “Office Space” is the backhanded love letter to all the frustrations and hypocrisies of workplace culture — from do-nothing management failing upward to the absurdity of memos and “flair.” It’s a rallying cry for anyone who’s mad as hell and so entirely quotable that it instantly became a cult classic despite its meager box office. The entire cast is note-perfect in how game they are, bringing to life such uninspiring schmoes (Gary Cole and John C. McGinley, in particular, are entertaining blowhards). “Office Space” is elegant in its social commentary, making Judge akin to a Jane Austen of the tech world, and is clearly the ancestor of his (now Emmy-nominated) series “Silicon Valley.” — Hanh Nguyen

Up next: Carell, Cornettos and a can of vegetables

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