10 Best R-Rated Comedies of The 2000s, Ranked

The biggest laughs in Hollywood often live behind an R-rating. Freed from the constraints of a family-friendly cut, filmmakers can chase the profane and the gloriously uncomfortable. And no decade did it better than the 2000s, which produced some of the best R-rated comedies.

This was the era when Judd Apatow built an empire of lovable slackers, when Sacha Baron Cohen brought his satirical character to the big screen, and when a bachelor party in Vegas became a cultural event. Here are the ten films that defined the golden run of raunchy comedies, ranked based on how hilarious they were.

10 Wet Hot American Summer Defined the Cult Camp Comedy

David Wain’s summer-camp comedy was a critical and commercial failure upon release. But it is one of those movies that has gained much appreciation in retrospect. The movie is now regarded as one of the most influential comedies of its generation and even spawned a beloved Netflix franchise. The movie produced many actors, who later went on to become major movie stars, including Amy Poehler, Bradley Cooper, Elizabeth Banks, and Paul Rudd.

Set on the last day of camp in 1981, it is an absurd take on the era’s teen s*x romps. The premise was years ahead of its time. With its gleefully random humor, total commitment to the absurdity, and enormous influence, it earns a deserved spot in this list of the best 2000s R-rated comedies.

9 The 40-Year-Old Virgin Launched the Modern Apatow Era

Judd Apatow is one of the first names that comes to mind when talking about the raunchy comedies of the 2000s. And Steve Carell’s The 40-Year-Old Virgin, helmed by Apatow, is the movie that established the filmmaker’s reputation. The premise could have easily been a one-note joke, but the movie handles it with surprisingly tender care.

The story follows a middle-aged sweet man who undertakes some improvised riffs as per his co-workers’ advice to lose his virginity. His actions include the now-legendary chest-waxing scene. Carell plays the lead, with supporting performances from Seth Rogen, Paul Rudd, and Romany Malco. Nearly two decades later, it remains the blueprint of raunch plus relatability in Hollywood, and hence we are putting it at the ninth spot on this list.

8 Knocked Up Is a Slacker Romcom At Its Best

Katherine Heigl starred as Los Angeles reporter Alison Scott opposite Seth Rogen in Judd Apatow’s Knocked Up. The movie follows the story of how a one-night stand between an ambitious reporter and a slacker results in an unintended pregnancy. This brings both belly laughs and genuine emotional stakes, with some R-rated scenes incorporated into the movie.

Rogen recently revealed that Anne Hathaway passed on the lead role, and Heigl’s issue with the movie is publicly known. However, the film’s willingness to let characters be flawed, immature, and still worthy of growth became the Apatow signature. It’s crude when it wants to be, but never at the expense of its emotions.

7 Forgetting Sarah Marshall Introduced Us to Breakup Comedy

Jason Segel not only starred in this late-2000s comedy, but he also wrote the movie’s script. He played a heartbroken TV composer, Peter Bretter, who escapes to Hawaii after being dumped by his actress girlfriend, played by Kristen Bell. However, his woes follow him to the resort when she shows up there with her current boyfriend.

The outrageous humor, combined with Peter’s emotional vulnerability, made the movie one of the standouts among Apatow’s outings. The movie also nailed its casting. Kristen Bell’s titular Sarah Marshall was not portrayed as an outright villain, but rather as a sympathetic character.

6 The Royal Tenenbaums Made Misery Look Impossibly Stylish

The Royal Tenenbaums is the proud outlier in this list. Gene Hackman, Anjelica Huston, Ben Stiller, Gwyneth Paltrow, and Bill Murray form one of the great ensemble casts ever assembled. Wes Anderson‘s melancholy comedy earns its R-rating through raw emotional themes, like addiction, infidelity, and a genuinely shocking suicide attempt.

It is as heartbreaking as it is funny. It is proof that R-rated movies can mean something richer than shock value. It ranks sixth because its sophistication is a different flavor entirely. But it lacks the raunchiness of the other movies above it on this list.

5 Borat Pushed Shock Comedy to New Extremes

Sacha Baron Cohen’s 2006 mockumentary-style black comedy movie was a controversial one for many reasons. The protagonist makes some very offensive actions and comments throughout Borat, which some viewers found indigestible. However, many recognized Cohen’s real intention behind the character. It was a satirical tool to expose the prejudices in American society.

Those who saw this correct interpretation praised it as a genre-defining movie. It is considered to be one of the greatest comedy movies of the 21st century. Cohen’s performance as the cringe-inducing protagonist was definitely the highlight of the movie. What made it funnier was that the real-life Americans featured in the movie did not see the actor behind the character and were just outraged by him.

4 Tropic Thunder Is the Gold Standard for Spoof Comedy

Tropic Thunder was a star-studded spoof comedy that roasted the entire film industry with its over-the-top filmmaking premise. Ben Stiller brought together a pack of Hollywood A-listers, most notably Robert Downey Jr. and Tom Cruise. The former earned an Oscar nomination for his role in the movie.

Fans loved everything about this satire, from the funny characters to all the faux promotional materials of the movie. It is considered one of the sharpest showbiz takedowns. Following a group of pampered actors who mistake a real jungle war for their own film shoot, it thrives on its absurdity and vanity. It is wickedly smart and wildly entertaining.

3 Zombieland Reinvented the Zombie Horror Genre

Zombieland injected fresh blood into two tired genres at once. Its rules-based approach to surviving the zombie apocalypse gave the horror-comedy a slick video-game energy, while its odd-couple road trip supplied the heart. Jesse Eisenberg and Woody Harrelson made a perfect mismatched pair.

The movie brings in a jaw-dropping Bill Murray cameo on top of its incredible cast, which also includes Emma Stone. It’s gory yet charming, bloody yet endlessly quotable. For reinventing a formula and then making it look effortlessly cool, the movie earns third place in this best 2000s R-rated comedies list.

2 Superbad Became an Instant Cultural Phenomenon

This coming-of-age comedy still rules as one of the best comedy films of the 2000s. In Superbad, three teenagers, played by Jonah Hill, Michael Cera, and Christopher Mintz-Plasse, make plans to party and lose their virginity before their high school graduation. Writers Seth Rogen and Evan Goldberg based the characters of Hill and Cera on themselves during their senior year.

The film received positive reviews, with particular praise for the performances and Rogen and Goldberg’s writing. It’s the definitive teen comedy of its generation. Superbad ranks second because it’s not just hilarious. It became the language of modern coming-of-age comedies. While a sequel idea was floated, Rogen didn’t even want to ruin such a great movie with a bad sequel (via LADbible).

1 The Hangover Became the Blackout That Defined a Decade

No comedy defined the decade, or changed the genre’s fortunes, quite like The Hangover. Todd Phillips’ Vegas nightmare, in which three groomsmen retrace a blackout to find their missing groom, turned a simple mystery structure into comedy gold and became the highest-grossing R-rated comedy at the time.

Bradley Cooper maintained his leading-man swagger, while Zach Galifianakis and Ed Helms stole the comedic scenes. Its escalating chaos formula was later adopted by many comedy movies. It is endlessly rewatchable, and its influence is immeasurable.

Which of these movies will you pick up for a rewatch? Do you have any picks from here that you are excited to watch for the first time? Let us know in the comments below!