15 Funniest R-Rated Comedies Of All Time

Summary

• R-rated comedies push boundaries with raunchy humor & compelling narratives that stand the test of time.
• Iconic directors like Mel Brooks & Judd Apatow revolutionized the genre with their unique humor.
• Movies like American Pie, There’s Something About Mary, & Superbad are among the best R-rated comedies ever made.

With the freedom to depict sex and violence and little restriction on using vulgar language, R-rated comedies push the boundaries of audience expectations to produce some of the funniest movies ever made. While this often leads to crude and vulgar humor, that’s not to say that all R-rated comedies were shocking for the sake of it, and plenty were also categorized by sincerity and vulnerability as they told compelling narratives that have stood the test of time. From satirical classics of decades past to recent laugh-out-loud misadventures, R-rated comedies have left their mark on the cinematic landscape.

Some of the funniest movies ever made were rated R, and they used this freedom to go the extra mile and not hold back on the raunchy humor. While iconic directors like Mel Brooks were responsible for some of the best R-rated comedies, filmmakers like Judd Apatow revolutionized the genre with their own brand of humor for the 21st century. While there have been plenty of hilarious R-rated movies across different genres, such as the record-breaking box office takings of superhero films like Deadpool, true out-and-out R-rated comedies have carved out an important legacy for themselves and deserve recognition.

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15 There’s Something About Mary (1998)

Directed by Peter Farrelly and Bobby Farrelly

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There’s Something About Mary is a 1998 romantic comedy directed by Peter and Bobby Farrelly. The film stars Cameron Diaz as Mary, the object of affection for multiple men, including Ben Stiller’s character Ted. The story blends humor and romance as Ted attempts to reconnect with his high school crush, leading to a series of outlandish and comedic events. Matt Dillon also stars as a private investigator entangled in the pursuit.

Director Peter Farrelly , Bobby Farrelly Release Date July 15, 1998 Distributor(s) 20th Century Fox Writers Ed Decter , John J. Strauss , Peter Farrelly , Bobby Farrelly Cast Cameron Diaz , Matt Dillon , Ben Stiller , Lee Evans , Chris Elliott Runtime 119 Minutes Budget $23 Million Main Genre Comedy Expand

The Farrelly brothers had viewers laughing hysterically with their PG-13 directional debut, Dumb and Dumber, but it was with There’s Something About Mary where they proved their talents for an R-rated audience. This excellent raunchy comedy saw Ben Stiller, Matt Dillon, Lee Evans, and Chris Elliott all vying for the attention of the beautiful Mary, played by Cameron Diaz. While it doesn’t quite reach the comedic heights of the absolute best R-rated movies, the infamous hair gel scene alone earned There’s Something About Mary a spot here.

14 American Pie (1999)

Directed by Paul Weitz

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American Pie is a raucous teen comedy and the film that launched a revival of the genre. It follows a group of high school friends determined to lose their virginity before graduation and delves into the misadventures of the four boys as they navigate the complexities of relationships, peer pressure, and parental mishaps. You’ll never look at warm apple pie the same again.

Director Paul Weitz , Chris Weitz Release Date July 9, 1999 Writers Adam Herz Cast Jason Biggs , Chris Klein , Thomas Ian Nicholas , Alyson Hannigan , Shannon Elizabeth , Tara Reid Runtime 95 minutes Budget $11 million Main Genre Comedy Expand

A quarter of a century since its release, it’s easier to underestimate just how important American Pie was to the teen sex comedy genre. Packed with classic moments and iconic characters like Jason Bigg’s naive Jim or Seann William Scott as the notorious Stifler, American Pie captured the awkwardness of sexuality mortification and laid the groundwork for later Judd Apatow movies that managed to walk the fine line between sensitivity and obscenity. While not everything about the first installment of this long-running series has held up, American Pie is still hilarious all these years later.

13 21 Jump Street (2012)

Directed by Phil Lord and Christopher Miller

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An adaptation of the TV series of the same name, 21 Jump Street stars Channing Tatum and Jonah Hill as two police officers (and best friends) who are sent into a high school undercover in order to bust a drug ring. Learning that high school has changed considerably since they were teenagers, the pair are forced to adapt in order to maintain their cover, threatening their friendship in the process.

Director Phil Lord , Christopher Miller Release Date March 14, 2012 Writers Michael Bacall Cast Jonah Hill , Channing Tatum , Brie Larson , Dave Franco , Rob Riggle , DeRay Davis Runtime 109 minutes Franchise(s) 21 Jump Street Sequel(s) 22 Jump Street Budget $42 million Expand

Phil Lord and Christopher Miller jumped straight from kids’ animation with Cloudy with a Chance of Meatballs headfirst into the world of R-rated comedies with the excellent 21 Jump Street. As an adaptation of a 1980s police procedural series, 21 Jump Street could have fallen flat on its feet if not for the excellent chemistry between Jonah Hill and Channing Tatum, who played cops going undercover at a high school to absolute perfection. Both nostalgic and a satirical send-up of teen movie tropes, everything about 21 Jump Street just worked.

12 Clerks (1994)

Directed by Kevin Smith

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Kevin Smith’s Clerks is a comedy film that follows Dante Hicks and Randal Graves, two best friends who work at a conjoined storefront of a convenience store and a video rental store. Presented entirely in black and white, the film goes through a day in the life of the two characters as they deal with the mundane, the weird, and the flat-out nonsensical as Dante continues to lament his current state in life, providing sharp satire on various discussed topics.

Director Kevin Smith Release Date September 13, 1994 Studio(s) Lionsgate Distributor(s) Lionsgate Writers Kevin Smith Cast Brian O’Halloran , Jeff Anderson , Marilyn Ghigliotti , Lisa Spoonauer , Jason Mewes , Kevin Smith Runtime 92 minutes Sequel(s) Clerks 2 , Clerks 3 Budget $27 thousand Expand

Kevin Smith proved filmmakers didn’t need big budgets to have a serious influence on the movie industry, as his debut, Clerks, was shot for just $27,575 after maxing out ten credit cards (via Viewaskew.) Luckily, this gamble paid off as Clerks hilariously showcased a day in the life of New Jersey convenience store employees and all the wild customers they interacted with, including the debut of the dynamic duo Jay and Silent Bob. With snappy dialogue, memorable characters, and an everyday sense of realism, this black-and-white comedy had a serious effect on indie filmmaking for decades to come.

11 Forgetting Sarah Marshall (2008)

Directed by Nicholas Stoller

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Forgetting Sarah Marshall follows Peter Bretter, a musician who, following a bad breakup with his girlfriend, Sarah Marshall, goes on a vacation to a Hawaiian resort only to discover that Sarah is also at the resort with her new boyfriend. Jason Segel stars as Peter, alongside Kristen Bell, Mila Kunis, and Russell Brand. 

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Director Nicholas Stoller Release Date April 18, 2008 Studio(s) Universal Pictures Distributor(s) Universal Pictures Writers Jason Segel Cast Jason Segel , Kristen Bell , Russell Brand , Bill Hader , Jonah Hill , Mila Kunis Runtime 111 minutes Budget $30 million Expand

One unconventional rom-com that shook up the genre was Forgetting Sarah Marshall, a film that shifted its focus to heartbreak as Jason Segal dealt with a devastating breakup. After being dumped by Kristen Bell, as the titular Sarah Marshall, Segal traveled to Hawaii to mend his broken heart, only to stay at the same resort as his ex and her new rockstar boyfriend, who was played by Russell Brand. With the perfect blend of heartfelt vulnerability and raunchy humor, Forgetting Sarah Marshall was a clever, sweet, and laugh-out-loud look at heartache, recovery, and self-discovery.

10 Blazing Saddles (1974)

Directed by Mel Brooks

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Written and directed by Mel Brooks, Blazing Saddles stars Cleavon Little as Bart, a black sheriff appointed in a small frontier town by Hedley Lamarr, a railroad man who believes Bart’s appointment will destabilize the town enough to drive everyone out and allow him to build a new railroad line through it. Instead, with the help of gunslinger Jim the Waco Kid, Bart works to thwart Lamarr’s schemes. Gene Wilder and Harvey Korman star alongside Little.  

Director Mel Brooks Release Date February 7, 1974 Studio(s) Warner Bros. Pictures Distributor(s) Warner Bros. Pictures Writers Mel Brooks , Norman Steinberg , Andrew Bergman , Richard Pryor , Alan Uger Cast Cleavon Little , gene wilder , Slim Pickens , Harvey Korman , Madeline Kahn , Mel Brooks Runtime 93 minutes Budget $2.6 million Expand

Blazing Saddles was one of the most important comedy movies of the 1970s, as it blended post-modern humor and satirical comedy with a production that broke down racial boundaries. As a true cult classic, Blazing Saddles defied the expectations of contemporary cinema and took influence from Broadway musicals to network television sketch comedy. As a true high point in the career of Mel Brooks, Blazing Saddles was a Western spoof that went the extra mile into social commentary, with the jokes coming a mile a minute for the entire runtime.

9 Planes, Trains, and Automobiles (1987)

Directed by John Hughes

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Directed by John Hughes, Planes, Trains and Automobiles stars Steve Martin as Neal Page, a busy advertising executive who finds himself the unwilling traveling companion of salesman Del Griffith as the two attempt to return to Chicago for the Thanksgiving holiday. Beset by bad weather and a continuing comedy of errors in attempting to make travel plans, Neal and Del must work together, however unwillingly, to accomplish their shared goal. John Candy also stars alongside Martin as Del. 

Director John Hughes Release Date November 25, 1987 Studio(s) Paramount Pictures Distributor(s) Paramount Pictures Writers John Hughes Cast John Candy , Steve Martin , Kevin Bacon Runtime 93minutes Budget $15million Expand

Steve Martin and John Candy made the perfect mismatched comedic couple in John Hughes’ beloved road trip comedy Planes, Trains, and Automobiles. As the story of two men forced to work together to make it from New York to Chicago in time for Thanksgiving, this R-rated odyssey was a change of pace for Hughes, previously known for teen movies like The Breakfast Club. Planes, Trains, and Automobiles was the perfect vehicle, pun intended, for its two stars as Martin’s frustration at the endless but unintentional annoyances of Candy’s character was true comedic gold.

8 I Love You, Man (2009)

Directed by John Hamburg

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I Love You, Man is a 2009 comedy film directed by John Hamburg, starring Paul Rudd as Peter Klaven, a real estate agent who discovers he has no male friends to be his best man at his upcoming wedding. He embarks on a series of awkward “man-dates” to find a suitable candidate and eventually forms a close bond with Sydney Fife, played by Jason Segel, leading to a comedic exploration of male friendship.

Director John Hamburg Release Date March 20, 2009 Writers John Hamburg , Larry Levin Cast Paul Rudd , Rashida Jones , Sarah Burns , Greg Levine , Jaime Pressly , Jon Favreau Runtime 105 Minutes Main Genre Comedy Expand

I Love You, Man was the quintessential bromance movie as Paul Rudd and Jason Segal gave hilarious and heartfelt performances as a friendless real estate agent forging a friendship with an idiosyncratic oddity. The two newfound best friends bonded over their mutual love of the band Rush, and Rudd’s character appeared to have finally found someone to be the best man at his upcoming wedding. Like the best R-comedies, I Love, Man was raunchy and over-the-top, but it was also categorized by real vulnerability as it highlighted the difficulties and excitement of making a new friend well into adulthood.

7 Step Brothers (2008)

Directed by Adam McKay

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Adam McKay, Will Ferrell, and John C. Reilly joined forces in 2008 to create this now iconic Comedy. The film sees two grown men that still live at home with their parents, forced to adapt to living with one another when their parents get married.

Director Adam McKay Release Date July 25, 2008 Studio(s) Sony , Columbia Pictures Distributor(s) Sony , Columbia Pictures Writers Adam McKay Cast Adam McKay , Will Ferrell , John C. Reilly , Adam Scott , Richard Jenkins Runtime 98minutes Budget $65 million Expand

At first glance, Step Brothers seemed like it could devolve into pure ridiculousness as it told the story of two middle-aged losers acting like embittered teenagers when forced to live together. Yet through the performances of Will Ferrell and John C. Reily, the absurdity of Step Brothers became part of its charm as its relentless immaturity and crude humor just worked. While Adam McKay may have since made a name for himself with clever satirical releases like The Big Short, his earlier movies like Step Brothers, Anchorman, and Talladega Nights were among the best comedies of the 2000s.

6 Bridesmaids (2011)

Directed by Paul Feig

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Bridesmaids follows Annie (Kristen Wiig), a perpetual underachiever in her thirties who is asked to serve as maid of honor for her friend Lillian’s (Maya Rudolph) wedding. After a string of misfortunes leaves Annie feeling inferior to bridesmaid Helen, she begins questioning her life and her friendship with Lillian. Rose Byrne, Melissa McCarthy, Wendi McLendon-Covey, Ellie Kemper, and Chris O’Dowd also star.

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Director Paul Feig Release Date May 13, 2011 Studio(s) Apatow Productions , Relativity Media Distributor(s) Universal Pictures Writers Kristen Wiig , Annie Mumolo Cast Kristen Wiig , Rose Byrne , Maya Rudolph , Melissa McCarthy , Ellie Kemper , Wendi McLendon-Covey Runtime 125 minutes Budget $32.5 million Main Genre Comedy Expand

The sorrowful few who wrongfully claim that women can’t do comedy only need to watch Bridesmaids to witness their thesis be obliterated in real time. As one of the funniest comedies of the 21st century, Bridesmaids combined compelling characters with R-rated humor to produce a comedy that connected with male and female viewers alike. With Kirsten Wiig as a hapless woman acting as her best friend’s maid of honor, Bridesmaids took the wedding-centric comedy of movies like Wedding Crashers and gave it an R-rated female-centric spin.

5 The Blues Brothers (1980)

Directed by John Landis

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After being released from prison, Jake Blues (John Belushi) reunites with his brother Elwood (Dan Aykroyd) to save a catholic home where they were raised together. To raise money, they put bring their old band back together and put on a show as “The Blues Brothers.” Set in Chicago and based on Saturday Night Live characters, The Blues Brothers features several musical celebrity cameos such as Ray Charles, Cab Calloway, Aretha Franklin, and James Brown.

Director John Landis Release Date June 20, 1980 Studio(s) Universal Pictures Distributor(s) Universal Pictures Writers Dan Aykroyd , John Landis Cast John Belushi , ray charles , Cab Calloway , James Brown , Dan Aykroyd , Aretha Franklin Runtime 133 minutes Sequel(s) blues brothers Budget $27 million Expand

The Blues Brothers was the perfect blend of action, musical excitement, and R-rated comedy as John Belushi and Dan Aykroyd went on a “mission from God” to save the orphanage they grew up in. Based on characters first seen on Saturday Night Live, the titular brothers were joined by blues and soul legends like James Brown, Aretha Franklin, and Ray Charles for a film that had it all. This was a tale of redemption for the sunglass-and-suit-wearing Elwood brothers, as The Blues Brothers quickly became an all-time classic due to its over-the-top energy, incredible musical numbers, and unique comedic sensibilities.

4 Tropic Thunder (2008)

Directed by Ben Stiller

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Written and directed by Ben Stiller, Tropic Thunder follows a group of bumbling actors attempting to make a Vietnam War film, who find themselves dropped into a real-life warzone when they are abandoned in the middle of the jungle they are shooting the film in. Stiller also stars in the film, with an ensemble cast that includes Jack Black, Robert Downey Jr., and Jay Baruchel. 

Director Ben Stiller Release Date August 13, 2008 Studio(s) DreamWorks Distribution Distributor(s) DreamWorks Distribution , Paramount Pictures Writers Justin Theroux , Etan Cohen , Ben Stiller Cast Ben Stiller , Robert Downey Jr. , Matthew McConaughey , Tom Cruise , Jack Black Runtime 107 minutes Budget $92 million Expand

The satirical R-rated action comedy Tropic Thunder was an excellent send-up that tackled everything from actors’ inflated sense of importance, the money-hungry reputation of studio executives, and Hollywood’s obsession with the glorification of war. Everything about Tropic Thunder just worked, but Robert Downey Jr. especially deserved praise for his characterization of Kirk Lazarus, the five-time Oscar winner, using blackface to portray his character in a fictional Vietnam War movie-within-a-movie. Ironically, Downey himself was nominated for an Academy Award for his performance, which hilariously held a mirror up to the ridiculous extremities of some method actors.

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Robert Downey Jr.’s blackface in Tropic Thunder should have sparked controversy, but it didn’t – here’s how RDJ used blackface for social commentary.

3 The Big Lebowski (1998)

Directed by Joel and Ethan Coen

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One of Joel and Ethan Coen’s most successful crime comedies, The Big Lebowski follows Jeffrey “The Dude” Lebowski (Jeff Bridges) after he is assaulted in a case of mistaken identity. After becoming tangled with the millionaire who shares his name, the Dude is tasked with delivering a ransom in order to save Lebowski’s wife from a group of hardened criminals. The Dude is joined by his bowling buddies Walter (John Goodman) and Donny (Steve Buscemi), who complicate Lebowski’s plans.

Director Joel Coen , Ethan Coen Release Date March 6, 1998 Studio(s) Working Title Films Distributor(s) Gramercy Pictures Writers Ethan Coen , Joel Coen Cast Julianne Moore , Jeff Bridges , Steve Buscemi , John Turturro , John Goodman , David Huddleston , Phillip Seymour Hoffman Runtime 117 Minutes Budget $15 Million Expand

The Coen Brothers hit on something special with The Big Lebowski, as all the stars aligned to make it one of their greatest achievements. From Jeff Bridges’ career-best performance, incredible script, and a unique world populated by eccentric characters, this neo-noir comedic story was loosely inspired by the hardboiled detective fiction of Raymond Chandler to tell an outrageous mystery that slowly unraveled. The Big Lebowski was clever, engrossing, and, most importantly, hilarious, as it stood among the best comedies of the 1990s.

2 The Hangover (2009)

Directed by Todd Phillips

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The Hangover follows a group of friends who head to Las Vegas for a bachelor party. With Doug (Justin Bartha) preparing for his wedding, his friends Phil, (Bradley Cooper), Stu (Ed Helms), and Alan (Zach Galifianakis) take him on a night he’ll never forget, After blacking out, the group – who call themselves the “Wolf Pack” – realize that they’ve lost Doug, and must retrace the steps of the most outrageous night of their lives in order to find him.

Director Todd Phillips Release Date June 5, 2009 Studio(s) Warner Bros. Pictures , Legendary Pictures , Green Hat Films , BenderSpink Distributor(s) Warner Bros. Pictures Writers Scott Moore , Jon Lucas Cast Ed Helms , Heather Graham , Justin Bartha , Zach Galifianakis , Bradley Cooper , Jeffrey Tambor Runtime 100 minutes Franchise(s) The Hangover Sequel(s) The Hangover Part II , The Hangover Part III Budget $35 million Expand

The Hangover had all the makings of a perfect R-rated comedy as the absurdity of the Wolf Pack’s forgotten night of misadventure was revealed with increased intensity and ridiculousness throughout. As a group awoke the night after a bachelor party with no memory of what came before, they were inexplicitly confronted with a Bengal tiger in their hotel room, a mattress impaled on a statue outside, and a wayward baby in the closet. The Hangover was truly hilarious, and although its legacy was somewhat tarnished by two lackluster sequels, when viewed on its merits alone, it’s a true comedy classic.

1 Superbad (2007)

Directed by Greg Mottola

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Written by Seth Rogen and Evan Goldberg and produced by Judd Apatow, Superbad follows high school seniors Seth (Jonah Hill) and Evan (Michael Cera), two best friends who are desperate to join the popular kids’ party before heading off to college. After asking their friend Fogell (Christopher Mintz-Plasse) – A.K.A. McLovin – to use his fake ID to purchase alcohol, Seth and Evan end up getting drawn into a night of criminal misfortunes that threatens the very fabric of their friendship.

Director Greg Mottola Release Date August 17, 2007 Studio(s) Sony Distributor(s) Sony Writers Seth Rogen , Evan Goldberg Cast Seth Rogen , Bill Hader , Jonah Hill , Christopher Mintz-Plasse , Michael Cera , Emma Stone Runtime 113 minutes Budget $20 million Expand

The coming-of-age teen comedy Superbad cemented Judd Apatow as the most important comedy producer of the 21st century and was a defining moment in the careers of co-writer Seth Rogen and its stars Michael Cera, Jonah Hill, and Emma Stone. Superbad pushed the boundaries of what could be depicted in an R-rated comedy but also maintained a level of sincere vulnerability that blanched its crudeness with charm. As an authentic take on friendship and awkwardness of high school, Superbad was not only the best R-rated comedy but also among the greatest high school movies ever made.

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