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The Greatest R-Rated Comedies of the 2000s – TheFantasyTimes

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By Jitin Gambhir

The Greatest R-Rated Comedies of the 2000s



Comedy films are designed to elicit laughter from the audience, and sometimes that involves pushing the boundaries. In the 2000s, the comedy scene was all about testing limits, resulting in several movies earning R-ratings. Typically, rated-R films feature crude humor, graphic violence, strong language, or a combination of all three. However, when done correctly, these films can be outrageously funny without being entirely offensive or disgusting.

Looking at comedy movies from the 2000s, some actors stand out as mainstays, including Vince Vaughn, Jonah Hill, and Paul Rudd. These actors seemed to have mastered the formula, making viewers laugh hysterically while still maintaining a strong focus on character development, plot, and narrative structure. These films took full advantage of their R-rating, delivering big laughs and putting smiles on viewers’ faces.

Here are some of the top R-rated comedies from the 2000s:

10. Superbad (2007)

The funniest movie of 2007 was undoubtedly Superbad. The film follows two high school kids, Seth (Jonah Hill) and Evan (Michael Cera), who are determined to party and score with girls. They plan to supply alcohol for a massive party but quickly realize they cannot fulfill their promise. Instead, their night is filled with hijinks, run-ins with the cops, and accidental fights. Superbad features hilarious one-liners, raunchy language, and tons of swear words. The film establishes strong characters that are well-acted by Hill, Cera, and a very funny ensemble cast. Ultimately, the dim-witted duo learns that friendship is the most important thing they have.

9. Forgetting Sarah Marshall (2008)

Forgetting Sarah Marshall is one of the most underrated R-rated comedies of the 2000s. When Peter (Jason Segel) is dumped by his girlfriend Sarah Marshall (Kirsten Bell), a Hollywood star, he goes on a dream vacation to get away. The only problem is that Sarah is also at the resort he’s staying at, complete with a new, hot boyfriend in tow (Russell Brand). The film pulls comedy from Peter’s self-pity, giving him hilarious lines and putting him in awkward situations. Forgetting Sarah Marshall features a scene near the beginning where viewers see Segel naked, a funny and unexpected moment that helps the film earn its R-rating. The film culminates with Peter achieving his vision of composing an epic vampire opera in a scene that scores big laughs.

8. Shaun of the Dead (2004)

Shaun of the Dead stars Simon Pegg as a lazy electronics sales assistant named Shaun, who lives with his equally deadbeat buddy Ed (Nick Frost) in a small apartment in London. Shaun’s girlfriend Liz (Kate Ashfield) is always on his case to grow up and get a job to no avail. When a zombie apocalypse threatens to take over the world, Shaun must take up arms and fight back. Dylan Moran and Bill Nighy also star and add some hilarious dialogue. Shaun of the Dead earns its R-rating through excessive amounts of blood, gore, and filthy language. As Shaun encounters more and more zombies, he’s forced to find more creative ways to kill them. Director Edgar Wright doesn’t hold back, making for a violent, original, and very satisfying movie. Whenever Pegg and Frost are together, you know there will be some funny scenes as well.

7. Old School (2003)

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Old School stars Luke Wilson as Mitch, a middle-aged loser who walks in on his girlfriend cheating on him. Realizing that his life isn’t where he wants it to be, he reluctantly decides to join a fraternity and move into a college frat house with his buddies Bernard (Vince Vaughn) and Frank (Will Ferrell). The gang throws an epic party, but the dean of the school (Jeremy Piven) wants them out as he doesn’t consider their group to be a real fraternity. Old School mixes hilarious lines with nudity, featuring some strong but funny language. The best parts of Old School are when Frank, a former alcoholic, reverts to his old ways and drinks too much. He decides to go streaking, but nobody joins him, leading to a humorous confrontation with his wife.

6. Tropic Thunder (2008)

In Tropic Thunder, Ben Stiller plays Tug Speedman, a Hollywood star who is cast in a movie about the Vietnam War. Unable to control his cast and crew, the movie’s director Damien (Steve Coogan) has an epic meltdown and sends the cast into the jungle to shoot the movie using hidden cameras. The team, rounded out by comedian Jeff Portnoy (Jack Black) and award-winning actor Kirk Lazarus (Robert Downey Jr.), doesn’t realize that they’re in an actual war zone. The comedy in Tropic Thunder comes from Stiller, Black, and Downey Jr. playing up the stereotypes of their characters. It’s mildly offensive and pushes the boundaries of good taste at times, but the film is also unafraid to hold back on language and subject matter, which makes it wickedly funny. Despite the controversy, Ben Stiller, who also co-wrote the film, doesn’t believe he should apologize for Tropic Thunder. Tom Cruise also has a legendary and hilarious cameo that can’t be overlooked.

5. The Hangover (2009)

The Hangover is the ultimate R-rated comedy. After a night of drinking, three friends wake up in a trashed suite in Las Vegas with no recollection of what happened. The problem is that their friend Doug (Justin Bartha) is missing and he’s about to get married in the coming days. It’s up to Phil (Bradley Cooper), Stu (Ed Helms), and Alan (Zach Galifianakis) to piece together clues and find Doug before his wedding is canceled. The Hangover took R-rated comedies to new heights when it was released in 2009. It features so many crude jokes, sexual innuendos, and foul-mouthed characters that it’s impossible not to laugh while watching it. From adopting a baby to stealing Mike Tyson’s tiger, the group’s choices get funnier as the movie plays out. The movie was a smash hit, spawning two sequels and ideas for a gender-swapped reboot.

4. Borat (2006)

Borat is an incredibly divisive movie. Whether you love it or hate it, there’s no denying that it pushes the limits of good taste in unimaginable ways. Borat (Sacha Baron Cohen) is a fictional character from Kazakhstan who is sent to America to document life on a different continent. He soon realizes that America is very different from his homeland, and Cohen purposely plays up awkward confrontations for maximum laughs. Some of his subjects were in on the joke, while others were not. Borat contains almost everything that could earn a movie an R-rating: offensive language, crude sexual jokes, and blatant nudity. If you can stomach the whole thing, it’s actually pretty funny. Some fans even consider it one of the best mockumentaries. Borat is not for everyone, but it does hold an impressive 90% rating on Rotten Tomatoes.

3. I Love You, Man (2009)

I Love You, Man is about a guy named Peter Klaven (Paul Rudd) who works hard and has almost everything a man could want in life. Unfortunately, Peter is getting married and doesn’t have many friends. He needs to pick the best man, so he tries to be more outgoing and meet new people. Peter runs into Sydney (Jason Segel) at an open house, and the two hit it off pretty quickly. The comedy in I Love You, Man comes from the bromance between Peter and Sydney. Rudd and Segel have great on-screen chemistry, and the R-rated laughs come from Sydney’s free spirit and willingness to say or do anything to earn a chuckle. He takes it a bit too far and insults Peter, making him feel like…

Comedy movies are meant to make the audience laugh and sometimes that means taking things to the limit. The comedy scene in the 2000s was all about pushing boundaries, and it earned several movies’ R-ratings. Generally, rated-R movies contain gross-out humor, graphic violence, strong language, or sometimes all of the above. When done right, rated-R comedy can be absolutely hilarious while not being completely disgusting or offensive.


Looking at the comedy movies of the 2000s, a few actors pop up as mainstays. Actors like Vince Vaughn, Jonah Hill, and Paul Rudd, to name a few, seemed to have nailed the formula. They made viewers spit out their drinks in laughter while still challenging them to think about characters, plot, and narrative structure. These films were especially good at using the R-rating to their advantage, giving us big laughs and putting smiles on our faces.

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10 Superbad

Superbad
Sony Pictures Releasing

The (unofficial) award for the funniest movie of 2007 goes to Superbad. Seth (Jonah Hill) and Evan (Michael Cera) are two boneheaded high school kids whose sole mission is to party and score with chicks. They hatch a plan to supply all the alcohol for a massive party but soon realize they won’t be able to deliver on their promise. Instead, their night consists of hijinks, run-ins with the cops, and accidental fights.

Superbad has everything viewers could want in an R-rated comedy: hilarious one-liners, raunchy language, and tons of swear words. Through it all, the movie establishes strong characters that are well-acted by Hill, Cera, and a very funny ensemble cast. In the end, the dimwitted duo scores big laughs and learns that friendship is the most important thing they have.

9 Forgetting Sarah Marshall

Forgetting Sarah Marshall
Universal Pictures

Forgetting Sarah Marshall is one of the best underrated R-rated comedies of the 2000s. When Peter (Jason Segel) is unceremoniously dumped by his Hollywood star girlfriend Sarah Marshall (Kirsten Bell), he goes on a dream vacation to get away. The only problem is that Sarah is also at the resort he’s staying at, complete with a new, hot boyfriend in tow (Russell Brand).

The movie pulls comedy from Peter’s self-pity, giving him hilarious lines and putting him in awkward situations. There’s also a scene near the beginning where viewers see Segel naked, a funny and unexpected bit that helps the film earn its R rating. Forgetting Sarah Marshall is one of the movies that made 2008 a great year for comedy. It all culminates with Peter achieving his vision of composing an epic vampire opera in a scene that scores big laughs.

8 Shaun of the Dead

simon-pegg-shaun-of-the-dead
StudioCanal

Simon Pegg stars as a lazy electronics sales assistant named Shaun in Shaun of the Dead. Shaun lives with his equally deadbeat buddy Ed (Nick Frost) in a small apartment in London. His girlfriend Liz (Kate Ashfield) is always on his case to grow up and get a job to no avail. When a zombie apocalypse threatens to take over the world, Shaun must take up arms and fight back. Dyland Moran and Bill Nighy also star and add some hilarious dialogue as well.

Shaun of the Dead earns its R rating through excessive amounts of blood, gore, and filthy language. As Shaun encounters more and more zombies, he’s forced to find more creative ways to kill them. Blood spills everywhere and director Edgar Wright doesn’t hold back. It’s a violent, original, and very satisfying movie. Whenever Pegg and Frost are together you know there’s going to be some funny scenes as well.

RELATED: 6 Most Realistic Zombie Movies of All Time

7 Old School

Ferrell Old School 2003 Montecito
DreamWorks Pictures

Old School stars Luke Wilson as Mitch, a middle-aged loser who walks in on his girlfriend cheating on him. Realizing that his life isn’t where he wants it to be, he reluctantly decides to join a fraternity and move into a college frat house with his buddies Bernard (Vince Vaughn) and Frank (Will Ferrell). The gang throws an epic party but the dean of the school (Jeremy Piven) wants them out as he doesn’t consider their group to be a real fraternity.

Old School scores its R-rating by mixing hilarious lines with nudity. It’s a highly quotable movie that contains some strong but funny language. The best parts of Old School are when Frank, a former alcoholic, reverts to his old ways and drinks too much. He decides to go streaking but nobody joins him, leading to a humorous confrontation with his wife.

6 Tropic Thunder

Some of the cast of Tropic Thunder trecking through the forest in military gear
DreamWorks Pictures

In Tropic Thunder, Ben Stiller plays Tug Speedman, a Hollywood star who is cast in a movie about the Vietnam War. Unable to control his cast and crew, the movie’s director Damien (Steve Coogan) has an epic meltdown and sends the cast into the jungle to shoot the movie using hidden cameras. The team, rounded out by comedian Jeff Portnoy (Jack Black) and award-winning actor Kirk Lazarus (Robert Downey Jr.), doesn’t realize that they’re in an actual war zone.

The comedy in Tropic Thunder comes from Stiller, Black, and Downey Jr. playing up the stereotypes of their characters. It’s mildly offensive and pushes the boundaries of good taste at the best of times. But the film is also unafraid to hold back on language and subject matter, which makes it wickedly funny. Despite the controversy, Ben Stiller, who also co-wrote the film, doesn’t believe he should apologize for Tropic Thunder. Tom Cruise also has a legendary and hilarious cameo that can’t be overlooked.

5 The Hangover

the hangover
Warner Bros. Discovery

The Hangover is the ultimate R-rated comedy. After a night of drinking, three friends wake up in a trashed suite in Las Vegas with no recollection of what happened. The problem is that their friend Doug (Justin Bartha) is missing and he’s about to get married in the coming days. It’s up to Phil (Bradley Cooper), Stu (Ed Helms), and Alan (Zach Galifianakis) to piece together clues and find Doug before his wedding is canceled.

The Hangover took R-rated comedies to new heights when it was released in2009. It features so many crude jokes, sexual innuendos, and foul-mouthed characters that it’s impossible not to laugh while watching it. From adopting a baby to stealing Mike Tyson’s tiger, the group’s choices get funnier as the movie plays out. The movie was a smash hit, spawning two sequels and ideas for a gender-swapped reboot.

4 Borat

Borat
20th Century Fox

Borat is an insanely divisive movie. Whether you love it or hate it, there’s no denying that it pushes the limits of good taste in the most unimaginable ways possible. Borat (Sacha Baron Cohen) is a fictional character from Kazakhstan who is sent to America to document life on a different continent. He soon realizes that America is much different from his homeland, and Cohen purposely plays up awkward confrontations for maximum laughs. Sometimes his subjects were in on the joke, other times they weren’t.

Borat contains almost everything that could earn a movie an R-rating: offensive language, crude sexual jokes, and blatant nudity. And, if you can stomach the whole thing, it’s actually pretty funny too. Some fans even consider it one of the best mockumentaries. Borat is not for everyone, but it does hold an impressive 90% rating on Rotten Tomatoes.

3 I Love You, Man

I love you man
Paramount Pictures

I Love You, Man is about a guy named Peter Klaven (Paul Rudd) who works hard and has almost everything a man could want in life. Unfortunately, Peter is getting married and doesn’t have many friends. He needs to pick the best man, so he tries to be more outgoing and meet new people. Peter runs into Sydney (Jason Segel) at an open house and the two hit it off pretty quickly.

The comedy in I Love You, Man comes from the bromance between Peter and Sydney. Rudd and Segel have great on-screen chemistry, and the R-rated laughs come from Sydney’s free spirit and willingness to say or do anything to earn a chuckle. He takes it a bit too far and insults Peter, making him feel like he’s being tied down by getting married.

RELATED: Best Paul Rudd Movies, Ranked by Rotten Tomatoes Score

2 The 40 Year-Old Virgin

The 40-Year-Old-Virgin
Universal Pictures

Director Judd Apatow’s 2005 movie The 40-Year-Old Virgin is gut-wrenchingly funny. Steve Carrell plays Andy, a middle-aged single guy who has never had sex. Once his friends find out this fact, they make it their mission to help Andy get some. Andy soon meets Trish (Catherine Keener) and soon his prospects for getting lucky are looking up.

The 40-Year-Old Virgin is credited with bringing back the R-rated comedy in the 2000s and it suits the label well. With over-the-top language and crude sexual references throughout the movie, it’s hard to picture The 40-Year-Old Virgin working any other way.

1 Knocked Up

Knocked Up
Universal Pictures

The premise of Judd Apatow’s next big comedy Knocked Up is almost the opposite of The 40-Year-Old Virgin. It stars Seth Rogan as Ben Stone, a stoner without a job who just wants to sit around all day thinking about video games and women. He meets Alison (Katherine Heigl) at a local club and the two end up going home together. Alison accidentally winds up pregnant, but Ben is not father material (yet).

Knocked Up is full of funny sex jokes and crude humor. Ben and his buddies provide the bulk of this, running their filthy mouths and spitting out some hilarious lines. In the end, Ben realizes that Alison and the baby need him to grow up and be confident. With a great story, funny acting, and anything-goes dialogue, Knocked Up earns its R-rating. It also has enough heart to be one of the best comedies of the 2000s.

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