The 10 Funniest R-Rated Comedy Movies Of The Past 20 Years

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R-Rated comedy movies have been gracing the silver screen for decades, yet they weren’t commonplace until the early 2000s. Although movies such as Caddyshack and Animal House laid the foundation for adult comedies, it wasn’t until after the turn of the century that they would start making loads of money and be given critical praise. The past twenty years have given fans some of the greatest comedy films of all time and for many years they seemed to get raunchier and even became somewhat controversial.

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However, fans should remember that these movies are made for laughs and they don’t need to be cinematic masterpieces. While most of these comedies include sex, drugs, alcohol, and everything in between, the best of the best have a good story and feature some of the most talented actors in the world today. There have been many successful R-Rated comedies over the past two decades, but some bring the laughs more than others.

10 The Change-Up (2011) Was A Fun Freaky Friday-like Movie For Adults

the change up 2011 movie

Anytime a movie brings together two talents like Jason Bateman and Ryan Reynolds, it usually means it will be hilarious. The Horrible Bosses star and the Deadpool star play off each other so well, especially when they swap bodies accidentally and have to act outside their normal element. In addition to Bateman and Reynolds, the supporting cast includes Olivia Wilde, Leslie Mann, and Alan Arkin, with the latter playing Ryan Reynold’s Mitch’s father.

Jason Bateman plays Dave, a husband, and father trying to become a partner in his law firm. Reynold’s Mitch is Dave’s best friend and is a free spirit that loves women and loves smoking marijuana. When the two are out drinking, they make a wish in front of a  magical statue and wish they had each other’s lives. Dave and Mitch switch bodies and hilarity ensues as the two try to balance each other’s lives.

9 21 Jump Street (2012) Was A Hilariously & Unique Reboot Of The TV Show

21 jump street 2011

The beloved TV show 21 Jump Street ran from 1987 to 1991, launching Johnny Depp into superstardom and making household names out of the entire cast. When it was announced that they were doing a 21 Jump Street reboot movie, many fans worried it wouldn’t live up to the show. Thankfully, the movie was wonderfully written and had two amazing actors in Jonah Hill and Channing Tatum leading the way.

Although they start off as high school adversaries, the two quickly bond during boot camp and become partners on the police force. The two are sent to Jump Street, an undercover group of officers who infiltrate high schools and try to find the deadly new drug, HFS. The jokes are non-stop, as the two twenty-somethings pretend to be students, with Jonah Hill’s nerdy Schmidt becoming the popular one and Tatum’s Jenko hanging with a less popular crowd.

8 Step Brothers (2008) Featured Amazing Improv From Will Ferrell & John C. Reilly

step brothers 2008 movie

John C. Reilly and Will Ferrell have worked on several projects together but none were as good and as hilarious as 2008’s Step Brothers. Both play 40-year-old men that still live at home and are forced to live together when their parents meet and get married. Ferrell’s Brennan and Reilly’s Dale start off with disdain for each other but soon bond over their hatred of Brennan’s real brother and their love of obscure hobbies. Derek, Brennan’s brother played by the multitalented Adam Scott, shows up and starts making fun of both Dale and Brennan.

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This leads to Dale punching him in the face and he falls out of their treehouse, leading to the Step Brothers becoming close and doing karate in the garage. Mary Steenburgen and Richard Jenkins play the flustered parents to perfection and the rest of the cast keeps up with the improving geniuses Ferrell and Reilly. Every scene is laugh-out-loud funny but none stand out as much as the musical finale at The F’n Catalina Wine Mixer.

7 Forgetting Sarah Marshall (2008) Had A Beautiful Setting & Nice Love Story

forgetting sarah marshall 2008

In 2008, Jason Segel was just starting to break out as a comedic actor, starring in the hit sitcom How I Met Your Mother and having previously been involved with projects such as Freaks and Geeks and Knocked Up. Forgetting Sarah Marshall really brought out the best in Segel and featured some amazing comedy, including a few hilarious scenes that are burned in the viewer’s brain.

The movie is about a man who is heartbroken by his ex-girlfriend and decides to take a trip to Hawaii to get his mind off it. Unfortunately for Peter (Segel), his ex, Sarah Marshall (Kristen Bell), is staying at the same hotel with her new rockstar boyfriend. Thankfully, he meets Rachel (Mila Kunis) and the two become close as Sarah and her rockstar boyfriend start to fall apart. The supporting cast is amazing, especially Russell Brand’s rockstar Aldis Snow and his biggest fan, Matthew (Jonah Hill).

6 Tropic Thunder (2008) Featured An Amazing Cast & Was A Movie Inside Of A Movie… Inside Of A Movie

tropic thunder 2008 movie

Tropic Thunder is one of the greatest comedies of all time, thanks to amazing performances from Ben Stiller and Robert Downey Jr. In addition to Stiller and Downey, the cast is loaded with amazing talents like Jack Black, Matthew McConaughey, Nick Nolte, and Tom Cruise. Robert Downey Jr. won awards for his portrayal of actor Kirk Lazarus and Tom Cruise was amazing as the explosive Les Grossman.

Tropic Thunder was a movie within a movie and showed the inner workings of what it’s like to film an expensive movie and shows how narcissistic actors and directors can be. In addition to the comedy and the action-packed story, the “movie’s” fake trailers at the beginning of the story are worth the price of admission alone.

5 Superbad (2007) Was Jonah Hill’s & Michael Cera’s Breakout Performances

superbad 2007 movie

Some of the best comedy movies ever made revolve around high school students, so when Superbad hit theaters in 2007 it attracted a certain audience. Revolving around a group of high school seniors trying to buy alcohol for a party, Superbad reminds viewers how funny and how difficult it can be to be a teenager getting ready to go to college.

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Whether it’s Michael Cera’s Evan arguing with Jonah Hill’s Seth about girls or Christopher Mintz-Plasse’s McLovin bonding with two police officers, every scene provides a lot of laughs. Seth Rogen and Bill Hader play the two police officers that bond with McLovin and even take him out for a wild night on the town. The movie also has a sentimental vibe that comes to a head at the end when Evan and Seth realize that their lifelong relationship will change as the two go to different colleges.

4 The 40-Year-Old Virgin (2005) Was A Risque2 But Fun Take On One’s Love Life

the 40 year old virgin movie

Steve Carell broke out of his usual supportive role and became a superstar when 2005’s The 40-Year-Old Virgin hit theaters. Carell plays Andy, a 40-year-old man who has never had any luck in the love department, prompting his co-workers to do anything to help him lose his virginity.

The supporting cast included Paul Rudd, Seth Rogen, and Romany Malco as Andy’s co-workers and Catherine Keener as Trish, Andy’s girlfriend later in the movie. The constant sex jokes and awkward situations Andy finds himself in are hilariously uncomfortable, reminding the viewer how hard it can be to get intimate with the opposite sex. The movie is filled with gags and laughs but none funnier than Andy getting his body hair waxed, which Steve Carell actually did so it would feel authentic.

3 Knocked Up (2007) Was Seth Rogen’s Coming Out Party As A Comedy Megastar

knocked up movie 2007

After having smaller, yet hilarious roles in Freaks and Geeks, Anchorman, and The 40-Year-Old Virgin, Seth Rogen became a made man in Hollywood after the release of Knocked Up. Rogen and Katherine Heigl star in the story as two twenty-somethings who hook up randomly one night and Heigl’s Alison later finds out she’s pregnant. Rogen’s Ben is a pothead who lives with a group of his friends and runs a website.

The cast is loaded with talents such as Paul Rudd, Jason Segel, Jonah Hill, Leslie Mann, and so many more that make this movie a must-watch for all fans. The story is a reminder of why people should practice safe sex but sometimes things happen and they happen for a reason. Sometimes love comes in different ways and being a parent can be done with the love and support of family and friends.

2 The Hangover (2009) Was An Adult Buddy Comedy With A Mystery Element

the hangover 2009 movie

When a group of friends goes to Vegas for a bachelor party, they get so drunk that they lose the groom and it’s their job to piece together the previous night. Starring Bradley Cooper, Ed Helms, Zack Galifinacus, and a great ensemble cast, The Hangover mixed comedy and partying to perfection. It also had a mystery element to it, as the three men do everything possible and go everywhere possible to find out what happened to their friend, Doug.

Whether it’s their interactions with Mr. Chow or stealing a tiger from Iron Mike Tyson, the movie is a non-stop laugh machine that makes the viewer constantly ask themself, did that really just happen? Additionally, it’s a reminder to anyone that they should be careful what they drink. Looking at you, Alan.

1 Wedding Crashers (2005) Reminded Viewers Why Weddings Are So Fun & Why Friends Are So Important

wedding crashers 2005 movie

Vince Vaughn and Owen Wilson have amazing chemistry and have made several successful movies together, but it’s the 2005 global phenomenon Wedding Crashers that everyone remembers. John Beckwith (Wilson) and Jeremy Grey (Vaughn) are lifelong friends that have made a living as lawyers by day and professional wedding crashers by night.

The two friends are charming and full of personality as they bond with everyone at each wedding they crash and take over the entire ceremony, which seems to impress attractive women. It’s not until they crash the wedding of Secretary Cleary’s daughter that the two of them find the loves of their lives. The movie constantly has the audience in hysterics and is the perfect mix of partying, love, and friendship.

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