10 Best R-Rated Comedies Of The 1990s

Summary

• 1990s R-rated comedies had creative freedom and big names, leading to some unforgettable movies.
• The Coen brothers, Spike Jonze and Richard Linklater all produced creative comedies which pushed the limits of the genre.
• Movies like American Pie pushed boundaries in teen comedy, influencing a wave of similar movies in the early 2000s.

The 1990s were a great time for comedy movies, with big studios and independent productions willing to take risks on adult-oriented humor. Looking back at the R-rated comedies of the 1990s highlights how studios have recently moved away from such movies. It’s a big financial risk to market big-budget comedies exclusively to adults, and this is something that may be falling out of fashion.

Studios gave plenty of creative control to comedic talents in the 1990s, resulting in some unforgettable comedy movies starring big names such as Robert De Niro, Cameron Diaz and Chris Tucker. R-rated comedies became somewhat homogenized in the 2000s. There are still hilarious R-rated comedies from the 21st century, but the 1990s were a particularly good time for them.

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10 Analyze This (1999)

Robert De Niro Flips His Gangster Movie Roles

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Robert De Niro gets a rare chance to show off his comedy chops in Analyze This, but he’s still playing the familiar role of a hardened mob boss. Far from the style of the Martin Scorsese movies that he’s often associated with, Analyze This is a comedy about a gangster who decides to see a therapist after he starts having panic attacks. In this way, Analyze This seems similar to The Sopranos, but the two projects came out in the same year. Their similarities are nothing more than a coincidence.

De Niro has played a few comedic roles since 1999, but none have been as funny as
Analyze This.

De Niro has played a few comedic roles since 1999, but none have been as funny as Analyze This. His surprisingly natural dynamic with Billy Crystal is a big reason why the movie works so well. When De Niro’s character is a fragile but potent danger, Crystal handles him with a gentle, firm hand. The constantly shifting power dynamic between the two characters is a joy to watch. The therapist wants to lead the sessions and establish some personal boundaries, but he knows what happens to people who cross the mob.

9 The Full Monty (1997)

The Full Monty Uses Stripping To Look At Some Serious Topics

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The Full Monty

Director Peter Cattaneo Release Date August 13, 1997 Cast Robert Carlyle , Tom Wilkinson , Mark Addy , Wim Snape , Steve Huison , Paul Barber , Hugo Speer , Lesley Sharp

The Full Monty is a raunchy British comedy about a group of unemployed steel mill workers in Yorkshire who form a male striptease act to make some money. Their main advantage over the Chippendales, they believe, is that they are willing to go “the full monty” by stripping completely nude. The men aren’t in the typical mold of strippers, but they still manage to generate a lot of interest.

The Full Monty
deals with some serious themes, including body image, homosexuality and fatherhood, but it always does so with humor and heart.

The Full Monty deals with some serious themes, including body image, homosexuality and fatherhood, but it always does so with humor and heart. Gaz’s relationship with his son is what drives him to become a stripper. It’s certainly an unorthodox story, but the love between the two reads as genuine and sweet. The Full Monty received a follow-up TV series on Hulu in 2023.

8 American Pie (1999)

The Quintessential Raunchy Teen Comedy Of The Time

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American Pie Where to Watch

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Director Paul Weitz , Chris Weitz Release Date July 9, 1999 Cast Jason Biggs , Chris Klein , Thomas Ian Nicholas , Alyson Hannigan , Shannon Elizabeth , Tara Reid

American Pie is responsible for the wave of teen comedies that came out in the early 2000s, as it set a new template for the genre. There have been many more American Pie movies since 1999, but none have yet lived up to the original. Part of this is due to the fact that it’s impossible to replicate the shocking impact that the original movie had. American Pie pushed the boundaries of good taste, creating an unforgettable teen comedy that defines American high school life in the 1990s.

American Pie
pushed the boundaries of good taste, creating an unforgettable teen comedy that defines American high school life in the 1990s.

Jason Biggs and Alyson Hannigan are the movie’s two romantic leads, but the ensemble comedy has a few other standout characters. Seann William Scott is superb as the ultra-macho, sex-obsessed Stifler, and Jennifer Coolidge is even harder to ignore as Stifler’s mom. There have been persistent rumors that American Pie 5 could be on the cards. Reuniting the original cast once more would be the only way to make another sequel work.

7 Dazed & Confused (1993)

Richard Linklater’s High School Comedy Is Absorbing And Hilarious

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Dazed and Confused Where to Watch

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Director Richard Linklater Release Date September 24, 1993 Cast Jason London , Wiley Wiggins , Matthew McConaughey , Rory Cochrane , Joey Lauren Adams , Milla Jovovich

Many of Richard Linklater‘s best movies can evoke a time and place with incredible accuracy. Boyhood, Apollo 10 1/2 and Everybody Wants Some draw from the director’s own experiences to transport audiences back in time, and Dazed and Confused is no different. Although it is sometimes described as a stoner comedy, it’s really a hangout movie about high school kids who sometimes happen to smoke. The drug use is just one part of the immersive feel of the movie.

Although it is sometimes described as a stoner comedy, it’s really a hangout movie about high school kids who sometimes happen to smoke.

Dazed and Confused is a brilliant movie to spend some time with. It uses a cast of likable characters and the setting of a single day to pull audiences into its world. Its loose structure is also more realistic, as characters bounce between interactions with different high school cliques naturally. Dazed and Confused helped make Matthew McConaughey into a star, but he isn’t the only young actor in fine form.

6 Office Space (1999)

A Workplace Comedy With Real Bite

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Office Space Where to Watch

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Director Mike Judge Release Date February 19, 1999 Cast Stephen Root , Ron Livingston , Gary Cole , John C. McGinley , Jennifer Aniston

Office Space is a brilliant workplace satire, dissecting the pointless bureaucracy and busywork of most office jobs. Ron Livingston plays a man who grows tired of his pencil-pushing tasks, so he decides to do as little as possible while at work in the hope of getting fired. His subsequent promotion shows him the nonsensical hierarchy at his workplace, and he conspires with his two friends to tear the company down from the inside.

Office Space
is painfully relatable for anyone who has ever found themselves working long hours in a job they don’t care about.

Office Space is painfully relatable for anyone who has ever found themselves working long hours in a job they don’t care about. There are obnoxious bosses and utterly bizarre coworkers all throughout the office. Peter realizes he can either play the game of office politics, or he can act like a normal human being and reject the phony artifice of work. Office Space is detailed enough to work over 20 years later, even when there are no more fax machines to destroy.

5 South Park: Bigger, Longer & Uncut (1999)

The Controversial Cartoon’s First Movie Was A Huge Success

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South Park: Bigger, Longer & Uncut (1999) Where to Watch

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Director Trey Parker Release Date June 30, 1999 Cast Trey Parker , Matt Stone , Mary Kay Bergman , Isaac Hayes , George Clooney , Brent Spiner , Minnie Driver , Dave Foley

The fact that the title of the South Park movie contains a joke about male genitalia was the first indication that creators Trey Parker and Matt Stone were ready to push their raunchy style of humor to its limits. South Park: Bigger, Longer and Uncut is designed to shock and offend, but it does so with a lot of intelligence. Ultimately, the joke is on the people who decry the low morals of a cartoon, people like Kyle’s mom.

The fact that the title of the
South Park
movie contains a joke about male genitalia was the first indication that creators Trey Parker and Matt Stone were ready to push their raunchy style of humor to its limits.

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South Park: Bigger, Longer and Uncut is a musical movie, with plenty of hilarious songs, including “Blame Canada,” “It’s Easy, Mmmkay,” and some others too profane to be repeated here. The show often uses the crude Canadian comedy duo Terrance and Phillip as a way of commenting on its own controversies, and the movie is no different. Trey Parker and Matt Stone didn’t quite spark a global conflict with the South Park movie, but they did attract a firestorm of criticism, all of which they predicted in the movie itself.

4 Being John Malkovich (1999)

Spike Jonze’s Surreal Comedy Is Weird And Wonderful

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Being John Malkovich

Director Spike Jonze Release Date October 29, 1999 Cast John Cusack , John Malkovich , Cameron Diaz , Catherine Keener

Being John Malkovich is one of the most creative comedies of the 1990s, but its quirky premise is more than just a gimmick. The movie follows a puppeteer who discovers a portal that allows him to briefly inhabit the body of John Malkovich. Craig is willing to sacrifice everything for fame and fortune, even his own identity. Naturally, this backfires horifically, eventually leading to a tragic ending in which he becomes trapped in a young girl’s body, and he must watch the woman he loves enjoy a life without him.

Being John Malkovich
is one of the most creative comedies of the 1990s, but its quirky premise is more than just a gimmick.

Being John Malkovich is wildly original, and this allows it to keep plenty of surprises throughout. The twisty narrative also helps the comedy. There’s no way of knowing what bizarre scenario may come up next, whether it’s two women using John Malkovich’s body as a vessel to act out their sexual fantasies, or a world populated entirely by John Malkoviches, saying nothing but “Malkovich” over and over again.

3 Friday (1995)

Ice Cube And Chris Tucker Make A Perfect Pair In Friday

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Friday

Director F. Gary Gray Release Date April 26, 1995 Cast Ice Cube , Chris Tucker , Nia Long , Tom Lister Jr. , John Witherspoon , Anna Maria Horsford , Regina King , Paula Jai Parker

Many of Ice Cube’s movies since Friday seem to be his attempts to recapture the brilliant chemistry he shares with Chris Tucker. He often plays gruff, no-nonsense straight men, but Tucker is the perfect funny man to bring the best out of him. Their dynamic is just one part of what makes Friday hilarious, however. The supporting cast of Friday is also filled with fantastic comedic actors, including the late, great Bernie Mac.

With an endless supply of memorable quotes and a smooth hip-hop soundtrack,
Friday
is worth rewatching long after the initial impact of the jokes has worn off.

Friday takes place over the course of one day in a south central Los Angeles neighborhood. The story takes in both the mundane and the bizarre, as the two main characters struggle to find money fast so that they can stay out of trouble. With an endless supply of memorable quotes and a smooth hip-hop soundtrack, Friday is worth rewatching long after the initial impact of the jokes has worn off.

2 There’s Something About Mary (1998)

Cameron Diaz Stars In A Romcom About The Absurdity Of Romcoms

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There’s Something About Mary

Director Peter Farrelly , Bobby Farrelly Release Date July 15, 1998 Cast Cameron Diaz , Matt Dillon , Ben Stiller , Lee Evans , Chris Elliott

There’s Something About Mary takes a fairly standard romcom trope to absurd new heights. While it’s common for romcoms to feature some kind of love rivalry, There’s Something About Mary features a staggering number of potential suitors fawning over Mary, including NFL star Brett Favre. Cameron Diaz delivers a superb performance as Mary. She is both likable and naive enough to attract dysfunctional men who can project their own ideals onto her.

There’s Something About Mary
has a strong enough premise to work as a PG-13 comedy, but it makes full use of its R rating with some wonderfully immature humor.

There’s Something About Mary has a strong enough premise to work as a PG-13 comedy, but it makes full use of its R rating with some wonderfully immature humor. The plot does enough intelligent, subversive work to allow for some surprisingly hilarious gags about sex and a pathetic fist fight. Each of Mary’s potential partners is terrible in their own special way, and their petty conflict provides the source for endless jokes.

1 The Big Lebowski (1998)

Jeff Bridges Delivers A Deadpan Masterclass In The Coen Brothers’ Strange Crime Comedy

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Director Joel Coen , Ethan Coen Release Date March 6, 1998 Cast Julianne Moore , Jeff Bridges , Steve Buscemi , John Turturro , John Goodman , David Huddleston , Phillip Seymour Hoffman

The Big Lebowski starts with a case of mistaken identity like many other dark comedy capers, but it quickly spins into something far weirder and less predictable. The world of The Big Lebowski is populated by flamboyant bowlers, spiritual cowboys and violent pornography magnates. It’s a surreal crime comedy, but the protagonist wants nothing to do with any of it.

The world of
The Big Lebowski
is populated by flamboyant bowlers, spiritual cowboys and violent pornography magnates.

The Big Lebowski is one of the best Coen brothers movies. It has a captivating crime plot just like Fargo and Raising Arizona, but its approach is much looser. Rather than ratcheting up the tension, The Big Lebowski frequently dips into inconsequential conversations with quirky side characters. There’s also a beautiful dream sequence that draws parallels between the Dude’s twin passions of bowling and sex.

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