While maybe not a pure comedy in the traditional sense, Martin Scorsese's epic biographical black comedy is undeniably hilarious in its depiction of excess, greed, and depravity on Wall Street. Leonardo DiCaprio gives a powerhouse performance as Jordan Belfort, a stockbroker who rises to immense wealth through illegal means. The film is long, intense, and filled with unbelievable true stories, but the sheer absurdity and comedic timing in many scenes make it a riot. It's a wild, drug-fueled ride through the world of finance that will leave you laughing and gasping.

An iconic teen sex comedy that helped define the genre for a generation. The film follows a group of high school friends who make a pact to lose their virginity before graduation. Its humor is often crude and relies on classic teen movie tropes, but it also has a surprising amount of heart. The scene involving Jim (Jason Biggs) and an apple pie is legendary and instantly cemented the movie's R-rated status. It's a nostalgic trip back to the late 90s with plenty of laughs and awkward moments.

Definitely not your typical Christmas movie! Billy Bob Thornton stars as Willie T. Soke, a miserable, foul-mouthed con man who poses as a department store Santa Claus each year to rob the place on Christmas Eve. This dark comedy is hilariously cynical and features a surprisingly sweet (in its own twisted way) relationship between Willie and a naive, overweight kid. Tony Cox and Bernie Mac also provide great support. It's the perfect antidote if you're tired of overly saccharine holiday films.

Seth MacFarlane brings his signature Family Guy-style humor to the big screen with this story about a man (Mark Wahlberg) whose childhood teddy bear magically came to life and is now his crude, hard-partying best friend. The film mines comedy from the absurdity of a talking teddy bear in the real world and the strain his presence puts on the man's relationship. MacFarlane voices Ted himself, and the humor is exactly what you'd expect from the creator of Family Guy - irreverent, pop-culture heavy, and often R-rated. It's a buddy comedy with a very fluffy, very foul-mouthed twist.

Seth Rogen and Evan Goldberg's directorial debut is a meta-comedy where actors play exaggerated versions of themselves facing the apocalypse during a party at James Franco's house. The humor comes from the stars' self-deprecating portrayals and their often-improvised reactions to biblical events. It's a chaotic, star-studded, and genuinely funny take on friendship, fame, and the end of the world, featuring hilarious cameos and outrageous special effects. Prepare for celebrity in-jokes and demonic mayhem!

Blending stoner comedy with action, Pineapple Express follows a process server (Seth Rogen) and his dealer (James Franco) who go on the run after witnessing a murder linked to a rare strain of weed. Produced by Judd Apatow and directed by David Gordon Green (known for indie dramas!), the film successfully mixes genuine peril with laugh-out-loud moments fueled by the duo's escalating panic and drug-induced antics. James Franco received a Golden Globe nomination for his comedic performance. It's a wild, funny ride, especially if you enjoy high-stakes silliness.

Who would have thought a reboot of a late 80s TV drama could be this hilarious? Jonah Hill and Channing Tatum have surprisingly fantastic comedic chemistry as two undercover cops sent back to high school. The film smartly pokes fun at reboots and updated high school tropes while delivering genuinely funny action sequences and character moments. Directors Phil Lord and Christopher Miller brought their unique comedic sensibilities to make this much more than just a retread. It's a surprisingly clever and laugh-out-loud action-comedy.

Will Ferrell is Ron Burgundy, a clueless but confident San Diego news anchor in the 1970s. This film, directed by Adam McKay, is a highly quotable, absurdist comedy that has built a massive cult following. The chemistry between Ferrell, Paul Rudd, Steve Carell, and David Koechner as the KVWN news team is fantastic. While not a massive box office hit initially, its unique brand of humor and unforgettable gags (like the jazz flute scene or the epic news team brawl) made it a comedy phenomenon. Stay classy, San Diego!

Ben Stiller directs and stars in this sharp satire of Hollywood and the lengths actors will go for their craft. A group of pampered actors are dropped into a real war zone for their method acting, leading to chaos and hilarity. The film features pitch-perfect performances, including Robert Downey Jr.'s controversial but undeniably funny turn as an Australian actor playing a Black man (a commentary on Hollywood's history), and Tom Cruise in a hilarious, uncredited role as a foul-mouthed studio executive. It's a smart, action-packed comedy that doesn't pull any punches.

Will Ferrell and John C. Reilly as Brennan and Dale, two grown men forced to live together when their single parents marry? Pure comedic gold. Directed by Adam McKay, this film is a masterclass in absurd, quotable humor and the comedic power of two actors fully committed to ridiculous characters. Their sibling rivalry and eventual bond provide endless laughs. The movie's improvisational feel and unforgettable lines have solidified its place as a cult comedy classic.

Kristen Wiig leads an incredible ensemble cast in this comedy that proved female-led R-rated humor could be a box office powerhouse and critically acclaimed. The film follows Annie, a down-on-her-luck baker navigating the chaotic and often competitive world of being a maid of honor. From disastrous dress fittings to cringe-worthy speeches, the movie finds humor in relatable anxieties and absurd situations. Melissa McCarthy received an Oscar nomination for her scene-stealing performance. It's hilarious, heartwarming, and features one of the most infamous food poisoning scenes in cinema history!

Breaking the fourth wall and breaking all the rules, Deadpool is the R-rated superhero movie we didn't know we needed! Ryan Reynolds IS Wade Wilson, bringing the Merc with a Mouth to life with perfect comedic timing and relentless meta-humor. The film is a fantastic blend of action, romance (in its own twisted way), and genuinely hilarious gags. It wasn't a guaranteed hit, especially with its smaller budget compared to other superhero flicks, but its irreverent attitude and direct address to the audience made it a massive success. It's crude, clever, and outrageously fun!

Talk about a bachelor party gone wrong! This movie redefined the 'guys' trip' comedy with its brilliant premise: three friends wake up in Vegas with no memory of the previous night and a missing groom. The chaotic search through the aftermath of their debauchery is filled with outrageous situations and unexpected cameos. Director Todd Phillips masterfully balances the mystery with laugh-out-loud physical comedy and sharp dialogue. It's a wild ride from start to finish that spawned two sequels, but nothing beats the original's shock value and sheer comedic energy.

This absolute gem of a teen comedy perfectly captures the awkwardness and desperation of high school seniors trying to score alcohol for a party. Seth Rogen and Evan Goldberg poured their own teenage experiences into the script, which they started writing when they were just 13! The chemistry between Jonah Hill and Michael Cera is electric, and Christopher Mintz-Plasse's portrayal of McLovin' became an instant pop culture icon. It's a hilarious, heartfelt, and surprisingly authentic look at friendship on the cusp of adulthood. Prepare for non-stop laughs and maybe a little bit of cringe!