The 25 funniest R-rated comedies of the 21st century

One of 2005’s biggest hits, is an Apatow-adjacent comedy that invests its raunchy set pieces with a surprisingly effective dose of heart. In the film, two professional bachelors—played by Vince Vaughn and Owen Wilson—struggle to maintain their passion for crashing weddings when they start falling in love with Isla Fisher and Rachel McAdams, respectively. Directed by David Dobkin, Wedding Crashers is a flawed but extremely entertaining comedy bolstered by the stars’ chemistry and the very quotable script. By the time Will Ferrell’s hilarious cameo hits (“Mom! The meatloaf!”), you’ve already succumbed to the movie’s charms.

One of the great stoner comedies, pairs John Cho with Kal Penn—who have endless on-screen chemistry—as they embark on a very funny and trippy journey to satisfy their munchies. Directed and co-written by Danny Leiner, Harold & Kumar is a perfect rainy Saturday comedy watch, as it coasts on the charisma of its two leads and its never-dull premise.

Before winning deserved Oscars for , writer-directors Phil Lord and Chris Miller cemented their reputation as go-to guys for making successful movies out of concepts that most wouldn’t think would make for successful movies with . Adapted from the dated Fox TV series about adult cops going undercover as high school students, the movie version of 21 Jump Street takes the core premise of the series and pluses it with Lord and Miller’s seemingly endless supply of funny and inventive answers to the question “Wouldn’t it be cool if this happened?” What happens is a highly quotable, and extremely funny, R-rated buddy cop movie that helped turn Channing Tatum and Jonah Hill into movie stars.

Two years after their first Jump Street outing, Lord and Miller—and Tatum and Hill—returned for , which some fans consider to have pulled a and surpassed the original in the comedy and meta department. This time, cops Tatum and Hill take their partnership to college to stop a new drug and the dealers selling it. 22 Jump Street not only embraces the symptoms of “sequelitis”—like bigger and better stunts—it also skewers them with in-story commentary and satire that make for a lively and, refreshingly, heartfelt Part 2. Comedy franchises rarely hit as many laughs with second installments as they did with the first, but 22 Jump Street is the rare exception—especially the very meta end-titles exploration of future, cameo-filled sequels.

A cult-favorite comedy from summer 2008, , directed by future Oscar-winner Adam McKay (), centers on two grown adults behaving like unruly preteens. We’re not sure that formula would have worked nearly as well without Will Ferrell and John C. Reilly delivering their particular brand of magic, as their effortless on-screen chemistry and penchant for improv make for one of the genre’s best and most watchable pairings.

“Yer my boy, Blue!” Blame l, Todd Phillips’ popular frat boy comedy, for the R-rated comedy boon of the early aughts. After a ginormous housewarming party gets out of hand, a suburban family man nicknamed Frank the Tank (Will Ferrell) reunites with college buddies Mitch Martin () and Beanie () to start up a fraternity and relive their beer-filled glory days. Ferrell steals the show here, especially with his now-iconic streaking scene, and Vaughn cements himself as one of comedy’s funniest leading men with his snarky, rapid-fire line readings.

It’s tough to argue with the sheer amount of comedic talent assembled for . Another R-rated hit from the school of Judd Apatow players—it’s co-directed by Seth Rogen and his long-time writing partner Evan Goldberg—This Is The End features a who’s who of popular American comedians, including Jonah Hill, Craig Robinson, and Danny McBride. The twist is that they all play a version of themselves as they grapple with the impending Armageddon while trapped in James Franco’s house in the Hollywood Hills. But beneath all the supernatural spectacle and zaniness is a surprisingly earnest story about two friends growing apart, who find themselves in literal Heaven. With the Backstreet Boys. Because movies.

If a stoner comedy and hooked up, their offspring would be . A bigger hit on home video than it was on the big screen, Super Troopers centers on a group of Vermont State Troopers in danger of getting shut down due to budget issues as they “police” a small but vital stretch of freeway. Led by Brian Cox’s Captain John O’Hagan, the Super Troopers (Jay Chandrasekhar, Kevin Heffernan, Steve Lemme, Paul Soter, and Erik Stolhanske) attempt to do their jobs under the threat of budget crisis, and mostly pass the time by playing practical jokes on motorists and each other. Shit gets real when the troopers’ mettle is tested by a drug bust, and that’s when the comedy troupe Broken Lizard really shines.

, the middle entry in director Edgar Wright’s Cornetto Trilogy, is by far the lightest of the three. Wright’s spoof of action-cop movies doesn’t have as much to get off its chest as or . (That’s not to say it’s a movie about nothing, though. Its satirical jabs at small-town living and hero-cops are quite clever.) And yet, Hot Fuzz is so damn funny. It’s a near-perfect joke machine, with a narrative structure that clicks into place like safe tumblers—full of set-ups nestled into callbacks that slot right into incredible sight gags and clockwork wordplay. Timothy Dalton playing the smarmiest man alive! Nick Frost pulling a Keanu! The swan! Ultimately, though, Hot Fuzz doesn’t need to be too much more than what it is—an incredible action-comedy.

The sleeper hit of Summer 2005, marked Judd Apatow’s feature-directorial debut and paved the way for nearly a decade’s worth of similarly minded comedies that would forever change the genre. It kicked off Apatow’s unique blend of R-rated laughs centered around likable and relatable characters with the story of the titular virgin, Andy (Steve Carrell), a mid-level employee at a Circuit City-like tech store trying to get laid for the first time. Seth Rogen was only 22 when he filmed his breakthrough role as Andy’s crass coworker, but he seemed much older, thanks to that raspy bark and worldly one-liners. He often stole the movie, alongside his heartbroken colleague played by Paul Rudd. Almost 20 years after its release, The 40-Year-Old Virgin is still Apatow’s best, most complete, film.

Coming-of-age high school comedies don’t get much funnier, or more sincerely sweet, than . Michael Cera and Jonah Hill are both at the top of their game in this modern classic about two geeky friends hellbent on losing their virginity before high school ends. It’s a hilarious romp that stays at ground level with our teen cast, but it also focuses a great deal on the strained friendship at the movie’s core in a way that invests the story with producer Judd Apatow’s uniquely gooey, emotional center.

There is life before, and life after, watching . A not-so-subtle send-up of early ’80s teenage sex comedies, Wet Hot American Summer is a pitch-perfect parody of mid-level programmers like that has since become a cult classic. It not only blessed audiences with some of the greatest comedic talents of the last 20 years—including Amy Poehler, Elizabeth Banks and Ken Marino—it also spun off two popular TV series on Netflix: and .

is, and will likely forever remain, Sacha Baron Cohen’s defining comedy—a masterpiece of mockumentary laughs. It’s the rare example of a successful TV character finding even more—and more enriching—success on the big screen, as Cohen’s crass and weapons-grade offensive Kazakh TV interviewer goes all out on a trip to America that leaves no PC stone unturned. Borat is an equal opportunity offender, a comedy full of subtle jabs at our most incredulous ways of life as well as one where two (very hairy) grown men wrestle naked in a hotel room. While the 2020 sequel approaches the comedy highs of Borat, nothing tops the original.

Few comedies in the past two decades have struck as big a chord as . The premise is very elevator pitch friendly: Three pals-turned-groomsmen struggle to track down the wayward groom after a night of drunken debauchery in Vegas. Between the constantly escalating hijinks and the strong chemistry among the main trio—Bradley Cooper, Ed Helms, and, in a star-making turn, Zach Galifianakis—it’s no surprise this sleeper 2009 summer hit inspired a successful R-rated comedy franchises.

After many years of male-centric raunchy comedies, audiences were more than ready for Paul Feig’s —a modern comedy classic headlined by one of the funniest female ensembles the genre has ever seen. Co-written by star Kristen Wiig, Bridesmaids is more than just a gender flip of The Hangover. It’s a complex, character-driven comedy about Annie (Wiig) struggling to figure out her life in the lead-up to her best friend Lillian’s (Maya Rudolph)’s wedding. The movie’s more outrageous (and memorable) moments—like a wedding dress shopping scene that ends with Lillian taking a dump in the middle of a busy street—are perfectly balanced with the film’s more heartfelt, charming beats. As landmark comedies go, they don’t get much better than Bridesmaids.