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

Released on Hulu during the first year of pandemic lockdown, Palm Springs struck a considerable nerve with audiences as they watched a movie tackle the trope of being stuck in a time loop just as many of us were stuck in our homes. Trying to escape the confines of a Groundhog Day-like scenario are Andy Samberg and Cristin Milioti, two wedding guests who spark a burgeoning romance despite being forced to live the same day over and over again. But it’s in the repetition of their daily existential prison where the potential lovers find both meaning and context for their lives, despite the futility that comes with discovering them while repeating the same 24-hour period. With strong performances from the cast, coupled with an inventive take on both time loops and rom-coms, Palm Springs is a refreshingly assured entry in the genre.

It’s a shame Popstar didn’t make a bigger splash at the box office upon its initial release, because it’s basically the best music rockumentary since This Is Spinal Tap. Star Andy Samberg and the rest of his Lonely Island trio effortlessly tackle the rise and fall of a ridiculous, ego-centric popstar—and their brand of slapstick and deadpan humor has never been funnier (or more quotable). Even better are the surprisingly catchy songs peppered throughout this hidden gem, which are worth the price of admission alone.

Despite being one of the biggest flops at the box office for a movie based on a Saturday Night Live sketch, MacGruber has endured thanks to a passionate fanbase who can’t get enough of their favorite throat-ripping government operative. Starring Will Forte as a MacGuyver-esque American action hero, MacGruber races against the clock—and his own ineptitude as an explosives expert who sucks at disarming bombs—to save the world from Val Kilmer’s evil Van Cunth. Kirsten Wiig and Ryan Phillippe are along for the very R-rated ride, which heavily skewers ’80s action films like Cobra and the oeuvre of Steven Seagal. The end result is both an infinitely quotable and watchable laughfest that, 13 years later, spawned a long-deserved sequel series on Peacock.

Another R-rated LOL-filled comedy from the Bridesmaids team of director Paul Feig and star Melissa McCarthy, Spy is an action-packed send-up of James Bond and Jason Bourne movies that actually elevates both the comedy and espionage genre with a story that’s as hilarious as it is riveting. McCarthy stars as Susan Cooper, a Moneypenny-type desk jockey to a super suave secret agent (played by Jude Law). When Law’s character is seemingly assassinated, Susan is forced to go into the field to find his killers and stop a deadly arms dealer. Feig’s deft handling of the “fish out of water” comedy pairs well with the action-packed scope a globe-trotting spy movie would need, with McCarthy and scene-stealers Jason Statham and Rose Byrne providing Spy with most of its greatest and funniest bits.

The general premise of Tropic Thunder is memorable enough, with a group of actors stranded in a jungle and forced to adapt when their fictional war movie becomes all too real. But it’s really the performances that put this one over the top, specifically the main trio of Ben Stiller, Robert Downey, Jr., and Jack Black. But our favorite turn comes from an unrecognizable Tom Cruise, playing a very eccentric, dance-happy Hollywood executive.

What We Do In The Shadows is the rare big screen comedy to spawn a TV series that is just as funny—if not funnier. Part mockumentary, part horror movie parody, Taika Waititi and Jemaine Clement’s 2014 film is a brisk comedy full of dry humor and sarcastic observations about the everyday life of a vampire clan. Waititi and Clement, who also star and wrote the screenplay, find most of the film’s clever humor in the more mundane aspects of being an immortal bloodsucker. It’s a tonal tightrope, but the filmmakers walk it effortlessly.

Given the inspired ensemble cast and road trip comedy premise, Girls Trip was expected to be a hit. But no one was prepared for how big a hit it was. Regina Hall, Queen Latifah, Tiffany Haddish (in a star-making turn) and Jada Pinkett-Smith headline this inspired laffer that subverts the road-trip comedy premise with some very clever narrative swerves and legit heartwarming beats in a story about friendship and empowerment. Here’s hoping that one of the biggest comedy hits in recent memory gets its long-in-development sequel.

Knocked Up proved that writer/director Judd Apatow was not a one-hit wonder, and that his charming mix of hilarious but relatable situations was something audiences couldn’t get enough of when it came to R-rated comedies. Apatow seemed to have perfected his comedy formula in Knocked Up, where he pulled triple duty as writer, director, and producer. This sleeper hit from the summer of 2007 features an all-star lineup of Apatow faves and a satisfying story of unlikely romance between Seth Rogen and Katherine Heigl’s characters. And as with so many Apatow films, the characters are allowed to grow and evolve even as they behave like total stoner goofballs.

Forgetting Sarah Marshall is almost an anti-rom-com; it combines the tropes of that tried-and-true genre with a healthy (and hilarious) dose of raunchy comedy. After breaking up with his titular girlfriend (Kristen Bell), Jason Segel retreats to Hawaii where he struggles to avoid her and her new, libido-fueled lover (Russell Brand) when they end up staying at the same resort. Sarah Marshall is one of producer Judd Apatow’s most rewatchable R-rated comedies, thanks to the full-throated commitment of the cast headlined by Segel, who transitions from supporting player in previous Apatow films (see: Knocked Up) to endearing leading man.

High school comedies are well-trodden territory, offering few opportunities for “fresh takes.” Olivia Wilde, in her feature directorial debut, subverts that truism with Booksmart, an often moving comedy that belongs right up there with Superbad as one of the best teenage comedies ever made. Written by Emmy-winning scribe Emily Halpern (Black-ish), Booksmart follows best friends Amy (Kaitlyn Dever) and Molly (Beanie Feldstein) as they use the last days of their senior year in high school to reclaim their social status before college and the specter of adulthood take over. Reckless for the first time in their lives, Amy and Molly go to parties, flirt with sexual conquests, and literally car race to graduation as Wilde chronicles their right of passage with unflinching honesty and go-for-broke comedy. Her and the script’s attention to this world feels very lived-in and relatable, which makes all the witty punchlines land even harder.

One of 2005’s biggest hits, Wedding Crashers 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, Harold & Kumar Go To White Castle 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 Spider-Man: Into The Spider-Verse, 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 21 Jump Street. 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 22 Jump Street, which some fans consider to have pulled a Toy Story 2 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, Step Brothers, directed by future Oscar-winner Adam McKay (The Big Short), 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 Old School, 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 (Luke Wilson) and Beanie (Vince Vaughn) 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 This Is The End. 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 Police Academy hooked up, their offspring would be Super Troopers. 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.

Hot Fuzz, 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 Shaun Of The Dead or The World’s End. (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, The 40-Year-Old Virgin 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 Superbad. 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 Wet Hot American Summer. 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 Meatballs 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: First Day of Camp and Ten Years Later.

Borat 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 Hangover. 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 Bridesmaids—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.