As the 1990s gave way to the 21st century, Hollywood comedies saw a slow but certain paradigm shift. Profoundly informed by the internet and the jagged-edge zaniness of indie cinema, 2000s-era comedies toned down on experimental concepts for improvised scripts, smaller budgets, and lots and lots and lots of R-rated antics. The new millennium was funny as heck. Amid ܫa riotous decade, what comedies are actually the greatest of all time?
While the old ways still remained in place – with star-led vehicles and genre-bending productions occasionally eclipsing the weekend box office – the 2000s are forever remembered by its raunchiness, its simplicity, and a🤡ll the quotable zingers you'd repeat to your friends.
The 2000s are now a thing of the past. But let's remember the best of the෴m with the greatest 2000s comedies of all time.
35. Bruce Almighty (2003)
Jim Carrey reigns supreme in Bruce Almighty, a surprisingly secular comedy about a man who inherits God's powers. Carrey stars as a frustrated TV news reporter who is invited by God (Morgan Freeman) to wield his almighty powers on Earth. While God's omnipotent powers are fun for a while, Carrey's title character Bruce eventually finds that even all thཧe power in the universe can't control free will. A high-concept co𒊎medy blockbuster with then-cutting edge VFX, Bruce Almighty is a biblically good time.
34. Idiocracy (2006)
Since its 2006 release, Idiocracy has enjoyed a rather dubious legacy as a movie predictive of society and politics. From director Mike Judge, Idiocracy follows an Army librarian (Luke Wilson) who undergoes suspended animation and wakes up 500 years into the future. However, the futureಞ is anything but a utopia as Wilson re-enters a world dumbed down due to unchecked capitalism, poor infrastructure, and other societal ills. Idiocracy enjoys an unfortunate legacy, its name is mentioned anytime a politician says something ridiculous.
33. Miss Congeniality (2000)
She's got beauty, she's got grace – and she's got a license to uphold the law. Sandra Bullock stars in this hilarious comedy as Gracie Hart, a tough-as-nails FBI agent who gets a glamorous makeover to go undercover as a contestant in a national beauty pageant. Along for the ride is Michael Caine as her pageant mentor, who teaches Bullock to charm and glide her way to the crown and prevent a terrorist plot. Part romantic comedy (Benjamin Bratt plays her coworker and love interest), part ugly duckling narrative in 🦋the style of My Fair Lady and She's🐷 All That, Miss Congeniality hits just right, like April 25th.
32. Knocked Up (2007)
After Judd Apatow ch𓂃anged the vibe of studio comedies with The 40-Year-Old Virgin, the comedy auteur did it again with the help of Seth Rogen and Katherine Heigl. Two strangers – a slacke💜r (Rogen) and an ambitious entertainment journalist (Heigl) – deal with sudden parenthood after their one-night stand leads to pregnancy. Featuring more of Apatow's popular plain-spoken comedy style and an appealing central message of accidents becoming fate, Knocked Up is a real gut-buster.
23. Kung Fu Hustle (2004)
From action-comedy mastermind Stephen Chow and renowned ꦦchoreographer Yuen Woo-ping, Kung Fu Hustle packs a fist of hilarious fury. Set in 1940s China, an 𝓰aspiring gangster (played by Chow) stumbles into a slum ruled by eccentric landlords who are actually the world's greatest kung fu masters. Chow's main character soon finds himself at the center between the notorious Axe Gang and the high-kicking slumlords as the battle of the century begins. Kung Fu Hustle puts the "chop" in chop socky, blending absurd comical humor with legitimately dazzling fight scenes.
22. Dodgeball: A True Underdog Story (2004)
If you can dodge a wrench, you can dodge a ball. In Dodgeball: A True Underdog Story, Vince Vaughn competes against a comically over-the-top (and ⭕gloriously mustached) Ben Stiller as they dodge, dip, duck,🔯 dive, and dodge big red balls. The two men play rival gym owners who compete in professional dodgeball competition, with Vaughn's group rising from zeroes to heroes. From director Rawson Marshall Thurber, Dodgeball affectionately spoofs sports classics while giving its own spin on the genre. It has a lasting legacy in ESPN 8: The Ocho, a real cable channel for obscure sports that airs annually on April Fools' Day.
21. Superbad (2007)
Never has losing one's virginity been so hilarious. In Superbad, from director Greg Mottola and written by Seth Rogen and Evan Goldberg, a few try-hard high schoolers (played by Michael Cera, Jonah Hill, and Christopher Mintz-Plasse in his film debut) atﷺtempt to buy alcohol to get into a house party. Amid their final weeks in school, the party is their last chance to hook up with their crushes (Martha MacIsaac and Emma Stone, also in her film debut). What unfolds is a night unlike any other, with unexpected bonds forged with irresponsible cops. One of the last truly great high school comedies of the 2000s, Superbad was a toast to an end of an era.
20. Clerks 2 (2006)
Over a decade after Kevin Smith asserted his voice in the indie filmmaking scene, the New Jersey auteur returned to his ♍roots behind the counter in Clerks 2. Brian O'Halloran and Jeff Anderson return to their roles as Dante and Randal, two unambitious best friends who work for a burger chain after their home, the Quik-Stop convenience store, burns down. Now in their 30s and fearing the world is passing them by, Dante and Randall struggle through one more day of work before Dante moves away. A surprisingly heartwarming story about friendship tested against time, Clerks 2 boa✱sts a heart of gold with a filthy mouth.
19. Forgetting Sarah Marshall (2008)
When a TV show composer Peter (Jason Segel) is dumped by his celebrity girlfriend Sarah Marshall (Kristen Bell), Peter vacations in Hawaii only to run into Sarah and her obnoxious new boyfriend (R🔥ussell Brand) at the same resort. With the help of a kind and beautiful hotel receptionist (Mila Kunis), Peter learns to move on from heartbreaking in this compulsively rewatchable 2000s classic. Since its release, Jason Segel has at times promised to release the music of Peter's vampire musical.
18. Wet Hot American Summer (2001)
On the last day of a Maine summer camp in 1981, the overly hormonal counselors try to settle their final scores before the sun sets. Featuring an all-star ensemble including Janeane Garofalo, David Hyde Pierce, Elizabeth Banks, Christopher Meloni, Paul Rudd, Michael Ian Black, and even Bradley Cooper in his movie debut, Wet Hot American Summer is a sun-drenched satire of nostalgic 🐓teen and sex comedies of the '80s and '90s that cements its own R-rated legacy. While the movie bombed at the box office, its cult following throughout the 2000s led to a short-lived Netflix revival.
17. The Royal Tenenbaums (2001)
Following his breakout movies Bottle Rocket and Rushmore, Wes Anderson attained auteur status with his celebrated comedy-drama The Royal Tenenbaums. Billed as being based on a novel (which doesn't exist), The Royal Tenenbaums chronicles the unfulfilled potential of the Tenenbaums, a family of prodigies who wind up as disappointments i♊n their adulthood. While The Royal Tenenbaums grapples with heavy themes like abandonment, expectations, and the pains of old wounds, the movie exhibits Anderson's signature sensibilities that made him a creative force in the years to come.
16. Role Models (2008)
Floundering in their job hawking poisonous energy drinks to kids, irresponsible friends Danny (Paul Rudd) and Wheeler (Seann William Scott) wind up legally forced to perform community service mentorඣing troubled kids; Bobb'e J. Thompson and Christopher Mintz-Plasse co-star as the young boys in question. While Danny and Wheeler struggle at first to bond with their assigned kids, they later grow into deeply involved guardians. They even end up on the epic battlefields of a fantasy LARP to prove it. Filled with quotable zingers, Role Models is indeed a picture-perfect comedy to learn from.
15. Legally Blonde (2001)
Graduating from Harvard Law – what, like it's hard? In the movie that crowned Reese Witherspoon as Hollywood's premier sorori𓆉ty queen, the actress stars as a fashion merchandising student who attends Harvard Law School initially to win back her ex-boyfriend. But Elle Woods' priorities change when she discovers a real knack for the American judicial system. Based on Amanda Brown's then-unpublished novel (inspired by her own experiences as a law student who didn't fit in because of her interest in fashion), Legally Blonde made Wit🐼herspoon a star as she became the new face for beauty with brains.
14. Harold & Kumar Go to White Castle (2004)
After a night on the couch leads to the munchies, John Cho and Kal Penn – playing best friends Harold and Kumar – hit the road for some juicy White Castle burgers. But a quick ride through New Jersey suddenly becomes the adventure of a lifetime when Harold and Kumar get sidetracked and encounter all kinds of outlandish obstacles, from freaky mechanics to obnoxℱious skaters to runaway cheetahs to even Neil Patric꧑k Harris. In an era when Hollywood comedies were predominantly the domain for straight white guys, Harold and Kumar introduced a whole new shade to bromances.
13. School of Rock (2003)
All hail the God of Rock! In School of Rock from director Richard Linklater, down-on-his-luck👍 guitarist Dewey (Jack Black) becomes a substitute teacher and forms a rock band with his students to win a Battle of the Bands competition. Through the awesome power of music, Dewey becomes the teacher these prep 🌌school students actually needed as Dewey sees their singular talent and passions when no one else would. Heartwarming as it is hilarious, School of Rock totally shreds.
12. Borat! Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan (2006)
In the middle of the 2000s, you couldn't escape Borat. Spinning off from Sascha Baron Cohen's HBO series Da Ali G Show, th🍨e mockumentary Borat follows an inept journalist from Kazakhstan (played by Cohen) who is dispatched to America to educate his people on Western culture. Eventually the job goes sideways as Borat becomes obsessed with marrying Pamela Anderson after watching Baywatch reruns. While Cohen plays the hilarious role of an insensitive foreigner, it's Americans who are the butt of his jokes as our commercial-driven culture is roasted like flame-broiled fast food. In 2020, a long-awaited, similarly controversial sequel arose in Borat Subsequent Moviefilm.
11. Burn After Reading (2008)
Shortly after Joel and Ethan Cohen released their neo-noir masterpiece ෴No Country for Old Men, the directors brought some fresh air back into the room with their breezy black comedy Burn After Reading. Two inept and dimwitted gym employees, played by Frances McDormand and Brad Pitt, mistake a retired CIA analyst's memoir for top secret intel and try to sell it for a big payday. Chaos ensues. A lampoon of espionage 💖movies from a more grounded perspective, Burn After Reading is a hot mockery of Washington amid the problematic War on Terror.
10. Wedding Crashers (2004)
Owen Wilson and Vince Vaughn show what it means to really score in Wedding Crashers, a mega-hit comedy from 2005. John (Wilson) and Jeremy (Vaughn) are best friends who have mastered the art of crashing weddings to hook up with single women. But John and Jeremy are forced to change their ways when John actually falls in love☂ with a bridesmaid (Rachel McAdams); their attempts to keep up their ruse soon spiral out of control. With its even balance of raunchy and sweet, along with an enchanting McAdams as the lead love interest, it's no surprise that Wedding Crashers became the first-ever R-rated comedy to gross over $200 million at the American box office.
9. Hot Fuzz (2007)
In his third feature film, British director Edgar Wright blows up American action movies with his epic cop comedy🀅 Hot Fuzz. A razor-sharp London cop, Nicholas Angel (Simon Pegg) is promoted and transf💯erred to a quiet English village where almost nothing happens. But amid a series of murders and deaths, Angel teams up with buffoonish constable and action movie obsessive Danny (Nick Frost) to restore law and order. In its clever juxtaposition of bombastic Hollywood-style action with small-town English living, Hot Fuzz really booms as a sublime genre spoof.
8. The 40-Year-Old Virgin (2005)
When 40-year-old electronics store salesman Andy (Steve Carell) is revealed to be a virgin, his work buddies try their hardest to get him some overdue acti✃on. Although mishaps and misunderstandings keep shy Andy from finally surrendering his V-card, opportunity arises when he meets and falls in love with attractive single mother Trish (Catherine Keener). A game-changing movie that set a whole new tone for studio comedies to come, The 40-Year-Old Virgin is as foul as it i♒s sincere, a film loaded with rude zingers that come from a place of love.
7. Mean Girls (2004)
Fetch may still never happen, but Mean Girls is truly forever. Released in 2004 from director Mark Waters and writer Tina Fey (who has a supporting role), Mean Girls follows naive teenager Cady (Lindsay Lohan) who transfers to a suburban American high school after being homeschooled a🌳broad. As Cady befriends two other outcasts (Daniel Franzese and Lizzy Caplan), she draws the heat of ruthless rich girl Regina George (Rachel McAdams) who oversees a clique known as "The Plastics." A touchstone for multiple generations, Mean Girls succeeds on the strengths of its cast and its searing script that confronts high school drama with honesty.
6. Meet the Parents (2000)
Talk about a bunch of Fockers! In the box office smash Meet the Parents, directed by Jay Roach, male nurse Greg Focker (Ben Stiller) meets his girlfriend's parents (Robert De Niro and Blythe Danner) for the first time. Pressured to live up to lofty expectati♈ons, Greg tries to assert himself as a worthy romantic partner for their daughter Pam (Teri Polo), but it's really hard convincing De Niro when he's a no-nonsense retired CIA agent. With its universally relatable predicament and original execution, Meet the Parents is proof that first impressions are everything.
5. Little Miss Sunshine
An indie comedy classic, Little Miss Sunshine charts the comical cross-country road trip of a dysfunctional family as they pack into a Volkswagen Microbus for their daughter's beau📖ty pageant. Across many setbacks and heartbreak, the family grows closer than they ever have been. Unlike other major hit comedies, Little Miss Sunshine veers away from raunchiness and rambunctiousness for something more earnest and sincere; its subsequent success proves that audiences were eager to go along for the ride.
4. Kiss Kiss, Bang Bang (2005)
In this underrated crime classic from writer/director Shane Black, Robert Downey Jr. plays a petty thief who accidentally lands the role in a Hollywood crime project. Downey's character is tasked with shadowing a private eye (Val Kilmer) while he gets caught up in a real murder mystery that happens to involve an old childhood crush (Michelle Monaghan). Set in the seedy underworld that exists beneath gla🐠morous Los Angeles, Shane Black's genre homage toys with mystery detective 🎀tropes while delivering something totally fresh and new.
3. Ocean's Eleven (2001)
Brad Pitt, George Clooney, Matt Damon, and a murderer's row of supporting actors pull off the heist of the century in Ocean's Eleven. A modern remake of the Rat Pack classic from 196𒅌0, career criminal Danny Ocean (Pitt) assembles a team to steal $160 million from a Las Vegas casino magnate who just so happens to be the new lover of his ex-wife (played by Julia Roberts). A perfect studio com﷽edy that plays its winning hand just right, Ocean's Eleven is a cinematic jackpot.
2. Napoleon Dynamite (2004)
Perfectly capturing the new zeitgeist of new millennium malaise, the indie smash Napoleon Dynamite follows an awkward teenager (Jon Heder) in small-town Idaho who takes it upon himself to get 🍌his new friend, quiet Pedro (Efren Ramirez) elected as class president. From Jared and Jerusha Hess, Napoleon Dynamite remains renowned for its hilarious portrait of small-town America and a sense of humor found only on the margins. An idiosyncratic classic, Napoleon Dynamite signaled a vibe shift in American comedies to come.
1. Tropic Thunder (2008)
A Hollywood satire that no one could geꦉt enough of, Ben Stiller takes point in the ensemble blockbuster Tropic Thunder. Co-written and directed by Stiller, the movie follows a group of pampered Hollywood stars – played by Stiller, Jack Black, Brandon T. Jackson, and Robert Downey Jr. (in an Oscar-nominated performance) – who are dropped into Vietnam as pꦯart of prep work for an upcoming Vietnam War production. What no one expects is for them to land in real danger in the jungles of 'nam. Along with an exceptionally memorable performance by Tom Cruise as a ruthless studio executive, Tropic Thunder is all dynamite and napalm as one of the biggest and best comedies of the 21st century.
Eric Francisco is a freelance entertainment journalist and graduate of Rutgers University. If a movie or TV show has superheroes, spaceships, kung fu, or John Cena, he's your guy to make sense of it. A former senior writer at Inverse, his byline haꦛs also appeared at Vulture, The Daily Beast, Observer, and The Mary Sue. You can find him screaming at Devils hockey games or dodging enemy fire in Call of Duty: Warzone.
