Top 81 Ranked

The Greatest 2000s Comedy Movies Ranked

Relive the Decades Most Iconic Laughs and Cult Classics

Discover the ultimate list of the best comedy movies from the early millennium. From teen classics to slapstick hits, find your next favorite rewatch.

Draft Best 2000s Comedy Movies with friends and our judges will crown a winner!

About 2000s Comedy Movies

The turn of the millennium was a strange, frantic time for the movie business, but for comedy, it was the beginning of a golden age that we are only now starting to fully appreciate. The 2000s did not just produce funny movies; they fundamentally rewrote the rules for how humor functioned on the big screen. We entered the decade still lingering in the shadow of the nineties high-concept slapstick, but we left it with a brand of comedy that was grounded, improvised, and deeply obsessed with the awkward beauty of the human condition.

The early years of the decade were defined by a certain kind of fearless absurdity. This was the era of the Farrelly brothers and Ben Stiller, where the goal was often to see how far the boundaries of good taste could be pushed. Zoolander and Old School captured a specific kind of frat-boy energy that ruled the box office, leaning heavily on the rising power of the Frat Pack. This informal group of actors, including Will Ferrell, Vince Vaughn, and Owen Wilson, dominated the culture by playing men who refused to grow up. Anchorman: The Legend of Ron Burgundy remains the pinnacle of this style, a film so quotable it practically replaced the English language for teenagers in 2004.

However, the most significant shift occurred mid-decade with the ascent of Judd Apatow. With The 40-Year-Old Virgin and Superbad, the genre pivoted away from caricatures and toward something far more recognizable. Apatow ushered in the age of the conversational comedy. Gone were the tight, stage-managed scripts of the past. In their place came long, sprawling scenes of characters just talking, riffing on pop culture and their own insecurities. This era prioritized chemistry over choreography. It was during this time that actors like Seth Rogen and Jonah Hill became the unlikely faces of a new, relatable masculinity.

Cultural shifts played a massive role in this evolution. The post-9/11 landscape created a vacuum that comedy rushed to fill with both escapism and satire. While some films offered pure distraction, others like Mean Girls used humor to dissect the brutal social hierarchies of American life with surgical precision. Mean Girls proved that smart, female-led comedies could be both massive commercial hits and enduring cultural touchstones. Simultaneously, the rise of the internet began to change how we consumed jokes. Filmmakers started to bake meme-worthy moments into their scripts, knowing that a funny face or a specific line of dialogue would live forever on message boards and early social media.

By the time the decade closed with The Hangover in 2009, comedy had become bigger and more expensive, yet also more comfortable with silence and cringe. The 2000s taught us that a movie could be crude and heartfelt at the same exact time. It was a decade of transition where the gross-out humor of the past met the character-driven depth of the future, creating a library of films that still define what makes us laugh today. We may have moved on to different trends, but the DNA of the 2000s comedy still runs through everything from modern sitcoms to the latest indie darlings.

The Complete Rankings

Based on the top picks in drafts on SnakeDrafts

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81
2000s Comedy in Nacho Libre (2006)
Nacho Libre
2006

Ignacio, a disrespected cook at a Mexican monastery, can barely afford to feed the orphans who live there. Inspired by a local wrestling hero, he decides to moonlight as the not-so-famous Luchador "Nacho Libre" to earn money for the monastery -- not to mention the admiration of beautiful nun Sister Encarnación.

Comedy
1h 32m
Jared Hess
Jack Black, Ana de la Reguera, Héctor Jiménez, Darius Rose
80
2000s Comedy in Paul Blart: Mall Cop (2009)
Paul Blart: Mall Cop
2009

When a shopping mall is taken over by a gang of organized crooks, it's up to a mild-mannered security guard to save the day.

Action
Adventure
1h 31m
Steve Carr
Kevin James, Keir O'Donnell, Jayma Mays, Raini Rodriguez
79
2000s Comedy in Just Married (2003)
Just Married
2003

Although Tom Leezak and Sarah McNerney come from different worlds, they are both unexpectedly swept off their feet after their first meeting. They quickly fall in love and plan to get married, despite opposition from Sarah's uptight, rich family. After their wedding, the happy couple sets off - with the highest of hopes and ideals about love and marriage - on what they expect will be the perfect honeymoon in Italy. Thanks to a relentless string of bad luck with one disaster after another, and an impromptu visit from Sarah's wealthy one-time ex-lover Peter Prentiss, the newlyweds experience the honeymoon from hell that tests the limits of their young love. Is it worth throwing away their love and marriage?

Romance
Comedy
1h 35m
Shawn Levy
Ashton Kutcher, Brittany Murphy, Christian Kane, David Moscow

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78
2000s Comedy in Jackass Number Two (2006)
Jackass Number Two
2006

Jackass Number Two is a compilation of various stunts, pranks and skits, and essentially has no plot. Chris Pontius, Johnny Knoxville, Steve-O, Bam Margera, and the whole crew return to the screen to raise the stakes higher than ever before.

Action
Comedy
1h 32m
Jeff Tremaine
Johnny Knoxville, Bam Margera, Steve-O, Chris Pontius
77
2000s Comedy in Scary Movie (2000)
Scary Movie
2000

A familiar-looking group of teenagers find themselves being stalked by a more-than-vaguely recognizable masked killer! As the victims begin to pile up and the laughs pile on, none of your favorite scary movies escape the razor-sharp satire of this outrageously funny parody!

Comedy
1h 28m
Keenen Ivory Wayans
Anna Faris, Regina Hall, Marlon Wayans, Shawn Wayans
76
2000s Comedy in Talladega Nights: The Ballad of Ricky Bobby (2006)
Talladega Nights: The Ballad of Ricky Bobby
2006

The fastest man on four wheels, Ricky Bobby, is one of the greatest drivers in NASCAR history. A big, hairy American winning machine, Ricky has everything a dimwitted daredevil could want, a luxurious mansion, a smokin' hot wife, and all the fast food he can eat. But Ricky's turbo-charged lifestyle hits an unexpected speed bump when he's bested by flamboyant Euro-idiot Jean Girard and reduced to a fear-ridden wreck.

75
2000s Comedy in The Dukes of Hazzard (2005)
The Dukes of Hazzard
2005

Cousins, Bo and Luke Duke, with the help of their eye-catching cousin, Daisy and moonshine-running Uncle Jesse, try and save the family farm from being destroyed by Hazzard County's corrupt commissioner, Boss Hogg. Their efforts constantly find the 'Duke Boys' eluding authorities in 'The General Lee', their 1969 orange Dodge Charger that keeps them one step ahead of the dimwitted antics of the small southern town's Sheriff, Roscoe P. Coltrane.

Comedy
Adventure
1h 44m
Jay Chandrasekhar
Johnny Knoxville, Seann William Scott, Jessica Simpson, Willie Nelson
74
2000s Comedy in Nancy Drew (2007)
Nancy Drew
2007

Intrepid teenage private eye Nancy Drew heads to Tinseltown with her father to investigate the unsolved murder of a movie star in this old-fashioned whodunit based on Carolyn Keene's popular series of books for young adults. But can the small-town girl cut through the Hollywood hype to solve the case?

Family
Adventure
1h 39m
Andrew Fleming
Emma Roberts, Max Thieriot, Josh Flitter, Rachael Leigh Cook
73
2000s Comedy in The Sweetest Thing (2002)
The Sweetest Thing
2002

Christina's love life is stuck in neutral. After years of avoiding the hazards of a meaningful relationship, one night while club-hopping with her girlfriends, she meets Peter, her perfect match. Fed up with playing games, she finally gets the courage to let her guard down and follow her heart, only to discover that Peter has suddenly left town. Accompanied by Courtney, she sets out to capture the one that got away.

Romance
Comedy
1h 24m
Roger Kumble
Cameron Diaz, Christina Applegate, Selma Blair, Thomas Jane
72
2000s Comedy in Johnny English (2003)
Johnny English
2003

A lowly pencil pusher working for MI7, Johnny English is suddenly promoted to super spy after Agent One is assassinated and every other agent is blown up at his funeral. When a billionaire entrepreneur sponsors the exhibition of the Crown Jewels—and the valuable gems disappear on the opening night and on English's watch—the newly-designated agent must jump into action to find the thief and recover the missing gems.

Adventure
Action
1h 27m
Peter Howitt
Rowan Atkinson, Natalie Imbruglia, Ben Miller, John Malkovich
71
2000s Comedy in Disaster Movie (2008)
Disaster Movie
2008

Over the course of one evening, an unsuspecting group of twenty-somethings find themselves bombarded by a series of natural disasters and catastrophic events.

Comedy
Science Fiction
1h 27m
Aaron Seltzer
Matt Lanter, Vanessa Lachey, Gary 'G. Thang' Johnson, Nicole Parker
70
2000s Comedy in Jackass: The Movie (2002)
Jackass: The Movie
2002

Johnny Knoxville and his band of maniacs perform a variety of stunts and gross-out gags on the big screen for the first time. They wander around Japan in panda outfits, wreak havoc on a once civilized golf course, they even do stunts involving LIVE alligators, and so on.

Action
Comedy
1h 25m
Jeff Tremaine
Johnny Knoxville, Bam Margera, Steve-O, Chris Pontius
69
2000s Comedy in Wild Hogs (2007)
Wild Hogs
2007

Restless and ready for an adventure, four suburban bikers leave the safety of their subdivision and head out on the open road. But complications ensue when they cross paths with an intimidating band of New Mexico bikers known as the Del Fuegos.

Action
Adventure
1h 40m
Walt Becker
68

After a mobster agrees to cooperate with an FBI investigation in order to stay out of prison, he's relocated by the authorities to a life of suburban anonymity as part of a witness protection program. It's not long before a couple of his new neighbours figure out his true identity and come knocking to see if he'd be up for one more hit—suburban style.

Comedy
Crime
1h 38m
Jonathan Lynn
67
2000s Comedy in Accepted (2006)
Accepted
2006

A high school slacker who's rejected by every school he applies to opts to create his own institution of higher learning, the South Harmon Institute of Technology, on a rundown piece of property near his hometown.

Comedy
1h 33m
Steve Pink
Justin Long, Jonah Hill, Blake Lively, Adam Herschman
66
2000s Comedy in Sweet Home Alabama (2002)
Sweet Home Alabama
2002

New York fashion designer, Melanie Carmichael suddenly finds herself engaged to the city's most eligible bachelor. But her past holds many secrets—including Jake, the redneck husband she married in high school, who refuses to divorce her. Bound and determined to end their contentious relationship once and for all, Melanie sneaks back home to Alabama to confront her past.

Comedy
Romance
1h 48m
Andy Tennant
Reese Witherspoon, Josh Lucas, Patrick Dempsey, Candice Bergen
65
2000s Comedy in Click (2006)
Click
2006

A married workaholic, Michael Newman doesn't have time for his wife and children, not if he's to impress his ungrateful boss and earn a well-deserved promotion. So when he meets Morty, a loopy sales clerk, he gets the answer to his prayers: a magical remote that allows him to bypass life's little distractions with increasingly hysterical results.

Comedy
Drama
1h 47m
Frank Coraci
64
2000s Comedy in American Pie 2 (2001)
American Pie 2
2001

After a year apart - attending different schools, meeting different people - the guys rent a beach house and vow to make this the best summer ever. As it turns out, whether that will happen or not has a lot to do with the girls. Between the wild parties, outrageous revelations and yes, a trip to band camp, they discover that times change and people change, but in the end, it's all about sticking together.

Comedy
Romance
1h 51m
J.B. Rogers
Jason Biggs, Thomas Ian Nicholas, Chris Klein, Seann William Scott
63
2000s Comedy in Analyze That (2002)
Analyze That
2002

The mafia's Paul Vitti is back in prison and will need some serious counseling when he gets out. Naturally, he returns to his analyst Dr. Ben Sobel for help and finds that Sobel needs some serious help himself as he has inherited the family practice, as well as an excess stock of stress.

Comedy
Crime
Robert De Niro, Billy Crystal, Lisa Kudrow, Joe Viterelli
62
2000s Comedy in Just Friends (2005)
Just Friends
2005

While visiting his hometown during Christmas, a man comes face-to-face with his old high school crush whom he was best friends with – a woman whose rejection of him turned him into a ferocious womanizer.

Comedy
Romance
1h 34m
Roger Kumble
Ryan Reynolds, Amy Smart, Anna Faris, Chris Klein
61
2000s Comedy in The Benchwarmers (2006)
The Benchwarmers
2006

A trio of guys try and make up for missed opportunities in childhood by forming a three-player baseball team to compete against standard little league squads.

Comedy
1h 25m
Dennis Dugan
Rob Schneider, David Spade, Jon Heder, Molly Sims
60
2000s Comedy in White Chicks (2004)
White Chicks
2004

Two FBI agent brothers, Marcus and Kevin Copeland, accidentally foil a drug bust. To avoid being fired they accept a mission escorting a pair of socialites to the Hamptons--but when the girls are disfigured in a car accident, they refuse to go. Left without options, Marcus and Kevin decide to pose as the sisters, transforming themselves from black men into rich white women.

Comedy
Crime
1h 49m
Keenen Ivory Wayans
Shawn Wayans, Marlon Wayans, Frankie Faison, Terry Crews
59
2000s Comedy in Charlie Bartlett (2008)
Charlie Bartlett
2008

Awkward teenager Charlie Bartlett has trouble fitting in at a new high school. Charlie needs some friends fast, and decides that the best way to find them is to appoint himself the resident psychiatrist. He becomes one of the most popular guys in school by doling out advice and, occasionally, medication, to the student body.

Comedy
Drama
1h 37m
Jon Poll
Anton Yelchin, Robert Downey Jr., Hope Davis, Kat Dennings
58

When North Korean ruler Kim Jong-il orchestrates a global terrorist plot, it's up to the heavily armed, highly specialized Team America unit to stop his dastardly scheme. The group, which has recruited troubled Broadway actor Gary Johnston, not only has to face off against Jong-il, but they must also contend with the Film Actors Guild, a cadre of Hollywood liberals at odds with Team America's 'policing the world' tactics.

Adventure
Action
1h 38m
Trey Parker
Trey Parker, Matt Stone, Kristen Miller, Chelsea Marguerite
57
2000s Comedy in Envy (2004)
Envy
2004

A man becomes increasingly jealous of his friend's newfound success.

56
2000s Comedy in The Ringer (2005)
The Ringer
2005

Pressured by a greedy uncle and a pile of debt, lovable loser Steve Barker resorts to an unthinkable, contemptible, just-crazy-enough-to-work scheme. He pretends to be mentally challenged to rig the upcoming Special Olympics and bring home the gold. But when Steve's fellow competitors get wise to the con, they inspire him to rise to the greatest challenge of all: becoming a better person.

Comedy
1h 34m
Barry W. Blaustein
Johnny Knoxville, Brian Cox, Katherine Heigl, Luis Ávalos
55
2000s Comedy in Kangaroo Jack (2003)
Kangaroo Jack
2003

Two childhood friends — a New York hairstylist and a wanna-be musician — get mixed-up with the mob and are forced to deliver $50,000 to Australia, but things go all wrong when the money is lost to a wild kangaroo.

Action
Adventure
1h 29m
David McNally
Jerry O'Connell, Anthony Anderson, Estella Warren, Christopher Walken
54

When the local FBI office receives a letter from a terrorist known only as 'The Citizen', it's quickly determined that he's planning his next act at the Miss America beauty pageant. Because tough-as-nails Gracie Hart is the only female Agent at the office, she's chosen to go undercover as the contestant from New Jersey.

Comedy
Crime
1h 50m
Donald Petrie
Sandra Bullock, Benjamin Bratt, Heather Burns, Michael Caine
53
2000s Comedy in Starsky & Hutch (2004)
Starsky & Hutch
2004

Join uptight David Starsky and laid-back Ken "Hutch" Hutchinson as they're paired for the first time as undercover cops. The new partners must overcome their differences to solve an important case with help from street informant Huggy Bear and persuasive criminal Reese Feldman.

Comedy
Crime
52
2000s Comedy in Zack and Miri Make a Porno (2008)
Zack and Miri Make a Porno
2008

Lifelong platonic friends Zack and Miri look to solve their respective cash-flow problems by making an adult film together. As the cameras roll, however, the duo begin to sense that they may have more feelings for each other than they previously thought.

Comedy
Romance
Seth Rogen, Elizabeth Banks, Craig Robinson, Gerry Bednob
51

Andrew returns to his hometown for his mother’s funeral, a journey that reconnects him with old friends. The trip coincides with his decision to stop taking his powerful antidepressants. A chance meeting with Sam—a girl also struggling with various maladies—opens up the possibility of rekindling emotional connections, confronting his psychologist father, and perhaps beginning a new life.

Comedy
Drama
1h 42m
Zach Braff
Zach Braff, Natalie Portman, Ian Holm, Peter Sarsgaard
50
2000s Comedy in Get Over It (2001)
Get Over It
2001

When Berke Landers, a popular high school basketball star, gets dumped by his life-long girlfriend, Allison, he soon begins to lose it. But with the help of his best friend Felix's sister Kelly, he follows his ex into the school's spring musical. Thus ensues a love triangle loosely based upon Shakespeare's "A Midsummer Night's Dream", where Berke is only to find himself getting over Allison and beginning to fall for Kelly.

Comedy
Romance
1h 27m
Tommy O'Haver
Kirsten Dunst, Ben Foster, Melissa Sagemiller, Sisqó
49
2000s Comedy in Made of Honor (2008)
Made of Honor
2008

Tom and Hannah have been platonic friends for 10 years. He's a serial dater, while she wants marriage but hasn't found Mr. Right. Just as Tom is starting to think that he is relationship material after all, Hannah gets engaged. When she asks Tom to be her 'maid' of honor, he reluctantly agrees just so he can attempt to stop the wedding and woo her.

Comedy
Romance
1h 41m
Paul Weiland
Patrick Dempsey, Michelle Monaghan, Kevin McKidd, Kadeem Hardison
48
2000s Comedy in Failure to Launch (2006)
Failure to Launch
2006

At 35, Tripp has an interesting job, a hip car, a passion for sailing, an active dating life, and a great house - trouble is, he still lives with his parents, Al and Sue, who are not happy about it. Al and Sue are fascinated when friends whose adult son has recently moved away from home reveal they hired an expert to help. In desperation to push Tripp out of the nest once and for all, Al and Sue hatch a plan to hire Paula, an "interventionist," who has a formula in these cases.

47
2000s Comedy in Along Came Polly (2004)
Along Came Polly
2004

Reuben Feffer is a guy who's spent his entire life playing it safe. Polly Prince is irresistible as a free-spirit who lives for the thrill of the moment. When these two comically mismatched souls collide, Reuben's world is turned upside down, as he makes an uproarious attempt to change his life from middle-of-the-road to totally-out-there.

Comedy
Romance
1h 30m
John Hamburg
46
2000s Comedy in Shallow Hal (2001)
Shallow Hal
2001

After taking his dying father's advice, Hal dates only the embodiments of female physical perfection. But that all changes after Hal has an unexpected run-in with self-help guru Tony Robbins. Intrigued by Hal's shallowness, Robbins hypnotizes him into seeing the beauty that exists even in the least physically appealing women. Hal soon falls for Rosemary, but he doesn't realize that his gorgeous girlfriend is actually a 300-pound-not-so-hottie.

Comedy
Romance
1h 54m
Bobby Farrelly
Jack Black, Gwyneth Paltrow, Jason Alexander, Joe Viterelli
45
2000s Comedy in Fun with Dick and Jane (2005)
Fun with Dick and Jane
2005

After Dick Harper loses his job at Globodyne in an Enron-esque collapse, he and his wife, Jane, turn to crime in order to handle the massive debt they now face. Two intelligent people, Dick and Jane actually get pretty good at robbing people and even enjoy it -- but they have second thoughts when they're reminded that crime can hurt innocent people. When the couple hears that Globodyne boss Jack McCallister actually swindled the company, they plot revenge.

Comedy
Crime
1h 30m
Dean Parisot
44
2000s Comedy in The Break-Up (2006)
The Break-Up
2006

Pushed to the breaking-up point after their latest 'why can't you do this one little thing for me?' argument, Brooke calls it quits with her boyfriend Gary. What follows is a hilarious series of remedies, war tactics, overtures and undermining tricks – all encouraged by the former couple's friends and confidantes …and the occasional total stranger! When neither ex is willing to move out of their shared apartment, the only solution is to continue living as hostile roommates until one of them reaches breaking point.

43
2000s Comedy in 50 First Dates (2004)
50 First Dates
2004

Henry is a player skilled at seducing women. But when this veterinarian meets Lucy, a girl with a quirky problem when it comes to total recall, he realizes it's possible to fall in love all over again…and again, and again. That's because the delightful Lucy has no short-term memory, so Henry must woo her day after day until he finally sweeps her off her feet.

Comedy
Romance
1h 39m
Peter Segal
42
2000s Comedy in 28 Days (2000)
28 Days
2000

After getting into a car accident while drunk on the day of her sister's wedding, Gwen Cummings is given a choice between prison or a rehab center. She chooses rehab, but is extremely resistant to taking part in any of the treatment programs they have to offer, refusing to admit that she has an alcohol addiction.

Comedy
Drama
1h 43m
Betty Thomas
41
2000s Comedy in Burn After Reading (2008)
Burn After Reading
2008

When a disc containing memoirs of a former CIA analyst falls into the hands of gym employees, Linda and Chad, they see a chance to make enough money for Linda to have life-changing cosmetic surgery. Predictably, events whirl out of control for the duo, and those in their orbit.

40
2000s Comedy in The Devil Wears Prada (2006)
The Devil Wears Prada
2006

A young woman from the Midwest gets more than she bargained for when she moves to New York to become a writer and ends up as the assistant to the tyrannical, larger-than-life editor-in-chief of a major fashion magazine.

Drama
Comedy
1h 49m
David Frankel
39
2000s Comedy in Hot Fuzz (2007)
Hot Fuzz
2007

Former London constable Nicholas Angel finds it difficult to adapt to his new assignment in the sleepy British village of Sandford. Not only does he miss the excitement of the big city, but he also has a well-meaning oaf for a partner. However, when a series of grisly accidents rocks Sandford, Angel smells something rotten in the idyllic village.

Crime
Action
2h 1m
Edgar Wright
Simon Pegg, Nick Frost, Jim Broadbent, Paddy Considine
38
2000s Comedy in I Love You, Man (2009)
I Love You, Man
2009

Peter Klaven is a successful real estate agent who, upon getting engaged to the woman of his dreams, Zooey, discovers, to his dismay and chagrin, that he has no male friend close enough to serve as his Best Man. Peter immediately sets out to rectify the situation, embarking on a series of bizarre and awkward "man-dates."

Comedy
Romance
1h 45m
John Hamburg
37
2000s Comedy in Adventureland (2009)
Adventureland
2009

It's the summer of 1987, and recent college grad James Brennan can't wait to begin his long-anticipated dream trip to Europe. Unfortunately, James' plans come to a screeching halt when his parents announce that they are unable to subsidize his trip. Forced to take a job at the local amusement park, James prepares for the worst summer ever, until he finds love with a captivating co-worker named Em.

Comedy
Drama
1h 47m
Greg Mottola
36
2000s Comedy in Mr. & Mrs. Smith (2005)
Mr. & Mrs. Smith
2005

A husband and wife struggle to keep their marriage alive until they realize they are both secretly working as assassins. Now, their respective assignments require them to kill each other.

Action
Comedy
2h 0m
Doug Liman
35
2000s Comedy in Juno (2007)
Juno
2007

Faced with an unplanned pregnancy, sixteen year old high-schooler, Juno MacGuff, makes an unusual decision regarding her unborn child.

Comedy
Drama
1h 36m
Jason Reitman
Elliot Page, Michael Cera, Jennifer Garner, Jason Bateman
34

A stoner and his dealer are forced to go on the run from the police after the pothead witnesses a cop commit a murder.

Action
Comedy
1h 51m
David Gordon Green
33

When megalomaniacal White Goodman, the owner of a trendy, high-end fitness center, makes a move to take over the struggling local gym run by happy-go-lucky Pete La Fleur, there's only one way for La Fleur to fight back: dodgeball. Aided by a dodgeball guru and Goodman's attorney, La Fleur and his rag-tag team of underdogs launch a knock-down, drag-out battle in which the winner takes all.

Comedy
1h 33m
Rawson Marshall Thurber
Vince Vaughn, Christine Taylor, Ben Stiller, Rip Torn
32

Eight very different couples deal with their love lives in various loosely interrelated tales all set during a frantic month before Christmas in London.

Comedy
Romance
2h 15m
Richard Curtis
31
2000s Comedy in Role Models (2008)
Role Models
2008

Two salesmen trash a company truck on an energy drink-fueled bender. Upon their arrest, the court gives them a choice: do hard time or spend 150 service hours with a mentorship program. After one day with the kids, however, jail doesn't look half bad.

Comedy
1h 39m
David Wain
Seann William Scott, Paul Rudd, Christopher Mintz-Plasse, Bobb'e J. Thompson
30
2000s Comedy in Yes Man (2008)
Yes Man
2008

Carl Allen, a guy whose life is going nowhere, signs up for a self-help program based on one simple covenant: say yes to everything…and anything.

Comedy
Romance
1h 44m
Peyton Reed
Jim Carrey, Zooey Deschanel, Bradley Cooper, John Michael Higgins
29
2000s Comedy in 13 Going on 30 (2004)
13 Going on 30
2004

After total humiliation at her thirteenth birthday party, Jenna Rink wants to just hide until she's thirty. Thanks to some magic wishing dust, Jenna's prayer has been answered. With a knockout body, a fabulous wardrobe, an athlete boyfriend, a dream job, and superstar friends, this can't be a better life. But soon Jenna realizes that adult life isn’t as easy as she hoped for.

Comedy
Fantasy
1h 38m
Gary Winick
28
2000s Comedy in The Girl Next Door (2004)
The Girl Next Door
2004

Exceptionally ambitious high schooler Matthew has aspirations for a career in politics when he falls in love with his gorgeous 19-year-old neighbor, Danielle. But Matthew's bright future is jeopardized when he finds Danielle was once a porn star. As Danielle's past catches up with her, Matthew's love for her forces him to re-evaluate his goals.

Comedy
Romance
1h 50m
Luke Greenfield
Emile Hirsch, Elisha Cuthbert, Timothy Olyphant, Christopher Rodriguez Marquette
27
2000s Comedy in EuroTrip (2004)
EuroTrip
2004

When Scott learns that his longtime cyber-buddy from Berlin is a gorgeous young woman, he and his friends embark on a trip across Europe.

Comedy
1h 32m
Jeff Schaffer
Scott Mechlowicz, Jacob Pitts, Michelle Trachtenberg, Travis Wester
26

In the deep south during the 1930s, three escaped convicts search for hidden treasure while a relentless lawman pursues them.

Adventure
Comedy
1h 47m
Joel Coen
25

You'd better watch out - Santa Claus Willie T. Soke is coming to town, and he doesn't care if you've been naughty or nice. Wille's favorite holiday tradition is to fill his sacks with loot lifted from shopping malls across the country. But this year his plot gets derailed by a wisecracking store detective, a sexy bartender, and a kid who's convinced Willie is the real Santa Claus.

Drama
Comedy
1h 32m
Terry Zwigoff
Billy Bob Thornton, Tony Cox, Lauren Graham, Brett Kelly
24

Royal Tenenbaum and his wife Etheline had three children and then they separated. All three children are extraordinary --- all geniuses. Virtually all memory of the brilliance of the young Tenenbaums was subsequently erased by two decades of betrayal, failure, and disaster. Most of this was generally considered to be their father's fault. "The Royal Tenenbaums" is the story of the family's sudden, unexpected reunion one recent winter.

23

When actress Sarah Marshall dumps aspiring musician Peter Bretter for rock star Aldous Snow, Peter's world comes crashing down. His best friend Brian suggests that Peter should get away from everything and to fly off to Hawaii to escape all his problems. After arriving in Hawaii and meeting the beautiful receptionist Rachel Jansen, Peter is shocked to see not only Aldous in Hawaii, but also Sarah.

Comedy
Romance
1h 51m
Nicholas Stoller
Jason Segel, Kristen Bell, Mila Kunis, Russell Brand
22
2000s Comedy in Harold & Kumar Go to White Castle (2004)
Harold & Kumar Go to White Castle
2004

Nerdy accountant Harold and his irrepressible friend, Kumar, get stoned watching television and find themselves utterly bewitched by a commercial for White Castle. Convinced there must be one nearby, the two set out on a late-night odyssey that takes them deep into New Jersey. Somehow, the boys manage to run afoul of rednecks, cops and even a car-stealing Neil Patrick Harris before getting anywhere near their beloved sliders.

Comedy
Adventure
1h 28m
Danny Leiner
John Cho, Kal Penn, Paula Garcés, Neil Patrick Harris
21

Bruce Nolan toils as a "human interest" television reporter in Buffalo, NY, but despite his high ratings and the love of his beautiful girlfriend, Bruce remains unfulfilled. At the end of the worst day in his life, he angrily ridicules God — and the Almighty responds, endowing Bruce with all of His divine powers.

Fantasy
Comedy
1h 41m
Tom Shadyac
20

Fashionable sorority queen Elle Woods has it all, but, she wants nothing more than to be Mrs. Warner Huntington III. But he dumps her before heading to Harvard Law School. Elle rallies all of her resources and gets into Harvard, determined to win him back. While there, she figures out that there is more to herself than just good looks.

Comedy
1h 36m
Robert Luketic
Reese Witherspoon, Luke Wilson, Selma Blair, Matthew Davis
19
2000s Comedy in Hitch (2005)
Hitch
2005

Dating coach Alex 'Hitch' Hitchens mentors a bumbling client, Albert, who hopes to win the heart of the glamorous Allegra Cole. While Albert makes progress, Hitch faces his own romantic setbacks when proven techniques fail to work on Sara Melas, a tabloid reporter digging for dirt on Allegra Cole's love life. When Sara discovers Hitch's connection to Albert – now Allegra's boyfriend – it threatens to destroy both relationships.

Comedy
Drama
1h 58m
Andy Tennant
Will Smith, Eva Mendes, Kevin James, Amber Valletta
18

A family loaded with quirky, colorful characters piles into an old van and road trips to California for little Olive to compete in a beauty pageant.

Comedy
Drama
1h 42m
Jonathan Dayton
17

Fired from his band and hard up for cash, guitarist and vocalist Dewey Finn finagles his way into a job as a fifth-grade substitute teacher at a private school, where he secretly begins teaching his straight-A students the finer points of rock 'n' roll and the power of sticking it to the man. But as the school’s stern principal closes in and the Battle of the Bands looms, Dewey risks everything to prove that rock ’n’ roll can change lives.

16
2000s Comedy in Old School (2003)
Old School
2003

Three friends attempt to recapture their glory days by opening up a fraternity near their alma mater.

15

A listless and alienated teenager decides to help his new friend win the class presidency in their small western high school, while he must deal with his bizarre family life back home.

Comedy
1h 35m
Jared Hess
Jon Heder, Efren Ramirez, Tina Majorino, Aaron Ruell
14

John and his buddy Jeremy are emotional criminals who know how to use a woman's hopes and dreams for their own carnal gain. Their modus operandi: crashing weddings. Normally, they meet guests who want to toast the romantic day with a random hook-up. But when John meets Claire, he discovers what true love – and heartache – feels like.

Comedy
Romance
1h 59m
David Dobkin
13

A slacker and a career-driven woman accidentally conceive a child after a one-night stand. As they try to make the relationship work, they must navigate the challenges of parenthood and their differences in lifestyle and maturity.

Comedy
Romance
2h 9m
Judd Apatow
12

A group of self-absorbed actors set out to make the most expensive war film ever. After ballooning costs force the studio to cancel the movie, the frustrated director refuses to stop shooting, leading his cast into the jungles of Southeast Asia, where they encounter real bad guys.

Action
Comedy
11

Andy Stitzer has a pleasant life with a nice apartment and a job stamping invoices at an electronics store. But at age 40, there's one thing Andy hasn't done, and it's really bothering his sex-obsessed male co-workers: Andy is still a virgin. Determined to help Andy get laid, the guys make it their mission to de-virginize him. But it all seems hopeless until Andy meets small business owner Trish, a single mom.

Comedy
Romance
1h 56m
Judd Apatow
Steve Carell, Catherine Keener, Paul Rudd, Romany Malco
10

Greg Focker is ready to marry his girlfriend, Pam, but before he pops the question, he must win over her formidable father, humorless former CIA agent Jack Byrnes, at the wedding of Pam's sister. As Greg bends over backward to make a good impression, his visit to the Byrnes home turns into a hilarious series of disasters, and everything that can go wrong does, all under Jack's critical, hawklike gaze.

Comedy
Romance
1h 48m
Jay Roach
Why it ranks

The film perfected the comedy of excruciating discomfort by pitting Ben Stiller’s everyman neurosis against Robert De Niro’s intimidating legacy, turning domestic tension into a high-stakes psychological battlefield.

9
2000s Comedy in Elf (2003)
2003

When young Buddy falls into Santa's gift sack on Christmas Eve, he's transported back to the North Pole and raised as a toy-making elf by Santa's helpers. But as he grows into adulthood, he can't shake the nagging feeling that he doesn't belong. Buddy vows to visit Manhattan and find his real dad, a workaholic.

Comedy
Family
Why it ranks

Rarely does a modern holiday film capture such unadulterated sincerity. Will Ferrell’s fish-out-of-water performance bypasses irony entirely to deliver a masterclass in joyful, wide-eyed physical humor.

8
2000s Comedy in Shaun of the Dead (2004)
Shaun of the Dead
2004

Shaun lives a supremely uneventful life, which revolves around his girlfriend, his mother, and, above all, his local pub. This gentle routine is threatened when the dead return to life and make strenuous attempts to snack on ordinary Londoners.

Horror
Comedy
1h 39m
Edgar Wright
Simon Pegg, Nick Frost, Kate Ashfield, Lucy Davis
Why it ranks

Edgar Wright’s kinetic direction birthed the 'Zom-Com,' a meticulously paced tribute to horror tropes that manages to be as emotionally resonant as it is breathtakingly clever and gore-streaked.

7

Clear the runway for Derek Zoolander, VH1's three-time male model of the year. His face falls when hippie-chic Hansel scooters in to steal this year's award. The evil fashion guru Mugatu seizes the opportunity to turn Derek into a killing machine. It's a well-designed conspiracy and only with the help of Hansel and a few well-chosen accessories like Matilda can Derek make the world safe for male models everywhere.

Comedy
Why it ranks

This satire of the fashion industry thrives on a unique brand of high-concept vacancy, utilizing Ben Stiller’s impeccable physical comedy to lampoon the vanity and vapidity of the turn-of-the-century elite.

6
2000s Comedy in Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan (2006)
Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan
2006

Kazakh journalist Borat Sagdiyev travels to America to make a documentary. As he zigzags across the nation, Borat meets real people in real situations with hysterical consequences. His backwards behavior generates strong reactions around him exposing prejudices and hypocrisies in American culture.

Comedy
1h 24m
Larry Charles
Sacha Baron Cohen, Ken Davitian, Luenell, Pamela Anderson
Why it ranks

Sacha Baron Cohen’s fearless commitment to his persona blurred the lines between reality and scripted farce, creating a confrontational mockumentary that exposed the absurd underbelly of the American psyche.

5
2000s Comedy in Mean Girls (2004)
Mean Girls
2004

Cady Heron is a hit with The Plastics, the A-list girl clique at her new school, until she makes the mistake of falling for Aaron Samuels, the ex-boyfriend of alpha Plastic Regina George.

Drama
Comedy
1h 37m
Mark Waters
Lindsay Lohan, Rachel McAdams, Lizzy Caplan, Lacey Chabert
Why it ranks

Tina Fey’s razor-sharp screenplay serves as a sociological dissection of high school hierarchy, blending acerbic wit with a timeless cautionary tale about the toxic allure of popularity.

4
2000s Comedy in Step Brothers (2008)
Step Brothers
2008

Brennan Huff and Dale Doback might be grown men. But that doesn't stop them from living at home and turning into jealous, competitive stepbrothers when their single parents marry. Brennan's constant competition with Dale strains his mom's marriage to Dale's dad, leaving everyone to wonder whether they'll ever see eye to eye.

Comedy
1h 38m
Adam McKay
Why it ranks

Adam McKay pushed the boundaries of cinematic arrested development here, crafting a fever dream of suburban nihilism that succeeds entirely on the sheer, committed insanity of its central duo.

3

It's the 1970s and San Diego anchorman Ron Burgundy is the top dog in local TV, but that's all about to change when ambitious reporter Veronica Corningstone arrives as a new employee at his station.

Why it ranks

Will Ferrell’s magnum opus of confident stupidity dismantled 1970s machismo with a surrealist, improvisational energy that remains the gold standard for meme-worthy absurdist satire.

2

Two co-dependent high school seniors are forced to deal with separation anxiety after their plan to stage a booze-soaked party goes awry.

Comedy
1h 53m
Greg Mottola
Jonah Hill, Michael Cera, Christopher Mintz-Plasse, Bill Hader
Why it ranks

A masterpiece of adolescent vulnerability, this film elevated the raunchy teen subgenre through its hyper-literate dialogue and a genuine, beating heart found amidst the chaos of a single, desperate night.

1

When three friends finally come to after a raucous night of bachelor-party revelry, they find a baby in the closet and a tiger in the bathroom. But they can't seem to locate their best friend, Doug – who's supposed to be tying the knot. Launching a frantic search for Doug, the trio perseveres through a nasty hangover to try to make it to the church on time.

Why it ranks

Todd Phillips redefined the R-rated landscape with this relentless exercise in comedic mystery, anchored by a volatile chemistry that turned a missing-groom premise into a definitive generational touchstone.

FAQ

Frequently Asked Questions

Everything you need to know about this list and SnakeDrafts

The comedy of the 2000s is characterized by a shift towards grounded, improvised humor that often blends with other genres like romance and horror. Films such as "Shaun of the Dead" and "The 40 Year Old Virgin" exemplify this trend by combining sharp wit with relatable, real-world scenarios.

2000s comedies moved away from exaggerated slapstick to emphasize character-driven narratives and social satire. Movies like "Mean Girls" and "Borat" introduced smart, culturally aware humor that resonated with audiences eager for more nuanced comedy.

Yes, directors like Adam McKay and Judd Apatow have multiple notable comedies on the list. McKay's "Anchorman" and "Step Brothers," as well as Apatow's "The 40 Year Old Virgin" and "Knocked Up," showcase their influence on 2000s comedy through their signature comedic styles.

Genre mashups are a hallmark of 2000s comedies, with many films blending humor with elements of horror, romance, or action. For example, "Shaun of the Dead" mixes horror and comedy, while "Tropic Thunder" incorporates action and comedy to deliver a unique viewing experience.

"Superbad" stands out as a quintessential coming-of-age comedy of the 2000s, portraying teenage friendships and the awkwardness of adolescence with humor and heart. Similarly, "Mean Girls" explores high school social dynamics with sharp comedic insight.

Improvisation played a significant role in creating the natural, spontaneous humor found in many 2000s comedies. Films like "Anchorman" and "The Hangover" benefited from actors' improvisational skills, which added unpredictability and freshness to the comedic scenes.

Absolutely, ensemble casts are a common and successful element in these comedies. Movies like "Wedding Crashers" and "Tropic Thunder" bring together diverse characters whose interactions and chemistry greatly enhance the comedic impact.

These comedies stay relevant by addressing timeless themes like friendship, social awkwardness, and cultural satire with humor that feels authentic and often nostalgic. Their blend of wit, relatable characters, and innovative comedy techniques continues to attract new audiences and encourage rewatching classic favorites.
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