The 2000s left us with unusual and memorable comedy films, ranging from dramedies and animated adventures to satires and rom-coms. Aside from making us laugh, those movies also have one more feature that marked the entire epoch — they dared to push the envelope. Comedies from the 2000s dared to be more adult, controversial, and meta.
So, here are the 20 best comedies of the 2000s that you must watch again, whether to appease your nostalgia or just for laughs.
1. I Love You, Man (2009)
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Peter Klaven (Paul Rudd) proposes to his great love (Rashida Jones). However, soon he realizes he has no guy friends he could ask to be his best man. That’s all about to change when he gets to know Sydney (played by Jason Segel).
Movies usually portray men’s friendships as tough, yet the relationship between these two is pure and hilarious. The casting is also spot-on because both Rudd and Segel are very charismatic and bring their own energy into the story. The movie scores 83% on Rotten Tomatoes, making it one of the best comedies of the 2000s.
2. A Serious Man (2009)
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When it comes to making movies, the Coen Brothers don’t really stick to any rules, and this comedy is no exception. The story is about an ordinary guy and the temptations that try to pull him away from his seemingly flawless life. Michael Stuhlbarg plays the main character, Larry Gopnik, and the plot is set in the late 1960s.
It’s a kind of parable with a quality, dark and direct humor, which is why this movie isn’t for everyone. But, if you want something more than just a typical shallow comedy, A Serious Man will give you enough food for thought. The Rotten Tomatoes gives this 00’s classic a 90% score.
3. Adventureland (2009)
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It’s the summer of 1987 when James Brennan (Jesse Eisenberg) halfheartedly accepts a job of an underpaid theme park employee. But things start to look up when he befriends a coworker Em (Kristen Stewart).
The great cast, amazing acting, and lovingly awkward characters place this movie on the list of the best comedies of the 2000s. Rotten Tomatoes agrees with this estimation with a score of 88%.
4. 500 Days of Summer (2009)
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Tom Hansen (played by Joseph Gordon-Levitt) has a crush on his coworker in this offbeat dramatic comedy. But soon, he discovers that she does not believe in true love.
The movie is clever, utterly charming, and refreshingly honest, which is why it landed a spot on this list of the best comedies of the 2000s. It also received numerous positive reviews leading many critics to label it the best film in 2009. Rotten Tomatoes gives this movie an 85% score.
5. Zombieland (2009)
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Zombieland is a movie that took the zombie genre and turned it into something funny instead of scary. The story is about Columbus (played by Jesse Eisenberg), a shy student trying to reach his family during a zombie pandemic. Along the way, he meets strangers who help him out — sisters Little Rock (Abigail Breslin) and Wichita (Emma Stone), and a gun-toting tough man named Tallahassee (Woody Harrelson).
As for the acting, Woody Harrelson is electric, and Emma Stone terrific as always. This top-grossing zombie movie in the US got 89% on Rotten Tomatoes.
6. Cloudy With a Chance of Meatballs (2009)
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This is an animated film from two of the finest comedy brains in the business, Christopher Miller and Phil Lord. Miller and Lord were on top of their game at the time, and this movie only gave them an even bigger boost.
Cloudy with a Chance of Meatballs is created using a unique art style and lots of imagination. The plot involves Flint Lockwood (voiced by Bill Hader), an inventor who makes an awkward contraption that causes food to shower from the sky.
He becomes a local hero and catches the eye of Sam Sparks (voiced by Anna Faris), a weather reporter. However, Flint’s machine turns rogue and soon threatens to destroy the world. Rotten Tomatoes gives it an 86% score.
7. Forgetting Sarah Marshall (2008)
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When it comes to getting over an ex, Forgetting Sarah Marshall is the movie to choose. As one of the best comedies of the 2000s, it talks about the universal experience of heartbreak but in a somewhat light and comical manner. After his celebrity lover breaks up with him, songwriter Peter Bretter tries to put some distance by going to Hawaii. But soon, he learns she is vacationing in the same hotel.
The cast is fantastic, with Jason Seagel playing the protagonist and Mila Kunis as his ideal romantic interest. Kristen Bell, Russell Brand, and Bill Hader play supporting roles, making the movie even more awesome. Rotten Tomatoes scores this movie at 83%.
8. In Bruges (2008)
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In Bruges is a pretty unusual comedy. The script was written by Martin McDonagh and won an Oscar for Best Original Screenplay. It chronicles the story of two hitmen hiding out in Bruges, Belgium, guilt-stricken after a job gone wrong. The movie touches some pretty dark themes while managing to portray the harsher scenes with elegance and humor.
Colin Farrell and Brendan Gleeson are fantastic on-screen duo. Ralph Fiennes is also excellent at playing the hilarious and menacing Harry Waters. Rotten Tomatoes gives this masterpiece an 84% score. So, if you decide to rewatch this comedic gem in 2022, you will once again be impressed by its ingenuity.
9. Superbad (2007)
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Superbad is a coming-of-age teen film and one of the best comedies of the 2000s. Two codependent best friends, Evan (Michael Cera) and Seth (Jonah Hill), get a once-in-a-lifetime chance to join a high-school party. But they face separation anxiety and make terrible decisions as they try to get the liquor ready.
Many memes we use today come from this movie, which only highlights how much of an impact it made. In fact, Superbad was the highest domestic grossing high school comedy at the time. Rotten Tomatoes confirms this by giving the film an 88% score.
10. Hot Fuzz (2007)
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Police constable Nicholas Angel (Simon Pegg) is sent to the countryside and partnered with a mediocre cop. That’s why he believes the glorious days on the force are behind him. However, as weird happenings occur in their little town, he becomes suspicious of a grander scheme.
Hot Fuzz is a buddy cop parody with hilarious jokes and scenes fans remember to this day. Legendary actors such as Nick Frost, Simon Pegg, Bill Nighy, and Timothy Dalton are all part of the cast and are considered one of the finest crews in the comedic stratosphere. As a testament of its greatness, Rotten Tomatoes gives this movie a 91% score.
11. Juno (2007)
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Juno is another coming-of-age movie and one of the best comedies of the 2000s, starring Michael Cera. Smart-talking teenager Juno (Ellen Page) faces hard life decisions when she learns she is pregnant. After realizing she isn’t ready to become a parent, she meets a charming couple, Mark (Jason Bateman) and Vanessa (Jennifer Garner), to arrange an adoption.
Critics generally praise this movie as one of the funniest, brightest comedies. On Rotten Tomatoes, you can notice it gets a pretty high score — 94%.
12. Knocked Up (2007)
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An energetic and successful journalist Alison Scott (Katherine Heigl), has a one-night stand with a slouch, Ben Stone (Seth Rogen), which results in an unplanned pregnancy. So, the two now have to reconsider their relationship status for the baby’s sake.
This is one of the best comedies of the 2000s and the film that launched Seth Rogen’s career. It is also a pretty amusing movie about growing up, being open-minded, and accepting responsibility for your actions but never stopping having fun. With cameos from Jason Segel, Paul Rudd, Leslie Mann, and James Franco, Knocked Up has a remarkable group of comedians all under one roof. Rotten Tomatoes gives it a 90% score.
13. Borat! Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan (2006)
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As you probably assumed from the title, the movie is as ludicrous as it can be. Borat, a Kazakh TV talking head, gets sent to the US to report about the world’s greatest country. However, he grows more interested in finding and marrying Pamela Anderson with the help of his documentary team. Still, the real twist is in the way Borat depicts an absurd world that actually appears very similar to ours.
Sasha Baron Cohen, who plays Borat, became an international celebrity after this mockumentary, and is now performing in more serious projects. Borat also became a cultural phenomenon, and it’s worth revisiting to check if things in society have improved since the film’s release. The Rotten Tomatoes score is 91%, making this movie one of the best comedies of the 2000s.
14. Little Miss Sunshine (2006)
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When Olive (Abigail Breslin), a brilliant seven-year-old, is given a rare chance to participate in California’s Little Miss Sunshine competition, her chaotic family climbs into a VW bus and heads to the pageant. The movie is a tragicomedy with a delightfully funny script and a strong message.
The cast also includes Alan Arkin, Toni Collette, Steve Carell, and Greg Kinnear. The movie scored 91% on Rotten Tomatoes and was included in the 1001 Movies You Must See Before You Die.
15. Kiss Kiss Bang Bang (2005)
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Kiss Kiss Bang Bang is a hard-core detective genre parody. A struggling actress Harmony Lane (Michelle Monaghan), requests a private investigator Gay Perry (Val Kilmer) and ex-thief, Harry Lockhart (Robert Downey Jr.), to investigate her sister’s death. Shane Black is the mastermind behind this story, and he uses tons of black humor and sharp dialogues to create a powerful tale of mystery, love, and plenty of laughs.
This movie also relaunched Robert Downey Jr.’s career, and it gave Val Kilmer the opportunity to play a brilliant comedy part for the first time. There would be no MCU as we know it today if this film did not exist. With the Rotten Tomatoes score of 86%, you definitely won’t be bored.
16. The 40-Year-Old Virgin (2005)
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Andy Stitzer (played by Steve Carell), a shy but sweet employee, admits that he is still a virgin, so his coworkers Cal (Seth Rogen), Jay (Romany Malco), and David (Paul Rudd) make it their mission to help him change that status. The 40-Year-Old Virgin is a charming movie about being comfortable in your own skin and how that type of confidence might just be the sexiest thing of all.
There are, of course, a plethora of amusing moments that arise naturally from this fantastic premise. The film is worth seeing just because it has a slew of actors who were then on the verge of becoming popular. Looking back, it’s evident that having them all together in the same movie was a stroke of luck. Rotten Tomatoes gives this comedy an 85% score.
17. Elf (2003)
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Buddy (Will Ferrell) is a human that was raised as an elf. But he always felt like an outsider at the North Pole. That’s why he decides to journey to New York City with Santa’s aid to see his birth father and spread some Christmas joy.
The whole idea is ridiculous, yet the story and the jokes are hilarious, which is why Elf belongs on this list of the best comedies of the 2000s. The rest of the cast is equally impressive, and once you see the movie, you will rewatch it every Christmas. Rotten Tomatoes gives Elf an 84% score.
18. Shrek (2001) and Shrek (2004)
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Shrek was a brilliant idea. The creators were able to build a story that is both a conscious fairy tale and a meta-commentary on storytelling in general. The animation may appear obsolete by today’s standards, but the voice acting and humor remain relevant.
The major characters are brilliantly voiced by Mike Myers, Cameron Diaz, and Eddie Murphy. Their efforts on the film really paved the way for new elite talent to enter the world of voice acting. Rotten Tomatoes gives Shrek an 88% and Shrek 2 an 89% score.
19. Mean Girls (2004)
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After relocating to the United States from Africa, Cady (Lindsay Lohan) tries to fit in at her new high school. But she quickly learns that cliques and the popular girl, Regina George (played by Rachel McAdams), rule the place.
Mean Girls was an instant modern classic that launched the careers of several of its cast members. It is also one of those films that have endured the test of time due to its quotability. For this reason, it keeps inspiring countless internet memes even today. Rotten Tomatoes gives the movie an 84% score.
20. Shaun of the Dead (2004)
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In this horror-comedy, Shaun (Simon Pegg), a store clerk, surprises his pals and himself as he takes command amid a zombie attack. Shaun of the Dead may appear to be a typical low-budget zombie movie from the outside. However, once you start watching, you will discover that it is loaded with witty comedy, outstanding editing, and even a profound, heartfelt core.
The movie is smart satire plucked from the limits of a genre case. It is also the film that launched Edgar Wright’s career. Rotten Tomatoes gives it a 91% score.
