One of the best things that came out of the 2000s was the plethora of funny comedy films in cinematic history. Some of these comedic offerings have aged well and are now considered cult classics. Additionally, Several funny scenes from iconic 2000s comedy movies still contribute to references in modern pop culture. It was an era when filmmakers experimented with new formats to fit into the new millennium, and it worked.
This list of funniest comedy films from the 2000s contains a mix of family comedies, rom-coms, action comedies, buddy comedies, and more. From the second installment in the Rush Hour franchise to The 40-Year-Old Virgin, some of the most amazing entries in the comedy genre were made during this golden era of great humor. Read and comment on the ones you think should make the list.
1. Legally Blonde (2001)
Based on Amanda Brown‘s novel of the same title, Legally Blonde was inspired by the author’s personal experience as a blonde student at Stanford Law School. Like the main character, Elle Woods (played by Reese Witherspoon), Brown was obsessed with beauty, fashion, and Elle magazine. Witherspoon received praise for her portrayal of Elle, a blonde sorority girl who breaks stereotypes to become a successful lawyer while trying to win back her ex-boyfriend. The movie flawlessly teaches life lessons like believing in oneself, and the perfect comic timing was top-notch.
2. Mr. Bean’s Holiday (2007)
Rowan Atkinson is a legend in slapstick comedy, and Mr. Bean’s Holiday is a constant reminder. A family-friendly comedy, Mr. Bean’s Holiday follows the title character on his way to Cannes, France, after winning a trip there. The trip turns into a funny nightmare when Bean is roped into an accidental kidnapping. The movie is absolutely hilarious, with sidesplitting gags from the iconic Mr. Bean (Atkinson) as he displays his most absurd and awkward problem-solving skills. Interestingly, Bean doesn’t have to utter a word to elicit laughter from audiences.
3. What Women Want (2000)
What happens to a cocky chauvinist when he can suddenly hear women’s thoughts? Nick Marshal, an advertising executive played by Mel Gibson, learns the hard way that he’s not as charming as he thought after an accident gave him the gift of hearing what women around him are thinking. As a chauvinist, his ego is brutally bruised. Despite the mixed reviews, What Women Want has several witty moments that set it apart as one of the funniest movies of the 2000s.
4. Rush Hour 2 (2001)
The Rush Hour movie franchise made cinematic history with adrenaline-pumping buddy cop action-comedy, led by Chris Tucker (Detective James Carter) and Jackie Chan (Chief Inspector Lee). The palpable chemistry between them in the first film, Rush Hour (1998), made the movie a hit, and Rush Hour 2 turned it up a notch, flawlessly striking a balance between action and comedy. It also solidified the cultural crossover appeal that made the first entry a global hit.
5. The Hangover (2009)
On their Vegas trip for a bachelor party, three friends wake up with a hangover and no idea what happened the night before. Things spin out of control when they realise the groom was missing, there’s a baby in the closet, and a tiger in the bathroom. With an approval rating of 79% on Rotten Tomatoes, The Hangover received generally positive reviews for its raunchy humor and comedic approach. The movie’s acclaimed cast includes Bradley Cooper, Ed Helms, Zach Galifianakis, Heather Graham, and Justin Bartha.
6. Miss Congeniality (2000)
In this thrilling action-comedy film, Sandra Bullock plays Gracie Hart, a tomboyish FBI agent tasked with infiltrating the Miss United States beauty pageant as a contestant following a bomb threat. What follows is an exciting adventure as FBI agents race to thwart the terrorist attack. Miss Congeniality is widely loved for its lighthearted comedy, with Bullock’s outstanding performance gaining massive acclaim for keeping audiences engaged.
7. Zoolander (2001)
Zoolander stands out as one of the funniest comedy films of the 2000s for its flawless satire, slapstick, and pure absurdity. The movie follows dimwitted male model Derek Zoolander (Ben Stiller), who is tricked into assassinating the Malaysian prime minister by fashion mogul Jacobim Mugatu (Will Ferrell). Stiller perfectly embodied his role, turning every pose and expression into cinematic gold that still holds up today. His chemistry with Owen Wilson, who played Hansen, his rival in the fashion industry, led to some of the most memorable and hilarious moments. Zoolander still stands out as a comedic cult classic.
8. Bruce Almighty (2003)
With Jim Carrey‘s exhilarating performance and an exceptional premise, Bruce Almighty became an instant hit upon its release. In the movie, Carrey plays Bruce Nolan, a disgruntled television reporter blaming God for his frustrating life on what seems to be the worst day of his life. What he didn’t expect was to be bestowed with God’s powers for one week. The film also stars Jennifer Aniston, Steve Carell, and Philip Baker Hall.
9. Superbad (2007)
Superbad is one of those comedy movies everyone must watch at least once. The coming-of-age teen comedy follows unpopular high schoolers Seth (Jonah Hill) and Evan (Michael Cera), who set out to make the most of the final days in high school. However, losing their virginity and getting their hands on some alcohol proved harder than the two friends expected. Rotten Tomatoes summarizes the movie as “an authentic take on friendship and the overarching awkwardness of the high school experience.”
10. The 40-Year-Old Virgin (2005)
Steve Carell delivers a career-defining performance as the 40-year-old virgin (Andy) in this classic rom-com, solidifying his status as a comedy legend. The story revolves around the over-the-top mission launched by Andy’s colleagues to help him lose his virginity. Directed by Judd Apatow (in his feature directorial debut), The 40-Year-Old Virgin leverages heartfelt humor and awkward situations delivered by an amazing ensemble cast. The award-winning movie also left viewers with memorable quotes that still hold up after two decades.
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