These Are Officially The Funniest Movies Of The Last 20 Years


Sometimes it can seen as if the end of the world truly is nigh.

Global warming is accelerating, Donald Trump is President of the United States, and him and Kim Jong-un are engaged in a battle of words that threatens all of humanity. In light of all this chaos, it can often be nice to zone out and have a few laughs. – What perfect way to do this than to settle down with a good old comedy film.

We’ve looked at IMDb and Rotten Tomatoes to find the very best comedies of the last 20 years (because, let’s face it, anything before that just isn’t that funny to us millennials).

30. The 40 Year-Old Virgin (2005)


Written and produced by Judd Apatow, The 40 Year-Old Virgin follows a middle-aged man’s hilarious journey to finally have sex. Following the success of the film, Apatow went on to direct other comedies such as Knocked-Up and Trainwreck.

29. Little Miss Sunshine (2006)


A particularly touching comedy that shows the ups and downs that come with family life. Truly heart-warming whilst managing to be comical at the same time. Highlights include Olive’s talent segment at a beauty pageant.

28. Hot Fuzz (2007)

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British comedy Hot Fuzz was directed by Edgar Wright and stars the hilarious duo of Simon Pegg and Nick Frost. Pegg and Frost play small-town policemen attempting to solve mysterious deaths happening in a backwater English village. Not only is this film hilarious, it’s also pretty scary.

27. School of Rock (2003)

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Jack Black isn’t normally someone who I consider as legitimately funny, but he shines in musical comedy School of Rock as struggling musician Dewey Finn.

26. Don’t Think Twice (2016)

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This entertaining film follows the trials and tribulations of members of an improv troupe. One member auditions for a fictional TV programme called Weekend Live (based on Saturday Night Live) as others watch on in jealousy.

25. As Good as It Gets (1997)

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Starring Jack Nicholson as an obsessive-compulsive novelist, Helen Hunt as a single mother, and Greg Kinnear as a gay artist, As Good as It Gets is an absolutely classic comedy. Both Nicholson and Hunt even ended up winning Academy Awards for their efforts.

24. Monsters, Inc. (2001)

"MONSTERS, INC. 3D" ©2012 Disney•Pixar. All Rights Reserved.

Animated comedy Monsters, Inc. is one of those childhood films that was hilarious for both children and their parents. A truly golden watch.

23. Step Brothers (2008)

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Step Brothers follows two ‘men-children’ (played by Will Ferrel and John C. Reilly) who are still living at home. Expect all the usual gaffs that come with incompetent adulting.

22. Rush Hour (1998)

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Mismatched cops Jackie Chan and Chris Tucker attempt to rescue the Chinese consul’s kidnapped daughter. While this film isn’t exactly sophisticated, it is pretty funny.

21. Bad Teacher (2011)

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Cameron Diaz plays a half-arsed teacher who is forced to return to her job. After her rich fiancé ends their engagement, Diaz attempts to raise enough money for breast implants. Not a particularly high-brow comedy but good fun nevertheless. Plus, the film also stars Justin Timberlake, who is just yummy.

20. Anchorman: The Legend of Ron Burgandy (2004)


Directed by Adam McKay, Anchorman is inspired by popular 1970s action news formats. Critics and lay people alike seemed to love the silliness of the film along with the abundance of hilarious quotable lines.

19. Without a Paddle (2004)

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Three reunited friends embark upon a troublesome filled trip up a remote river in order to discover the hidden treasure of an airplane hijacker. An instance commercial success, Without a Paddle is full of more than a few laughs.

18. Dodgeball: A True Underdog Story (2004)


Many love to hate Ben Stiller and Dodgeball is one of those films where his annoying nature fits perfectly to the character he plays. What’s not funny about a group of mishaps entering a dodgeball tournament in order to rescue their subpar gym from corporate takeover.

17. Pineapple Express (2008)


Pineapple Express stars well established comedy duo Seth Rogen and James Franco and the plot follows a process server and his petty weed dealing friend having to flee from not only a corrupt police officer but also various hitmen. Pretty much a laugh a minute, this film even landed Franco a nomination for a Golden Globe.

16. American Pie (1999)

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Following five best friends and their high school pact to lose their virginity before graduation, this film is hilarious and crude.

15. Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan (2006)


Every Halloween it’s impossible to get away from those iconic Borat costumes. This mockumentary is entertaining, cringeworthy, and inspired a whole generation.

14. Johnny English (2003)

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Rowan Atkinson is one of those actors who is just brilliant in everything they star in. Johnny English is no exception, with Atkinson playing incompetent MI7 agent Johnny English. British humour at its finest.

13. The Big Sick (2017)

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Released this year, The Big Sick is based on the real life romance between writers Emily V. Gordon and Kumail Nanjiani as they struggle with some amusing cultural differences in their relationship. The film is so far one of the highest-grossing independent films of 2017 and is definitely worth a watch if you’re looking for a laugh.

12. Chicken Run (2000)

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Aardman Animation’s Chicken Run is probably the funniest film you’ll ever see about chickens. Hilariously relatable and one for all ages, I honestly never tire of sitting down to watch this.

11. Wedding Crashers (2005)

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Any film with Owen Wilson is usually a no-go for me… there’s just something about his face… Anyway, Wedding Crashers is a genuinely funny film and is also a pretty easy watch. Just the kind of thing to enjoy on a lazy Sunday.

10. Kick-Ass (2010)

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If you can get past the gore then Kick-Ass is actually hilarious. Based on a comic book of the same name, this film follows an ordinary teenager (played by Aaron Johnson) who embarks upon a mission to become a real-life superhero. This film is a brilliant dark comedy.

9. Zoolander (2001)


While it doesn’t star my favourite three actors (Ben Stiller, Owen Wilson, and Will Ferrell), Zoolander is funny enough for me to look past this. Panned by critics but a complete box office success, this is definitely a film that is worth a watch.

8. Four Lions (2010)


Four Lions is one of those films that makes you laugh even though it just feels wrong. The film shows a group of home-grown terrorists from Sheffield as they attempt- very ineptly- to become suicide bombers.

7. Napoleon Dynamite (2004)


Weird and wonderful, Napoleon Dynamite has gained a sturdy cult following. A must watch comedy.

6. Austin Powers: International Man of Mystery (1997)


Spy action comedy Austin Powers: International Man of Mystery was so hilarious that it led to two sequels Austin Powers: The Spy Who Shagged Me, and Austin Powers in Goldmember. This film is lovably silly and also features some pretty iconic suits.

5. The Full Monty (1997)

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One of the few times it paid off to sit down and watch a film that your parents recommended, The Full Monty is genuinely brilliant humour. Set in Sheffield, the plot follows six inept unemployed men who end up creating a male striptease act. Expect some brilliant routines.

4. The Hangover (2009)


The first film in The Hangover franchise is funny. The other two, however, are not really. Despite the sequels tailing off, the original is one of those things you are not going to regret watching.

3. We’re the Millers (2013)

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The film that made Will Poulter’s eyebrows famous, We’re the Millers had me laughing out loud. One golden scene involves the entire family (Jennifer Aniston, Jason Sudeikis, Emma Roberts, and Will Poulter) singing TLC’s song ‘Waterfalls’. Any film that involves Nick Offerman (Ron in Parks and Rec) is basically guaranteed to be hilarious.

2. Logan Lucky (2017)

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Containing eye-candy and humour, Logan Lucky was released this year to rave reviews. It also had a pretty star-studded cast including Channing Tatum, Daniel Craig, Seth MacFarlane, and Katie Holmes.

1. Superbad (2007)


Directed by Greg Mottola and produced by Judd Apatow, watching Superbad is basically a comic act of rite. The film stars Jonah Hill and Michael Cera as lead characters Seth and Evan, who were named after writers Seth Rogen and Evan Goldberg. Easy to quote and full of sketches, this film received universal acclaim and is definitely a must watch. Ah McLovin’.

Do you agree? Let us know in the comments.

Images via You Tube/ HBO / Pixar / Disney / 

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