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Film

The 10 funniest comedies of the 21st century

@Russellisation

Comedy is one of the most subjective things in all of the entertainment industry, which makes this list of the ten funniest films of the 21st century something of a tricky task. Depending on your age, cultural background and life history, a film that could have one person rolling around in laughter, in dire need of emergency assistance, might have another shrugging their shoulders in confusion. 

For the following list of ten modern classics, we’ve put tastes to one side in an attempt to capture the ten funniest modern comedies that have had the most obvious impact on contemporary pop culture. After all, surely the very best comedies are the ones that manage to grab the hearts of the most people, no matter of critical rating or status in the wider history of movies. 

Looking back at 22 years of comedy cinema to choose out just ten of the funniest was no easy feat, with the following list regrettably omitting the likes of Wedding Crashers, The 40-Year-Old Virgin, Knocked Up and In Bruges, with each of these films being excellent in their own right. This just goes to show how exclusive the following list of ten contemporary classics is. 

The 10 funniest comedies of the 21st century:

10. Step Brothers (Adam McKay, 2008)

Though not for everyone, Adam McKay’s Step Brothers has a lot of love across the world for its puerile comedy that makes the most out of its two lead actors Will Ferrell and John C. Reilly. Telling the story of two middle-aged step brothers who are forced to share rooms when their parents marry, this immature comedy is undeniably hilarious throughout, leading to several jokes in the film becoming commonly thrown around in contemporary culture. 

Bolstered by an excellent supporting cast that includes Mary Steenburgen, Richard Jenkins, Kathryn Hahn and Adam Scott, Step Brothers remains a fan-favourite long after its release.

9. Role Models (David Wain, 2008)

David Wain has done a lot for modern comedy behind the scenes, directing Wet Hot American Summer in 2001 as well as writing the surprisingly funny spoof comedy They Came Together in 2014. Neither of these projects compare to the success of 2008s Role Models, however, a hilarious comedy that follows a pair of energy drink representatives who avoid jail by enrolling in a Big Brother program.

Such leads to a heartwarming tale that never lets up its comedic pressure, with the likes of Paul Rudd, Seann William Scott, Christopher Mintz-Plasse and Jane Lynch each contributing to the humour. 

8. Mean Girls (Mark Waters, 2004)

Many of the jokes from Mark Waters’ Mean Girls have suffused into the language of popular culture, and for good reason too, with Tina Fey’s watertight script providing for a film that is both hilarious and irresistibly charming. Bolstering the careers of Lindsay Lohan, Rachel McAdams, Ana Gasteyer, Amanda Seyfried and Amy Poehler, Mean Girls was arguably one of the most important films of early 21st-century comedy. 

Based on the book Queen Bees and Wannabes by Rosalind Wiseman, Mean Girls follows a new girl at an American high school who is forced to abide by the unusual playground politics. 

7. Bridesmaids (Paul Feig, 2011)

Speaking of influential comedy movies, Paul Feig’s Bridesmaids, written by Kristen Wiig and Annie Mumolo, provided a breath of fresh air in 2011, an antidote to the macho frat-boy comedies that had long dominated Hollywood comedy throughout the era. Making the likes of Wiig, Rose Byrne, Rebel Wilson and Melissa McCarthy household names, among many others, Bridesmaids would lead to bigger things for everyone involved.

A hilarious and heartfelt comedy, Feig’s movie tells the story of a competition between a maid of honour and a bridesmaid at a wedding as to who’s the best friend of the bride. 

6. 22 Jump Street (Chris Miller, Phil Lord, 2014)

Emerging almost out of nowhere to be two of the most sought-after comedy directors in all of Hollywood, Chris Miller and Phil Lord both found initial success in the animated comedy Cloudy with a Chance of Meatballs before hitting a home run with The Lego Movie and the Jump Street series. Though the first movie, 21 Jump Street, is also a modern great, we think the sequel marginally pips it to the comedy post. 

Starring Jonah Hill and Channing Tatum, the 2014 comedy follows two undercover cops who pretend to be high-school students to bust a drug ring. It’s silly, fast-paced and hilariously sharp. 

5. Hot Fuzz (Edgar Wright, 2007)

There are few directors in contemporary cinema quite as creative as the British filmmaker Edgar Wright, a modern master who first found success with Shaun of the Dead in 2004. Though a hysterical horror-comedy, Wright bettered himself three years later with the release of the action-packed cop-drama Hot Fuzz starring Simon Pegg, Nick Frost, Olivia Colman and Martin Freeman.

A rare comedy that boasts an intricate story, smart characters and a witty sense of humour that’s suffused throughout the movie, Hot Fuzz is a fan-favourite that still remains fresh to this day.

4. Borat (Larry Charles, 2006)

Having a monumental impact on popular culture upon its release in 2006, Borat was born from the instant camcorder pranks of the YouTube and Jackass generation, arriving in Hollywood at the perfect moment. Led by its star and co-writer Sacha Baron Cohen, Borat garnered great critical and commercial acclaim, popular for its sharp satirical criticism as well as its self-deprecating comedy. 

Giving birth to several pop-cultural phrases, Borat became an international sensation, catapulting Sacha Baron Cohen to bigger (but not necessarily better) things.

3. Anchorman: The Legend of Ron Burgundy (Adam McKay, 2004)

Will Ferrell might be the single most influential comedic figure in the whole of the 21st century, responsible for making countless movies international hits. Anchorman: The Legend of Ron Burgundy is likely his very best work, with his later films edging on the side of facial a little too much. Don’t get us wrong though, Anchorman is a very silly and very funny movie. 

Ferrell isn’t left to make all the jokes on his own either, with the actor joined by an impressive supporting cast that includes Paul Rudd, Steve Carell, David Koechner, Christina Applegate, Fred Armisen and Seth Rogen.

2. Superbad (Greg Mottola, 2007)

With a countless number of imitators, Greg Mottola’s Superbad was the movie that introduced Hollywood to Jonah Hill, Michael Cera, Christopher Mintz-Plasse and even Emma Stone. Telling the story of three high-school seniors who embark on a wild night of partying and accidental adventure, Superbad is widely recognised as a side-splitting modern classic. 

Having produced previous hits with 40-Year-Old Virgin and Knocked Up, Superbad also made the name of Judd Apatow who is now a prominent figure in modern Hollywood comedy. 

1. Team America: World Police (Trey Parker, 2004)

Not just a comedy classic, but also an innovative cinematic feat, the makers of South Park, Trey Parker and Matt Stone created a timeless satire with Team America: World Police, a criticism of American foreign policy made entirely using puppets. Idiotic and farcical yet also strangely insightful, Parker and Stone created an enigma of the comedy genre back in 2004, with several of the film’s quotes remaining iconic to this day.

Telling the story of a Broadway actor who is recruited to an elite counter-terrorism team, Trey Parker’s film takes the group across the world, from Paris to Cairo to North Korea, leaving a trail of destruction in their wake.