Top 21 Comedy Movies of Each Year (2000 - 2020)
Trivia Top 21 Comedy Movies of Each Year (2000 - 2020)



Top 21 Comedy Movies of Each Year (2000 - 2020)

VOICE OVER: Rebecca Brayton WRITTEN BY: Nick Spake
The 21st century has been one of the best when it comes to comedies! For this list, we'll be looking at the most hilarious films released throughout the 21st century. Our countdown includes "Jojo Rabbit", "Superbad", "21 Jump Street", “The Grand Budapest Hotel”, "Zoolander", and more!

Top 21 Comedy Movies of Each Year between 2000 to 2020

Welcome to WatchMojo, and today we’re counting down our picks for the Top 21 Comedy Movies of Each Year between 2000 to 2020.

For this list, we’ll be looking at the most hilarious films released throughout the 21st century. We’re leaving off superhero and animated flicks this time around, so apologies to Deadpool and Lego Batman.

What’s your favorite comedy movie of the past 21 years? Let us know in the comments.

2000: “Best in Show”

We learned a lot about animals in 2000. While “Meet the Parents” taught us about milking cats, “Best in Show,” introduced us to the competitive world of dog shows. We’ve all heard of stage parents, but dog owners and trainers can be just as over-the-top. This Christopher Guest mockumentary isn’t so much about dogs as it is about human nature. We’ve all met somebody who treats their pet as their child. So the characters here, as bizarre as they might be, are oddly relatable. The film is carried by an all-star comedic cast comprised of Guests’ usual suspects improvising much of their dialogue. Arguably the funniest actor is Fred Willard, who impressively maintains a straight face while providing completely ludicrous commentary.

2001: “Zoolander”

“Zoolander” was a mild box office success upon release. At the time, Ben Stiller, Owen Wilson, and Will Ferrell were just on the cusp of comedic super-stardom. As their profiles continued to grow, so did the film’s fan base. Nowadays, you’ll be hard-pressed to find anybody who doesn’t know what Blue Steel, Le Tigre, or Magnum is. Derek’s looks might not have much variety to them, but the film possesses too many hilarious one-liners to count. It also has one of cinema’s funniest examples of product placement. We’re still waiting for Starbucks to make Orange Mocha Frappuccino a regular menu item! If there’s a science to producing “stupid” comedy, then “Zoolander” deserves a Nobel prize. Even the film’s DVD menu is brilliant.

2002: “Punch-Drunk Love”

This Paul Thomas Anderson film is often cited as Adam Sandler’s first foray into drama. Although Sandler shows a more serious side of himself than audiences were used to, the film is just as much a romantic comedy. While Anderson and Sandler seemed like an odd pairing, both creators are known for surreal humor. “Punch-Drunk Love” finds the middle ground between Sandler’s silliness and Anderson’s dark edge to produce a strange yet sincere romance. In many respects, the film isn’t a huge departure for Sandler. Like “Happy Gilmore”, Barry Egan is a short-tempered yet sensitive soul. It’s still very much an “Adam Sandler movie,” but Anderson finds layers we never realized were there.

2003: “School of Rock”

While not Jack Black’s first star vehicle, “School of Rock” proved he had what it took to carry a film. Black plays Dewey Finn, a would-be rocker who cons his way into a teaching gig that presents an unlikely opportunity. This high-energy role plays to Black’s comedic and musical strengths. It also showcases his knack for working with children, including a young Miranda Cosgrove. ‘School of Rock” is also rounded out by an excellent supporting cast that includes Joan Cusack, Sarah Silverman, and screenwriter Mike White. Black received a Golden Globe nomination and an MTV Movie Award for his performance. While it was a good year for him, 2003 was also a breakout year for Will Ferrell with hilarious turns in “Old School” and “Elf”.

2004: “Anchorman: The Legend of Ron Burgundy”

“Anchorman” set the gold standard for Will Ferrell comedies. More than a decade and a half later, this throwback to 1970s culture is still the one to beat. It stood out as the funniest film of 2004, which is saying a lot in a year that brought us cult classics like “Shaun of the Dead” and “Napoleon Dynamite.” From Brian’s “60%” line to Ron’s German translation of San Diego, everybody has a quote that they constantly reference. “Anchorman” also provides an outlet for Ferrell’s physical and surreal humor. The film was not only a landmark for Ferrell, but also the entire Frat Pack. Paul Rudd, Steve Carell, David Koechner and behind-the-scenes talent like producer Judd Apatow all got to shine.

2005: “The 40-Year-Old Virgin”

Speaking of Apatow, “The 40-Year-Old Virgin” marked his feature directorial debut, as well as Steve Carell’s first film as a lead. While regarded as a comedy classic now, expectations weren’t through the roof at the time. The title suggested that audiences were in store for a one-joke premise poking fun at middle-aged virgins. People were not only surprised that the film had one laugh after another, but there was cleverness behind the humor. Although it’s a sex comedy, the film challenges the way intercourse is depicted in media. It outright rejects the idea that everybody needs to lose their virginity by a certain age. Between this film and “Wedding Crashers,” 2005 brought the R-rated comedy back while giving the genre some heart.

2006: “Borat”

If you weren’t familiar with Sacha Baron Cohen already, you definitely knew his name after 2006. In addition to stealing the show in “Talladega Nights,” he took the world by storm with “Borat.” Although Cohen plays a Kazakhstani journalist, America is the primary target of satire here. The social commentary shockingly blends with reality every time Borat’s interviewees don’t hold back from sharing their true thoughts. At the time, most reviews focused on Cohen’s shocking, fearless antics. Behind the public indecency, though, the film made commentary on problems in America that have only grown more prevalent in recent years. Cohen’s outrageous performance won him a Golden Globe while the clever screenplay was nominated for an Academy Award.

2007: “Superbad”

It feels like whenever a comedy becomes a runaway hit, there’s always a group of naysayers that deems it “overrated.” But “Superbad” has never really faced such a backlash. It’s still regarded by many as one of the funniest teen comedies ever made. So, why does “Superbad” still hold up? Sure, it’s a laugh riot, but the same can be said about other entries on our list. Perhaps it’s because the film found a balance that few other teen comedies have. While the humor is unapologetically vulgar, the characters are more thoughtful than the ones you’d find in “Porky’s.” The result is a comedy that’s immature and progressive in all the right ways, borrowing the best elements from 80s comedies and contemporary comedies. Also, McLovin!

2008: “Tropic Thunder”

Was 2008 the century’s best year for comedies? Let’s just say that in another year, “Forgetting Sarah Marshall,” “Pineapple Express,” or “Step Brothers” easily could’ve been deemed the best. Since we’re obliged to single out one, we’re going with “Tropic Thunder.” As far as ensemble pieces go, few can contend with this film’s lineup of hilarious heavyweights. It also features several dramatic actors who surprised us with their comedic chops. Although it seems like a parody of war movies, “Tropic Thunder” is also a sendup of Hollywood. It’s debatable whether it inspired lasting change. However, this fearless comedy did force Hollywood to reflect on whitewashing, the portrayal of the mentally handicapped, and other increasingly relevant issues. Sometimes satire speaks the most truth.

2009: “The Hangover”

By 2009, the R-rated comedy was officially back. But “The Hangover” achieved levels of success that hadn’t been seen since the ‘80s. Todd Phillips’ film exceeded expectations by becoming the highest-grossing R-rated comedy domestically at the time. It made a star out of Zach Galifianakis while advancing the careers of Bradley Cooper and Ed Helms. “The Hangover” combination of a zany story with a fantastic cast was truly lightning in a bottle. Although the sequels might not have been able to recapture the magic, that doesn’t take away from the original’s lasting impact. Winning the Golden Globe for Best Picture – Musical or Comedy was just the cherry on top. We just wish that Helms had gotten an Oscar nomination for Stu’s tiger song.

2010: “Scott Pilgrim vs. the World”

2010 gave us a few unlikely action heroes like the titular “Other Guys”. But there’s never been a more unlikely action star than Scott Pilgrim. Edgar Wright’s adaptation of Bryan Lee O’Malley’s graphic novels is a love letter to video games, manga, and everything nerd culture. Of all the films on this list, “Scott Pilgrim” may have the most ingenious visual gags. But that doesn't mean it lacks quotable one-liners or colorful characters either. Every time you watch it, you find something new to appreciate, as is the case with the best comedies. The film notoriously and inexplicably bombed upon release, but a comedy this inventive was born for cult status. So much so that a theatrical re-release was announced for its 10th anniversary.

2011: “Bridesmaids”

Directed by Paul Feig, “Bridesmaids” marked several milestones. It saw Kristen Wiig blossom from a quirky supporting player into a hilarious leading lady. Melissa McCarthy evolved from a sitcom actress to an Oscar nominee. Wiig was also nominated for her screenplay co-written with Annie Mumolo. Not only was it the first Judd Apatow production to gain this much attention from the Academy, but it was also his studio’s highest-grossing film. Most notably, “Bridesmaids” was something of a turning point for female-driven comedies, specifically of the R-rated variety. It may sound unusual, but our central female characters shattered a comedic glass ceiling after losing control of their bowels during a bridal fitting. For every gross-out gag, there’s a heartfelt moment to go with it.

2012: “21 Jump Street”

Sometimes comedies can catch you off-guard, be it the story of a foul-mouthed teddy bear or an upscale couple living among hippies. Still, who would’ve guessed that an adaptation of “21 Jump Street” would be 2012’s funniest movie? If you’ve never seen the original TV series, don’t worry. This film ignores everything about its source material outside of the basic premise and the fact that Johnny Depp had a part. On that note, the film features one of the century’s most epic cameos. But Jonah Hill and Channing Tatum are the true stars here. They’re not the only duo who went above the call of duty. Directing duo Phil Lord and Christopher Miller’s reputation for spinning seemingly bad ideas into gold debatably started here.

2013: “This Is the End”

Between “21 Jump Street” and his Oscar-nominated performance in “The Wolf of Wall Street,” Jonah Hill starred in this comedy of biblical proportions. Hill, Seth Rogen, James Franco, and too many other familiar celebs to count also play exaggerated versions of themselves facing an apocalyptic scenario. End-of-the-world movies typically focus on average Joes triumphing against the odds. “This Is the End”, on the other hand, shifts the focus to entitled stars—and none of them are exactly Will Smith in “I Am Legend.” Like “Tropic Thunder,” this is a high-concept comedy that peels back the facade of Hollywood by revealing how self-centered celebs can be. With nothing left to lose, we see the gang at their worst and their funniest.

2014: “The Grand Budapest Hotel”

You could say that 2014 was the year of the auteur comedy. Jemaine Clement and Taika Waititi turned in the wickedly original mockumentary “What We Do in the Shadows.” Meanwhile, Wes Anderson delivered his Best Picture-nominated magnum opus. “The Grand Budapest Hotel” sees all of Anderson’s trademarks taken into overdrive. However, the film never comes off as repetitive. It’s an example of an artist mastering his craft, delivering his best-looking, most well-acted, and funniest feature to date. As is the case with most Anderson pictures, the humor is a blend of visual jokes, surrealism, and lines that are hysterical in or out of context. The film exists in its own world, and it’s one that we never want to leave.

2015: “Trainwreck”

“Trainwreck” follows a familiar formula seen in other Judd Apatow movies: an immature party animal learns to take personal responsibility and settles down into a committed relationship. This comedy, however, is distinguished by Amy Schumer, who stars and wrote the screenplay. “Trainwreck” almost feels like a response to the common criticism that women in comedies are usually the supportive love interests while the guys have all the fun. Schumer shows that the ladies can be every bit reckless, crude, and hilarious. Of course, the dudes also get in on the laughs with strong supporting performances from Bill Hader, Colin Quinn, and LeBron James as LeBron James. There’s more to the film than a simple gender swap, as Schumer makes the Apatow formula her own.

2016: “Popstar: Never Stop Never Stopping”

Audiences missed some of 2016’s best comedies. We mean, why go see “The Angry Birds Movie” when “The Nice Guys” starred a much funnier Gosling and Crowe? “Popstar” is the box office bomb that bewilders us the most, though. We guess since “The Lonely Island” really rose to fame on TV and online, their fans were less willing to get out of the house and go to the theater. Thanks to home media, “Popstar” is starting to gain the cult following it deserves. The story is essentially every other movie about an egotistical musician who needs to learn humility. But within the stereotypical plot, we get an onslaught of cameos and absurd musical stylings that put Lonely Island on the map. “Popstar” delivers in spades.

2017: “The Big Sick”

2017 was a breakout year for a couple of comedic talents, including the fantastic Tiffany Haddish. Kumail Nanjiani hit the big time with his Oscar-nominated screenplay for “The Big Sick”, which he co-wrote with his real-life spouse Emily V. Gordon. The film is loosely based on their relationship, with Nanjiani channeling himself while the delightful Zoe Kazan fills the Emily role. While their complicated love story is at the rom-com’s core, “The Big Sick” is also about balancing family, culture, and one’s passion. Kumail shows us that’s easier said than done. By getting to know Emily’s parents, however, Kumail undergoes a personal journey that brings about growth, tears, and laughs. It may be the most mature comedy yet from director Michael Showalter and producer Judd Apatow.

2018: “Game Night”

While “Crazy Rich Asians” deservingly became the decade’s highest-grossing romantic comedy, no film released in 2018 brought more laughs than “Game Night.” The film starts with a promising set-up centered on a mystery game that spirals into an actual crime caper. “Game Night” makes the most of its premise with gleefully violent action, a screenplay full of surprises, and a well-oiled ensemble. The standout is Jesse Plemons, who’s known for playing comedic relief characters and mysterious creeps. His character here is a little bit of both and giving him an adorable dog only adds to the uncomfortable hilarity. Directors John Francis Daley and Jonathan Goldstein have a hit-and-miss track record, but “Game Night” rolls nothing but sixes.

2019: “Jojo Rabbit”

From “Booksmart” to “Jojo Rabbit,” 2019 was a year of unconventional coming-of-age stories. This is especially true for the latter film, which revolves around a Hitler Youth who realizes that der Führer isn’t the cool guy he’s been imagining. The titular Jojo also grows closer to a young Jewish girl. In an age where some comedians are afraid to tackle controversial subjects, writer/director Taika Waititi goes all in. He does so with an almost-naive sincerity by telling the story through a child’s eyes. At the same time, Waititi explores the horrors of Nazi Germany and sends a clear anti-hate message. This balance of edgy comedy, quirkiness, and drama amounted to a Best Picture nomination and a Best Adapted Screenplay win for Waititi.

2020: “Palm Springs”

When the world needed laughter more than ever in 2020, Hollywood delivered comedies like “The King of Staten Island.” “Borat Subsequent Moviefilm” was another hilarious film that we needed for more reasons than one. However, “Palm Springs” was the year’s most rewatchable comedy… and we’re not just saying that because of the time loop premise. While we’d seen this sort of idea in other comedies, “Palm Springs” ranks among the funniest and most sharply edited. It also might be the most romantic with Andy Samberg and Cristin Milioti wonderfully complementing one another. In a way, the sci-fi flick was a perfect representation of 2020. We kept waking up in what felt like the same day, but through love, personal growth, and humor, we made it out.