10 Most Underrated Comedy Films of the Last 20 Years

Who doesn’t love a good laugh? And one of the best can come from a hilarious film. Despite how entertaining a good comedy can be, there aren’t many original additions to the genre each year — especially in our age of reboots, sequels, and big-budget blockbusters.

That’s why it’s unfortunate that these 10 comedy films flew under the radar and were missed by a wide swath of the movie-going public. Stream one of these titles the next time you’re in need of a laugh.


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10 Surf’s Up (2007)

This animated mockumentary is less laugh riot than laid-back chuckler, but it will keep you smiling throughout its run time. The story mimics the format of a surfing documentary, as a teenage penguin named Cody Maverick leaves Antarctica to follow his dream of becoming a professional surfer just like his hero Big Z.

The voice cast, especially Jeff Bridges as Big Z, is top notch and the movie's format is creative, especially for an animated film. There were a lot of successful penguin-centric movies released around the time Surf’s Up came out, and unfortunately Surf’s Up was the least seen of the bunch. Even if you couldn’t care less about surfing, this fun film is worth checking out.

9 The Spy Who Dumped Me (2018)

This spy caper/buddy comedy pairs Mila Kunis and Kate McKinnon as best buds who find themselves in the middle of an international conspiracy after one discovers her ex is a spy. The pair travel across Europe attempting to outrun assassins and figure out what’s going on to hilarious effect.

While the movie can be busy and violent at times, it's also incredibly funny to watch the friends attempt to navigate a world of undercover intrigue. And McKinnon aces her hysterical role as an overly confident fish out of water.

8 Thank You for Smoking (2005)

Aaron Eckhart in Thank You For Smoking

Before Jason Reitman made Juno or Up in the Air, he directed this satire starring Aaron Eckhart as a tobacco lobbyist whose job is to defend the tobacco industry. The character’s also a member of a group that includes a firearm lobbyist and an alcohol lobbyist. All these individuals know that what they’re selling is dangerous, but they believe in personal responsibility — at least as much as they believe in anything — and are willing to spin things in whatever way best serves their purpose.

If you like your comedies black, this is a great choice. Although the movie’s presented from the perspective of a tobacco lobbyist, its goal isn’t to persuade its audience about the joys of smoking. It’s to explore the choices we make and the people who try to influence how we make them. It’s a smart movie with a great cast that elicits knowing laughter.

7 Zack and Miri Make a Porno (2008)

Zack and Miri, played by Seth Rogen and Elizabeth Banks, are 10 years out of high school and going nowhere fast. They don't even make enough money at their dead end jobs to pay their rent and bills. And just as Thanksgiving rolls around they find both their power and water shut off. So they do what any hard-up twenty-somethings would do — they decide to make an adult movie.

Wait, don’t walk away yet! Despite the premise, the movie is surprisingly touching. It’s directed by Kevin Smith, so it has its share of gross-out humor and edgy jokes, some of which feel outdated by today's standards. However, the movie is genuinely funny with great performances by its leads, characters who know their lives aren’t where they want them to be but are doing their best with what they have.


6 Hoodwinked! (2005)

This animated fairy tale mash-up uses the framework of Little Red Riding Hood to explain why the Wolf was at Granny’s house from several different points of view, Rashoman-style. Needless to say, what we know from the fable turns out to be a matter of perspective.

It’s true that the animation isn’t top notch, but if you can overlook that, the story is incredibly entertaining. The movie also includes funny songs and fantastic voice work by talent like Anne Hathaway, Glenn Close, and Patrick Warburton. If you enjoyed the TV shows Once Upon a Time or Grimm or were a fan of Into the Woods, give Hoodwinked! a try.

5 Role Models (2008)

Role Models stars Paul Rudd and Seann William Scott as two energy drink salesmen who find themselves stuck doing community service at a Big Brothers-type charity. At first, things don’t go so well between the pair and their assigned little brothers. Then they start to bond over breasts, KISS, and live-action role-playing.

Given the stars involved, it’s no surprise that the movie’s funny, but it’s also sweet and endearing. Sure, there’s some raunchy humor, but you also genuinely care about the characters. By the end, you may even decide LARPing is a great bonding activity.

Related: Which Romantic Comedy Are You, Based On Your MBTI®

4 Best in Show (2000)

Schitt's Creek

In the late 1990s and early 2000s, Christopher Guest had a particularly prolific period as a director churning out improvised mockumentaries like Waiting for Guffman and A Mighty Wind. Best in Show was another entry in Guest's accomplished canon. It follows the quirky owners of five dogs as they prepare to compete in an upcoming dog show.

The film’s loose structure allows it to mine comedy from the situation as well as its ridiculous characters. And those characters are played by an accomplished cast, which includes Eugene Levy, Catherine O’Hara, and Jane Lynch.

3 Game Night (2018)

Jason Bateman and Rachel McAdams in Game Night

As its title suggests, Game Night involves friends gathering for a game night that goes horribly awry. Soon, the board games are left behind for what the group thinks is a live-action role-playing scenario, until they realize they’re going up against a real criminal organization.

The movie is full of twists and turns and is laugh-out-loud funny in scene after scene. It boasts a fantastic cast who completely buy into the zany premise. Special shout out to Rachel McAdams, whose reaction to vanquishing a bad guy is a comedic highlight.

Related: 10 Comedy Actors From The 90s We Wish Were Still Making Movies

2 Sleepwalk With Me (2012)

Stand-up comedian Mike Birbiglia wrote, directed, and starred in this indie based on his struggles with his career, his relationship, and his increasingly dangerous bouts of sleepwalking. While the main character is definitely having a rough time, the movie’s presentation of his challenges is hilarious.

At the same time though, the film does a good job of presenting the life of a stand-up comedian and the difficulties faced by someone who sleepwalks. It’s from that honesty that the movie expertly mines its comedy.

1 Tucker & Dale vs. Evil (2010)

Tucker and Dale just want to renovate their new vacation cabin in the woods. But instead they find their property overrun with college kids who believe they're psycho-killer rednecks. This horror comedy is heavy on both the horror and the comedy as the college kids keep accidentally offing themselves in hilarious ways. Meanwhile, both Tucker and Dale and the group of students continue to draw the wrong conclusions about one another.

The movie makes everyone’s points of view clear, which adds plausibility when things get completely out of hand. Plus, Alan Tudyk and Tyler Labine turn in endearing performances as the title characters who continuously have their good intentions misinterpreted. Even if you’re not a fan of horror, the comedy makes this movie worth a watch.


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