Top 20 Comedy Movies of the Century So Far

Script written by Savannah Sher
Sometimes we just need a good laugh. Welcome to WatchMojo, and today we’ll be counting down our picks for the Top 20 Comedy Movies of the Century (So Far).

For this list, we’ll be looking at our favorite comedic films released between 2000 through 2019. We’re only looking at live action movies featuring real actors. so animated films like “The Lego Movie” and puppet based films like “Team America: World Police” won’t make the cut.

#20: “What We Do in the Shadows” (2014)

Taika Waititi has become one of the major comedic auteurs in the last decade, and while he has created some great (and hilarious) flicks, our favorite has to be 2014’s “What We Do in the Shadows,” which he co created with another New Zealand funnyman, Jemaine Clement. This movie takes a satirical look at the vampire genre and employs the mockumentary style to flawless comedic effect. The story is set in Wellington and focuses on a group of vampire roommates. Waititi and Clement both star in the film, which works on both obvious physical jokes and more clever subversive ones, making for a well rounded horror comedy that we could watch again and again.

#19: “Walk Hard: The Dewey Cox Story” (2007)

The trend of satirizing common film genres started, of course, long before “What We Do in the Shadows”. In 2007, “Walk Hard: The Dewey Cox Story” took a stab at the tropes found in the standard music biopic, seeming to pay particular attention to “Walk the Line” and “Ray.” John C. Reilly stars in the titular role, and is as hilarious as he always is, but brings his comedic musical talents to the table as well. The original songs are a feat of their own, and while this movie hasn’t become a pop culture phenomenon like some of the others on our list, we’d say it’s seriously underrated.

#18: “Wet Hot American Summer” (2001)

This movie was a total box office bomb, making under $300 thousand despite a $1.8 million budget, but that doesn’t mean it isn’t beloved. “Wet Hot American Summer” received mixed-to-negative reviews and clearly didn’t bring people out to theaters, but with an all star cast that included Bradley Cooper, Amy Poehler, Elizabeth Banks, and Paul Rudd before they were household names, how could you go wrong? It too is a satire, taking a comedic look at summer camp culture and - despite its poor fiscal performance - was picked up by Netflix for a prequel series that spawned a sequel.

#17: “This Is the End” (2013)

The concept of a bunch of A-list celebrities getting together during the apocalypse seems almost too good to be true. But Seth Rogen and Evan Goldberg used their celeb clout to pull it off with “This Is The End”. They called in all their famous friends and managed to convince the likes of Emma Watson, Mindy Kaling, James Franco and Rihanna to play over the top fictionalized versions of themselves as they band together for the end of the world. There’s a certain behind the scenes enjoyment that viewers get from this movie, because it begs the question of whether this is really what these guys are like in real life.

#16: “Step Brothers” (2008)

The storyline of “Step Brothers” is just so delightfully weird that it works. Two adult men (played flawlessly by Will Ferrell and John C. Reilly) become step brothers when their parents get together, and act like children throughout the process. The plot is full of twists and turns though, because while at first it seems that the conflict will be between the two man children, they quickly realize how much better things will be if they decide to be friends. The flick is full of iconic moments, and gave us phrases that most of us have probably forgotten are even from the film. That’s right: this is the movie that prompts us to comment on how much extra space “for activities” a room may have.

#15: “21 Jump Street” (2012)

Who would have thought that Jonah Hill and Channing Tatum were the buddy cop duo that we had all been waiting for? This unconventional pairing made for a great partnership in “21 Jump Street”, where two cops have to go undercover to bust a high school drug ring. This story has so much going for it, tackling teenage stereotypes in a way that’s really funny and yet also kind of heartfelt. Sequels aren’t always worth talking about, but 2014’s “22 Jump Street” actually holds up pretty well to its predecessor.

#14: “Bridesmaids” (2011)

After 2011, people were forced to stop saying that “female comedians aren’t funny” anymore. “Bridesmaids” was like anything else that came before it: a major studio comedy with an all female primary cast that employed as much over the top and gross out humor as anything the boys were making. The film was a massive financial success, bringing in almost ten times its budget in box office revenue. In fact, it’s the biggest box office success that Judd Apatow has ever had. It also reignited Melissa McCarthy’s career as a comedic actress and has become something of a modern classic.

#13: “Pineapple Express” (2008)

Not all stoner comedies are worth writing about, but this one definitely is. Judd Apatow, Seth Rogen and Evan Goldberg were behind “Pineapple Express”, which pretty much made it a shoe-in for comedic success. It’s about a regular guy and his drug dealer who find themselves on the run from the law and shows their situation quickly escalating out of control. It’s full of admittedly gratuitous violence that’s used for comedic effect and the sort of humor that makes you feel guilty for laughing, but hey, things don’t always have to be high brow to be good.

#12: “Mean Girls” (2004)

Tina Fey’s screenplay for “Mean Girls” proved that she was so much more than an SNL star, as she adapted a teen self help book into this biting and satirical yet oh so funny critique of high school girl culture. There are so many iconic characters and moments in this film, which has flawlessly stood the test of time despite being released more than a decade and a half ago. Saying it has a cult following seems like a major understatement, because “Mean Girls” has simply become part of the cultural zeitgeist, with phrases from the movie being part of our cultural lexicon. You go, Glen Coco!

#11: “Tropic Thunder” (2008)

Telling the story of a movie within a movie, “Tropic Thunder” looks at a group of privileged actors who find themselves in dire circumstances while filming. Though most of “Tropic Thunder” would be easily read as being straight up ridiculous, it was one of the rare comedies of this sort that received awards season recognition. Robert Downey Jr. even received an Oscar nod for his performance! While there was controversy about the treatment of mental disability in the movie, one of the writers stated that it was in fact the opposite, saying, "Some people have taken this as making fun of handicapped people, but we're really trying to make fun of the actors who use this material as fodder for acclaim.”

#10: “Zoolander” (2001)

The premise for “Zoolander” may be absurd, but that doesn’t make us love it any less. Someone is trying to brainwash models to assassinate the Prime Minister of Malaysia, but the plot doesn’t really matter because this movie is all about Ben Stiller absolutely killing it playing a vain and vapid male model. He has to go up against Owen Wilson’s Hansel (so hot right now), who is his foe before becoming his friend. Will Ferrell is perfection as fashion mogul Mugatu, who plays an outlandish stereotype of the type of people who work in the industry. Parts of this flick may make us feel guilty for laughing because they’re so dumb, but we can’t help ourselves.

#9: “The Grand Budapest Hotel” (2014)

While most of the comedies on this list are of the big, blockbuster, laugh-out-loud variety, we’re going to take a detour for this entry. Wes Anderson has become known for his distinctive filmmaking style, his pastel color palette and his ever so symmetrical framing. All of his movies have an element of humor to them, and we were definitely tempted to include “The Royal Tenenbaums”, but our favorite has to be 2014’s “The Grand Budapest Hotel”. It has a simmering undercurrent of comedy running throughout the tale that is both subtle and incredibly clever.

#8: “Shaun of the Dead” (2004)

We would have loved to put every film in Simon Pegg’s Cornetto Trilogy on our list, but while we love “Hot Fuzz” and “The World's End”, we had to go with the earliest of the three, “Shaun of the Dead”. Pegg managed to take the zombie horror genre and make it into comedy in a way that ushered in many attempts to replicate the formula that he had perfected. The movie is not only funny, but actually kind of touching in a way we wouldn’t expect from films in this genre. “Shaun of the Dead” was put together by comedy auteur Edgar Wright, who also penned and directed the stellar “Scott Pilgrim vs. the World”.

#7: “Napoleon Dynamite” (2004)

We pity anyone who is too young to remember what a big deal “Napoleon Dynamite” was back in 2004. It’s the sort of movie that suffers retroactively because so many tried to imitate the awkward and dorky style that it created, almost making us forget how great the original really was. It was made on a shoestring budget of less than half a million dollars, with the film’s star only making $1000 for his work until he negotiated for a share of the profits following its massive success. The fact that we saw so many Vote for Pedro shirts out in the world for years following its release is an indicator of its cultural success.

#6: “School of Rock” (2003)

Not everyone loves Jack Black, but we’re pretty such we can all agree that this movie is a masterpiece. A comedy that makes us laugh this much but which also manages to be incredibly heartwarming is truly something special. When Dewey Finn starts impersonating a substitute teacher at a fancy prep school, he uses the only skills he has to teach the kids about rock n’ roll. It’s easy to forget that this film was directed by Richard Linklater, who is better known for his more serious and artsy endeavors. The songs in the movie are catchy as hell, and the child actors do a much better job than you’d think. Not only that, but it makes even the biggest hater love Jack Black.

#5: “The Hangover” (2009)

The premise of “The Hangover” is such a simple one, but the execution made this movie one of the biggest comedies of the 2000s. A group of guys goes to Vegas for a bachelor party and things escalate into chaos. But this flick is full of unexpected twists and turns that keep you guessing and which never take you where you think you’re going. The cast is full of great comic actors like Ed Helms and Zach Galifianakis along with Bradley Cooper, whose career skyrocketed after the film was released. In case you don’t already know this, feel free to skip the two sequels because they do not hold up to the original.

#4: “Superbad” (2007)

“Superbad” wasn’t exactly going into uncharted territory. On paper, it seems like a run of the mill high school comedy about two dorky teens who want to lose their virginities before graduation and end up having a big night out. But the comedic duo that is Jonah Hill and Michael Cera elevated this movie into something iconic that was not only a huge financial and critical success, but one that has gone on to enter the realm of best teen movies of all time. The chemistry between the two leads gives this story a much sweeter undercurrent than other more cynical films and we could watch it again and again.

#3: “Borat” (2006)

Did anyone NOT see “Borat” when it hit theaters in 2006? Back then it seemed like everyone and their mother was testing out their Borat impression by saying “very nice” and “great success”. Sacha Baron Cohen’s idea behind this film was nothing short of genius: impersonate a journalist from Kazakhstan and go around the US interviewing unsuspecting citizens, showing just how backwards things are in our own backyards. Sure, there are aspects of this approach that haven’t aged all that well, but keeping in mind what Cohen’s intention was, you know his own views aren’t the ones to be concerned about.

#2: “The 40-Year-Old Virgin” (2005)

Though “The Office” began airing a few months before this movie was released, it was really “The 40-Year-Old Virgin” that made Steve Carell a star. He penned the screenplay for the film alongside Judd Apatow, and it seems like it was flawlessly written for his personal brand of adorable awkwardness. Though it’s a story filled with silliness, there’s also something going on below the surface, which has come to characterize Apatow’s movies, whether he directed, wrote, or produced. In fact, it was Apatow’s directorial debut and remains one of his best comedies, though more modern picks like “Trainwreck” also give it a run for its money.

Before we unveil our top pick, here are a few honorable mentions.

“Game Night” (2018)

“Zombieland” (2009)

“Popstar: Never Stop Never Stopping” (2016)

“Super Troopers” (2001)

“MacGruber” (2010)

“The Nice Guys” (2016)

#1: “Anchorman: The Legend of Ron Burgundy” (2004)

We’ve already seen a handful of great Will Ferrell comedies on this list, but none can top “Anchorman”. A piece about a group of misogynistic TV newscasters in the 1970s may not have seemed like fodder for comedy gold, but you can’t possibly explain the appeal of this movie on paper. It’s full of quotable lines that have become part of our everyday speech patterns, whether we realize it or not. It’s one of those films that somehow never gets old, even though the jokes aren’t exactly clever. There may be no rhyme or reason to it, but there was no question that it had to be at the top of our list. You stay classy, San Diego!