Top 30 Comedy Movies of the Century (So Far)

This 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.

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.

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.

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.

“Best in Show,” was a stellar introduction 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.

It’s not unusual to suddenly discover that your fiancé has been hiding an intimidating millionaire family from you. Not in a romcom, anyways. “Crazy Rich Asians” invigorated that familiar concept with new life, turning it into one of the biggest hits of 2018. Based on Kevin Kwan’s novel, the movie depicts amiable professor Rachel as she struggles to win over her future-husband’s eccentric relatives and matriarch. Critics and audiences applauded its affectionate representation of multiple cultures and demographics, and its diverse casting made the film’s success an inspiration. Supported by kooky characters, a smart screenplay and a pitch perfect cast, “Crazy Rich Asians” is a milestone for inclusivity while still being downright hilarious.

Nothing matches hot pink better than… existential dread! Not only did “Barbie” reach new heights both culturally and financially, it dazzled audiences with its empowering messaging, visually stunning direction, and standout performances. Even with all that aside, the film is simply hilarious! Ryan Gosling’s Ken is easily one of the most quotable characters in recent film history– we’re still laughing at his “sublime” delivery. And when you have the likes of Kate McKinnon, Will Ferrell, and Michael Cera in your cast, you know you’re in for a great time! We predict that “Barbie” will continue to be beloved beyond the peak of its popularity, for decades to come!

“Jojo Rabbit” 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.

It’s bewildering that, for how funny it is, “Popstar” was a box office bomb. 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.

Sometimes, the best comedies are the ones that know exactly what they are and run with it. Rather than dodge its potential shortcomings as a predictable rags-to-riches story, “Dodgeball” embraces them completely and is all the better for it. With Vince Vaughn and a roided out Ben Stiller leading the pack, it’s the kind of movie that’s at it’s best when at it’s most nonsensical. A worthy successor to the profane and over-the-top sports comedies of the 90s, what “Dodgeball” lacks in surprises, it more than makes up for in endlessly quotable lines and a wholesome ensemble of lovable losers.

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.

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.

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.

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.

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.

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.

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.

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.

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!

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.”

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.

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.

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”.

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.

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.

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.

“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.

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.

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.

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!