What’s So Funny? Comedies From The 21st Century That Are Worth The Giggle Fest

Since the turn of the century, there have been a ton of movies where we giggle to the point where we might pee our pants. There’s something about comedies in this day-and-age that always makes us want more. Humor is a subjective topic, and it’s fair to look at all of the movies from this century that left us laughing out loud.

This list represents the best cross-section of comedy from our very young millennium. From rom-coms, raunch-coms, new-and-improvised takes on comic types, there’s a little something for everyone here, no matter what you find funny. Go ahead, start a heated argument about which film is the funniest of them all!

Harold And Kumar Go To White Castle


Photo Credit: New Line Cinema/MovieStillsDb

In this classic stoner comedies, a couple of twentysomething dudes head out for a “road trip” to feed their munchies. Kal Pal and John Cho take the audience down the perfect detour as this generation’s Cheech and Chong.

They even learn that being young and dumb to devote their night for a fast-food craving is on another level. Of course, the cameos from Christopher Meloni and Neil Patrick Harris are nothing but comedic gold.

Mean Girls


Photo Credit: Paramount Pictures/MovieStillsDb

Welcome to high school hell. A world full of jocks, nerds, and girls who eat their feelings. Along those same lines, there are the wannabees and the burnouts. Then, there are the Plastics led by Regina George who cause nightmares for everyone else.

Tina Fey was sure to establish herself as one of America’s best comedy writers thanks to this teen-classic. Of course, lines like “On Wednesdays, we wear pink” and “It’s October 3rd” can never go unsaid.



Photo Credit: DreamWorks Pictures/MovieStillsDb

Will Ferrell did a fantastic job of transitioning from Saturday Night Live to movie stardom. Ferrell and his frequent collaborator, Adam McKay, found a great delivery device for the actor’s hilarious ascension by being a news anchor.

The movie helped establish Ferrell’s brilliant oddness by having him play the jazz flute to fighting with a rival news network. But, who could forget Burgandy and his foolish co-workers doing an a cappella performance of “Afternoon Delight?” Just ahead, a few years after Anchorman, Ferrell and McKay teamed up again. This time, with John C. Reilly.

Tropic Thunder


Photo Credit: DreamWorks Pictures/Paramount Pictures/MovieStillsDb

Ben Stiller’s 2008 Hollywood fiasco was spot on, especially with the studio logos and the opening’s fake trailers. The movie is an Apocalypse Now-style war movie with the film’s cast and crew being stranded in a jungle.

The ensemble cast is complete with Nick Nolte, Jack Black, Jay Baruchel and Robert Downey Jr. as the hardcore method actor. Also, under so many pounds of makeup, Tom Cruise is a loathsome executive just dying for that MVP status.



Photo Credit: Universal Pictures/MovieStillsDb

What’s the opposite of The Hangover? Champagne and cupcakes and party favor puppies wrapped up in the string. Not only that, but Kristen Wiig throwing tantrums is the best thing to happen to this movie.

Years from now, it’ll make even more sense why this story about a thirtysomething whose stuck in a rut is so relatable. Fresh faces such as Rebel Wilson, Ellie Kemper, and Chris O’Dowd get plenty of room to make an impact. But then, there are moments that really make this the all-girl version to Todd Phillips 2009 comedy.

Step Brothers


Photo Credit: Columbia Pictures/MovieStillsDb

Ferrell and McKay are at it again with a new sidekick, John C. Reilly. The duo played stunted adults who are forced into the same family when their single parents re-marry. They’re nothing but a bunch of manchildren, which is what makes Ferrell and Reilly comedic geniuses.

Since the release of the movie in 2008, their back and forth idiocy has only built a cult following, and forever made this movie a modern classic. The next movie ahead features director Edgar Wright’s breakthrough film that takes aim at zombie flicks and post-apocalyptic dramas.

The 40-Year-Old Virgin


Photo Credit: Universal Pictures/MovieStillsDb

Judd Apatow was best-known for Freaks and Geeks until his big-screen directorial debut took movie-goers by storm. Steve Carell plays the title character, a geek who’s never had a real relationship despite being 40 years old.

A team of supporting players, including Romany Malco, Jane Lynch, Seth Rogen, and Paul Rudd, offer horrible romantic advice to a guy who’s never sealed the deal. But it starts here because as everyone should know, you never forget about your first time.

Punch Drunk Love


Photo Credit: Columbia Pictures/MovieStillsDb

Adam Sandler has come a long way since his Billy Madison days. Paul Thomas Anderson teases Sandler’s usual high-energy comedy styo around a love story. The actor plays Berry Egan who falls for Lena, a friend of one of his many sisters.

They’re two people who are somewhat misfits who belong together. We have to mention that the Provo, Utah phone-sex operator was none other than the late Philip Seymour Hoffman.

Shaun Of The Dead


Photo Credit: Universal Pictures/Rogue Pictures/MovieStillsDb

Director Edgar Wright’s breakthrough film takes aim at horror movies, zombie flicks, and post-apocalyptic dramas. It’s really funny, but frightening at the same time with each tone over-throning the other.

This was co-writer Simon Pegg’s early stages of the cheeky, stylish irreverence that would solidify the British actor’s trademark for future films. It’s so comical, in fact, that it takes a moment to fully understand how weirdly emotional it can be. Pegg and co-star Nick Frost would team up for the movie just ahead, which is a buddy-cop British comedy.

Legally Blonde


Photo Credit: MGM Distribution CO./MovieStillsDb

Sorority president Elle Woods was dumped by her Harvard-bound boyfriend for being too much like Marilyn Monroe and not enough like Jackie Kennedy. Woods thinks she’s both and sets out to prove it.

From out of nowhere, this cute blonde girl is acing her LSAT, but let’s not forget her video essay for Cambridge’s law school in a pink bikini. Reese Witherspoon makes us fall in love with her, with a heart of gold and a comedy full of laughter.



Photo Credit: Columbia Pictures/MovieStillsDb

Seth Rogen and Evan Goldberg went back to their youth and created a teen comedy with plenty of dirty jokes. Two high-school dudes are trying to have one last night of fun before high school wraps up.

The antics are pretty simple, involving a patty, period blood and some kid who wanted a fake ID with the name “McLovin.” But underneath all the teen-boys and shenanigans is a thread of deep-seated insecurity. Oh, and Michael Cera singing “These Eyes” to a room full of drug addicts was the highlight of it all.

Hot Fuzz


Photo Credit: Universal Pictures/Rogue Pictures/MovieStillsDb

Simon Pegg and his partner-in-crime, Nick Frost, are back with a buddy-cop action flick. Pegg plays a London detective who is reassigned to a provincial police force. The pair has come a long way since their Shaun of the Dead days.

Between Hot Fuzz’s big set pieces and those epic references to Bad Boys II and Point Break, the movie is full of big laughs with a dose of small-town anarchy in the United Kingdom. The next movie ahead was Trey Parker and Matt Stone’s universe away from a little town called South Park.



Photo Credit: 20th Century Fox/MovieStillsDb

Sasha Baron Cohen pretends to be a dimwitted, bigoted Kazakh journalist on a journey through America. There’s a lot of shenanigans happening in this movie, even if people try their best to refrain from saying “my wife” in that accent.

Borat has nothing to lose and it’s nothing but a laughing machine with no end in sight. Sometimes, it feels that the film captured and embodied something rotten deep down in the American soul.

Jackass: The Movie


Photo Credit: MTV Films/MovieStillsDb

“Hello, I’m Johnny Knoxville and welcome to Jackass.” Want to see a topless man bike in shorts while rolling around on hundreds of mouse traps? Or a dude who shoved a toy car up in their butt? Say no more.

Johnny Knoxville and his stunt-hooligan gang were pioneers long before YouTube even existed. It’s gut-busting, even if you are concerned about these overgrown skateboarders who may need to go to the hospital.

Team America: World Police


Photo Credit: Paramount Pictures/MovieStillsDb

Trey Parker and Matt Stone turned the old, obscure sixties kids’ show, Thunderbirds, and made it into a take-no-crap puppet-apalooza. The South Park creators are quick to rip into military jingoists, foreign-policy hawks, and liberal movie stars.

The fact that the movie has not been made out-dated shows that it’s, in fact, more timely than it ever was. But then, you remember the movie is full of puppets who have the sudden passion to blurt out “Amer-i-ca! F*** Yeah!” A movie that featured Christopher Meloni and other up-and-coming actors from the late nineties is still on the way!

The School Of Rock


Photo Credit: Paramount Pictures/MovieStillsDb

Jack Black’s passion for the guitar gods of the past was on full display. It’s why he was the best choice to fake his way into a fifth-grade substitute teaching gig. But, it wouldn’t take long for his character to turn his musically gifted students into his backing band.

Black is perfectly in his element, but his poor rumbled knowledge of what it means to be a teacher is supposed to be his downfall. His little act toward Joan Cusack to “Edge of Seventeen” by Steve Nicks is worth the laugh over-and-over again.

The Royal Tenenbaums


Photo Credit: Buena Vista Pictures/MovieStillsDb

Wes Anderson’s feature has laughs and pathos from a family’s decades of pent-up resentment, disappointment, and desires. Gene Hackman portrays the neglectful Tannenbaum, and is featured with his ex-wife and three children who never lived up to their early potential.

The three children include a burned-out athlete, a failed playwright and a paranoid stockbroker. The clever dialogue, tracksuit-clad children, and wannabe cowboy authors make the movie funny from start to finish.

Wet Hot American Summer


Photo Credit: USA Films/MovieStillsDb

Law & Order: SVU’s Christopher Meloni learns some valuable life lessons from taking a can of vegetables that can pleasure itself. The cast of soon-to-be-superstars included: Bradley Cooper, Amy Phoeler, Elizabeth Banks, and Paul Rudd, and literally a ton of other future stars.

This raunchy Reagan-era teen comedy is worth the laugh after a long day of work. The cult-following film spawned into two Netflix spinoff series, but the movie is still the bar setter.

Knocked Up


Photo Credit: Universal Pictures/MovieStillsDb

Katherine Heigl might not have enjoyed her time when filming the movie where Judd Apatow’s script features a one-night stand that goes horribly wrong. With Seth Rogen coming out of the gates after getting Heigl pregnant, Apatow was sure to add some screw-ball friends to make his a laugh out loud comedy.

As for all of the rom-com’s cheesy gags, it has a heartstring kind of story that keeps you rooting for both, but especially Rogen, who was the underdog until the final scene.

High Fidelity


Photo Credit: Buena Vista Pictures/MovieStillsDb

The adaption to Nick Hornby’s novel does a great job at tackling record store gatekeepers. John Cusack plays a stubborn romantic, and then there’s Jack Black, who’s breakout performance provided a glimpse at all hey had in store for us later in life.

After seeing the film, Hornby was happy with Cusack’s performance. He even said that “at times, it appears to be a film in which John Cusack reads my book.” Oh, and the movie wouldn’t be complete without a cameo from Bruce Springsteen.