The 15 Best Comedies Released in the Past 25 Years

The 15 Best Comedies Released in the Past 25 Years

Comedy is one of those rare things that never goes out of style. No matter how much the world changes, we’ll always need movies that make us laugh so hard our stomachs hurt. Over the past two decades, filmmakers have delivered comedies that became instant classics—some outrageous, some heartwarming, and some so quotable they’ve become part of everyday conversation.

1. Superbad (2007)

Few comedies capture the awkwardness of teenage life as perfectly as Superbad. Jonah Hill and Michael Cera play two high school friends desperate to make the most of their final days before college. Their quest to score alcohol for a party turns into an epic night of misadventures.

What makes this movie so great isn’t just the raunchy jokes—it’s the heart underneath. The film perfectly balances crude humor with a surprisingly touching story about friendship.

And, of course, it gave us one of the most iconic side characters of all time: McLovin. If you’ve ever looked back on your teenage years and cringed, laughed, or both, Superbad will hit you right in the nostalgia.

2. The Hangover (2009)

When three friends wake up in Las Vegas with no memory of the night before—and a missing groom—the chaos begins. The Hangover thrives on escalating absurdity. Each new discovery (a tiger in the bathroom, a baby in the closet, Mike Tyson singing) tops the last.

The cast chemistry is spot-on, with Bradley Cooper as the smooth talker, Ed Helms as the panicked dentist, and Zach Galifianakis stealing every scene as the socially clueless Alan. What sets the movie apart is how it turns a simple “bachelor party gone wrong” concept into an unforgettable comedy adventure.

It’s outrageous, unpredictable, and endlessly quotable—making it the kind of film you can watch over and over without losing its spark.

3. Bridesmaids (2011)

Sometimes the funniest movies are the ones that feel the most real. Bridesmaids dives into the chaos of wedding planning, female friendships, and life’s unexpected curveballs. Kristen Wiig’s down-on-her-luck character tries to juggle it all while competing with a perfect new rival for her best friend’s attention.

The film is packed with memorable moments—from the infamous airplane scene to the wedding dress meltdown that no one saw coming. But beyond the big laughs, Bridesmaids works because it captures the highs and lows of friendship in a way that feels honest and relatable.

Add in Melissa McCarthy’s scene-stealing performance, and you’ve got a comedy that’s as heartfelt as it is hilarious.

4. Anchorman: The Legend of Ron Burgundy (2004)

Will Ferrell’s portrayal of a clueless 1970s news anchor is comedy at its most absurd. Ron Burgundy is confident, charming, and completely ridiculous—a combination that makes every scene unforgettable.

From the epic news team street brawl to Burgundy’s bizarre jazz flute performance, Anchorman is full of random but brilliant moments. It satirizes the macho culture of old-school journalism while giving us some of the most quotable lines in comedy history.

The supporting cast, including Paul Rudd, Steve Carell, and Christina Applegate, rounds out the chaos beautifully. It’s the kind of movie that’s so over-the-top, you can’t help but laugh, even when you know the punchlines are coming.

5. Step Brothers (2008)

Sometimes, the funniest comedies are also the dumbest—and Step Brothers is proof. Will Ferrell and John C. Reilly play two middle-aged men forced to live together when their parents marry. What follows is pure, chaotic immaturity.

The humor works because the characters fully commit to their ridiculous behavior, from building bunk beds to starting a terrible family band. Despite their childish antics, Ferrell and Reilly create characters you weirdly care about.

By the time they start to grow up (just a little), you’re rooting for them. The movie’s absurd premise and nonstop quotable lines make it one of the most rewatchable comedies of the 21st century.

6. Tropic Thunder (2008)

Making a comedy about making a movie is tricky, but Tropic Thunder nails it. The film follows a group of actors shooting a war movie who accidentally find themselves in real danger.

The cast is stacked: Ben Stiller, Jack Black, and a nearly unrecognizable Robert Downey Jr. deliver some of their funniest performances. The movie skewers Hollywood egos, blockbuster culture, and even awards season, all while delivering outrageous action sequences.

It’s bold, self-aware, and unafraid to cross lines, which is exactly why it’s so memorable. Tropic Thunder proves that when comedy meets sharp satire, the result can be explosively funny.

7. Borat (2006)

Sacha Baron Cohen’s creation, Borat Sagdiyev, is one of the most outrageous characters in comedy. The mockumentary follows Borat, a journalist from Kazakhstan, as he travels across America—exposing cultural quirks and awkward truths along the way.

The brilliance of Borat lies in its mix of scripted absurdity and real reactions. Cohen’s commitment to staying in character no matter how insane things get is jaw-dropping. While the humor is often cringeworthy and shocking, it also reveals uncomfortable truths about society.

Whether you laugh nervously or hysterically, Borat is impossible to forget. It’s the kind of comedy that pushes boundaries—and somehow makes it work.

8. 21 Jump Street (2012)

Who knew a reboot of an ’80s TV show could be this funny? 21 Jump Street takes the premise of undercover cops in high school and flips it on its head with brilliant comedic timing.

Channing Tatum and Jonah Hill make an unexpectedly perfect duo. Watching them struggle to fit in with modern high school cliques is hilarious, especially as roles reverse—Hill’s nerd becomes popular, while Tatum’s jock becomes the outcast.

The film doesn’t just rely on slapstick; it pokes fun at teen drama tropes and the very idea of Hollywood reboots. It’s smart, self-aware, and endlessly entertaining.

9. Hot Fuzz (2007)

British humor doesn’t always hit with American audiences, but Hot Fuzz is the glorious exception. Directed by Edgar Wright, the film blends buddy-cop tropes with small-town mystery, all wrapped in rapid-fire comedy.

Simon Pegg and Nick Frost make a fantastic pair, balancing action and absurdity with perfect chemistry. The gags come fast, from subtle background jokes to outrageous explosions. What sets Hot Fuzz apart is how clever it is—it works both as a parody of action films and as a genuinely thrilling story.

By the time the over-the-top finale hits, you’re laughing just as much as you’re on the edge of your seat.

10. The 40-Year-Old Virgin (2005)

Steve Carell’s breakthrough role showed the world that awkward comedy could also be sweet. Playing Andy, a middle-aged man who has somehow never had sex, Carell balances cringe-worthy moments with genuine heart.

The supporting cast—including Paul Rudd, Seth Rogen, and Catherine Keener—elevates the story, turning what could have been a one-note joke into a layered, hilarious film. The humor ranges from raunchy banter to painfully awkward silences, making it endlessly rewatchable.

What really makes The 40-Year-Old Virgin special, though, is that beneath the comedy, it’s ultimately a story about vulnerability, connection, and finding love when you least expect it.

11. Shaun of the Dead (2004)

Zombies aren’t usually funny—but leave it to Edgar Wright and Simon Pegg to make them hilarious. Shaun of the Dead is part zombie horror, part British rom-com, and part comedy of errors.

Shaun, a slacker trying to win back his girlfriend, accidentally becomes the leader of a zombie survival crew. The film’s humor comes from its sharp writing and clever visual gags, but it also works because it has heart.

Even while laughing at the absurdity of using bar stools and records to fight zombies, you find yourself caring about the characters. It’s a unique mix of gore, laughs, and surprisingly touching moments.

12. Napoleon Dynamite (2004)

Quirky, awkward, and unlike anything else, Napoleon Dynamite became a cult classic almost instantly. Jon Heder’s portrayal of the oddball Napoleon—complete with moon boots, dance moves, and llama care—is as unforgettable as it is hilarious.

The humor is dry, the pacing is slow, and the characters are bizarre—but somehow, it all works. From Uncle Rico’s football obsession to Pedro’s campaign for class president, the movie thrives on its small-town weirdness.

It’s the kind of comedy that sneaks up on you, where the funniest moments are often the most understated. If you get it, you love it—and chances are, you’re still quoting it years later.

13. Mean Girls (2004)

High school cliques have never been roasted harder than in Mean Girls. Written by Tina Fey, the movie follows Cady Heron as she navigates the ruthless world of popularity, gossip, and “The Plastics.”

What makes it timeless is how sharp the humor is. Every line feels quotable, from “You can’t sit with us” to “On Wednesdays we wear pink.” The cast—led by Lindsay Lohan, Rachel McAdams, and Amanda Seyfried—brings the script to life with perfect comedic timing.

Beneath the jokes, though, is a smart commentary on teenage culture and identity. It’s funny, it’s relatable, and it’s endlessly rewatchable.

14. Elf (2003)

Christmas comedies often rely on charm, but Elf takes it to another level. Will Ferrell’s Buddy is pure childlike energy in a grown man’s body, and his antics in New York City are comedy gold.

From guzzling syrup to singing loudly in public, Buddy’s naive optimism creates endless hilarious situations. But what keeps audiences coming back every holiday season is the heart.

Elf is funny, yes, but it’s also about family, kindness, and believing in the Christmas spirit. The combination of slapstick humor, quotable lines, and genuine warmth has made it a modern holiday classic.

15. The Nice Guys (2016)

Ryan Gosling and Russell Crowe might not seem like a natural comedy duo, but The Nice Guys proves otherwise. Set in 1970s Los Angeles, the film pairs a bumbling private eye with a tough enforcer on a wild case involving murder, corruption, and porn scandals.

What makes it so funny is the mix of slapstick and sharp dialogue. Gosling leans into physical comedy, often failing spectacularly, while Crowe plays the straight man with just enough dry wit. Together, they create a dynamic that feels both fresh and classic.

Stylish, chaotic, and laugh-out-loud funny, The Nice Guys is one of those underappreciated gems you’ll want to recommend to everyone you know.