Top 22 Funniest Comedy Movie Moments of Each Year (2000 - 2021)
Trivia Top 22 Funniest Comedy Movie Moments of Each Year (2000 - 2021)



Top 22 Funniest Comedy Movie Moments of Each Year (2000 - 2021)

VOICE OVER: Rebecca Brayton WRITTEN BY: Nick Spake
These are the comedy movie moments that have defined the far. For this list, we'll be looking at moments that made us laugh the hardest throughout the 21st century. Our countdown includes “Zoolander”, “Anchorman: The Legend of Ron Burgundy”, "Superbad", “Booksmart”, "Free Guy", and more!

Top 22 Funniest Comedy Movie Moments of Each Year 2000-2021

Welcome to WatchMojo, and today we’re counting down our picks for the Top 22 Funniest Comedy Movie Moments of Each Year 2000-2021.

For this list, we’ll be looking at moments that made us laugh the hardest throughout the 21st century.

What’s your favorite comedy of the past 22 years? Let us know in the comments.

2000: I Have Nipples, Greg

“Meet the Parents” (2000)

When Greg covers up a lie by saying that he grew up on a farm, it’s funny, yet seemingly inconsequential. The filmmakers build upon this in the subsequent scene, though, as Greg’s little white lie snowballs into an elaborate faux backstory. Although Greg is visibly digging himself deeper and deeper, he remains committed to his tale about milking his sister’s cat. Greg’s assessment that anything with nipples can be milked is met with a classic response from Jack. The AFI would even shortlist Jack’s response as one of the 400 most memorable quotes in American cinema. The scene is made even funnier in the sequel when we learn Greg doesn’t even have a sister. We’re not sure why he named the fictional cat Geppetto either.

2001: Center for Ants

“Zoolander” (2001)

Ben Stiller was on fire in the early 2000s. While only a modest success upon release, “Zoolander” took on a life of its own thanks to moments like this. After dousing an unsuspecting Todd with a foamy latte, Mugatu reveals a model for Derek’s educational center. The brainless Derek is confused about its size, however. While Derek occasionally runs the risk of coming off as too stupid, it’s impossible not to laugh as he angrily chucks the model aside, noting that only ants could fit inside. It’d be one thing if the scene ended there, but Stiller goes the extra mile. We can practically see the hamster wheel spinning in Derek’s head as he concludes that the center needs to be three times bigger.

2002: Meeting Future In-Laws

“My Big Fat Greek Wedding” (2002)

Meeting parents was a popular trend in early 2000s comedies and “My Big Fat Greek Wedding” remains one of the funniest examples. While Toula’s family puts Ian through a lot of hoops, he remains a good sport throughout. It’s when Ian’s parents meet Toula’s whole family that matters get awkward. Mr. and Mrs. Miller can see how outnumbered they are pulling up to the lively Portokalos household. As if being swarmed by their future in-laws wasn’t overwhelming enough, Gus emphasizes what they’re getting into as he lists off every single family member, about ten of whom are named Nick. As baffled as the Millers are, Maria is even more confused when they present her with a cake missing its center.

2003: Neck Tranquilizer

“Old School” (2003)

Steve Carell came close to landing a regular spot on “SNL,” but they went with Will Ferrell. Fortunately, 2003 was a breakout year for both of these rising comedy giants. Carell briefly stole the spotlight from Jim Carrey in “Bruce Almighty.” Fresh off his “SNL” tenure, Ferrell cemented his film career with “Old School.” Just when you thought nothing would outshine Frank’s streaking, Ferrell outdoes himself with a tranquilizer. It hurts just hearing the dart blast into his neck, but Frank is so tripped out that he can’t comprehend what Mullett Stifler is saying. While the setup is funny enough, viewing all of this from Frank’s perspective in slow motion is what makes the scene so ingenious. Good thing Frank is built like a tank.

2004: Escalated Quickly

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

Everyone was doing (or at least watching) the Napoleon Dynamite dance in 2004, but we’re going back to the 1970s for this entry. Continuing their winning streaks, Ferrell and Carell appeared together in “Anchorman,” along with several other comedy heavyweights. Many of them clash in this unexpected showdown when a heated news ratings competition gets real. From Luke Wilson, to Tim Robbins, to Ben Stiller, the scene tops itself with each cameo. That’s only the beginning, as an all-out war breaks out, complete with severed limbs, pitchforks, and a grenade that hilariously never goes off. The battle is so random that by the time it’s over, even the participants aren’t sure how it escalated so quickly. They still reflect on the bloodfest quite casually.

2005: Kelly Clarkson!

“The 40-Year-Old Virgin” (2005)

Even in a cameo, Ferrell walks away with the funniest line: “Meatloaf!” Yet, 2005 officially solidified Carell as a leading man. Carell demonstrates how far he’ll go for a laugh as Andy gets his beastly chest waxed. While they could’ve turned to special effects or a body double, Carell knew that real pain always amplifies the comedy. Andy’s obscenities are priceless, but the funniest thing to come out of his mouth is the most G-rated: “Kelly Clarkson!” Even more than “Since U Been Gone,” the real Clarkson has stated that she’s best known for this unscripted moment. The scene is so painfully funny that even the actors can’t maintain straight faces, which still works marvelously in the film’s context. Suffering for your art has never been more hysterical.

2006: Freaky Family

“Little Miss Sunshine” (2006)

2006 was full of moments that had us laughing and cringing uncontrollably, from Ricky Bobby's grace to the Baby Jesus to Borat’s nude confrontation with Azamat. However, the climax of “Little Miss Sunshine” perhaps caught us off guard the most. Considering that grandpa coached Olive, we figured that her routine wouldn’t exactly be conservative. Nothing could prepare us for a striptease set to “Super Freak,” though. Shock value aside, this twist also proves clever commentary about child beauty pageants. Parading little girls in makeup and swimsuits is accepted, but a Rick James song is a step too far? It’s a surprisingly sweet moment as well with Olive’s whole family joining the dance. They didn’t drive 800 miles to let the act end abruptly.

2007: McLovin

“Superbad” (2007)

Rod Kimble and his crew weren’t the only ones who liked to party in 2007. So did the made trio from “Superbad.” Before they can party, it’s up to Fogell to purchase them some booze. There are more than a few problems with Fogell’s newly acquired fake ID, however. For starters, it says that he’s 25 when Fogel barely looks 18. The card claims that he’s from Hawaii, which raises several other red flags. Most glaring of all, Fogel changes his name to McLovin. Like Seal, no last name is required. With virtually nothing right about the card, Evan and especially Seth rip into Fogel. Regardless, it’s all they have to work with. They might think it’s laminated incompetence, but we’re McLovin it.

2008: Les Grossman Doesn’t Negotiate

“Tropic Thunder” (2008)

Between the bunk beds mishap in “Step Brothers” and Red’s many brushes with death in “Pineapple Express,” 2008 was a peak year for comedy. No character made us scream laugh more than Les Grossman, played by an unrecognizable Tom Cruise. Beyond Cruise’s extreme physical transformation, the character is unlike any other in the Oscar-nominated actor’s filmography. Grossman is at his most Grossman when he takes the reins of a phone conversation, laying into a group that’s taken one of his actors hostage. Dropping almost ten profanities before abruptly hanging up, Grossman concludes that Tugg is more valuable dead than alive. Whether you think Grossman is evil, mad, a genius, or an evil mad genius, we can all agree he’s the master of the dance floor.

2009: Head-Turning Credits

“The Hangover” (2009)

Unless it’s a Marvel movie, people generally bow out when the credits roll. “The Hangover” not only got the audience to stay put, but the credits delivered a cherry on top of what was already a satisfying sundae. While most of the loose ends seem to be tied up, we’re still left with numerous questions about the Wolfpack’s wild night. How did Phil end up in the hospital? How did they sneak out Tyson’s tiger? This is all hilariously explored through a photo montage, adding new layers to several jokes. Sometimes it’s funnier when a movie lets the mystery be, but in this case, we’re so happy that the filmmakers filled in the gaps. We still don’t know where exactly the chicken came from, though.

2010: Aim for the Bushes

“The Other Guys” (2010)

Seeing how the movie is called “The Other Guys,” we assumed that Samuel L. Jackson and Dwayne Johnson’s super cops would eventually be cast aside. Nobody could’ve predicted how they exit the film, though. In hot pursuit, Highsmith and Danson take a leap of faith. As they draw closer to the pavement, the audience grows increasingly skeptical of their plan. They say, “aim for the bushes,” but there are no bushes in their vicinity. Do they have parachutes or something to break their fall at the last minute? No, they end up dying as they lived: not thinking things all the way through. And let’s be honest. If all buddy cop movies were realistic, our “invincible” heroes would be dead less than thirty minutes in.

2011: Hot Lava

“Bridesmaids” (2011)

Watching the trailers for “Bridesmaids,” a lot of people categorized it as a “chick flick.” Granted, it is a “flick” and the cast is primarily comprised of “chicks,” but “Bridemaids” redefined what a “chick flick” could be. Nowhere is this better exemplified than at a bridal shop where lunch comes back to haunt the ladies from every end. With only one toilet, the others need to get creative, turning to the sink and the street. Like the characters, we can barely contain ourselves, although Annie somehow keeps it in. “Vomit,” “Defecation,” and “Revolutionary” are three words that aren’t often grouped together. In 2011, however, few other female-driven comedies were as unapologetic when it came to gross-out humor, breaking down barriers in its own twisted way.

2012: Teddy Ruxpin

“Ted” (2012)

Can you think of a stranger duo than Jonah Hill and Channing Tatum in a “21 Jump Street” reboot? How about Mark Wahlberg and a teddy bear? Given Wahlberg’s reputation for talking to animals, we suppose the premise for “Ted” isn’t that far-fetched. As the Thunder Buddies endure the stormiest weather of their friendship, John and Ted say what they’ve been bottling up. John takes things a step too far when he wishes he had gotten a Teddy Ruxpin instead, driving the bear to go “Revenant” on him. We’re not sure how Ted packs such a powerful punch, as he’s literally stuffed with fluff. Maybe it was part of John’s childhood wish? In any case, such surreal imagery could only emanate from Seth MacFarlane’s mind.

2013: When Life Gives You Lemmons

“The Wolf of Wall Street” (2013)

Martin Scorsese has been repeatedly praised for his crime dramas, but people sometimes forget about his black comedies. “The Wolf of Wall Street” is arguably his funniest film, bringing down the house with this outrageous scene. Jordan Belfort is already an unreliable narrator, and his reality becomes even more warped as the quaaludes kick in. While the film is largely driven by its uproarious dialogue, this is where Leonardo DiCaprio’s talents for physical comedy creep up. Simply dragging himself to his car is a perilous journey. More crazy hijinks await at home where Jordan and Donnie get tangled in another mess. Apparently, DiCaprio wore a neck brace after spending three days shooting this scene. Well, at least the car’s unscathed… oh spoke too soon.

2014: Schmidt & The Captain’s Daughter

“22 Jump Street” (2014)

Given Captain Dickson’s intense impulses, Schmidt might’ve thought twice about sleeping with Maya had he known she was his daughter. Schmidt connects the dots when he meets Maya’s parents at lunch. Being undercover, Schmidt and Dickson can’t unleash all the thoughts swarming through their heads, but they can exchange awkward glances. Oh, and since Schmidt previously bragged about hooking up with someone, the Captain knows everything! The only thing funnier than this twist is Jenko’s reaction when he puts two and two together. To say that Jenko isn’t discreet with this information would be an understatement. It’d be one thing if Jenko just laughed uncontrollably, but having him run around, proclaiming what happened is next level. Nothing that a shock to the crotch can’t resolve.

2015: You Always Do This to Me

“Trainwreck” (2015)

If we were watching a movie starring Daniel Radcliffe as a dog walker and Marisa Tomei as a dog owner, we’d want absolute silence in the theater. So, we can understand one patron’s frustration when John Cena’s Steven takes this time to sort out his relationship issues with Amy. When the fellow audience member gets coarse, Steven is less concerned about his derogatory remarks towards Amy and more upset about the Mark Wahlberg comparison. He fires back with several threats, which he probably could’ve worded better. The evening only goes downhill from there as Steven realizes that Amy likes to keep her relationships open, destroying his plan to marry her and start a basketball team with their six boys. Can we see that alternate universe?

2016: Message Received

“The Nice Guys” (2016)

“The Nice Guys” allows Russell Crowe and Ryan Gosling to play against type. While a tough guy doesn’t sound like a stretch for Crowe, we severely underestimated his comedy chops until this point. Gosling, usually the coolest person in the room, is turned into a bumbling P.I. who never learns his lesson. Gosling’s March finds himself in over his head when Crowe’s Healy introduces himself. March makes multiple attempts to turn the tables, but he doesn’t get the message until Healy leaves him squealing like a little kid. And speaking of which, Healy meets March’s daughter outside, who offers him a Yoo-hoo. The way Healy lights up at the prospect of a chocolate beverage perfectly contradicts the violence that just transpired.

2017: Zip-Line

“Girls Trip” (2017)

A word of advice: always use the bathroom before you go ziplining. Jada Pinkett Smith’s Lisa learns this the hard way when she gets stuck halfway. While the audience can sense where this scene is going, we weren’t ready for Lisa to pop like a shaken-up champagne bottle. Thankfully for Lisa, her embarrassing public display is quickly overshadowed by Tiffany Haddish’s Dina. Giving her friend a push to the other side, Dina rains upon the spectators below like a fire hose out of control. And this is why Bourbon Street doesn’t actually have a zipline. What happens in New Orleans stays in New Orleans, right? Or is that another city? Either way, no amount of restraint can hold in our laughter.

2018: Removing the Bullet

“Game Night” (2018)

It takes a while for Max and Annie to piece together that their role-playing game has spiraled into the real deal. Playtime officially ends when Annie accidentally shoots Max in the arm with a very real gun. The good news is that you can pretty much get everything needed to remove a bullet from a convenience shop. Of course, under normal circumstances, we’d recommend the ER. Even when one of them is recouping from a gunshot wound, Max and Annie still make for an adorable couple. They try to remain positive, treating Max more like a kid who scraped his knee. The deeper Annie searches for the bullet, though, the more the situation bears down on them. The funniest part? There’s no bullet to remove!

2019: A Doll’s Life

“Booksmart” (2019)

The tripping out scene is a staple of high school comedies, but we’ve never seen one this inventive. Having consumed some hallucinogenic strawberries, Molly and Amy’s world is turned into the demented stop-motion version of “Toy Story.” Envisioning each other as playthings, the friends realize how unrealistically fashion dolls are designed. Nevertheless, Amy can’t help but give in to the illusion as they strip down to their plastic bodies. We don’t think we need to censor any of this, but we’re never going to look at Barbie the same way again. It’s not surprising that animation studio ShadowMachine previously worked on “Robot Chicken.” As the scene ends, the perspective shifts to the live-action partygoers as Molly and Amy stiffly make their way out the door.

2020: Rudy Giuliani

“Borat Subsequent Moviefilm” (2020)

For a period, Rudy Giuliani was a widely respected politician. Over time, though, he became a much easier target for comedy. With his surprise appearance in “Borat Subsequent Moviefilm,” Sacha Baron Cohen turned him into the ultimate punchline. Watching this shocking scene, you can see why Maria Bakalova scored an Oscar nomination, remaining in character as Giuliani makes unfounded statements, toasts his drink after coughing during a pandemic, and follows her into the bedroom. Whether you believe Giuliani was “tucking in [his] shirt” as he claims or that he had other intentions, we’re glad Borat showed up when he did. We’d say that this is the craziest thing to ever happen in modern politics, but there’s A LOT to unpack from the past several years.

2021: Dude

“Free Guy” (2021)

“Free Guy” was already into production when Disney acquired 20th Century Fox. This enabled the filmmakers to incorporate several familiar properties into Guy’s climactic fight against Dude. Although he seems outmatched, Guy has a red, white, and blue ace up his sleeve. We’re not sure if Ryan Reynolds’ Deadpool will ever meet the MCU’s Steve Rogers. For the time being, though, Chris Evans’ cameo here is all we need. Guy reaches even deeper into the Mouse’s vault, conjuring the Hulk’s fist and a lightsaber. Keeping with the film’s video game theme, we also get some references to “Fortnite,” “Half-Life,” and “Portal.” Guy ultimately manages to subdue his nemesis by showing him the light, although he may still need to deal with Evans in the “se-quel.”