WEEKEND SPECIAL: The 100 Funniest Movies Of The 21st Century
And The Inevitable Pledge Drive
While I was in prison, a curious theory spread through the world of cinema, that comedy was dead. Some people blamed “woke”, some people blamed MAGA, some people blamed the growing overseas market. Personally, I have my theories. But the point is, there were less comedies being made, and they were being greeted by a contentious audience.
Fortunately, that means a smaller canon. So I’m staking my claim on this — a century that is a quarter of the way complete, has produced a considerable list of comedic classics. There have been some stinkers, too, and some years produced far less than others. But in 2025, we can look back on the 21st century and look specifically at the laughs.
Now, worth noting, my criteria, which was fungible and unprofessionally-flexible:
-Firstly, I am talking about the movies that made me laugh the hardest. I’m not talking about the BEST comedies, as many of them were great not because of laughs, but because they were dramatically potent. The films of Charlie Kaufman could be considered comedies, and I love them dearly, but I usually finish them wiping away tears and considering my place in the universe. So a number of Kaufman films are not here. Maybe I will change my mind in a year and put them in. Anyway, some of the lower ranked movies are more dramatically satisfying than the ones above them. Oh well.
-Secondly, I am talking about films that were primarily comedies. We all laughed a lot during “Moonfall”, but, c’mon.
-Thirdly, what does it mean to laugh? Some of these movies I found funny because, in the moment, I threw back my head and roared. Others were funny because they would grow in my memory, and I would recall the depth and meaning of the joke, which had only grown stronger over the years. And some movies, in small doses, made me laugh a few times, while others made me only chuckle, but constantly and consistently. It’s not a fine science. Regardless, these are movies that induced laughter-type mouth-sounds from me.
Fourth, this goes without saying — people make lists like this for debate, and to recommend little-known movies. Don’t hesitate to speak up. I’m just a guy, I might have missed one!
Fifth, if you hate to laugh, I apologize, this list may not be for you. I am sorry that you suffer from sadness.
Sixth, if I reviewed the movie on this Substack, I will simply let the link do the talking. Several of these which fall between 2014-2023 will likely eventually receive a review.
HONORABLE MENTION: Our Idiot Brother, Happiness Of The Katakuris, OSS 117: Cairo Nest Of Spies, The Little Hours, Norwegian Ninja, Hell Baby, Smiley Face
Hamlet 2
Not the most laugh-for-laugh comedy. But the sheer absurdity of the “Hamlet 2” stage show in this film, complete with “Rock Me, Sexy Jesus”, is an all-timer comedy setpiece.
Save The Green Planet
Is the boss an alien, or an innocent? Are we human or are we dancer? No Bugonia required.
The Other Guys
Right before Adam McKay lost his fastball, he delivered a textbook cop buddy comedy that manages to shoehorn in a number of his topical interests, enriching what was already a fairly-amusing Ferrell/Wahlberg two-man act.
Divine Intervention
Absurdist Palestinian comedy plays like “Playtime” in a war zone.
The Nice Guys
Gosling and Crowe, a surprising comedic A-team.
The Invention Of Lying
Doesn’t really have an end, Ricky Gervais’ own ambitions tumbling over each other. But what a concept, the idea of one man inventing the concept of the lie. At its best, a deeply funny, timeless parable.
Ratatouille
Stealthily Pixar’s best, teaming witty banter with clever animated slapstick.
Wolf Of Wall Street
Leo and Marty and their irresponsible pro-fraud bad-boy movie, and thank God we were here for it.
Thunder Road
The birth of a miraculous satirist in Jim Cummings, somehow finding the right temperature between anguished melodrama and silly antagonistic comedy.
Good Boys
Underrated caper about young boys running loose on an R-rated mission. Admirable restraint in keeping the kids clean and earnest as dirty shenanigans occur around them, boosted by ringers like Lil Rel, Will Forte and Sam Richardson.
Funny Pages
Cringe comedy at it’s most mortifying, as much an interpersonal horror story as it is a comedy in that final half hour, a “Flirting With Disaster”-flavored sequence of cinematic chaos where everything fall apart.
Big Man Japan
Ridiculous multimedia comedy where a kaiju-fighting superhero has to cope with diminished self-respect and dignity while being followed by a camera crew and fighting a series of increasingly-embarrassing monsters.
World’s Greatest Dad
One of Robin Williams’ last amazing performances as a man who loves his pathetic incel dirtbag son and yet still uses the boy’s suicide to further his own career.
The People’s Joker
Vera Drew killing it with a dizzying genre-hopping exploration of the Batman villain’s mythos that doubles as a lacerating critique of the current comedy pipeline.
Problemista
Julio Torres’ gently-subversive sensibility arrives onscreen fully intact in a story about immigration, workplace abuse, and that guy named Craigslist.
Give Me Pity!
In this bizarre curio, variety superstar Sissy St. Claire is starring in her own TV special. But she can’t defeat her own doubts and concerns. Surreal enough that I believe it was on Shudder for a while. Wildly, weirdly committed to the bit.
Sasquatch Sunset
A delightful troll job, a full ninety minutes of a family of Sasquatches eating, defecating, and humping everything in the forest.
Scott Pilgrim Vs. The World
Mad respect to the Vegan Police.
Deerskin
Oscar winner Jean Dujardin stars as a maniac who listens to the spoken wishes of his sweet deerskin jacket to destroy all of the world’s other jackets.
Elf
With anyone else, a sweet Christmas fable for kids. But with Will Ferrell, this becomes an anarchistic flight of fancy always teetering on the edge of yuletide-flavored violence.
This Is The End
Despite a proud career as a writer, producer and actor, Danny McBride’s finest moment may be when he shows up a half hour into this and immediately steals the movie from an all-star lineup of funny people.
American Splendor
Paul Giamatti and Hope Davis are legendarily funny together, but one cannot ignore Judah Friedhandler’s “Revenge Of The Nerds”-worshipping Toby Radloff.
Young Adult
Charlize Theron teaching a masterclass on how to be a brilliantly funny garbage fire of a woman.
Brüno
A genuine gay dirty bomb tossed into 3000 unsuspecting theaters in 2009. Sacha Baron Cohen nearly dying for his comedy.
Wonder Boys
Where Michael Douglas plays an academic version of Jeff Lebowski in a low-key excellent ensemble of actors who have all never been funnier.
Klown
“The Hangover” but from Germany and with genuine balls.
The TV Set
Little-know Judd Apatow joint that is basically what happened behind the scenes of “Freaks And Geeks”, with David Duchovny doing a hilariously-accurate Apatow.
Team America: World Police
Lawless puppet satire from the “South Park” guys.
Booksmart
Beanie Feldstein catapults through this like a lethal weapon of comedy.
Me And You And Everyone We Know
))<>((
Talladega Nights: The Ballad Of Ricky Bobby
Savage takedown of Bush-era jingoism that NASCAR, somehow, embraced.
In Bruges
If you’re wondering why Colin Farrell gets to star in movies after movies that lose millions, it’s because of just how hysterical he is in this.
I Heart Huckabee’s
Madcap slapstick nonsense with sly politics from a dream cast. Is it wrong to look at Lange?
Pineapple Express
Franco and Rogen in their most iconic team-up, in a cast loaded with ringers. There’s a reason Franco received a Golden Globe nomination for this movie.
Tropic Thunder
Not nearly as biting as it thinks, but the comedic drive-by that was “The Fatties Fart Two” is a real dark moment.
A Different Man
Has that modern sensitivity and meta-warping meeting the anarchism of early Woody Allen.
Bad Trip
Obscenely funny COVID-era hidden camera movie that deserves canonization.
Superbad
Come for the Hill/Cera teaming, stay for Emma Stone becoming a star.
53. Bottoms
ZAZ-flavored nonsense filtered through xilennial lesbian chaos, with a finale that should have set Fox News aflame.
Frances Fergueson
From Bob Byington, an unsung comedic voice, about a woman slowly, sleepily tanking her entire life in slow-motion.
What We Do In The Shadows
A dizzying density of jokes and puns.
The Fantastic Mr. Fox
Whack Bat, we swear by it.
Bad Santa
Bill Murray was originally cast as Bad Santa, but can you envision anyone else other than Billy Bob Thornton just killing every single line reading?
Kung Fu Hustle
Stephen Chow running a martial arts comedy masterclass.
Tim And Eric’s Billion Dollar Movie
My favorite bit is probably Will Forte running that sword store, though he is paid by the local government specifically to not sell anyone swords on account of the rash of local sword killings. I’ll have a different favorite the next time I think of this movie.
Thor Ragnarok
The funniest of the MCU thus far, a movie that gleefully dismantles all dimwitted superhero tropes in favor of a candy-coated sci-fi free-for-all.
Goon
Seann William Scott’s greatest moments as a cheery dimwit recruited to wear skates and punch people.
Ghost World
There’s still time to retroactively give Steve Buscemi two Academy Awards for his single performance in this movie.
Black Dynamite
In a sea of blaxploitation spoofs, somehow Michael Jai White made the signature one.
Mystery Team
Deeply, preposterously dumb story of three boy detectives now well over the age of puberty.
21 Jump Street/22 Jump Street
A dumb IP extension disguising a savage takedown of the industry’s profound lack of imagination.
Red Rocket
Personally, I laugh with what feels like every other Sean Baker joint. But none have had a lead performance as recklessly, poetically stupid.
Girls Trip
Introducing the hurricane that is Tiffany Haddish.
The 40 Year Old Virgin
What stands out among the overlying sweetness of the premise is that impossible chemistry between an ensemble at their comedic peak.
The Squid And The Whale
The moment where Jeff Daniels’ son proudly admits to him that he’s a”philistine”, and the devastation on his face when he hears that is the type of tragedy that could fuel a massive Russian novel.
Toni Erdmann
Mildly funny until that legendarily-cringy nude work party, the stuff of absolute nightmares.
Jackass The Movie
This slot for each of the movies in this franchise of partnership and pain.
Step Brothers
Doback says, “The last time I laughed that hard I fell off my dinosaur”, and Huff retreats so quickly back into his shell that he’s just about ashen for the next four close-ups. Absolute devastation.
Sword Of Trust
Unsung indie comedy about misfits banding together to sell a Civil War-era sword, running into a hornet’s nest of conflicts.
Hot Rod
Cool beans!
A Serious Man
Michael Stuhlbarg running a typical Coen Bros. moral gauntlet like a comedic legend.
High Fidelity
As obnoxious as he’s become, it was hard to deny that, in Jack Black, this was a ten megaton star. To do this while not overshadowing a career-defining John Cusack turn is a minor miracle.
Adaptation
It’s technology… versus horse.
Best In Show
Christopher Guest and company continuing to dominate the mockumentary space.
Bridesmaids
Possibly the comedy with the largest collection of genuine female ringers, not a single weak link or a dull moment.
Yannick
Quentin Dupuiex’s funniest, a small, contained comedy of manners where a perturbed day laborer takes the cast of an underwhelming play hostage in the middle of the show.
Idiocracy
Oops, we elected President Camacho!
Observe And Report
Yep, Ronnie was definitely there on January 6th. Anna Faris with the line reading of the century in, “Physically yes, but psychologically NOOOOOOOOOOO!”
Four Lions
Wickedly, wildly funny terrorist satire that, for several reasons, will probably forever remain one of a kind.
Kiss Kiss Bang Bang
Val and RDJ were a dream duo — we should have gotten them together for at least three more movies.
The Royal Tenenbaums
Arguably the generation’s best comedy director at the height of his power.
Splitsville
A masterpiece of comic chaos. The goldfish bit will go down as legend.
Barbie
Ridiculous, and inconsistently clever (the Will Ferrell stuff is a non-starter). But this massive blockbuster had a handful of incredible one-liners.
A Town Called Panic
French stop motion animation about friendship and struggle between Cowboy, Indian and Horse. Maybe a metaphor for something, but who cares?
Between The Temples
Carol Kane undefeated never lost.
Shaun Of The Dead
The ur-text of a certain, very specific demographic.
Burn After Reading
Not exactly the best Coen work, arguably in the back half. But certainly the most brazen, dark-hearted laughs of any of their work.
Wet Hot American Summer
One of the few movies that I paused a half hour in, just so I could call everyone I knew to come over so I could restart the whole thing.
Walk Hard: The Dewey Cox Story
Even the songs are bangers. A comedy with the highest degree of difficulty, and they nailed it.
A Mighty Wind
One of those cases where the laughs are bigger simply because of the pathos generated by a never-better cast.
Borat: Cultural Learnings Of America For Make Benefit Glorious Nation Of Kazahkstan
Throughout this era, no one gave as much of themselves to laughs as Sacha Baron Cohen.
In The Loop
Washington insiders behaving badly, like a lineup of sluggers where, every time someone comes to bat they blast a grand slam. F-words never sounded so good.
Anchorman: The Legend Of Ron Burgundy
Subtly noticed at the time for its pessimistic undertone, one that time ended up validating. We all live within the legend of Ron Burgundy now, and Adam McKay saw it coming first.
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I want to thank you all for being supportive during these last few weeks. It’s been difficult. I received some costly medical news, which was during the same week I lost my father. Shortly after, I lost my full-time job after three years. I’ve been trying to rebuild, but there are limitations given my status as an ex-con. One battle after another, really.
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You will need to explain how “Hot Fuzz” is not on that list..
For me… Monty Pythons’ “The Life of Brian” is the funniest movie I’ve ever seen 👍😂. It’s one of the most quotable movies ever ✅