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The 50 Best Comedies of the 21st Century Thus Far

Written by on August 10, 2016 


No genre is more subjective than comedy. What makes one person laugh may make another cringe. Some “comedies” may only result in a few chuckles while watching, yet are heightened as one looks back. Others may cause constant laughter, yet are forgettable after theater’s lights come on.

With Seth Rogen‘s latest comedy, Sausage Party, arriving in theaters this week, we’ve set out to reflect on the millennium’s comedies that have most excelled. To note: we only stuck with feature-length works of 60 minutes or longer and, to make room for a few more titles, our definition of “the 21st century” stretched to include 2000.

Following our favorite sci-fi films and animations, check out our top 50 below and, in the comments, let us know your favorites. If you’re on Letterboxd, you can follow the list here.

50. Walk Hard: The Dewey Cox Story (Jake Kasdan)

Walk Hard

It is wholly possible that a more perfect spoof comedy will never be made. Picking up the mantle from comedy greats David Zucker, Jim Abrahams, and Jerry Zucker (Airplane!, The Naked Gun), Jake Kasdan and Judd Apatow primarily poke fun at musical biopics such as Walk the Line and Ray and get weirder from there. John C. Reilly’s performance — the man does impressions and runs the gamut of emotions while eliciting laughter — is proof that comedic turns deserve to get more serious awards consideration. – Dan M.

Best line/joke: “The wrong kid died.”

49. Tim & Eric’s Billion Dollar Movie (Tim Heidecker and Eric Wareheim)

Tim and Eric

I usually go by the notion that you should give all films their due, even if you aren’t clicking with the first act. However, if you aren’t laughing within the first minutes of Tim and Eric’s Billion Dollar Movie, it is simply not for you. Tim Heidecker and Eric Wareheim‘s feature-length film is a work of surrealist, inane art, complete with their brand of bizarre, finely tuned editing techniques emphasizing blank reactions and repeated phrases, to name but two standout components. It’s possible that, in the history of cinema, never before has this amount of work been put into something so stupid — and I mean that with the highest praise possible. Five bags of popcorn, at least. – Jordan R.

Best line/joke: Chef Goldblum and the Schlaaang Super Seat.

48. Enough Said (Nicole Holofcener)

Enough Said

Any conversation around Nicole Holofcener’s Enough Said inevitably comes back to its trite “twist.” But it’s a very good (and very funny) film on its own terms, and a belated gift in bringing together two of the best actors, comedic or otherwise, of this generation: James Gandolfini and Julia Louis-Dreyfus. For being released the year of Gandolfini’s untimely passing, Holofcener’s film carries a mournful glow, but there’s also a down-to-Earth giddiness. It’s like much of Holofcener’s work with a precisely calibrated, low-key story, and cutting self-reflection, and it’s also just deliriously entertaining to watch Gandolfini and Louis-Dreyfus genially snipe at each other about getting older and not necessarily wiser. – Michael S.

Best line/joke: “Yes, yes, the Container Store. The store that sells crap you can put your crap in so you can go out and buy some more crap.” “I love that store. I love crap.”

47. Four Lions (Chris Morris)

Four Lions

Chris Morris‘ fearless directorial debut, Four Lions, presents its audience with five main comedic protagonists: suicide bombers planning a terrorist attack on the city of London. What may appear to be rudimentary shock-comedy tactics slowly reveals itself to be a pained portrait of flawed, but lovable people, heads filled with lies and misinformation, sleepwalking toward a terrible fate. Instead of watching with morbid fascination, we’re so caught up in the lives and hearts of these misguided men that we are dragged to the edge of our seats, hoping they will come to their senses and abort their plans. Every nuance of the world feels exquisitely defined and real, as does every character within this dark comedy of errors — including the lead bomber’s wife and son, who encourage the men to go through with the attack, even as they begin having understandable doubts. “Don’t worry. You’ll be in heaven before your head hits the ceiling,” the son gently reminds his father with a smile. We laugh, though we could just as easily cry. – Tony H.

Best line/joke: As Omar attempts to talk Waj out of the bombing via cell phone, Omar says, “No, Waj! You’re confused!” Waj takes a selfie, examines it, and replies:”I’m not confused, brother! I just took a picture of my face, and it’s deffo not my confused face.”

46. Scott Pilgrim vs. the World (Edgar Wright)

Scott Pilgrim vs the World

The first viewings of Scott Pilgrim vs. the World are akin to being thrown in a pop-culture blender, references to video games, movies, television, comics, music, and historic events made at a relentless speed through direction and editing that are, at times, jaw-dropping. By the third or fourth viewing, things once obscured — most of all the characters’ complex psychological profiles and how the banal selfishness of their actions affect their heightened world — come to light. An amazing sensory experience, a painfully studied look at why and how we fail ourselves as much as we do others, and a time capsule of the late ’00s that already feels timeless. And with a part where a gorilla made of rock music fights two dragons composed of electronica. – Nick N.

Best line/joke: “What a perfect asshole.”

45. Right Now, Wrong Then (Hong Sang-soo)


Why is this the Hong Sang-soo movie that’s having a moment, insofar as a more-than-a-little-depressing and structurally baffling South Korean comedy can, in fact, have a moment? If nothing else, and as this placement will suggest, it’s among the funniest he’s made – bewitching in its Groundhog Day-like structure and devastating in its done-twice comedy of errors, one that anybody who’s ever been too stupid to nab a desired partner will relate to in some deep way. – Nick N.

Best line/joke: This exchange.

44. Love & Friendship (Whit Stillman)

Love and Friendship

I never thought I’d be laughing throughout a Jane Austen film, but there I was, just earlier this year, loving the experience of Whit Stillman‘s Love & Friendship. While there’s not much initial comedy as Stillman sets up all the characters, plotting, and dynamics, soon enough you ease into the lush landscapes and the quick wit displayed by its eclectic cast. The men are buffoons and the women take full advantage, none more than a delightfully sarcastic Kate Beckinsale. – Bill G.

Best line/joke: “Oh, so that’s what it’s called? Churchill? I was very confused at first, seeing neither a church nor a hill. Churchill… DELIGHTFUL!”

43. Frances Ha (Noah Baumbach)

Frances Ha

A coming-of-age story directed at anxious millennials newly cognizant of the responsibilities adulthood entails, Frances Ha technically qualifies as a comedy, except much of it isn’t funny. Put another way: this film meets the requirements of its genre through an abundant supply of gags and faux pas — but rather than tickling, these punchlines sting. Growing pains may be humorous in retrospect, but they ache in the moment, and Frances Ha’s story of one woman’s emotional maturation is told in the present-tense. Visually evoking the freewheeling mobility of the French New Wave even as its heroine becomes mired in one difficult situation after another, the film finds wisdom in cringe comedy and beauty in the act of embracing life’s awkwardness. – Jonah J.

Best line/joke: “You look across the room and catch each other’s eyes — but not because you’re possessive or it’s precisely sexual, but because that is your person in this life. And it’s funny and sad, but only because this life will end, and it’s this secret world that exists right there, in public, unnoticed, that no one else knows about.”

42. Black Dynamite (Scott Sanders)

Black Dynamite

The art of parody has suffered a lot recently. The glut of “[Genre] Movie” movies that substitute poor imitation for actual construction and comedy ruined the concept of a parody for a whole generation. Then comes Black Dynamite, with its faux-poor production values, groovy soundtrack, and relentless stoicism to turn your damn world upside down. The writing is snappy, the actors are committed to the cinematic reality of the Blaxplotation kung-fu flick they are making, and the story is just as manically “political” as you’d want from a ’70s throwback. – Brian R.

Best line/joke: Police chief: “I can’t have you running through the streets creating a river of blood.” Black Dynamite: “Tell me who did it and I’ll just leave a little puddle.”

41. Bridesmaids (Paul Feig)


Bridesmaids is remarkable, in part, because it ventures into the historically male-dominated territory of gross-out comedy with an all-female main cast — but, more importantly, it is also remarkable because it’s hilarious. This second attribute makes the first that much more significant, since it leads to this question: why isn’t Hollywood offering more female-led comedies that are this well-orchestrated? The titular bridesmaids take raunchiness and indecency to the level of art, breaking both gender- and non-gender-coded social conventions in the process of navigating a touching story of friendship and emotional resilience. When it first hit theaters, Bridesmaids was an event. Now, it’s well on its way to becoming a comedy classic. – Jonah J.

Best line/joke: Post-lunch dress shopping.

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