No genre is more subjective than comedy. What makes one person laugh may make another cringe. Some “comedines” 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.

40. State and Main (David Mamet)

State and Main

The circus-like world of Hollywood overtakes idyllic small-town America in David Mamet‘s pitch-black ode to the fateful meeting of art and commerce. Despite the fact that State and Main is undoubtedly the most puppy-dog-eager comedic work of Mamet’s career, the film is so much darker than I remembered. While the movie’s lead actor (Alec Baldwin) slobbers after underage girls, its crew rushes around behind the scenes, attempting to cover up any evidence of his lustful misdeeds. This reveal fails to scandalize the production until someone, a small-time busybody with big-city ambitions, decides to exploit it. The clichéd notion of Hollywood corrupting the values of good, old-fashioned, small-town America condescends to those very values. Instead, Mamet takes the higher road: the citizens of this tiny berg are intelligent and endearingly distinct, some bemused by the chaos while others quietly net a healthy profit from the production. At the end of the day, the studio needs a completed movie, no matter what happens. As an exhausted A.D. tries to calm his pregnant wife over the phone as she goes into labor, the cynical director demands to know if dinner reservations have been made. The assistant protests, explaining that his wife is having a baby. The irritated director replies, “Is that on the call sheet?!” – Tony H.

Best line/joke: After he’s informed that Alec Baldwin’s movie star character likes 14-year-old girls, William H. Macy‘s bluntly spoken director replies, “Well, get him something else. We want to get out of this town alive. Get him half a 28-year-old girl.”

39. Don’t Go Breaking My Heart (Johnnie To and Wai Ka-fai)

Dont Go Breaking My Heart

It’s probably cheating, but consider this an entry for much of Johnnie To’s comedy work from the past decade and a half. Short of possibly Sion Sono, To has been one of the most breathlessly prolific directors of the ’00s, spreading his time between immaculately directed crime films (e.g. Drug War) and superlative “comedies,” including Office and, here, Don’t Go Breaking My Heart. The latter is the most conventional of those three, but it nonetheless puts most American romantic comedies to shame. To, like Nicholas Ray before him, has a fundamental understanding of the relationship between space and emotion, and nowhere is that more apparent than in his understanding of comedy. He places characters whole buildings apart, but their rapport is always fluid as the camera skillfully skips back and forth and his characters build their relationship, piece-by-piece, onscreen. – Michael S.

Best line/jokeLouis Koo and Yuanyuan Gao flirting through the window.

38. Hot Rod (Akiva Schaffer)

Hot Rod

Andy Samberg battling with Ian McShane in the living room is a memory I won’t soon lose. Their sheer willingness to give into roles that were so positively absurd was delightful. Hot Rod never takes itself seriously — there’s no underlying message that it strives to achieve, and even the laughs are borderline childish. Yet there’s something alluring about that combination. Samberg is great at slapstick and this is the kind of film tailored to him — which is no wonder, considering it was The Lonely Island’s (a group made up of Samberg, Jorma Taccone, and Akiva Schaffer) first foray into feature films. It also sports a hell of a cast: Will Arnett, Danny McBride, Isla Fisher, and Bill Hader. – Bill G.

Best line/joke: “He died instantly… the next day.”

37. Klown (Mikkel Nørgaard)


It’s not so much the fact that Klown‘s characters are, to put it lightly, absolute fucking idiots, or that these absolute fucking idiots are, in a classic (but fairly tired) comedy set-up, put in charge of a young child that makes this movie so relentlessly funny. Rather, it’s the willingness to “go there,” no matter how awful a place “there” might be, and still avoid the sense of trying too hard. As far as I can tell, Mikkel Nørgaard‘s Curb Your Enthusiasm-esque comedy has no aspirations to any kind of social commentary or implicating the audience in its protagonists’ actions, and in that way it’s almost primal – much in the way an unwanted ejaculation on the face or semi-naked charge of a concert stage might be. – Nick N.

Best line/joke: “Frank, I was fucking raped.”

36. They Came Together (David Wain)


David Wain‘s latest feature, an affectionate dismantling of the romantic comedy genre, marks his most consistent and, for my money, the funniest comedy of the decade thus far. In an era where much of the spoof genre lazily repeats scenarios for cheap laughs, They Came Together is a remarkably brilliant dissection of tropes, led by two of the most likable actors in Hollywood — not to mention a gathering of exceptional (and unexpected) supporting players. You can say that again. (Tell me about it.) – Jordan R.

Best line/joke: Christopher Meloni‘s Roland covering up his fecal accident.

35. 21 Jump Street (Phil Lord and Chris Miller)

21 Jump Street

The world has seen its fair share of updates of old properties over the past sixteen years. Most times, these take the form of hilarious misjudged reboots that seek to add some grit and danger to inherently dumb ideas. 21 Jump Street reaches an almost critical level of meta humor when it directly addresses its origins, but still remains steeped in its comedic premise enough to pull off an actual story. Adding the glorious physical odd couple of Channing Tatum and Jonah Hill as former high school strangers who become gloriously goofy best friends brings heart to the proceedings. Genre and social awareness — for its crime story and its high school story, respectively — brings it all home. – Brian R.

Best line/joke: The increasing bonkers-ness of what will and will not explode during a major car chase.

34. MacGruber (Jorma Taccone)


Taking its ludicrous sensibilities and sprinting with it, MacGruber pleases on the simple idea of not talking down to its audience (a sure-fire understatement). Instead, it flails about in all its glory of absurd, juvenile, and, frankly, stupid humor, allowing Will Forte to run, throat-rip, and hump his way from gag to gag with Kristen Wiig, while a pitch-perfect Ryan Phillippe plays the appalled straight-man. Unafraid of going for low-brow, balls-out comedy, MacGruber pairs its excessive, R-rated action-comedy stylings with one of the funniest sex scenes in modern cinema and a supervillain named Dieter Von Cunth (Val Kilmer). Standing as one of the best SNL-style big screen comedies, MacGruber succeeds with often straightforward hilarity and an odd story of friendship and sorta-redemption. If you see it for one reason, let it be for the how-to on staging a proper distraction. – Mike M.

Best line/joke: The arc of the “distraction” gag.

33. Idiocracy (Mike Judge)


The scary thing about Mike Judge’s Idiocracy is how, as every year passes, its vision of the future seems less and less ridiculous. While initially seen as something of a disappointment compared to Office Space, time has been kind to Idiocracy, and it stands quite well on its own as a funny, all-too-real satire. Terry Crews and Dax Shepard both have a lot of fun with their characters, and Judge’s sense of humor is a perfect match for a dry actor such as Luke Wilson, who sometimes struggles to find roles that match his strengths. – John U.

Best line/joke: “The #1 movie in America was called Ass. And that’s all it was for 90 minutes. It won eight Oscars that year, including Best Screenplay.”

32. Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan (Larry Charles)


Sacha Baron Cohen’s recent comedies may have some retroactively questioning if his 2006 mammoth hit is all it’s cracked up to be, but, a decade later, the entire country could use a rewatch. On his tour through America, pushing every button possible along the way, the comedian satirically explores racism, bigotry, and jingoism, exposing the country’s underbelly through his most indelible character. Sure, the film ensures you’ll never again say “my wife” with the same tone, but there’s a sly brilliance to the comedic timing here, particularly considering how much is off-the-cuff. – Jordan R.

Best line/joke: Borat and Azamat’s “relationship.”

31. Kung Fu Hustle (Stephen Chow)

Kung Fu Hustle

After years of culturally specific comedies — including collaborations with fellow Hong Kong superstar auteur Johnnie To — 2001’s Shaolin Soccer arguably put Stephen Chow on the radar for many western critics, but his real breakthrough in the United States was Kung Fu Hustle. A meld of classic Hong Kong martial arts sensibilities and a visual style equally indebted to King Hu and Chuck Jones, this is an endless fountain of comic invention. Filled with memorable characters — Qiu Yuen’s perpetually irritated landlord is an easy highlight — crisp action scenes, and starring an endearingly doofy anti-hero, Kung Fu Hustle both pokes fun at and honors a stalwart cinematic tradition. – Michael S.

Best line/joke: Road Runner/Coyote chase between Sing and the landlady.

30. Dogtooth (Yorgos Lanthimos)


Yorgos LanthimosDogtooth is an acutely observed anthropological study that doubles as an obscene, hilariously cruel comedy. Lanthimos’ deadpan styling doesn’t allow for easy laughs — he wants the choked gasps and uncomfortable cackles. But he’s also not a sadist, and he knows the value of lightness in his films. The centerpiece dance sequence is still every bit as exquisite a piece of filmmaking as it is a comedic set piece. Dogtooth is foremost a marvel of tonal reconfiguration as conceptions of normalcy and absurdity are jumbled together so completely that the only possible reaction is to laugh. – Michael S.

Best line/joke: “I hope your kids have bad influences and develop bad personalities. I wish this with all my heart.”

29. Force Majeure (Ruben Östlund)


Ruben Östlund‘s Force Majeure is a rigorously assured exploration of the responsibility found in marriage, and also a remarkably funny one. With performances that rely on acute gestures and movements to convey things some films take an entire runtime to explore, this examination of gender roles and masculinity is brilliant. Despite a final scene that feels unnecessary, what comes before is some of the sharpest comedic filmmaking you’ll find this century as Östlund’s patiently traps us into the headspace of a man in crisis as the walls close in on him. – Jordan R.

Best line/joke: The world’s most extreme man crying.

28. Superbad (Greg Mottola)


I saw Superbad opening weekend in a packed theater, and the laughter from the audience was so frequent and so boisterous that I felt as if I missed half the jokes. Almost a decade later, the film holds up well: like the best of the Apatow-branded movies, no matter how crude or vulgar it becomes, there’s an underlying sweetness and good nature to the characters that justifies their actions. Superbad was largely responsible for launching the film careers of numerous actors, and, in retrospect, all their potential is onscreen here. It’s easy to see how Jonah Hill’s role, if played by a lesser actor, may have come across as overtly crude and unlikeable, but he plays him with a sympathetic side, and Michael Cera is equally strong. – John U.

Best line/joke: After Joe Lo Truglio‘s first encounter, he asks, “You guys have MySpace?”

27. Burn After Reading (Joel and Ethan Coen)

Burn After Reading

I’ve seen the Coen brothers Burn After Reading treated with hostility by their fans, most likely because it’s perceived as one of their more mainstream efforts, but there’s something to be said for a film in which George Clooney spends half its time working on a supposedly top-secret project, only for it to be revealed as a rocking chair with a dildo attached. Burn After Reading isn’t the Coens at their most incisive or quirky, but it’s still a very strong film with hilarious supporting turns from Brad Pitt and John Malkovich; the scene in which Pitt’s intellectually challenged fitness instructor calls Malkovich in the middle of the night in an attempt at blackmail had me in stitches. – John U.

Best line/joke: “I have a drinking problem? Fuck you, Peck, you’re a Mormon. Compared to you we all have a drinking problem!”

26. Magic Mike XXL (Gregory Jacobs)


Magic Mike XXL is a movie of improbably long sequences, triumphantly goofy digressions (the gas-station dance set to the Backstreet Boys), and a very special feel-good vibe that is not to be taken for granted. (Ignatiy Vishnevetsky summed up the feeling well: “Doggedly positive. Rare experience of leaving the theater feeling slightly better about the world than when I went in.”) Steven Soderbergh’s clinical cynicism is a necessary pill in a lot of contexts, but Gregory Jacobs‘ follow-up (photographed and edited by the former) is a big-hearted breath of fresh air that still possesses the Magic Mike director’s ecstatic powers of color, pace, and composition. – Danny K.

Best line/joke: Joe Manganiello + “I Want It That Way” + water bottle.

25. Tropic Thunder (Ben Stiller)

Tropic Thunder

It’s easy to forget what disarray Tom Cruise’s career was in back in 2008. Fresh from his bizarre talk-show appearances, a couple under-performing films at the box office, and becoming the object of tabloid fodder, Cruise’s star had plummeted. This is part of what made his extended cameo appearance in Tropic Thunder so riotously funny: buried under layers of prosthetics and sporting a pot belly, the sleazy, verbally abusive studio exec stole the show, arguably upstaging Robert Downey Jr.’s turn as a method acting dimwit who earnestly dons blackface in an attempt to play an African-American character. Ben Stiller’s directorial career has been shaky, but Tropic Thunder is probably his best work behind the lens. It may not boast the subtlest of satire, but it makes up for this by simply being very, very funny. – John U.

Best line/joke: “You never go full retard.”

24. School of Rock (Richard Linklater)

Funny and warmly infectious, School of Rock remains a cheerfully touching comedy classic nearly fifteen years later. While the work of director Richard Linklater, writer Mike White, and star Jack Black provide a winning trifecta, it’s the lead performance, along with a stunning cast of adept child actors, that make up the foundation of this film. White’s screenplay provided the perfect vehicle for Black’s talents, without whom the premise could have easily collapsed under its own predictability: Dewey, an unemployed rocker, poses as a teacher, inspiring a classroom of stuffy private-school kids to cut loose and form a class rock band. Admittedly, it’s the type of zany performance that could easily repulse and annoy by pushing over the top, were it not for the charms of their innately likable star. Indeed, Black swings wildly for the fences, but Dewey’s unbridled musical passion effectively sells each of this goof’s bizarre facial tics and thrusting gyrations, supporting the character rather than distracting from it. – Tony H.

Best line/joke: After he’s revealed as a fraud at parent-teacher night, Dewey tries desperately to explain himself: “I have been touched by your kids. And I’m pretty sure that I’ve touched them.” The parents react accordingly.

23. Mistress America (Noah Baumbach)

Mistress America

Noah Baumbach’s unofficial companion to Frances Ha navigates similar thematic territory as the 2012 film — i.e. the arrested development of millennials not yet ready to tackle the adult world — except Mistress America is even harder to watch, even more vicious in its deconstruction of narcissism and entitlement. Yet the film doesn’t altogether despise its characters, either, keeping us emotionally invested in their exploits even as we wince at their social and moral blunders. From this tension between empathy and derision, Baumbach has built a formidable screwball comedy filled with mile-a-minute patter and a glorious climactic set piece that evokes The Rules of the Game in its use of organized chaos to satirize the social elite. – Jonah J.

Best line/joke: “I’m an autodidact. Do you know what that means? […] That is one of the words I self-taught myself.”

22. Hill of Freedom (Hong Sang-soo)

Hill of Freedom

Hong Sang-soo‘s 16th feature is one of his greatest, and, to my mind, undoubtedly the most accessible: 65 minutes long, primarily in English, and powered by a great structural conceit (are you noticing a trend between this and Right Now, Wrong Then?) that one could pore over endlessly but need not worry about for the sake of simply enjoying its stranger-in-a-strange-land narrative. Hill of Freedom again resembles the other Hong entry – and almost every film he’s made in the last twelve-or-so years – for relying on misunderstanding to evoke laughs, but not in a cruel sense: others’ casual insanity matters no less than the main character’s affable cluelessness, making it among Hong’s most generous works. Each minute is as pleasurable as it is mysterious. – Nick N.

Best line/joke: A stiff, too-enthusiastic thumbs-up that encapsulates the film’s complex relationship with communication.

21. Sideways (Alexander Payne)


Offering up some of this century’s most genuine comedy, Alexander Payne has a way to inject even the most dramatic situations with a humorous levity. The fact that his films tow the line so carefully between genres is proof that, as in reality, the two rarely fail to be intertwined. This is never better exemplified than in Sideways, a full-bodied look at festering neuroses and romantic commitments that’s captured with an airy sincerity that could only come from Payne’s delicate touch. – Jordan R.

Best line/joke: “I’m not drinking any fucking Merlot.”

20. Shaun of the Dead (Edgar Wright)

Shaun of the Dead

It’s amazing to witness the creative zeal and potential on display in Edgar Wright‘s Shaun of the Dead, the story of a slacker’s attempt to win back his ex-girlfriend amidst the throws of a zombie invasion. Everything that Wright had created and would go on to create feels distantly visible in this film, a work that’s lovingly crafted and immensely cinema-literate in its execution. As with the best comedies, its laughs are driven from the eccentricities of Wright and co-writer Simon Pegg‘s deftly drawn cast of characters. Even the nastier folks, such as Pete (Peter Serafinowicz), are ones we gladly return to on repeat viewings to view their metamorphoses into the stumbling dead. Any movie worth its weight would be lucky to contain even one-tenth the gleeful joy of the barroom sequence set to Queen’s “Don’t Stop Me Now,” yet Wright’s debut continues building to a sincere emotional climax, transcending far beyond a mere comedic exercise. – Tony H.

Best line/joke: As “Don’t Stop Me Now” blares from the jukebox, Shaun attempts to regain order, shouting to David, “Kill the Queen!” Confused, David replies: “What?” Frustrated, Shaun shouts back, “The jukebox!”

19. The 40-Year-Old Virgin (Judd Apatow)

The 40 Year Old Virgin

Knocked Up gets a lot of credit for sparking the now-over-saturated comedy sub-genre of “Man-Child Grows Up,” but it’s The 40-Year Old Virgin that blazed the trail. With a star-making turn from Steve Carell and too many impressive supporting turns to list in full (Jane Lynch, Seth Rogen, Paul Rudd, and Romany Malco, to name a few), this comedy backs its provocative premise with an incredibly high joke-success rate and a memorably lovely performance from Catherine Keener. The chest-waxing scene alone will live forever in comedy infamy. – Dan M.

Best line/joke: “I always thought Matt Damon was like a Streisand, but I think that he’s rocking the shit in this one.”

18. Submarine (Richard Ayoade)


This film’s simple quality is baffling. Nearly everything about its approach — narrative, content therein, formal qualities, music, the put-on demeanor of actors — could be qualified as “tweet” in only the most nauseating sense of the word, but debut director Richard Ayoade makes it sing with a tenor that Submarine’s ilk so often and so significantly fail at communicating: earnestness. Its story of precocious, rejected love would almost recall Harold and Maude — the resemblance between Noah Taylor and Bud Cort is so strong as to not possibly be coincidence — but this supersedes that film for actually focusing on real people. – Nick N.

Best line/joke: “It’s rude to leave a film before it’s finished.” “Who to?” “To the filmmakers.” “How do they know?” “They just do.” “How?” “They do!”

17. Pineapple Express (David Gordon Green)

Pineapple Express

At the height of their hitting the adult comedy scene, director David Gordon Green and co-writer / star Seth Rogen created an R-rated, stoner action comedy that just worked. I watched this film so much as a teenager that I could quote entire scenes as they played out; the actors all feel as if they’re really playing in the space, allowing situations to settle in and unravel at a pace that feels natural. This type of effortless chemistry and flow makes a buddy comedy that could have fallen flat on its face, like countless others before — and after — it, instead feel fresh, alive, and, most importantly, very funny. The budding relationship works, with Rogen and James Franco working in tandem to find small moments of heart amidst all the crazy, silly humor. This is all packaged with some incredible physical comedy — especially during a three-way fight in a house and bathroom — to make for a memorable, often juvenile, and strangely touching bro-bonding adventure. – Mike M.

Best line/joke: The dead car-battery discussion.

16. What We Do in The Shadows (Taika Waititi, Jemaine Clement)


There seems to be no sub-genre more worn-out in Hollywood than that of the vampire. Thankfully, a pair of New Zealand’s finest comedic talents breathed new life into the blood-sucking mythology with their humbly brilliant vampire mockumentary. Jemaine Clement and Taika Waititi‘s comedy was perfectly enjoyable on first viewing, but it’s only on subsequent ones where I’ve fallen more in love with the characters as they go about their day in which no blood-sucking myth goes un-mocked. Waititi is keeping himself busy with Thor, and, once he has the opportunity to shoot it, it’s safe to say few comedies are more anticipated than the cleverly titled follow-up, We’re Wolves.  – Jordan R.

Best line/joke: “I think of it like this. If you are going to eat a sandwich, you would just enjoy it more if you knew no one had fucked it.”

15. The Informant! (Steven Soderbergh)

The Informant

Although mostly defined by his serious role, Matt Damon‘s delightful stint into deadpan comedy hits the mark perfectly. With the power of Steven Soderbergh behind the lens and Scott Z. Burns behind the script, The Informant! is whip-sharp and full of wonderful lines. Perhaps more important than its actual comedic moments — with internal monologues from Damon’s Whitacre that reminds myself of my own ADHD wanderings — is the fact that the central premise about a whistleblower taking down his own company without any clear sign of benefiting himself, initially, is so absurd and yet true. Why would someone damage their own standing in an industry without having been wronged or without a clear path of benefit ahead? In taking this wry, specific tone and approach, Soderbergh amusingly shows us. – Bill G

Best line/joke: “When polar bears hunt, they crouch down by a hole in the ice and wait for a seal to pop up. They keep one paw over their nose so that they blend in, because they’ve got those black noses. They’d blend in perfectly if not for the nose. So the question is: how do they know their noses are black? From looking at other polar bears? Do they see their reflections in the water and think, ‘I’d be invisible if not for that’? That seems like a lot of thinking for a bear.”

14. Adaptation (Spike Jonze)


It’s almost depressing to rewatch Adaptation in 2016, because it’s a reminder of how strong an actor Nicolas Cage is when he actually invests himself in good projects. It was soon after this that his career went off the rails, but he’s remarkably impressive here, playing the dual roles of Charlie Kaufman and his fictional twin brother, Donald. As much a mind-fuck as any other Kaufman screenplay, Adaptation blurs the lines between the real and the surreal, being partially an adaptation of Susan Orlean’s The Orchid Thief and, ultimately, more a story of adapting The Orchid Thief. Spike Jonze perfectly understands Kaufman’s comic rhythms, and Cage captures the scribe’s quirky mannerisms better than most actors could. The first time I saw Adaptation, I was turned off because I could not make heads or tails of it. In the years since, I have seen it countless times, and consider it to be one of the best comedies of the last couple of decades in general. – John U.

Best line/joke: “I’m putting in a chase sequence. So the killer flees on horseback with the girl, the cop’s after them on a motorcycle and it’s like a battle between motors and horses, like technology vs. horse.”

13. Step Brothers (Adam McKay)

Step Brothers

Step Brothers is a movie that I’m almost ashamed to admit I’ve seen more times than I could even attempt to guess, but, like some kind of comfort food, it always puts a smile on my face. Its mean-spirited humor seemed to be a point of contention for many people during release, but Will Ferrell and John C. Reilly are at their best when they’re unhinged and able to fly off the handle, unrestricted by the boundaries of a PG-13 rating, and there’s something childishly funny about seeing grown men act like spoiled kids. A movie such as this needs a straight man for the jokes to work, and so, to his credit, Richard Jenkins is perfect as the frustrated father who is at his wit’s end. And Adam Scott, always at his funniest when playing douchebags, steals every scene he’s in as Ferrell’s narcissistic older brother. – John U.

Best line/joke: “I haven’t had a carb since 2004.”

12. Living Trilogy (Roy Andersson)


Roy Andersson’s Living trilogy — which consists of Songs from the Second Floor, You, The Livingand A Pigeon Sat on a Branch Reflecting on Existence — brilliantly captures a sense of surreality and impending doom. Andersson’s absurdist comedy perfectly blends with his ghoulish attention to the detailed minutia of daily life, all of which is anchored by truly unforgettable and arresting visuals. Composed of a series of peripherally connected vignettes, the final film is easily the darkest entry in this trilogy as it builds to a sobering and deeply disturbing climax, searing unfathomable yet hauntingly photogenic imagery into the viewer’s mind. Andersson is a true auteur whose work remains unlike anything you’ve ever seen before — unless you’ve seen another Roy Andersson film. – Tony H.

Best line/joke: You, the Living‘s dream train sequence.

11. Punch-Drunk Love (Paul Thomas Anderson)

Punch Drunk Love

Following Boogie Nights and Magnolia, some initially took it as a joke that Paul Thomas Anderson would make a 90-minute Adam Sandler comedy, but Punch-Drunk Love is a resonant, beautiful film with an amazing soundtrack by Jon Brion and stunning images. Anchored by suitably bizarre narrative choices (e.g. the van in the street randomly flipping over), the film successfully deconstructs Sandler’s “man-child” persona while adding complexity and depth to it, essentially taking Happy Gilmore or Billy Madison and exploring how this kind of person might function in a real society, and what could have caused him to become this way. Sandler is, to his credit, at his best here, as he seems to understand Anderson’s angle and doesn’t over-play the character of Barry. Emily Watson is equally strong as Sandler’s love interest, convincing us how a woman of her nature would fall for this outwardly weird guy by seeing his good side. The late Philip Seymour Hoffman is also brilliant as Dean, a.k.a “The Mattress Man,” whose showdown with Barry at film’s end is darkly funny. – John U.

Best line/joke: “I have a love in my life. It makes me stronger than anything you can imagine.”

10. Wet Hot American Summer (David Wain)

Wet Hot American Summer

Even aside from providing an early glimpse at a staggering amount of comedic talent — including Janeane Garofalo, David Hyde Pierce, Molly Shannon, Paul Rudd, Christopher Meloni, Michael Showalter, Ken Marino, Michael Ian Black, Amy Poehler, Bradley Cooper, Elizabeth Banks, Joe Lo Truglio, Judah Friedlander, and more — Wet Hot American Summer excels at showing us David Wain and co.’s talents for blending absurdity with endearment. There’s not a character you don’t adore and a joke that doesn’t leave at least a smirk. The comedy kicked off a century in which we had spoof titles aplenty, but barely any measured up to the lovable goofiness on display here. – Jordan R.

Best line/joke: Paul Rudd’s facial expressions.

9. The Grand Budapest Hotel (Wes Anderson)


All of Wes Anderson‘s films could be considered comedies, so instead of including them all, we opted for the one that best exemplifies his funny bone — and which just so happens to be his biggest hit. The Grand Budapest Hotel is a furiously paced, immaculately detailed work of staggering beauty (through every frame, no less), in which the tragic stories at its center only reveal themselves to be as much after Anderson concludes his wildly entertaining caper. Due to his careful construction of characters and the increasingly preposterous situations they find themselves in, there isn’t a scene that fails to be delightful. – Jordan R.

Best line/joke: “You see, there are still faint glimmers of civilization left in this barbaric slaughterhouse that was once known as humanity. Indeed that’s what we provide in our own modest, humble, insignificant… oh, fuck it.”

8. Observe and Report (Jody Hill)

Observe and Report

Comedy can go to some dark, taboo places, and, boy, it doesn’t get much more dark and taboo than examining how the effects of bipolar disorder might lead a mall cop with delusions of grandeur to do some really awful things. Mall cops are a ready source of comedy, both successful and unsuccessful, due to the supposed importance of their position being both non-existent and, even if it were, hilariously pointless. Seth Rogen, however, finds levels of anger and pain and narcissism that exceed one’s wildest expectations for the profession. Given the dark, dark places that this movie goes, its a small miracle that Observe and Report never loses pace with its twisted comedic beat. – Brian R.

Best line/joke: Undergoing a psychological evaluation, Ronnie describes a deeply disturbing recurring dream.

7. In the Loop (Armando Iannucci)

In the Loop

If you want to recreate the world of global politics on a small scale, get a nest of vipers, throw it in a burlap sack with a coked-out mongoose, and throw that into the time-out corner of a preschool right after the biggest baby in class just got put away for eating too much post-Halloween candy. The screaming, braying, hissing, and utter fucking carnage of that moment is, on a micro scale, pretty much exactly what politics is. Filmed in a cinéma vérité style and cut with the focus and pacing of a scrap-booker on a meth bender, In the Loop shows this truth with ferocious humor and a black, cracked, oil-bleeding heart. Everyone in the cast excels at both reaching a fever-pitch of comic zaniness while still gnawing their profanity-filled lines like a mad dog chewing on a child’s leg. If the presidential election is making you want to say “what the fuck is going on,” then the Veep creator’s feature is exactly the shot of adrenaline you’ll need to snap your TV in half and, then, beat Wolf Blitzer to death with it. – Brian R.

Best line/joke: A particularly angry man, on opera: “Turn that fucking racket off! It’s just VOWELS! Subsidised… foreign… fucking… vowels!”

6. Hot Fuzz (Edgar Wright)

Hot Fuzz

The second film in Edgar Wright’s unofficial Blood and Ice Cream Trilogy, Hot Fuzz took all the best components of its predecessor Shaun of the Dead — the copious plants and pay-offs, the clever genre subversions, the snappy editing — and honed them into a more finely tuned, well-articulated modern comedy masterwork. Splashed in arguably more extreme violence and retro-fitted in a classic action movie sensibility, Wright’s picture even re-tooled some of the gags from Shaun, making for a delightful double-feature for the attentive. With a strong grasp on visual economy and pacing, Hot Fuzz is a movie unafraid of subtle humor balanced with spot-on sight gags and wonderful twists of the action (and horror) trope playbook that is a joy to be behold on countless rewatches. – Mike M.

Best line/joke: “SWAN!”

5. Inherent Vice (Paul Thomas Anderson)

Inherent Vice

Creating a fully realized world in which each supporting character seems capable of leading their own film and every line of dialogue is one that can be endlessly pored over, Paul Thomas Anderson‘s Inherent Vice is a dense, keenly faithful adaptation of Thomas Pynchon‘s novel. At once sprawling in its far-reaching, paranoia-drenched plotting and intimate, with the majority of scenes being prolonged, drug-laced conversations that superbly wrangle every word from the source material, this is, across the board, a feat of sublime assembly. Having already revisited the film a number of times since its release, it’s still a marvel in just how damn funny it is. Even divorced from Pynchon’s dialogue, Joaquin Phoenix‘s bumbling, one-step-out-of-reality demeanor is enough to delight for the entire runtime. – Jordan R.

Best line/joke: “It’s not groovy to be insane!” and Rudy Blatnoyd’s subsequent paranoia.

4. Best in Show (Christopher Guest)

Best in Show

Christopher Guest has had an exceptionally strong ’00s with A Mighty Wind and For Your Consideration, and it remains to be seen how his upcoming Mascots will be received, but his arguable peak is still the gloriously funny mockumentary Best in Show. Guest’s other films have lovingly skewered egotistical oddballs and the insanity of subjective or objective criticism, so Best in Show is one of his rare films that feels as deeply invested in its main conceit — the Mayflower Dog Show — as its neurotic participants. Gathering together a bulletproof human cast — including Parker Posey, Catherine O’ Hara, Michael McKean, and John Michael Higgins — and an equally capable animal ensemble, it’s among the best examples of the improvisatory form’s possibilities. – Michael S.

Best line/joke: “It worked for my family until my mom committed suicide.”

3. Kiss Kiss Bang Bang (Shane Black)

Kiss Kiss Bang Bang

Shane Black made a name for himself with witty scripts that merged action and comedy and character. He made his name as a director with one such script, the one that might be remembered as his absolute best once the dust settles. A story that at first seems shambolic and a little too zany slowly winds itself up into a tight, tense ball, with lives and honor on the line. All the while, we get to spend time with Harry (Robert Downey Jr.), Gay Perry (Val Kilmer), and Harmony (Michelle Monaghan) as they get shot, dress like a sexy Santa, and lose fingers… and not in that respective order. The velocity of its plot verges on being too fast, but the actors and the script keep pace perfectly. – Brian R.

Best line/joke: Russian roulette.

2. A Serious Man (Joel and Ethan Coen)

A Serious Man

“But I didn’t do anything,” cries Larry Gopnik at one point during Joel and Ethan Coen‘s A Serious Man, their beautifully deadpan ode to growing up Jewish in the suburbs of 1960s Minneapolis. He’s absolutely right. As Larry’s life unravels around him, his marriage dissolving and professional reputation at risk, he frets, panics, and worries while remaining meekly immobile. He dreams of a psychedelic sexual affair with the kooky woman next door and of saving his poor misunderstood brother; in reality, Larry is frozen, incapable of even explaining to the Columbia House Record Company that his kid forged his name on an application. Larry’s Job-like story mines the biggest laughs from its marvelous ensemble, particularly the horrified reactions of star Michael Stuhlbarg, which work as comedy because he plays them as drama. Impending dread and soul-crushing hopelessness have never been funnier. Nerve-jangling and bleakly hilarious, A Serious Man is a darkly orchestrated fable of unrelenting doom. – Tony H.

Best line/joke: As Larry loses his cool on the phone with a Columbia House representative, he exclaims, “I don’t want Santana Abraxas! I’ve just been in a terrible auto accident!”

1. In Bruges (Martin McDonagh)

In Bruges

After a hitman (Colin Farrell) botches the murder of a priest by accidentally also killing a young boy, he and his older mentor (Brendan Gleeson) go to Bruges, where the mentor may have to kill him if the hitman doesn’t commit suicide first. Are you laughing yet? Writer-director Martin McDonagh sets himself a difficult task by injecting a heavy dose of black humor into what could be a staid drama, but his hard work pays off by creating the century’s best comedy thus far. The humor lets us see the humanity underneath two men who have made murder their lives, and that human investment means the drama becomes all the more affecting as an inevitable climax takes hold. – Brian R.

Best line/joke: Two men in a gunfight hash out how the gunfight should proceed, and then argue over directions to a canal.

Honorable Mentions

Judging from the amount of great comedies this decade, we could’ve easily expanded this one to 100 entries. While it sits atop the box-office, The Hangover didn’t quite hit the top 50. A number of Apatow-backed films (and those featuring his alums) barely missed the cut, including I Love You, Man, Anchorman, Knocked Up, Forgetting Sarah Marshall, This is the End, Role Models, Wanderlust, and the Neighbors films.

There’s also a great deal to enjoy in Super Troopers, Extract, A Mighty Wind, Wedding Crashers, Mean Girls, Bring it On, Austin Powers in Goldmember, Undercover Brother, Goon, Hail, Caesar!, Ghost World, Damsels in Distress, Tucker & Dale vs. Evil, Thank You for Smoking, and I Love You Phillip Morris.

Darker comedies (e.g. Greenberg, Young Adult, Seven Psychopaths, World’s Greatest Dad, and the work of Todd Solondz) were bandied about. We also found a lot to like in smaller-budget comedies, including Humpday, Results, Obvious Child, and Kaboom, as well as a handful from across the world, including Michael Winterbottom‘s Trip films, Like You Know It All, and Offside.

We considered titles such as Vicky Cristina Barcelona, Adventureland, the Oceans trilogy, Brothers Bloom, Y Tu Mama Tambien, and The Good, the Bad, the Weird, but found they fit other genres a bit closer. We also didn’t repeat films we’ve included on past best-of-the-century-so-far lists (also seen below), including The Lobster, The World’s End, Fantastic Mr. Fox, Team America: World Police, and Shaun the Sheep.

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