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The 50 Best Comedies of the 21st Century Thus Far

Written by on August 10, 2016 

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.”

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