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The 40 Best Comedies on Netflix (May 2019)

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As Judi Dench is fond of saying, “Like a grand and miraculous spaceship, our planet has sailed through the universe of time; and for a brief moment we have been among it’s passengers.” Time never stops, and if it ever does, we are all royally screwed. And just as time passes unceasingly, so does the content on Netflix, the undisputed king and queen of the content stream. Every month—week—day they’re uploading new business to crack into, and that includes comedy. And not just the deluge of stand-up that they spray us down with every Tuesday, but movies, even. Funny movies, at that. Here are the best of them.

As expected, there have been some changes over the last few months. Stripes has gone AWOL, Bad Santa died of exposure on his way back to the North Pole, and Adam Sandler and Paul Rudd both had to deal with a couple of their movies evaporating off Netflix in the dead of night. Fortunately a solid spread of new films have hit the scene, including Pineapple Express, Legally Blonde, and the sad, smart, stand-up-centric dark comedy All About Nina, which features work from Paste’s own Jamie Loftus. And old favorites like Punch-Drunk Love and… uh, okay, just that have returned.

If you need something to take your mind off the world today, or just need a few laughs before nodding off to bed, you could do worse than dialing up any of these movies on your favorite Netflix device.

(Oh, and the standard reminder: although I do consider the overall quality of the movie when I make this list, my main concern is how much it makes me laugh. We’re looking at the quality of the comedy more than the craftsmanship of the film, although both are considered. Yes, it’s a highly scientific process. Punch-Drunk Love is a perfect example, actually: yeah, it’s the best movie Adam Sandler has ever been in, and it’s also very funny, but as silly and slapdash as they are, Billy Madison and Happy Gilmore are funnier movies, and would probably rank higher than Punch-Drunk Love if they were still on this list. Judge me all you want.)

40. Our Idiot Brother
Year: 2011
Director: Jesse Peretz
Netflix wasn’t making original movies in 2011, and yet that’s exactly what Our Idiot Brother feels like. It’s a movie that’s so relaxed and where the stakes are so low that it barely feels like it exists, but with a great cast full of funny and likable performers. Paul Rudd stars as a guileless modern day hippie failing to rebuild his life after a jail sentence, with Zooey Deschanel, Emily Mortimer, Elizabeth Banks, Kathryn Hahn, Steve Coogan and Rashida Jones playing the various siblings, exes and in-laws that he bothers. It’s a minor but pleasant film that stays afloat almost entirely because of that cast and its own lack of pretension.—Garrett Martin


39. Band of Robbers
Year: 2016
Directors: Aaron Nee, Adam Nee
As strong as the talent is in front of the camera (including the comedic sidekick duo of Hannibal Buress and Matthew Gray Gubler), consider the talent behind it even more. The Nees know their stuff, whether they’re setting up a punch line (of which Band of Robbers has many) or composing countless lovely shots in widescreen. They’ve made a film that’s as hilarious as it is beautiful. As Huck himself might say, it’s nothin‘ but magic.—Andy Crump


38. Goon
Year: 2011
Director: Michael Dowse
You’d think Slap Shot would’ve said all there is to say about violence as a crucial marketing tool for minor league hockey, but Goon carves out its own nook in the sports comedy pantheon thanks to a funny script from Jay Baruchel and Evan Goldberg and fine performances from Seann William Scott and Liev Schreiber. A sequel is actually being released a week from the day this list was originally published in March 2017.—Garrett Martin


37. Little Evil
Year: 2017
Director: Eli Craig
Seven years after he gave us Tucker & Dale vs. Evil, one of the best horror comedies in recent memory, director Eli Craig has finally returned with another horror comedy exclusive for Netflix, Little Evil. An obvious parody of The Omen and other “evil kid” movies, Little Evil wears its influences and references on its sleeve in ways that while not particularly clever, are at least loving. Adam Scott is the sad-sack father who somehow became swept up in a whirlwind romance and marriage, all while being unfazed by the fact that his new step-son is the kind of kid who dresses like a pint-sized Angus Young and trails catastrophes behind him wherever he goes. Evangeline Lilly is the boy’s foxy mother, whose motivations are suspect throughout. Does she know that her child is the spawn of Satan, or as his mother is she just willfully blind to the obvious evil growing under her nose? The film can boast a pretty impressive supporting cast, from Donald Faison and Chris D’elia as fellow step-dads, to Clancy Brown as a fire-and-brimstone preacher, but never does it fully commit toward either its jokes or attempts to frighten. The final 30 minutes are the most interesting, as they lead the plot in an unexpected direction that redefines the audience’s perception of the demon child, but it still makes for a somewhat uneven execution. Tucker & Dale this is not, but it’s still a serviceable return for Craig. —Jim Vorel


36. Mascots
Year: 2016
Director: Christopher Guest 
“Diminishing returns” might apply to Christopher Guest mockumentaries more than anything else on earth, but when you start from the unparalleled heights of Waiting for Guffman and Best in Show there’s a long way to plummet. To wit: Mascots, his latest film, is still full of great performances and good jokes. Much of his stock company returns for the Netflix exclusive (Parker Posey, Jane Lynch, Fred Willard and Ed Begley Jr. are still standouts), and although the absence of Eugene Levy and Catherine O’Hara is palpable, the ensemble is still stocked with capable improvisers. The satire isn’t as sharp as his earlier films, but there’s still an endearing goofiness at the movie’s heart.—Garrett Martin


35. To All the Boys I’ve Loved Before
Year: 2018
Director: Susan Johnson
To All the Boys I’ve Loved Before, the teen scene’s newest runaway hit, is a flat-out excellent film. It is not excellent “for a teen flick.” It is not excellent “for a romantic comedy.” It is excellent for a film. TATBILB fully inverts the 80/20 ratio: Within the first 20 minutes, all five of the deeply private love letters our daydreamy, emotionally buttoned-up protagonist Lara Jean (Lana Condor) has written to her childhood crushes over the years have been stolen and mailed out—including the one to her neighbor and best friend, Josh (Israel Broussard), who just happens to also be her older sister’s just barely ex-boyfriend. This swift puncturing of any protracted emotional dishonesty Lara Jean might have hoped to indulge in, well, forever, leaves the film’s final eighty minutes free for her to embrace some really radical emotional honesty. That TATBILB allows Lara Jean to accomplish this not in spite of but through the fanfic-favorite trope of “fake dating” another, less-risky letter recipient (Noah Centineo’s ridiculously charming Peter Kavinsky) is a story strength. Of course, all the emotional honesty in the world wouldn’t matter if TATBILB’s leads didn’t burn with chemistry. Fortunately, Lana Condor and Noah Centineo can get it. Condor and Centineo are undeniably the stars of the show, but TATBILB doesn’t rest on their charismatic laurels: Mahoro as Lucas is a foxy ball of friendliness; Madeleine Arthur as Lara Jean’s best (girl) friend, Chris, is just the wide-eyed punk weirdo she needs to be; Janel Parrish plays against type as the sweet and steel-spined Margot; Anna Cathcart steals every scene as Lara Jean’s meddling little sis, Kitty; and John Corbett plays the healthily engaged version of Kat Stratford’s single OBGYN dad with a discernible glee. The importance of Lara Jean and her sisters being half-Korean, and the majority of the cast (along with Mahoro) non-white, is hard to overstate, but it isn’t the most impressive thing about the cast by a long shot. In a genre that can so often see its characters lean too far into caricature, Lara Jean’s world is instead populated with teens—and through them, love—you can believe in. —Alexis Gunderson


34. The Waterboy
Year: 1998
Director: Frank Coraci
I saw The Waterboy in the theater on opening night and I’m still not sure if it’s the last of the classic Adam Sandler films or the first of the not-so-classic Adam Sandler films. It’s clearly a step below Billy Madison, Happy Gilmore and The Wedding Singer, but it’s not quite as obnoxious or depressing as pretty much every other comedy he’s made since The Waterboy. His manchild antics didn’t feel redundant yet, and here he has the help of a great supporting cast that includes Kathy Bates, Jerry Reed, Henry Winkler and Blake Clark. (And, uh, the Giant from WCW, aka the Big Show, also has a ton of charisma in his brief cameo.) If you’ve always hated Sandler, you should avoid this one; if you recognize those first three films as the classics that they are, you’ll probably enjoy The Waterboy enough to not feel like you’re wasting your time.—Garrett Martin


33. Legally Blonde
Year: 2001
Director: Robert Luketic
If you like the color pink and are currently between the ages of 25 and 45, there’s a good chance you’ve practiced the “Bend-and-Snap” at home at least once in your life. Legally Blonde, starring Reese Witherspoon as the lovable blonde-sorority-girl-turned-law-student who proves to her doubtful ex-boyfriend and all the other Harvard kids to be actually, like, really smart, is a perfect example of all of the girl power Rom-Coms released in the early 2000s. It’s smart, it’s quotable, and the outfits are downright iconic. There’s nothing high brow about it, it’s just pure, unadulterated fun. Just like the “Bend-and-Snap,” the film Legally Blonde works every time.—Annie Black


32. The Little Hours
Year: 2017
Director: Jeff Baena
Raunchy comedies rarely cop to such well-regarded sources: The Little Hours claims its basis lies within Giovanni Boccaccio’s 14th-century novella collection The Decameron, which makes its structure, bawdiness and characterizations all feel appropriately pithy. A series of incidents involving three horny nuns—Alessandra, Genevra, and Fernanda (Alison Brie, Kate Micucci and Aubrey Plaza, respectively)—and sexy farmhand-on-the-run Massetto (played by Dave Franco in full romance novel cover mode), The Little Hours finds writer/director Jeff Baena (who minored in Medieval and Renaissance Studies at NYU) delighting in updating The Decameron’s light and witty stories, helped by the fact that Boccaccio’s language was opposed to the flowery erudition of most of the period’s texts. That translates to a very vulgar (and funny) movie both indebted to and different than a wide spectrum of vulgar nun and nunsploitation movies that have spanned porn, hauntings and thrillers promising both nude nuns and big guns.—Jacob Oller


31. Scott Pilgrim vs. the World
Year: 2010
Director: Edgar Wright 
In many ways, all of Edgar Wright’s films have been romantic comedies in some fashion. Shaun of the Dead just happens to have zombies and Hot Fuzz just happens to have two males as its romantic leads. In this way, Scott Pilgrim vs. The World is perhaps Wright’s most clear-cut attempt at a rom-com. The story deals in a situation that is all too familiar in the relationship world—that of dealing with your romantic partner’s past romantic baggage. However, to paraphrase Scott Pilgrim’s own words, this emotional baggage (i.e., his girlfriend’s evil ex-boyfriends) is actively trying to kill him every 30 seconds. Just as in a musical, where characters start singing when emotions run too high, Scott Pilgrim dishes out videogame-style duels whenever emotional conflict comes into play. As heightened as Scott Pilgrim may seem at times, its undertones are all too relatable. —Mark Rozeman


30. Tucker & Dale vs. Evil
Year: 2010
Director: Eli Craig
Let’s face it, hillbillies and their ilk have been getting the short end of the pitchfork in movies since the strains of banjo music faded in 1972’s Deliverance. And whether due to radiation (The Hills Have Eyes) or just good old determined inbreeding (Wrong Turn and so, so many films you’re better off not knowing about), the yokel-prone in film have really enjoyed slaughtering innocent families on vacation, travelers deficient in basic map usage skills, and, best of all, sexually active college students just looking for a good time. But fear not, members of Hillbillies for Inclusion, Consideration & Kindness in Screenplays (HICKS)—writer/director Eli Craig has your hairy, unloofahed back. His film, Tucker & Dale vs. Evil, answers the simple question: What if those hillbillies are just socially awkward fellows sprucing up a vacation home and the young college kids in question are just prone to repeatedly jumping to incorrect, often fatal, conclusions? Think Final Destination meets the Darwin Awards.—Michael Burgin


29. The Incredible Jessica James
Year: 2017
Director: Jim Strouse
Jessica Williams plays Jessica James, a twenty-something theatre fanatic who’s trying to get one of her plays produced while simultaneously dealing with a breakup. The ex? Damon, played by the equally wonderful Lakeith Stanfield (Atlanta, Short Term 12), who can’t manage to stay out of Jessica’s dreams. When she meets a new fling, played by the comically refreshing Chris O’Dowd, she begins to re-evaluate her love life while clinging to her life goals. When do you know you’ve made it? As lighthearted as the film can be, it’s rooted in an exploration of the deeper questions that any artist, or person for that matter, grapples with. Williams is hilarious, which we all know from her time on The Daily Show. She’s also incredibly powerful, showcasing a feminine strength that’s so crucial to this generation and a passion for her craft that’s the opposite of the indifference often associated with millennials. The film is perfect for a popcorn and beer night with the gals and guys. —Meredith Alloway


28. Casa de Mi Padre
Year: 2012
Director: Matt Piedmont
Will Ferrell’s Spanish-language comedy is more than just a gimmick or one-note joke. It alternates between being a pitch perfect telenovela parody and a bloated, feature-length version of Ferrell’s more surreal Saturday Night Live work. Ferrell is wonderful, of course, but it also has great turns by Diega Luna and Gael García Bernal (who, yes, American film critics will always automatically associate with one another because of Y Tu Mamá También). There’s one scene with all three of them in a bar together that is one of the most scathing and hilarious criticisms of modern day America you’ll see in any comedy.—Garrett Martin


27. Burn After Reading
Year: 2008
Directors: Joel and Ethan Coen
This Coen Brothers favorite has an unsurprisingly incredible cast, but can we take a moment to give all of the awards and props to Frances McDormand? Her Linda Litzke is one of the strangest, most hilariously bizarre characters to ever appear in a film, and yet there’s something completely familiar about her. She’s pursuing her own version of the American Dream, and the mess she leaves in her wake makes up the crux of this very black, very funny comedy. That she does so while all the other members of this ensemble do the same, and manage to entangle their own personal dramas with hers, makes this movie an entertaining way to spend an evening. Along with McDormand, George Clooney, Brad Pitt, Tilda Swinton and Richard Jenkins (who plays the tragically adorable Ted) all give fantastic turns—unrecognizable, in many ways, from their typical fare which makes the story all the more enthralling.—Garrett Martin


26. Swingers
Year: 1996
Director: Doug Liman
With their breakout roles in Swingers, Vince Vaughn and Jon Favreau established the personalities that still define them 20 years later. Vaughn’s a fast-talking Eddie Haskell type who isn’t quite as charming as he thinks, and Favreau’s an affable everyman with a sensitive side. This carries over to their recent film work: Vaughn motormouths his way through comedies and dramas alike, while Favreau makes big budget Hollywood films that tend to be a little bit smarter and better crafted than most. The ease and charm of their friendship is what makes Swingers so memorable—it would’ve been called a bromance so often if that portmanteau existed in 1996. Swingers is a character-first comedy that captures a specific time and place in vivid detail.—Alan Byrd


25. All About Nina
Year: 2018
Director: Eva Vives
Eva Vives’ grimy, crusty black comedy about the comedy world works best in its primary mode: As a story about navigating that world as a woman, that woman being (surprise!) Nina (Mary Elizabeth Winstead), an acerbic, sharp, blisteringly funny stand-up with a life out of sorts, a brutal drinking problem, and worse taste in men than her alcoholic upheavals leave in her mouth. (Her ex, played by Chace Crawford, hits her, hard, within the film’s first five minutes, and just a minute after that, we see them together basking in the morning afterglow of late night sex.) All About Nina functions well as a profile of its lead, and her past (at first unspoken) trauma, and how the things she’s lived through have shaped her as both a woman and as a comic. It functions less well by comparison as a rom-com, as Nina slowly, cautiously falls for Rafe (Common), an older, but gentle, honest man, who shows her the curative power of real adult love. Sort of. The film skirts the edges of eye-rolling cliché, mostly thanks to the blunt, bleak hilarity of its central thread. It helps that Winstead carries that frank tenor through her work, such that even when All About Nina courts excess sentiment it still speaks in a bitter language; she gives an absolute knockout performance, making her the strongest (and perhaps only) recommendation anyone needs for checking the movie out in the first place. —Andy Crump


24. Observe and Report
Year: 2009
Director: Jody Hill

In 2009 comedy fans bought tickets for Observe and Report expecting Seth Rogen’s lovable stoner man-child schtick. Instead they had to confront the ugly, violent dark comedy that director Jody Hill perfected with his HBO shows Eastbound & Down and Vice Principals. Rogen is surprisingly good in a role that seems written for Danny McBride, a seething cocktail of confusion, depression, arrogance and anger. Anna Faris, Aziz Ansari, Michael Pena and a young Jesse Plemons round out a strong cast.—Garrett Martin


23. Spring Breakers
Year: 2013
Director: Harmony Korine
Watching James Franco in Spring Breakers, one has to ask: Is this a put-on? But the scarier question is, What if it’s not? The brilliance of his portrayal of Alien, a Scarface-aspiring dirt-bag, is that no matter how outlandishly over-the-top it goes—“Look at my shit!”—there remains a deeply unsettling edge to the performance that suggests a white-trash nightmare who could do real damage to those around him. We laugh at Franco as Alien, but the laughs get stuck in our throat: Just like the movie, his performance is a wickedly satiric look at our worst impressions of youth culture—until it gets so frighteningly real that we’re left dazed and amazed.—Tim Grierson


22. The Edge of Seventeen
Year: 2016
Director: Kelly Fremon Craig

Craig may not always get the details right, but her larger vision—alternately pitiless and forgiving of teenage foibles in the midst of adolescence—is still bracing. And the performances she encourages from her actors help pick up the slack. This is Hailee Steinfeld’s first major performance after she burst onto the scene in the Coen BrothersTrue Grit in 2010, and if she showed remarkable pluck and heart there, she shows a talent for comedy here that one might not have been able to guess at from the earlier film. And what a joy Woody Harrelson is here, putting on a master class in minimalist acting, inspiring giggles while barely seeming to move a muscle.—Kenji Fujishima


21. Wedding Crashers
Year: 2005
Director: David Dobkin
The frat pack boorishness that was all the rage in the ‘00s hasn’t aged too well in the post-#MeToo era, but that doesn’t completely deflate Wedding Crashers. Owen Wilson and Vince Vaughn are somehow charming as two Lotharios who hit up random weddings to pick up women, and the supporting cast, including Isla Fisher, Rachel McAdams, Christopher Walken, Bradley Cooper, Henry Gibson, Jane Seymour and an uncredited Will Ferrell, carry just as much of the comedic weight.—Garrett Martin


20. Obvious Child
Year: 2014
Director: Gillian Robespierre
Above all else, Obvious Child is a compassionate film. That might strike pro-life viewers as odd, even offensive, to say since this romantic comedy-drama features a main character getting ready to have an abortion. But in its modest, clear-eyed way, director and co-writer Gillian Robespierre’s feature debut goes beyond the issue’s moral implications to present a realistic, sensitive portrayal of how one young woman makes her decision to terminate her unwanted pregnancy. That the movie also manages to be funny and incredibly sweet is a small marvel. Obvious Child stars rising comic actress Jenny Slate as Donna, a struggling standup in New York. A few years shy of 30, Donna hasn’t quite gotten the hang of anything yet in her life—not her career and not her relationship. (In fact, as the film opens, she walks off stage from a small Brooklyn club to discover that her boyfriend is leaving her for her friend.) Thrown into depression, Donna alternates between stalking her ex and trying to turn her misery into standup material. But it’s not until she meets a wholesome, handsome guy named Max (Jake Lacy) at the club that she can see a possibility for new love—a vision that’s complicated by the fact that she gets pregnant after their one-night stand. Obvious Child seeks to rethink the typical twenty-something romantic comedy. The setup is almost a parody of the scenario usually visited upon a sad-sack protagonist: Not only does Donna lose her boyfriend, she also discovers her job is ending, leaving her in a state of total limbo. But Robespierre upends those conventions with the serious development at the film’s center. Obvious Child isn’t blind to the fact that abortion is the closing of a door and the ending of a possible life, but it’s grownup enough to assume that adults can watch one woman’s journey toward terminating a pregnancy and recognize the emotional intricacies that go into that decision. Touching on a red-hot issue, Obvious Child is agreeably gentle, and even wise. —Tim Grierson


19. Mindhorn
Year: 2016
Director: Sean Foley
Julian Barratt gives a charismatic lead performance, using those chiseled cheekbones and glorious mustache in concert with uncommonly sad eyes to make his washed-up actor Richard Thorncroft both recognizable and worthy of empathy, despite his arrogance and stupidity. The rest of the cast is also strong, though largely overshadowed by Barratt’s magnetism. If Steve Coogan, who also produced, wants to continue spending large chunks of his time in very small, brutally funny roles in comedy movies (see: The Other Guys, In the Loop, and technically Hot Fuzz), that’s fine by me. Kenneth Branagh, shockingly, cameos as himself in one early scene where he auditions Richard for a Hamlet adaption—it’s nice to see he has a sense of humor about still being the go-to Shakespeare guy. It’s clear, in any case, that Mindhorn is a labor of love for the cast and crew.—Deborah Krieger


18. Bull Durham
Year: 1988
Director: Ron Shelton
I believe in ridiculous names like Crash Davis and Nuke LaLoosh. I believe in romantic comedies about giving up on a certain phase of your life where characters stand up and deliver cliched “I believe” speeches that, despite being borderline cheesy, somehow ring completely true. And yes, I too believe there should be a Constitutional Amendment banning Astroturf and the designated hitter. I believe in Bull Durham. The most engaging presentation of the minor-league life on film—and a pretty salute to baseball, in general—this first installment in the unofficial Kevin Costner Baseball Trilogy proved that baseball could equal big box office. Costner and Susan Sarandon anchor this film that does its part to engender a love for the game and the people who court it. —Bonnie Stiernberg & Michael Burgin


17. The Legend of Drunken Master (Drunken Master II)
Year: 1994
Director: Lau Kar-leung

1994’s Drunken Master II (released in the U.S. as The Legend of Drunken Master) is Jackie Chan’s best movie—by far. It features everything uniquely awesome about Chan’s martial-arts movie stardom while showcasing each of his prime elements (fluidity of motion/technique, comedic timing, sheer athleticism) better than in any one of his other cinematic punch-outs, including the original 1978 Drunken Master (starring an obviously much younger Chan). Here he leads as Wong Fei Hung, a Chinese folk hero who employs his Zui Quan (Drunken Boxing) skills to stop the corrupt British consul set on illegally exporting Chinese artifacts out of the country. Although nearly all the action sequences are wonderfully exhaustive and memorable, the final fight is a breathless show-stopper. —K. Alexander Smith


16. Frances Ha
Year: 2012
Director: Noah Baumbach 
Frances Ha is endearing, kind and, in many ways, Noah Baumbach’s best movie to date. One could trace his films, from his debut (Kicking and Screaming) to his most recent (Greenberg) and see a slow but steady focus on the individual, as well as his abandonment of an ironic, sometimes caustic stance against the very characters he writes. It is as if Baumbach could only write a certain type of person—the privileged, socially crippled intellectual with either too much self-awareness or none at all—and for a while it seemed like even the writer himself couldn’t stand to be in the same room with such characters. This anger has faded, and what has emerged over his last few films, and culminated in Frances Ha, is an embrace of not only the flaws of his characters, but also his flaws as a filmmaker. He has settled down and created a film imbued with love, fun and melancholy. It feels simple and open and is a joy to watch.—Joe Peeler



15. Don’t Think Twice
Year: 2016
Director: Mike Birbiglia 

One of the most appealing aspects of Don’t Think Twice is the sense of close-knit community it depicts among its main characters, all of them members of a fictional New York City-based improv troupe named the Commune. They’re so attached to each other, at least in the film’s early stages, that they regularly spend their Saturday nights with each other watching Weekend Live, the Saturday Night Live-like late-night comedy show that represents the endgame for which they’ve devoted so many of their years toiling in relative obscurity.

When one of the Commune members, Jack (Keegan-Michael Key), finally reaches that aforementioned pinnacle and becomes a new member of Weekend Live, the ascension brings out into the open the sense of cutthroat competition that was perhaps always underlying the surface camaraderie. As close-knit as he, his mentor Miles (director Mike Birbiglia), Jack’s girlfriend Samantha (Gillian Jacobs) and the rest are, they’re all vying for the same highly coveted spots; no surprise that an unspoken sense of jealousy soon develops after Jack is picked. Therein lies Don’t Think Twice’s most poignant insight into this particular creative world: This “frenemies” dynamic takes place in an environment so brutal that it forces those who don’t make it to the top to wonder if they ever had the talent to begin with. Even Jack, who may have proved to be the “best” of the Commune members, finds himself still facing an uphill climb at Weekend Live.—Kenji Fujishima


14. Punch-Drunk Love
Director:   Paul Thomas Anderson  
Year: 2002
It may be hard to recall, but there was once a time when the world believed in Adam Sandler—and we have P.T. Anderson to thank for such a glimpse of hope. Compared to the scope of There Will Be Blood, or the melancholy of Boogie Nights, or the inexorable fascination at the heart of The Master, Punch-Drunk Love—a breath of fresh, Technicolor air after the weight of Magnolia—comes off like something of a lark for Anderson, setting the stage for the kind of incisive comic chops the director would later epitomize with Inherent Vice. But far from a bit of fluff or a reactionary stab at a larger audience, Punch-Drunk Love is what happens when a director with so much untapped potential just sort of throws shit at the wall to see what sticks. A simple love story between a squirmy milquetoast (Sandler) and the woman (Emily Watson) who yanks him from his stark blue shell, the film is part musical, part silent film and all surreal comedy. That this is Sandler’s best role is hardly up for debate; that this may be Jon Brion’s best soundtrack is something we can talk about later. That the rest of the film, which in any other director’s hands would be a total mess, feels so exquisitely felt is almost … magical. And that? That’s that, Mattress Man.—Dom Sinacola


13. The Trip to Spain
Year: 2016
Director: Michael Winterbottom
Sadly the first two of Steve Coogan, Rob Brydon and Michael Winterbottom’s comedy travelogues aren’t on Netflix. You don’t need to see them to enjoy the latest sequel, though, where they drive through Spain, sampling some fantastic looking restaurants. Watching two middle-aged men eat their way through scenic European vistas might not sound like a great recipe for laughs, but Coogan and Brydon are both brilliant comic minds, and together they have an easy and irresistible charm that makes their impression-heavy banter deeply enjoyable.—Garrett Martin


12. In Bruges
Year: 2008
Director: Martin McDonagh
You know you’ve tripped into the ambiguous realm of Postmodernism when medieval Europe, midget jokes and ultraviolence converge into a seamless whole. Theater auteur Martin McDonagh’s debut feature, In Bruges, thrives on these stylistic clashes with its narrative of two sympathetic hitmen who seek refuge in a European wonderland full of tourists and irony. The film’s visual appeal complements irreverent and hilarious dialogue—timed brilliantly with the Anglo-Saxon bravado of Fiennes, Farrell and Gleeson—to produce one of a most pleasant
dark-horse dramedy.—Sean Edgar


11. Pineapple Express
Year: 2008
Director: David Gordon Green 
Pineapple Express is a successful attempt to graft the kind of comedy that Judd Apatow’s crew was known for in the ‘00s onto a different genre. The result is a shaggy, ‘70s-style low-budget crime thriller turned into an absurd, low-brown stoner comedy starring Seth Rogen and James Franco. This is the best vehicle for these two after Freaks and Geeks. As ridiculous and violent as the comedy gets, it’s still rooted in character, and not just that of the two leads; almost everyone on screen, from Gary Cole’s crime boss, to Craig Robinson and Kevin Corrigan’s hitmen, to Danny McBride’s cartoonish small-time dealer, establishes a character that’s more than just a stereotype or bundle of comical tics.—Garrett Martin


10. Heathers
Year: 1988
Director: Michael Lehmann
Heathers might look like another teen comedy, but it’s probably the darkest and most brutal movie on this list. It’s a cynical deconstruction of the typical high school comedy, turning peer pressure fatal and elevating the stakes from social lives to actual lives. It smartly subverts one of the stalest genres of comedy, and still remains edgy 30 years later.—Garrett Martin


9. A Serious Man
Year: 2009
Directors: Joel and Ethan Coen

Working with few recognizable stars, the Coens have made a funny but odd and inquisitive film about guilt. It’s also their most Jewish film to date, a film about physics professor Larry Gopnik and the Jewish subculture of a medium-sized late-’60s American town. Larry’s life begins to fall apart when his wife says she wants a divorce, and in the great unraveling that follows, the Coens have made Kafka’s implications explicit. The K word is often slapped onto any old symbolic nightmare, but Kafka’s own work was actually very funny, even though he could slip into gray areas without much warning. The Coens can, too. A Serious Man is one of the most fascinating, maybe even heartfelt, renderings of a Kafkaesque sensibility that I’ve seen. —Robert Davis


8. Kung Fu Hustle
Year: 2004
Director: Stephen Chow
Stephen Chow is probably the biggest name in martial arts comedy since the days of Sammo Hung, and Kung Fu Hustle will likely remain one of his most well-regarded films both as a director and performer. Gleefully kooky, it combines occasional song and dance with extremely exaggerated kung fu parody in telling the tale of a young man who ends up overthrowing a large criminal organization, the “Deadly Axe Gang.” This is not a complex film—rather, it’s simply intended as popcorn entertainment at its most absurd. The action has no basis in reality, being closer to a real-world depiction of Looney Tune physics. The characters are broad pastiches and references to famous actors from the genre’s history abound. With comedy that teeters decidedly on the juvenile or inscrutable side, it’s a film that some will dismiss off-hand, but Chow’s style has always and will probably always be “entertain first, make sense later.” That’s what he does, and he does it better than anyone else. —Jim Vorel


7. She’s Gotta Have It
Year: 1986
Director: Spike Lee 
Spike Lee arrived as a fully-formed talent with this small-budget, black-and-white debut, which wound up being one of the most important movies in the rise of independent films in the 1980s. Lee brought a voice and verisimilitude to the screen that hadn’t been seen before, with a movie that’s smart, funny and audacious. The central theme—that women can sleep around as much as men, and that they shouldn’t be judged or scorned for it—is still relevant 30 years later. In fact, it’s so relevant Lee adapted the movie into a Netflix series that premiered last year.—Garrett Martin


6. Hot Fuzz
Year: 2007
Director: Edgar Wright 
The second chapter in the Three Flavours Cornetto trilogy (before there was ever such a thing), Hot Fuzz is clear evidence that Edgar Wright is capable of anything. A blockbuster action flick, a thriller, a pulp plot, a winking noir, a commentary on classism in an increasingly urbanized society—the movie is all of these things, down to the marrow of its very existence. Moreso than Shaun of the Dead or The World’s End, Hot Fuzz inhabits its influences with the kind of aplomb to which any cinephile can relate: Somewhere between fascination, revulsion and pure visceral joy there walks the Michael Bays, the Don Simpsons, the John Woos, the Jerry Bruckheimers, and Wright gives each stalwart his due. Plus, he does so with total respect, showing that he understands their films inside and out. And in that intimate knowledge he knows even better that filmmaking is a conflagration: Best to burn it all down and see what remains than build it from the ground up.—Dom Sinacola


5. The 40 Year-Old Virgin
Year: 2005
Director: Judd Apatow 
Judd Apatow’s first film as a director remains his best. Rather than being a film insulting Steve Carell’s Andy and his choice to wait for sex, it creates an understanding and sensitivity towards him, turning him into the voice of reason rather than just the lonely virgin. Despite the title, The 40 Year-Old Virgin isn’t really about sex at all, but about finding a person who is right instead of just a person for the night. It’s a surprisingly conservative take on the idea, but the result is a hilarious and surprisingly romantic story that twists typical ideals on its head, without ever condemning one way or the other.—Ross Bonaime


4. Wet Hot American Summer
Year: 2001
Director: David Wain
A cult film that’s long since surpassed that status, Wet Hot American Summer is a lot of things: It’s hilarious; it’s perfectly cast; and it’s a clear demonstration that Christopher Meloni has more range than simply playing a dour sex crime detective. But what makes it so brilliant, 15 years later and with a Netflix series on lock, is that it’s so painfully, relentlessly nihilistic. We could trade quotable lines for days (my personal favorites being what Jon Benjamin’s can of vegetables admits he’s acrobatically capable of, and then Paul Rudd bluntly refusing to make out with Elizabeth Banks’s character due to her burger flavor), but the key to the movie’s endurance—past its timelessness grounded in a specific brand of ’80s sex romp flick—is the way in which it treats nostalgia. Like Wain, Michael Showalter and Michael Ian Black’s Stella series, Wet Hot American Summer, which takes place over the course of Camp Firewood’s last day, exists in a bleakly amoral world. Here, bad things happen to good people—and really only to good people. Wain takes innocence and obliterates it, punishes it, gleefully destroying all nice memories anyone would ever hold dear about long lost summers, first loves and youth. Without a shred of wistfulness, Wet Hot American Summer surpasses its origins in parody and becomes something more: It earns its comedy. Taunting our very explicitly American tendency to let everything we touch devolve into sentimentality, the film proves that when we obsess over remembering ourselves at our best, we might as well be celebrating us at our worst. —Dom Sinacola


3. Monty Python’s Life of Brian
Year: 1979
Director: Terry Jones
Pretty much made on George Harrison’s dime and considered, even if apocryphally, by the legendary comedy troupe to be their best film (probably because it’s the closest they’ve come to a three-act narrative with obvious “thematic concerns”), Life of Brian got banned by a lot of countries at the butt-end of the ’70s. As a Christ story, the telling of how squealy mama’s boy, Brian (Graham Chapman) mistakenly finds himself as one of many messiah figures rising in Judea under the shadow of Roman occupation (around 33 AD, on a Saturday afternoon-ish), Monty Python’s follow-up to Holy Grail may be the most political film of its ilk. As such, the British comedy group stripped all romanticism and nobility from the story’s bones, lampooning everything from radical revolutionaries to religious institutions to government bureaucracy while never stooping to pick on the figure of Jesus or his empathetic teachings. Of course, Life of Brian isn’t the first film about Jesus (or: Jesus adjacent) to focus on the human side of the so-called savior—Martin Scorsese’s take popularly did so less than a decade later—but it feels like the first to leverage human weakness against the absurdity of the Divine’s expectations. Steeped in satire fixing on everything from Spartacus to Franco Zeffirelli’s Jesus of Nazareth, and buttressed by as many iconic lines as there are crucifixes holding up the film’s frames (as Brian’s equally squealy mother hollers to the swarming masses, “He’s not the messiah. He’s a very naughty boy!”), the film explores Jesus’s life by obsessing over the context around it. Maybe a “virgin birth” was really just called that to cover up a Roman centurion’s sexual crimes. Maybe coincidence (and also class struggle) is reality’s only guiding force. Maybe the standard of what makes a miracle should be a little higher. And maybe the one true through line of history is that stupid people will always follow stupid people, whistling on the way to our meaningless, futile deaths. —Dom Sinacola



2. The Graduate
Year: 1967
Director: Mike Nichols
In the undisputed king of movies for those headed out into the real world, a hyper-accomplished recent grad (Dustin Hoffman) panics at the prospect of his future and falls into an affair with the much older wife of his father’s business partner (Anne Bancroft). It helped define a generation long since embalmed by history, but the sense of longing for an alternative hasn’t aged. —Jeffrey Bloomer


1. Monty Python and the Holy Grail
Year: 1975
Director:
It sucks that some of the shine has been taken off Holy Grail by its own overwhelming ubiquity. Nowadays, when we hear a “flesh wound,” a “ni!” or a “huge tracts of land,” our first thoughts are often of having full scenes repeated to us by clueless, obsessive nerds. Or, in my case, of repeating full scenes to people as a clueless, obsessive nerd. But, if you try and distance yourself from the over-saturation factor, and revisit the film after a few years, you’ll find new jokes that feel as fresh and hysterical as the ones we all know. Holy Grail is, indeed, the most densely packed comedy in the Python canon. There are so many jokes in this movie, and it’s surprising how easily we forget that, considering its reputation. If you’re truly and irreversibly burnt out from this movie, watch it again with commentary, and discover the second level of appreciation that comes from the inventiveness with which it was made. It certainly doesn’t look like a $400,000 movie, and it’s delightful to discover which of the gags (like the coconut halves) were born from a need for low-budget workarounds. The first-time co-direction from onscreen performer Terry Jones (who only sporadically directed after Python broke up) and lone American Terry Gilliam (who prolifically bent Python’s cinematic style into his own unique brand of nightmarish fantasy) moves with a surreal efficiency. —Graham Techler

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