Video Get App
Music Movies TV Comedy Games Books Comics Drink Politics

The 40 Best Comedies on Netflix (October 2018)

Comedy Lists What to Watch
Pin

You gotta learn from the churn. Netflix adds and loses movies every month, throughout every month, even, meaning a list like this is never truly done. You can’t be comprehensive about something that’s always changing, always getting better or getting worse or even just staying the same but different, somehow.

October is a good month for new comedies on Netflix. We’ll miss Trading Places and The Commitments and Moonrise Kingdom, but some all time classics are now streaming here, both movies returning to Netflix after brief absences and favorites that haven’t been on Netflix for years, if ever. Two of our top three weren’t on Netflix a month ago—Blazing Saddles and Monty Python’s The Life of Brian. Our top ten is 40% different than it was a month ago, and that’s almost entirely because of additions and not subtractions. Again: this is a good month for comedies.

If you’re looking for something hilarious to wind down with at the end of a tough work day, or a top shelf chuckler to keep your mind off how you haven’t Netflix and chilled in so long that “Netflix and chill” was still a thing people actually said at the time, let this list guide you right and true.

(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.)

40. Nacho Libre
Year: 2006
Director: Jared Hess
Jared Hess’s mannered, overly calculated goofiness can be an acquired taste, and it’s definitely one I, personally, have not been able to cultivate. That silliness is on full display in Nacho Libre, a lucha libre comedy with Jack Black as an orphanage employee who wrestles under a mask at night. Black fully commits to the role, of course—full commitment is Black’s entire thing—and that helps carry some of the movie’s more annoying aspects. Older wrestling fans (and Jim Cornette) might appreciate that it keeps total kayfabe—Nacho’s matches are presented as real competitions, which fits the movie’s dusty, sepia-toned take on the ‘70s.—Garrett Martin


39. Game Over, Man!
Year: 2018
Director: Kyle Newacheck
Your response to this Netflix Original will hinge almost entirely on how you feel about Workaholics. This is basically a Workaholics movie, after all—not just one made by and starring that show’s cast (Adam DeVine, Anders Holme, Blake Anderson and Newacheck), but a movie that could’ve been made by the stoner slacker characters they played in Workaholics. It’s Die Hard with three stoner slacker videogame designers playing John McLane, and it’s exactly as shaggy, self-indulgent and tossed-off as you’d expect. It’s also really funny, if you appreciate the kind of comedy these guys do—vulgar, lightly absurd, occasionally mean-spirited, but rarely cynical or pretentious.—Garrett Martin


38. 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


37. 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


36. 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


35. Bad Santa
Year: 2003
Director: Terry Zwigoff
Billy Bob Thornton is sublimely degenerate, as only he can be, but the film’s ending has one of the most redemptive turns this side of It’s A Wonderful Life. A true masterpiece of a dark comedy, in Bad Santa we see the titular Anti-St. Nick pee himself, get wasted, swear at kids, disrespect authority and plan on robbing the very mall in which he (barely) works. That the aforementioned Bad Santa is not just a vulgar caricature is testament to Thornton’s these-are-the-facts deadpan, countered by two brilliant supporting performances from the late greats John Ritter and Bernie Ma, as well as Thornton’s genuinely touching rapport with innocent cherub Thurman Murman (Brett Kelly). —Greg Smith


34. 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


33. Magic Mike
Year: 2012
Director: Steven Soderbergh 
Hot producer-star Channing Tatum draws from his personal history for this raucous comedy-drama set in Tampa’s Xquisite Male Dance Revue. Tatum worked as a stripper for eight months early in his career, and if Magic Mike is any indication, it was a good time for both the ladies and the performers—the movie certainly is. Channing plays the titular main attraction at a weekend dive run by onetime-stripper-turned-manager Dallas (Matthew McConaughey). Mike is a popular performer, but stripping three nights a week doesn’t pay the bills on his swank beachfront pad and brand-new pickup truck, so he makes ends meet by working a construction gig. He’s also got a couple of entrepreneurial enterprises on the side, including a detailing business that may or may not actually have customers and a dream to custom-build furniture full-time. The guys’ hands-on performances, choreographed by Alison Faulk, are enthusiastic and energetic, if not always polished, with indelible set pieces like the part-Singin’ in the Rain, part-Matrix treatment of “It’s Raining Men” that introduces us to the act. What you may not have even known you wanted until you got it is a solo by McConaughey, an electrifying turn that marks the climax of the action. McConaughey is perfectly cast to begin with but then turns around and makes the role his own, even incorporating an allusion to his infamous bongos incident. He’s sleazy yet sexy, equally alluring to the women he services and the men he employs. The ladies in the small packed house go wild for these guys, and their excitement is infectious. Along with a solid script by Tatum’s producing partner Reid Carolin, director-cinematographer Steven Soderbergh (who took a low-budget, highly experimental look at the life of a high-end call girl in The Girlfriend Experience) brings a warm golden aesthetic that’s at once polished and serendipitous. The way the sunlight dapples the actors’ bodies during a sunset beach scene is particularly lovely. But Magic Mike would hardly be as magical without Tatum, whose good looks, athletic physicality, easygoing charm and heart-on-his-sleeve sincerity are as seductive to moviegoers as to the women he dances for on-screen. —Annlee Ellingson


32. Up in the Air
Year: 2009
Director: Jason Reitman 

Ryan Bingham (George Clooney) lives his life traveling, and he loves it, even though his job is to fire workers for employers who can’t break the news themselves. The gig’s a downer, but at least he gets to fly. His remote boss is played by the great Jason Bateman, Vera Farmiga plays a fellow traveler, and when these actors pair off they’re fantastic. The film is primarily a portrayal of Bingham’s isolation and the depressing circumstances of his job, and in doing so provides a spot-on illustration of the the life of the jaded business traveller who knows his way around an airport better than his own home. —Ryan Bort


31. 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


30. 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


29. Clerks
Year: 1994
Director: Kevin Smith 
Does Clerks hold up? That’s a tough question. It’s the exact same movie it was in 1994, obviously, as unapologetically raunchy and jaded as ever. It’s at once barely competent as filmmaking and yet probably the most artistically cohesive and competent work Kevin Smith has ever made. Clerks was never really a great movie, per se, but made a deep impression for two reasons. First off, the rags-to-riches story behind its creation was basically the ultimate summation of the entire 1990s fascination with indie films. Here’s a guy who made an ugly, lo-fi, black-and-white comedy without professional actors for less than a year’s worth of college, and because it had a voice and verisimilitude that hadn’t really hit the big screen yet, he got distribution through the biggest indie film company of the day and the movie wound up making millions. Secondly, if you were a teenager or twentysomething at the time, Clerks was legitimately hilarious. These characters spoke like your friends, or at least like amplified versions of them. It’s far from a great movie, and most of the acting is as terrible as you probably remember, but it still has that middle-class wastrel charm that made it stand out 24 years ago, and some of the jokes still land, even if your taste in comedy has changed greatly since you first saw it.—Garrett Martin


28. 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


27. The Truman Show
Year: 1998
Director: Peter Weir
Before reality shows took over the world and VH1, there was a prescient little movie called The Truman Show. Strange, that there was a time in our culture when the thought of putting someone on television and watching their life unfold in a somewhat (or completely) falsified manner was morally wrong. But The Truman Show was more than just a critique on the reality shows of the future; Jim Carrey was the everyman hero, weary of living a life where he took no risks and saw no change. As he attempted to make new moves, he was met with such resistance that it made the very act of living a revolutionary process in itself. Laura Linney, Noah Emmerich and Ed Harris (as Christof, the all-powerful man behind the curtain) made up Truman’s world and the cast of one of the most captivating and triumphant stories ever told.—Shannon M. Houston


26. 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


25. 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


24. 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


23. Role Models
Year: 2008
Director: David Wain

Even though it’s rated R, Role Models could easily be mistaken as a Judd Apatow-produced attempt at a family film. Much of what makes this feel like an Apatow film is how reliable the plot is. The end is no surprise to anyone who’s watched even a dozen Hollywood films, but what’s important is the journey. David Wain (Wet Hot American Summer) allows the characters to meander to their destined plot points for as long as the jokes will take them—which can be quite a while in some cases. But since the overall story isn’t in question, this time spent elsewhere doesn’t detract; it instead deepens the characters. The jokes aren’t revolutionary either, but they are spot on. Role Models is not experimental like some of Wain’s other comedy projects (Stella, The State). What it is, though, is well acted, well written and extremely polished. Most important of all, it’s really funny. Apatow should be flattered by the comparison..—Sean Gandert


22. I Love You, Man
Year: 2009
Director: John Hamburg
While Paul Rudd goes a little bit over the top with his awkward, almost-naive behavior at the beginning (think Michael Scott from The Office, who appears to be a clear influence on the character), Jason Segel and Rudd make for one dynamic duo. At times, one might assume there would be too much male bonding, but this film brings just the right amount of vulgar jokes, back-handed compliments, and sexual innuendo to the table.—Muriel Vega


21. Meet the Parents
Year: 2000
Director: Jay Roach
Robert DeNiro’s comedy chops were never more perfectly suited than with his role as Jack Byrnes, the over-protective father who brings out the absolute worst in his son-in-law to be, male nurse Gaylord Focker (Ben Stiller). Every boyfriend’s nightmare about making a good impression comes to pass as Focker makes every wrong-headed decision that you’d expect from a Stiller character at this point. Plenty of laugh-out-loud moments make this now-classic slapstick comedy of errors a fun, popcorn movie night.—Josh Jackson


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. 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


17. Amélie
Year: 2001
Director: Jean-Pierre Jeunet
A delicate, delicious little French trifle, Amélie is easily the most romantic film on this list. The adorable Audrey Tautou launched herself into the American consciousness as the quirky do-gooder waitress who sends her secret crush photos and riddles masking her identity in order to make their first encounter—and first kiss—the most romantic moment of her life. Endlessly imaginative and beautifully photographed, Amélie is a film to be treasured.—Jeremy Medina



16. 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


15. The Breakfast Club
Year: 1985
Director: John Hughes
We shouldn’t have to tell you what makes The Breakfast Club an all-time classic. There’s not a single weak link in the film’s ensemble cast, and Molly Ringwald holds her own as Claire, the princess forced to spend her Saturday in detention with a brain, a basket case, a jock and a criminal. She gives a richly layered performance, turning what could easily be a one-dimensional character into someone we pity, empathize with and root for—which, if you haven’t seen the movie, is kind of the whole point. —Bonnie Stiernberg


14./13. The Trip to Italy / The Trip to Spain
Year: 2014/2016
Director: Michael Winterbottom
Sadly the first of Steve Coogan, Rob Brydon and Michael Winterbottom’s comedy travelogues isn’t on Netflix. You don’t need to see it to enjoy the two sequels, though, which we’ve lumped together because they are equally great and hilarious. 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. Stripes
Year: 1981
Director: Ivan Reitman
Stripes might not be as beloved as Ghostbusters or Groundhog Day, but John Winger, the sarcastic, irreverent cabdriver who joins the army after his life falls apart, should be Bill Murray’s defining role. (Or, at least, early Murray, before he became a respectable actor.) Sure, Murray had already developed his voice at Second City and on Saturday Night Live, and premiered it on the big screen with Meatballs, but Stripes put Murray’s anti-authoritarianism up against the most authoritarian institution in America, allowing him to reach new heights of smarmy disrespect. And it’s not afraid to make him look like an asshole without trying hard to rehab him, something that can’t be said about Ghostbusters or Groundhog Day. Stripes has problems as a movie—it drags on too long, the last third is overblown and unrealistic, and the way it treats women was uncomfortable back then and would be downright unacceptable today—but between Murray, Harold Ramis, John Candy, Judge Reinhold, John Larroquette, and a fantastic straight man performance by Peckingpah tough guy Warren Oates as the drill sergeant, it might be, laugh for laugh, the funniest movie on this list.—Garrett Martin


11. 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


10. Billy Madison
Year: 1995
Director: Tamra Davis

There’s a strong case to be made that Billy Madison is the best Adan Sandler movie. Sure, it’s not as human as The Wedding Singer, and it’s hard to vote against Happy Gilmore, but Madison so thoroughly exceeded the abominably low expectations I had for it in 1995 that it wound up being one of the most memorable movies of the decade. It’s still hilarious today, a perfect vehicle for Sandler’s man-child persona, and one that surrounds him with a fantastic supporting cast, including Bradley Whitford, Darren McGavin, Norm Macdonald, Chris Farley, and a giant penguin, among others. It’s not the story or even the jokes that make Billy Madison so funny—it’s the surreal flourishes, the way lines are delivered, how Tamra Davis (both a woman and an outsider to the small circle of men who have directed most of Sandler’s movies since) is able to contrast Sandler’s weirdness with a world that feels recognizable in its everyday mundanity. Later Sandler movies feel lazy and untethered from the real world, but Madison doesn’t suffer from either flaw. It’s dumb comedy done with enough weirdness and intelligence to become a true classic.—Garrett Martin


9. 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 almost 30 years later.—Garrett Martin


8. 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


7. Happy Gilmore
Year: 1996
Director: Dennis Dugan
Adam Sandler could’ve retired in 1998, after his first three movies, and his comedy legacy would’ve been secured. (He maybe should’ve retired then, but let’s not get into that.) It’s hard to pick between The Wedding Singer, Billy Madison and Happy Gilmore, but that last one is the only one of the three on Netflix, so let’s talk about that. The tale of a failed hockey player becoming a champion golfer is an ideal vehicle for Sandler’s inchoate frat boy rage, and the absurd streak that elevated Madison above most Hollywood comedies of the day is even more visible here. It has some of the same problems as most Sandler movies—an underwritten, unbelievable love interest (here played by Modern Family’s Julie Bowen), a bare bones story that’s little more than a launching pad for jokes—but Gilmore is an ideal character for Sandler, and a great supporting cast (including Carl Weathers, Ben Stiller, Richard Kiel, Joe Flaherty, and Christopher McDonald as the iconic villain Shooter McGavin) help turn this into a legitimate classic. Also there’s a great chance this is the main thing younger people know Bob Barker from, which is actually kind of sad.—Garrett Martin


6. 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


5. Pee-Wee’s Big Adventure
Year: 1985
Director: Tim Burton 
Tim Burton’s full-length directorial debut is also one of his best. Pee-wee’s Big Adventure brings us into the bizarro world of Pee-wee Herman, the excitable, ageless protagonist that’s hopelessly attached to his bike. After it’s stolen in broad daylight, we see Herman travel across the U.S. to reclaim his baby. And through the adventure and its ongoing discoveries (who knew the Alamo didn’t have a basement?) we’re introduced to unforgettable characters like Herman; his (sort-of) love interest, Dottie; the horrifying trucker ghost Large Marge; the snotty, rich Francis; and Herman’s dog, Speck. Herman’s wacky world is fully realized through the eye of Burton, and this one stands alone as a film that kids and adults can both get a kick out of.—Tyler Kane


4. 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


3. Blazing Saddles
Year: 1974
Director: Mel Brooks
Mel Brooks’ greatest and most racially charged comedy has recently been mentioned in debates of political correctness, in the tone of “Nobody would be able to make Blazing Saddles today,” and for better or worse, it’s hard to refute. The film is a product of its time, a decency-stretching Wild West farce about a black sheriff trying to win over the white settlers of his frontier town and foil the plot of comically nebbish villain Harvey Korman in an all-time great comedy performance. Brooks regulars such as Madeline Kahn contribute great bits, and there’s the wonderfully understated Gene Wilder, but the reason the film remains such a classic today is that the surface-level gags are largely harmless and timeless. From its little diversions to do Loony Tunes parodies, to the genre satire of every person in town seemingly being named “Johnson,” it’s a surprisingly sweet film for one that’s also throwing around heavy themes of racism and discrimination. One thing that genuinely wouldn’t be done in a film today is its madcap, zany ending, as the cowboys spill out of their own movie and into the other Warner Bros. soundstages. Outside of Anchorman 2, nothing else in recent years has tapped into that level of reality-bending, plot-snapping absurdism.—Jim Vorel


2. 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


1. Groundhog Day
Year: 1993
Director: Harold Ramis
Bill Murray, director/co-writer Harold Ramis and screenwriter Danny Rubin take a Twilight Zone-esque comedic premise—a self-centered weatherman gets stuck experiencing February 2 again and again—and find unexpected profundity. A more conventional film would have love resolve the chronological predicament, but instead, it falls to Murray to become the best man he can possibly be. A Hollywood comedy that challenges middle-class Americans to better themselves, Groundhog Day doesn’t just elicit laughs, but leaves audiences more deeply moved than they ever expected.—Curt Holman

More from What to Watch
What to Watch Features
What to Watch Lists
What to Watch Video