The 25 Best Comedies on Hulu (May 2019)

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The 25 Best Comedies on Hulu (May 2019)

If you still think Hulu is just a place to watch sitcoms the day after the networks broadcast them, it must’ve been a few years since you last logged in. The streaming site has long been a full-service rival to Netflix, and arguably has a deeper and stronger lineup of films. It might not be quite as rich on great comedies at the moment—notice this is a list of 25 movies, whereas our Netflix list goes all the way to 40—but it’s a more diverse set of films, with something for all tastes and ages.

Before we jump in, let me include the standard disclaimer that I always start that Netflix comedy list with. I’m a comedy editor. I’m mostly looking at how much a movie makes me laugh when I’m putting together a list like this. So if you feel the need to go all Margaret Dumont about the sheer impropriety of these rankings, maybe go check out some of our more tasteful overall movie rankings, instead. If you can handle the very first movie on this list, though, the one coming in right here at number 25, you can probably make it through without getting too angry.

dirty work movie poster.jpg25. Dirty Work
Year: 1998
Director: Bob Saget

In 1998 hope was high that Dirty Work would be Norm Macdonald’s Billy Madison, a surprise hit (and surprisingly good) comedy that would propel him to Adam Sandler-level fame and success. Well, that didn’t happen. Dirty Work is still a greatly underrated film, one that fully integrates Macdonald’s distinctive comedic voice into a shaggy mainstream comedy full of clear ‘90s Hollywood signifiers. (Yes, “Semi-Charmed Life” is on the soundtrack. Yes, Christopher “Shooter McGavin” McDonald plays an uptight villain who, in a Hollywood comedy bingo twofer, is also an evil real estate developer who wants to evict Norm’s love interest’s grandmother. Yes, that love interest is played by a ‘90s sitcom actress, in this case Traylor Howard.) The film works because of Norm’s distinctive delivery and his character’s fractious relationships with his best friend and his best friend’s father, respectively played by Artie Lange and Jack Warden (in one of his final roles). Their chemistry, Norm’s charisma, and some sharp joke-writing elevates an otherwise predictable mediocrity.—Garrett Martin

hulu anger management.jpg24. Anger Management
Year: 2003
Director Peter Segal

Adam Sandler’s steady downward slide was momentarily halted almost entirely because of Jack Nicholson. The Hollywood legend unleashed his malevolent side as an unconventional therapist helping Sandler overcome his rage issues. Nicholson’s charisma—and the perverse appeal of seeing him in such a low stakes, low brow comedy—is a fine antidote to the increasing laziness of the Sandler formula. Nichoson’s not the only legitimately great actor in this movie—in addition to talented Sandler regulars like John Turturro and Luis Guzman, the cast also includes Woody Harrelson, Harry Dean Stanton, John C. Reilly, and, in a true coup, acting legend Rudy Giuliani.—Garrett Martin

hulu larger than life.jpg23. Larger Than Life
Year: 1996
Director: Howard Franklin

Yes, this is that elephant movie. If you want to know how great Bill Murray was during his ‘90s revival, just watch this movie, which is better than it ever should’ve been due to Murray. It’s nowhere near the brilliant level of his Quick Change / What About Bob? / Groundhog Day trifecta, but Murray’s so comfortable in his routine, which somehow has never really grown old, that he’s able to almost save this thoroughly mediocre movie. Arriving the same year as Kingpin, this was essentially Murray’s farewell to straight comedy, unless you count the Garfield movies, for some reason.—Garrett Martin

ace ventura poster.jpg22. Ace Ventura Pet Detective
Year: 1994
Director: Tom Shadyac

The character of Ace Ventura in Ace Ventura: Pet Detective is the definition of zany. And slightly deranged. And…bird-like. According to an Inside The Actors’ Studio interview, Carrey based Ace Ventura’s voice, clothes, walk, hair and mannerisms on the behavior of birds. To base an entire performance on birds or any animal and to get such hilarious results as Carrey had is a mark of an original actor.—Anita George

hulu poster jumanji 1995.jpg21. Jumanji
Year: 1995
Director: Joe Johnson

No, the Rock is nowhere in this version of Jumanji. This is the first adaptation of Chris Van Allsburg’s children’s book about an enchanted board game that magically makes rhinos and Robin Williams appear when you play it, or something like that. Williams was deep into his family friendly phase by this point, far removed from the coke-addled mania of his stand-up days, but he was still a warm and charming presence, and still brought a lot of comic weight to what is otherwise a fairly standard mid ‘90s children’s fantasy film. Jumanji can’t escape that studio blockbuster factory feel, and the special effects have not aged gracefully, but it’s worth watching for a solid Williams performance.—Garrett Martin

romy and michelle movie poster.jpg20. Romy and Michelle’s High School Reunion
Year: 1997
Director: David Mirkin

K, it’s not the hardest-hitting comedy in the world, but it is the film that canonized “I invented Post Its” as a rejoinder at my house. Romy and Michele (Mira Sorvino and Lisa Kudrow) are two not-especially-ambitious young women who have been best friends since high school and live together in Los Angeles. When they get a high school reunion invite, they realize they desperately want to descend on their hometown in Arizona and lay waste to the bitchy “A-List” girls who made their high school lives miserable, so they borrow a Jaguar, don pin-striped suits and concoct a pile of lies about their accomplishments as Serious Businesswomen. Of course they get into a huge fight on the way there and have to find their way back to each other as well as themselves, as it becomes clear that they are not the only ones at the reunion trying to deal with their high school unfinished business. Light to the point of near-self-parody and sometimes not quite funny enough to justify itself, the film nonetheless has tons of laughs for anyone in the mood to find something funny, and Kudrow and Sorvino are both hysterically deadpan-though the stealth comedic missile is Jeanane Garofalo as a foulmouthed, chain-smoking misanthrope classmate who has her own revelation at the event. If the Reagan administration was rough on you and you have mixed feelings about pastels, this is a film with some potential feel-good value.—Amy Glynn

hulu poster the oath.jpg19. The Oath
Year: 2018
Director: Ike Barinholtz

The Oath is a cutting indictment of all sides, reserving the most resentment for itself—or at least for writer-director Ike Barinholtz, who makes a dark comedy about a news-obsessed upper-middle-class woke white man, an identity which many of us both claim and resent ourselves for claiming. Which is why, even if you don’t fulfill all of the preceding quantifiers, the film can feel so painfully, hilariously relatable: It’s about being angry all the time when you have no real reason to be—about seeing the world so cynically you make the lives of everyone around you, everyone you love, just that much more miserable.—Dom Sinacola

tucker and dale vs evil poster.jpg18. 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

while you were sleeping movie poster.jpg17. While You Were Sleeping
Year: 1995
Director: Jon Turteltaub

While You Were Sleeping, a throwback romantic comedy in the screwball mode, is impossible not to like, a standout of the genre that holds up more than two decades after its release. More kind-hearted than My Best Friend’s Wedding and more grounded than Return to Me, the film turns a daffy plot into something touching and compulsively watchable. Much of the film’s appeal can be attributed to Sandra Bullock’s performance as Lucy, a lonely CTA employee who moved to Chicago with her ailing father, put her future on hold and never returned to it once he died. (That character description alone is enough to set this film apart from so many “high-powered lawyer” romantic comedies.) Lucy takes tokens from and pines for well-dressed lawyer Peter Callaghan (Peter Gallagher) before—long story short—he ends up in a coma. His family (comprising a number of delightful character actors) assumes she’s his fiancée, “adopting” her as one of theirs, but of course she falls in love with Peter’s furniture-building, salt-of-the-earth brother Jack (Bill Pullman). Aside from its focus on the El and life as a CTA employee (“I sit in a booth like a veal,” Lucy snaps), the film showcases the frigid-yet-twinkly reality of Chicago at Christmas, from Lucy hauling a tree up to her apartment in Logan Square, to exploring Peter’s swanky pad on Lake Shore Drive, to taking a freezing walk with Jack past the Chicago River, always quick to exploit the slapstick possibilities of Chicago cold.——Maura McAndrew

the baxter movie poster.jpg16. The Baxter
Year: 2005
Director: Michael Showalter

Showalter’s feature debut as a writer-director was poised to announce Showalter as a serious comedic film talent (not to mention re-affirm his penchant for ensembling, bringing on Wet Hot American Summer co-stars Elizabeth Banks, Paul Rudd, Zak Orth and Michael Ian Black). Instead, it’s a strange film, its tone a jumble of romantic comedy tropes, typical Showalter-Wain irony and real sad-sack dejection. That uneasy mixture may be why the film grossed a mere $180,000 and change, or in industry jargon, approximately .0129 the gross of Osmosis Jones. Too bad—The Baxter holds up as a unique, sometimes discomfiting experience about how things rarely work out the way they do in the movies.—Corey Beasley

hulu zombieland.jpg15. Zombieland
Year: 2009
Director: Ruben Fleischer

It seems like there’s a certain amount of blowback against Zombieland these days. Not among the general audience, where the film is still fairly well-liked, but among the horror and zombie geeks and “purists,” who don’t seem to consider it legitimate enough as a zombie film. I’m not sure why that is, in a genre where Shaun of the Dead is rightly hailed as the cream of the zombie comedy crop. Zombieland was certainly inspired on some level by the former, as it moved the action to the USA and brought together survivors who were anonymous to each other rather than a circle of friends, as in the tradition of Night of the Living Dead. Jesse Eisenberg’s Columbus is the type of character we hadn’t seen in a zombie film before, even in the comedies—somewhat neurotic, not particularly well-equipped to fight, but brainy and resourceful enough to get by on his own, he presents an entirely different mold of survivor. Of course it’s Woody Harrelson as Tallahassee who really steals the show, as a short-fused drifter on a seemingly pointless quest to find the world’s last box of Twinkies. Featuring zombies that are legitimately threatening, it tows a near-perfect line between comedic (but gory) violence and character-driven humor. And after an abominably long wait, the sequel is finally percolating as well.—Jim Vorel

in a world movie poster.jpg14. In a World
Year: 2013
Director: Lake Bell

Lake Bell’s directorial debut has heart, soul and a message without getting too preachy. In a World… is an examination of the male-dominated world of the voice-over industry. It opens with a short introduction to the men behind the microphone, including the late Don LaFontaine, who voiced more than 5,000 movie trailers during his career. It’s LaFontaine’s passing that sets the film in motion: Who will become the industry’s next godfather? Veteran voice actor Sam Sotto (Fred Melamed) says he doesn’t want the mantle, so instead grooms golden boy Gustav (Ken Marino) to win the next big gig. When his underachieving daughter Carol (Bell) finds herself also in the running for the quadrilogy, Sotto breaks his promise to groom Gustav and throws his own hat into the ring. It gets ultra-competitive with both hilarious and heart-breaking moments. In a World… provides great insight into the voice-over industry, but Bell does an even better job of bringing fresh characters, interesting relationship dynamics and multiple storylines to the screen through a crisp script that doesn’t pander to the audience.—Christine N. Ziemba

four-weddings.jpg13. Four Weddings and a Funeral
Year: 1994
Director: Mike Newell

The first of several Richard Curtis-penned rom-coms starring Hugh Grant, Four Weddings and a Funeral follows our favorite bumbling Englishman as he repeatedly runs into the love of his life at—you guessed it—four weddings and a funeral. While much of the movie is lighthearted and some of it borders on cheesy (see Andie MacDowell’s infamous “Is it still raining? I hadn’t noticed” line in its finale), its graver moments, like Fiona (Kristen Scott Thomas) dealing with unrequited love or the titular funeral, remind us that love may be goofy and complicated and wonderful, but finding that one true love is serious business. The Academy agreed, nominating the film for Best Picture in a stacked year that included Forrest Gump, Pulp Fiction and The Shawshank Redemption. —Bonnie Stiernberg

hulu the cable.jpg12. Cable Guy
Year: 1996
Director: Ben Stiller

Ben Stiller and Judd Apatow’s black comedy faltered at the box office, but it quickly became a cult classic due to Jim Carrey’s uncharacteristically dark performance and cameos by a who’s who of mid ‘90s alternative comedy greats. It’s a de facto Ben Stiller Show reunion, with Stiller, Bob Odenkirk, Janeane Garofalo and Andy Dick all putting in memorable appearances. Between Odenkirk, David Cross and Jack Black, it also felt like a bit of Mr. Show on the big screen, at a time when that HBO series was still new and unheralded. Cable Guy isn’t worth watching because of the other shows it’ll make you think of, though. It’s a hilarious movie in its own right, almost as cringeworthy and unsettling as Scorsese’s The King of Comedy, but not quite as violent or malevolent.—Garrett Martin

ITonya-poster.jpg11. I, Tonya
Year: 2017
Director: Craig Gillespie

The triple axel was Tonya Harding’s greatest trick—and making an audience think that it’s a comedy of some sort is I, Tonya’s. Craig Gillespie’s infuriating and entrancingly brilliant biopic gives its subject control, and with fury, glibness, regret and a smirk, Tonya (Margot Robbie) and the many others in her life spin her story, detailing the ways that trauma (and class marginality) has affected and shaped her. Scenes of abuse—in which Tonya is often pummeled by both her mom (Allison Janney) and her husband, Jeff (Sebastian Stan)—are bracingly uncomfortable but cut with snark, and the film then has the gall to ask why you could possibly be laughing at such a horrible thing. I, Tonya dares to embody a camp aesthetic and immediately rebuke it, making sure that everything about it, from its skating scenes—dizzingly filmed as if her skill should be admired, but without actually detailing the technical aspects of what she’s doing, as if to mimic white queer men and how they talk about character actresses—to its genre packaging (part wannabe gangster film, part confessional documentary), smears the ironic quotation marks of its framework with blood, sweat and tears: a roar and a snarl and a declaration of defiance. —Kyle Turner

major league hulu.jpg10. Major League
Year: 1989
Director: David S. Ward

Many can laugh at this crazy cast of oddballs, but only a select few can look back and laugh. Because for those in Cleveland and northeastern Ohio, it’s all too real. Not until the second film’s release did the Cleveland Indians finally break out of their 30-year slump. Some will say it was the new stadium. Others, the even more superstitious ones (most baseball fans), may point to the dominance and swagger of Rick “Wild Thing” Vaughn, as portrayed by Charlie Sheen. (Fun fact: Sheen was actually a star pitcher in high school.) Whatever the case, the really bad times are in the past, and let’s hope, for the sake of another one of these movies popping up, they stay there. —Joe Shearer

hulu poster up ins moke.jpg9. Up in Smoke
Year: 1978
Director: Lou Adler

Between Adler’s inexperience, the influence of Robert Altman’s intentionally shambolic aesthetic, and Cheech & Chong’s trademark pot humor, Up in Smoke is a comedy that’s exceptionally loose and shaggy. It’s essentially a series of vignettes based around the duo’s love of drugs and music, largely adapted from their series of hit stand-up albums. Like a lot of first-time movies by popular comedians, it’s less interested in creating a unified film than in capturing the essence of what made Cheech & Chong popular in the first place. That’s made it both an artifact of a very specific time and place, but also a comedy that has transcended its era and remained relevant for decades.—Garrett Martin

colossal-movie-poster.jpg8. Colossal
Year: 2016
Director: Nacho Vigalondo

Colossal is simply a much darker, more serious-minded film than one could possibly go in expecting, judging from the marketing materials and rather misleading trailers. It blooms into a story about sacrifice and martyrdom, while simultaneously featuring an array of largely unlikable characters who are not “good people” in any measurable way. I understand that description sounds at odds with itself—this film is often at odds with itself. But in the cognitive dissonance this creates, it somehow finds a streak of feminist individuality and purpose it couldn’t have even attempted to seek as a straight-up comedy. —Jim Vorel

hulu knocked up.jpg7. Knocked Up
Year: 2007
Director: Judd Apatow

For its many schlubby white-man sins—and its wolf-in-dog’s-clothing conservatism—Judd Apatow’s Knocked Up performs the essential romantic-comedy service of focusing on, in drawn-out detail, the consequences of not taking responsibility for oneself in any relationship. Though Alison (Katherine Heigl), television “journalist” and career-minded modern woman, is mostly just an impetus for a typical 20-something dude (Seth Rogen) to learn that it’s important to read a book sometimes instead of going out and getting drunk—Heigl’s character satisfied, despite all of her ambition, with someone whose only demonstrable sense of action is to read said book instead of going out and getting drunk—the two still have a very surprisingly ample amount of chemistry together. Which may just be that particularly Apatowan aspect of romantic comedies at its epitome—namely, that we’re willing to overlook a lot of bad storytelling if we like the characters despite ourselves. —Dom Sinacola

sorry-to-bother-you-movie-poster.jpg6. Sorry to Bother You
Year: 2018
Director: Boots Riley

Sorry to Bother You has so many ideas busting out of every seam, so much ambition, so much it so urgently wants to say, that it feels almost churlish to point out that the movie ends up careening gloriously out of control. This is rapper and producer Boots Riley’s first movie, and it shows, in every possible way—good, bad, incredible, ridiculous—as if he didn’t know if he’d ever be able to make another one, so he threw every idea he ever had into this. There are moments in Sorry To Bother You that will make you want to jump giddily around the theater. There are also moments that will make you wonder who in the world gave this lunatic a camera. (Some of those moments are pretty giddy too.) The former far outnumbers the latter. Lakeith Stanfield plays Cassius, a good-hearted guy who feels like his life is getting away from him and thus tries his hand at telemarketing, failing at it (in a series of fantastic scenes in which his desk literally drops into the homes of whomever he is dialing) until a colleague (Danny Glover, interesting until the movie drops him entirely) recommends he use his “white voice” on calls. Suddenly, Stanfield sounds exactly like David Cross at his most nasally and has become a superstar at the company, which leads him “upstairs,” where “supercallers” like him go after the Glengarry leads. That is just the launching off point: Throughout, we meet a Tony Robbins-type entrepreneur (Armie Hammer) who might also be a slave trader, Cassius’s radical artist girlfriend (Tessa Thompson), who wears earrings with so many mottos it’s a wonder she can hold up her head, and a revolutionary co-worker (Stephen Yeun) trying to rile the workers into rebelling against their masters. There are lots of other people too, and only some of them are fully human. It’s quite a movie. —Will Leitch

hulu borat.jpg5. Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan
Year: 2006
Director: Larry Charles

It’s easy to overlook or underrate Borat in 2019, or Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan, given the Sacha Baron Cohen movies that followed. The likes of Bruno and The Dictator managed to water down Cohen’s original statement, but his faux-documentary about an awkward Eurasian traveler remains kind of brilliant. It was a wide-release comedy that plainly and critically looked at an average American attitude of dismissiveness and outright xenophobia toward people we don’t understand, as well as a willingness to feign earnestness if they thought taking advantage of Borat might somehow benefit them. Borat might say things that are naive, but at least they’re sincere products of the character’s fictitious upbringing. Borat the character is no charlatan—the “real” people he meets in America, on the other hand, can’t make the same claim. One final aside: This film, along with Anchorman, is the loudest I’ve ever heard an audience laugh in a multiplex theater. —Jim Vorel

royal tenenbaums poster.jpg4. The Royal Tenenbaums
Year: 2001
Director: Wes Anderson

Wes Anderson’s first two films took place in the Texas of his youth. The Royal Tenenbaums moves his storytelling to his adopted city of New York. And the story is one that bridges childhood and adulthood and the tremendous effects one has upon the other. The “Royal” in the title refers to Gene Hackman’s character. Royal Tenenbaum is the patriarch of a family of childhood prodigies: Chas (Ben Stiller), a math genius with a head for business; Richie (Luke Wilson), a tennis star; and adoptive daughter Margot (Gwyneth Paltrow), a playwright. The movie begins with Royal announcing his separation from his wife, Etheline (Anjelica Huston) before picking up years later with the children having gone on to great success and failure. As Etheline prepares to re-marry to her longtime accountant (Danny Glover), Royal announces that he has stomach cancer and attempts to reconcile with the family he abandoned. The family disfunction and struggle for redemption would become hallmarks of Anderson’s oeuvre, but here, with a talented cast that also included frequent collaborators Bill Murray, Owen Wilson and Kumar Pallana, the auteur’s gift for wringing humor out of hopelessness is unmatched. As every piece of set dressing, every item of clothing seems and every symmetrical camera frame seems painstakingly managed, the characters are spiraling out of control; their despair is deeply felt, and their redemption serves as a euphoric release. It’s a beautiful movie both visually and emotionally and remains Anderson’s crowning achievement after all these years. —Josh Jackson

heathers_poster.jpg3. 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

office space poster.jpg2. Office Space
Year: 1999
Director: Mike Judge

Great comedy almost always has a dark heart. (The flipside is also true of great horror: It almost always teeters on the edge of farce). But this makes sense: Laughter is our response to absurd and unexpected contradictions; comedy needs its darkness to fully flourish. Mike Judge, the writer/director of Office Space, knows this well. His humor concerns the lowest, saddest schmucks on the corporate ladder (thus 99% of us can relate) who mostly feel dead inside, turning to Kung Fu films and cheap beer to escape. It’s a subject as old as capitalism itself: Most of us are unhappy, not doing what we want, feeling our dreams escaping us more and more with each passing day. For protagonist Peter Gibbons (Ron Livingston), his goal is a subversive joy: Independently, from no wellspring of societal angst (unlike, say, The Graduate’s Benjamin Braddock), he wants to do nothing. And besides being a hilarious antidote to scores of predictable, cookie-cutter hyperactive hero-protagonists, his needs feel absolutely real, and is what the corporate rat race deserves in an anti-hero. The do-gooder replaced by the do-nothing. It also helps that Judge has a cast perfectly on board with his tone. Together, they turn caricature into depth, a cartoon into vivid life. —Harold Brodie

hulu dazed.jpg1. Dazed and Confused
Year: 1993
Director: Richard Linklater

Set in 1976 Texas, Dazed and Confused flows from one group of high-school and middle-school students over the course of one night—the traditional cinematic one-night-that-changes-everything.— Richard Linklater’s follow-up to Slacker shows a variety of vantage points on a number of issues, philosophical, political and otherwise. The camera lingers, offering multiple perspectives, and allowing you to take your time and consider all sides of these various excursions. Ultimately, these digressions circle back on one another, and Linklater forms them into a coherent narrative that resembles an updated American Graffiti for a new generation. As the day begins, there is a very rose-tinted-glasses style outlook on the whole scene, one that is, layer by layer, peeled away over the course of the ensuing evening. For all the seeming importance placed on things like playing football, chasing romantic partners and finding some good old-fashioned visceral experiences, there isn’t much in the way of consequences. You may get your ass kicked a little bit, but there isn’t a lot at stake. Whatever happens, you’ll be fine. This is never more apparent than as Dazed and Confused draws to a close and the film takes a dark turn towards what can only be described as adulthood. —Brent McKnight