The Best Comedies on HBO Max Right Now (May 2022)

Comedy Lists HBO Max
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The Best Comedies on HBO Max Right Now (May 2022)

Can a streaming service have too much content?

Probably not, but HBO Max is determined to find out. Warner’s streamer has an overwhelming variety of movies, cartoons and TV shows from the last century of entertainment, and although I love that as a customer, it’s beyond daunting as a guy whose job involves making lists of the stuff you can stream on services like this. But after poring over the hundreds of movies currently available through HBO Max, I was able to strip them down to the absolutely funniest, and have been regularly updating it every month since the service first launched. You can find those results below.

As far as comedy movies goes, HBO Max has the best, deepest, and most varied selection of any streamer at the moment. Good luck finding this many classics or pre-’90s comedies on the other services. HBO Max today feels like Netflix did a decade ago, before the streaming world splintered into a dozen different walled off rivals. That’s a good thing.

Also, my standard disclaimer for these comedy lists: I’m not judging these exclusively on their cinematic qualities. Acting, storytelling, and technique are all apart of the equation, but the most important single facet is how much it makes me laugh.

With that out of the way, let’s get to it. Here are the funniest movies on HBO Max today.

1. Best in Show

best_in_show_poster.jpg Year: 2019
Director: Christopher Guest
Stars: Eugene Levy, Catherine O’Hara, Christopher Guest, Parker Posey, Jennifer Coolidge, Jane Lynch, Michael Hitchcock, John Michael Higgins, Michael McKean, Bob Balaban, Ed Begley Jr., Fred Willard
Rotten Tomatoes Score: 94%
Rating: PG-13
Runtime: 91 minutes

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The genius of Christopher Guest’s particular style of mockumentary is in his cast’s complete commitment to character, and none of his films are inhabited by a more hilarious ensemble than Best in Show. Parker Posey and Michael Hitchcock as Meg and Hamilton Swan project their own neuroses on their poor Weimaraner. Eugene Levy’s Gerry Fleck is outrageously outmatched by his wife Cookie, played by Catherine O’Hara—the secret weapon of most Guest films. The director himself plays Harlan Pepper, a Southern gentleman with no self-awareness and an ability to name all kinds of nuts. The more inane his rambling gets, the harder it is to keep from laughing. Finding the ridiculousness in something like the world of dog shows might not be difficult, but there’s no mocking tone to the subject, just to the quirks of human nature. The improvisation and dead-pan delivery from Jane Lynch, Bob Balaban, Jennifer Coolidge, Michael McKean and especially Fred Willard as the sports announcer who knows nothing about the subject he’s paid to talk about, elevate the medium by giving surprising dimension to their characters. It’s a symphony of creation from a troupe of performers at their peak. —Josh Jackson


2. The Great Dictator

chaplin_Great_dictator.jpg
Year: 1940
Director: Charles Chaplin
Stars: Charles Chaplin, Paulette Goddard, Jack Oakie, Reginald Gardiner
Rotten Tomatoes Score: 93%
Rating: G
Runtime: 126 minutes

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Charlie Chaplin’s first “talkie” was a biting satire that he wrote, directed, produced, scored, and starred in-as both of the lead roles, a fascist despot who bears a rather marked resemblance to Adolf Hitler and a persecuted Jewish barber. Good satire can be powerful, and this film was: Released while the United States was still formally at peace with Germany, it stirred greater public attention and condemnation of the Nazis and Mussolini, anti-Semitism and fascism. (That said, Chaplin later recounted that he could never have made the satirical film even a year or two later, as the extent of the horrors in German concentration camps became clearer.) The choice to play both the tyrant and the oppressed man was an inspired one, underscoring the frightening but inescapable truth that we all contain a little bit of both characters. This is a strikingly pertinent film for our particular moment in history, and well worth dusting off and queueing up not only for its incredible craft but for its resonance as a study in projection. —Amy Glynn


3. Coming To America

coming-to-america.jpg
Year: 1988
Director: John Landis
Stars: Eddie Murphy, Arsenio Hall, John Amos, James Earl Jones, Shari Headley, Madge Sinclair, Eriq La Salle, Allison Dean, Louie Anderson
Rotten Tomatoes Score: 72%
Rating: R
Runtime: 116 minutes

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If this movie consisted of the barbershop scenes inside of My-T-Sharp and nothing else, it would still be one of the greatest comedies of all time. Eddie Murphy and Arsenio Hall teamed up with director John Landis (Blues Brothers) and created a classic. As Prince Akeem from the fictional African country of Zamunda, Murphy travels to the great United States of America to evade his arranged marriage and find true love (in Queens, obviously). Akeem encounters all of the wonders of black America, but the satirical twist is genius—the black preacher (via Hall as the incomparable Reverend Brown), the club scene, the barbershop, hip-hop culture, and Soul Glo—it’s all here. Cameos from actors like Cuba Gooding Jr., Samuel L. Jackson, Louie Anderson, and Murphy’s Trading Places co-stars Don Ameche and Ralph Bellamy take the Coming to America experience to a whole new level. An excellent comedy and a great tribute to New York City, this story of a prince just looking to be loved is a must-see for everyone—including those of us who’ve already seen it.—Shannon Houston


4. The Philadelphia Story

philadelphia_story_poster.jpg
Year: 1940
Director: George Cukor
Stars: Katharine Hepburn, Cary Grant, James Stewart, Ruth Hussey, John Howard
Rotten Tomatoes Score: 100%
Rating: NR
Runtime: 112 minutes

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Can you believe there was a time when Katharine Hepburn was known in Hollywood as “box office poison”? This adaptation of a Broadway hit was a vehicle to get her career back on track after a series of flops. Her performance as icy heiress Tracy Lord in this “remarriage” comedy is a force of nature. Happily, her no-longer-drunken ex is played by Cary Grant, who is a fabulous foil. Jimmy Stewart and Ruth Hussey round out the cast as reporters in not-so-clever disguise. Pretty much everything about this movie is a pure delight, and the script is a masterpiece. —Amy Glynn


5. Caddyshack

caddyshack poster.jpg
Year: 1980
Director: Harold Ramis
Stars: Chevy Chase, Rodney Dangerfield, Ted Knight, Bill Murray, Michael O’Keefe
Rotten Tomatoes Score: 73%
Rating: R
Runtime: 98 minutes

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There are four faces on that poster to the left, and all of them are equally crucial to Caddyshack’s enduring popularity. From Ted Knight’s aristocratic bluster, to Rodney Dangerfield’s irreverent populism, to the glib playboy Chevy Chase, to Bill Murray’s iconic idiot, Caddyshack has one of the greatest casts of any comedy in memory. Add in a sharp script from National Lampoon co-founder Doug Kenney and amiably shaggy direction from Harold Ramis, and you have an all-time classic.—Garrett Martin


6. The 40-Year-Old Virgin

netflix 40 year old virgin.jpg
Year: 2005
Director: Judd Apatow
Stars: Steve Carell, Catherine Keener, Paul Rudd, Seth Rogen, Romany Malco, Kat Dennings, Elizabeth Banks, Leslie Mann
Rotten Tomatoes Score: 85%
Rating: R
Runtime: 112 minutes

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Judd Apatow emerged as a major new voice in the world of romantic comedy with his first directorial effort, The 40-Year-Old Virgin—a big, goofy, hilarious mess of a movie that is anchored by the easy charm of its two principal leads, Steve Carell and Catherine Keener. Their no-nonsense romance is surprisingly understated and adult in a movie with an outrageous premise and lewd jokes. Leslie Mann also deserves credit for that hilarious French toast scene.—Jeremy Medina


7. Clueless

clueless_netflix_poster.jpg
Year: 1995
Director: Amy Heckerling
Stars: Alicia Silverstone, Stacey Dash, Brittany Murphy, Paul Rudd, Dan Hedaya, Donald Faison, Breckin Meyer, Jeremy Sisto
Rotten Tomatoes Score: 81%
Rating: PG-13
Runtime: 97 minutes

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The Beverly Hills reboot of Jane Austen’s classic Emma was a sleeper-smash in 1995—and much more importantly, gave the phrase “As if!” to pop culture. Alicia Silverstone is Cher, a pretty, vain, superficial LA teen who goes on a mission to turn ugly-ducking classmate Tai (Brittany Murphy) into a Superswan, only to find herself eclipsed and adrift. A soft-edged satire of nouveau-riche Angeleno culture and simultaneously of the teen rom-com genre, Clueless is neither the most subtle nor the most hard-hitting film of its era, but it’s surprisingly seductive, in large part thanks to Amy Heckerling’s scrupulously researched script, which captured a dialogue style that both represented and influenced teen-speak of the time. —Amy Glynn


8. Friday

friday netflix poster.jpg
Year: 1995
Director: F. Gary Gary
Stars: Ice Cube, Chris Tucker, Nia Long, Tommy “Tiny” Lister, John Witherspoon, Anna Maria Horsford
Rotten Tomatoes Score: 78%
Rating: R
Runtime: 91 minutes

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In Straight Outta Compton we witness Ice Cube finish writing Friday with finality, as if he’d begun a week prior by declaring, “I will now write a screenplay,” and then a week later at his kitchen table putting down a pen and saying, “There. I’m finished.” We’re willing to accept that Ice Cube once did little more than decide to write a screenplay, and then did, and then made the movie, and then people loved it, because in that movie Ice Cube is our hero, a person who found no real difference, no barrier of entry, between wanting to do and then doing, despite much of his world forcefully telling him otherwise. In Friday, Ice Cube plays Craig, a young guy from south central L.A. whose best friend Smokey (Chris Tucker) implicates him in a $200 debt to Big Worm (Faizon Love), among the many problems Craig encounters throughout the course of the day. Chief among them: Deebo (Tony Lister Jr.), the neighborhood bully so without human empathy he’ll steal a man’s bike and then wait for the man to return just to uppercut him so hard the man’s lifted a few feet in the air. At least that’s how Smokey tells it. Craig even responds, laughing, “You’re lying,” but later Smokey’s story is proven true, at least in spirit, when Craig brains Deebo with a brick instead of shooting Deebo with a gun, which up until that point seemed to be the only viable option. The gun never fires, though it was introduced in the first act. Even if something like that matters to you, chances are that in Friday you never noticed. —Dom Sinacola


8. Bottle Rocket

bottle_Rocket_210.jpg Year: 1996
Director: Wes Anderson
Stars: Luke Wilson, Owen Wilson, James Caan, Lumi Cavazos, Robert Musgrave, Andrew Wilson
Rotten Tomatoes Score: 85%
Rating: R
Runtime: 91 minutes

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Bottle Rocket introduced us both to the singular world of Wes Anderson and the unique charm of the Wilson brothers. The film about a pair of friends planning a series of ambitious heists in Texas expands on Anderson’s first short of the same name, shot four years earlier. Co-writer Owen Wilson’s Dignan was the prototype Anderson protagonist with visions of grandeur and not enough common sense or self-awareness to back it up. Most adults who’ve forgotten to grow up are either repulsive in their adolescent behavior or the butt of the joke, but Dignan retains a certain boyish likability for all his crazy scheming. The original humor and stylistic quirks that feel so familiar now felt refreshing in 1996. And the music—a mixture of Mark Mothersbaugh score and classic rock (this time Rolling Stones and Love)—set the template for most Wes Anderson films.—Josh Jackson


9. Top Secret!


top_Secret_210.jpg Year: 1984
Director: Jim Abrahams, Dvaid Zucker
Stars: Val Kilmer, Lucy Gutteridge, Christopher Villiers, Omar Sharif, Peter Cushing, Jeremy Kemp
Rotten Tomatoes Score: 75%
Rating: PG
Runtime: 90 minutes

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This goofy, Monty Python-level silly, yet surprisingly narratively engaging parody of WWII-era propagandistic American spy thrillers is, for some maddening reason, not as popular or as well-known as Airplane and Naked Gun, two other groundbreaking comedy classics from the Zucker, Abrams, Zucker team. The fish-out-of-water plot features Elvis Presley-meets-The Beach Boys rock star Nick Rivers (Val Kilmer) finding himself as the savior of a group of anti-East German revolutionaries, and is of course used as a shoestring to hang as many cliché-skewering gags per minute as possible. As opposed to Airplane, where the parody was focused on story-based tropes, Top Secret’s gags mostly lean on bits that expose the various visual trickery that Hollywood uses to sell its fantasies. Looking from the inside of a train, you think the train is moving away from the station, when actually it’s the station that’s moving. A phone in the foreground of a shot turns out to actually be as massive as it looks. Cows seen through binoculars casually cross the masking of the POV effect. An Indiana Jones type map turns into a game of Pac-Man. The list goes on. Kilmer’s blistering charisma makes us fall in love with Nick Rivers the way the supporting characters are supposed to, providing the narrative glue that keeps it from feeling like a bunch of episodic sketches. Top Secret is the prototypical underrated comedy masterpiece.—Oktay Ege Kozak


9. Beetlejuice

beetlejuice_poster.jpg Year: 1988
Director: Tim Burton
Stars: Michael Keaton, Winona Ryder, Geena Davis, Alec Baldwin, Catherine O’Hara, Jeffrey Jones
Rotten Tomatoes Score: 85%
Rating: PG
Runtime: 92 minutes

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After a little vacation, Barbara and Adam Maitland find some uninvited guests in their homes. Okay, so maybe they died, and maybe their house was sold to some poor, unsuspecting (but equally annoying) couple—that doesn’t mean Geena Davis and Alec Baldwin have to like it. After some failed haunting attempts, the Maitlands make the mistake of hiring a “bio-exorcist” Betelgeuse (played perfectly by a never-more-revolting Michael Keaton) to fumigate the place of the living. As this situation tends to go, the hired gun gets out of control, and we’re left with Tim Burton’s wacky vision of a ghoul gone really bad. Its good humor and (sort of) likable antagonist make this one the rare cinematic ghost story that most of the family can enjoy, although Keaton certainly tosses out a few veiled adult jokes for the ages. —Tyler Kane


10. The Wedding Singer

wedding_singeR_poster.jpg
Year: 1998
Director: Frank Coraci
Stars: Adam Sandler, Drew Barrymore, Christine Taylor, Allen Covert, Matthew Glave
Rotten Tomatoes Score: 69%
Rating: PG-13
Runtime: 96 minutes

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Over 20 years removed, Frank Coraci’s vision of the mid-’80s by way of the late-’90s bears the pastel aesthetic and pop culture refuse of a parody of that decade more than a clear memory of what was actually going on, but all the better to ground the then-popular caricature of Adam Sandler in a tender role best suited to his natural baby-man weirdness. What Happy Gilmore and Billy Madison did for Sandler’s “stop looking at me swan” voice, The Wedding Singer did for every other aspect of the comic actor, not only mitigating all that past frat boy dipshittery, but demonstrating that he could be a quiet, lovable leading man—a persona he’d go on to hone with his best films (notably, Punch-Drunk Love and The Meyerowitz Stories). The story of a banquet hall’s in-house crooner, Robbie Hart (Sandler), suffering a broken heart (like his name!) to find his way to the true girl of his dreams (Drew Barrymore, simultaneously endearing and cloying) hits each rom-com beat so squarely it’s nearly impossible to not see where this thing is going, but its heady brew of ultra-nostalgia and surreal poptimism, as well as Sandler’s unforced hilarity, serves the genre beautifully. The movie’s only glaring miscue is the repeated lambasting of Robbie’s bandmate George (Alexis Arquette), who navigates an onslaught of audience booing every time he sings Culture Club’s “Do You really Want to Hurt Me?” Since the movie takes place in 1985, the song’s been a certifiable hit for more than two years. The audience’s revulsion is more of a cheap gag than a cultural reality, a mis-remembered joke from a manufactured history—like much of the ’80s of The Wedding Singer, as dated today as it was in 1998. —Dom Sinacola


11. Modern Times

modern-times.jpg Year: 1936
Director: Charles Chaplin
Stars: Charles Chaplin, Paulette Goddard, Henry Bergman
Rotten Tomatoes Score: 100%
Rating: G
Runtime: 88 minutes

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If time is a flat circle, then Modern Times is like a flat sprocket—the travails of the Little Tramp navigating a mechanical world being so incessant and repetitive that elements like luck and hope only serve to spur along Chaplin’s farce even though they hold little grip on his characters’ futures. Not much changes for the Little Tramp throughout: He tries to survive, and yet the institutional system craps him back out to where he started, desperately hungry and penniless, left with nothing to do but try again. This was also Chaplin’s last go as the Tramp, and it’s easy to imagine that, throughout the film’s many misadventures—joined by equally good-natured partner in crime, the gamin (Paulette Goddard)—as he gets sucked up and sublimated into the modern industrial machine, this “disappearance” was kind of by design. It’s a weird way for Chaplin’s beloved character to go out, but so are the many ways in which Chaplin shows how the modern industrial machine becomes part of the Tramp, too. He may get squeezed through a giant, sprocket-speckled apparatus, becoming one with its schematics, but so too does the assembly line—with all that twisting, wrenching, and spinning—impress itself onto the Tramp, leaving him unable after a long shift to do anything but waggle his arms about as if he’s still on the assembly line. It’s no wonder, then, that the President of Modern Times’ factory setting bears a striking resemblance to Henry Ford: Chaplin, who toured the world following the success of City Lights, witnessed the conditions of automobile lines in Detroit, how the drudgery of our modern times weighed on young workers. The Great Depression, Chaplin seems to be saying, was the first sign of just how thoroughly technology can kill our spirits, not so much discarding us as absorbing our individuality. Modern Times, then, is a film with a conscious far beyond its time, a kind of seamless blending of special effects, sanguine silent film methods and radical fury.—Dom Sinacola


12. The Birdcage

the_birdcage_poster.jpg Year: 1996
Director: Mike Nichols
Stars: Robin Williams, Gene Hackman, Nathan Lane
Rating: R
Runtime: 119 minutes

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You know what’s awkward? When you’re a middle-aged gay Jewish South Beach drag club owner (Armand, played by Robin Williams) and your straight son shows up and asks for your blessing to marry his girlfriend who is the daughter of a Neocon senator (Gene Hackman) who heads something called “The Coalition for Moral Order.” You want to support your kid, but you don’t love being closeted by him, and the dinner meet-up ends up meaning you and your partner, Albert (Nathan Lane), are forced into a whole new level of drag in which you are straight, a cultural attaché to Greece, and married to the one-night stand straight-sexperiment (Katherine, played by Christine Baranski) that led to the conception of your son. Your partner’s offended, the Senator’s being investigated by the tabloids, tensions are running high and your houseboy Agador (Hank Azaria) has agreed to transform into a Greek butler named “Spartacus,” but let’s face it, tensions are running high on all sides-and that’s before your baby-mama gets caught in traffic and Albert sees the opportunity for the drag role of a lifetime. Fully Shakespearean hijinks ensue. The 1996 Mike Nichols remake of Edouard Molinaro’s La Cage Aux Folles was not really blistering social commentary, but beneath its glib feel-good star-vehicle exterior there are some depths you could easily miss while you’re distracted by the batshit-crazy and heavily sequined antics of Williams and Lane. It’s actually not only rambunctious and witty but, as with many of Robin Williams’ film roles, The Birdcage has a serious streak where a genuine investigation of personal identity is underway, and hypocrisy, acceptance, snobbery, and most of all, everyone’s individual style of “drag” (and hey, we all have one, even if we don’t always express it by putting on fake lashes and singing Sondheim) gets taken out for a much-needed exam. —Amy Glynn


13. Broadcast News


broadcast-news.jpg
Year: 1987
Director: James Brooks
Stars: William Hurt, Albert Brooks, Holly Hunter, Robert Prosky, Joan Cusack
Rotten Tomatoes Score: 98%
Rating: R
Runtime: 132 minutes

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Broadcast News, against the backdrop of television news, lets play out that age-old cinematic gold mine: the love triangle. But rather than remain just a backdrop, the profession of journalism is the key to our three main characters’ identities: Jane (Holly Hunter) is an extremely driven producer, known for being cool under pressure and unwaveringly excellent at her job; Aaron (Albert Brooks as uber-mensch) is her steadfast partner at work, an intrepid reporter whose dynamism in the field remains overlooked; and then there’s Tom (William Hurt), the new pretty boy anchor way more clever than he seems. Aaron and Tom’s battle for career recognition, as well as Jane’s affection, mirrors the constant balance television journalists must strike between entertainment and hard news. And in typical Brooks fashion, there is no easy resolution to that balance. —Maura McAndrew


14. Safety Last!

safety-last-poster.jpg Year: 1923
Directors: Fred C. Newmeyer, Sam Taylor
Stars: Harold Lloyd, Mildred Davis, Bill Strother
Rotten Tomatoes Score: 97%
Rating: NR
Runtime: 80 minutes

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“I shouldn’t have bothered scoring the last 15 minutes,” Rodney Sauer of the Mont Alto Motion Picture Orchestra told me after accompanying Safety Last! at the San Francisco Silent Film Festival. He said he and his ensemble couldn’t even hear themselves over the uproarious laughter in the Castro Theatre during Harold Lloyd’s famous building-scaling sequence. The scene, with its iconic clock-hanging finale—is such a perfect mix of suspense and comedy that it doesn’t much matter that the rest of the film seems to exist merely as a lead-up. —Jeremy Mathews


15. Gremlins 2: The New Batch

gremlins-2-movie-poster.jpg Year: 1990
Director: Joe Dante
Stars: Zack Galligan, Phoebe Cates, John Glover, Robert Prosky
Rating: PG-13
Runtime: 107 minutes

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Joe Dante didn’t want to make a sequel to Gremlins. The first film exhausted him and was wrapped up so nicely, he didn’t see a need to carry the story forward. The studio, however, refused to give up and, out of desperation, gave him complete creative control. They sure got what they paid for, as the cult classic sequel throws absolutely everything at the viewer with zero interest in whether it will stick or not. It’s a slapstick comedy wrapped up in cartoonish violence and some sharp-edged satire about corporations and capitalism. Oh, and there’s a cameo by Hulk Hogan to boot. —Robert Ham


16. House

house.jpg Year: 1977
Director: Nobuhiko Obayashi
Stars: Kimiko Ikegami, Miki Jinbo, Kumiko Ohba
Genre: Comedy, Horror
Rotten Tomatoes Score: 90%
Rating: NR
Runtime: 88 minutes

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Movies are rarely, if ever, as whirringly rich and strange as House. The 1977 fairy-tale-as-fever-dream from Japanese director Nobuhiko Obayashi was the debut of a guy who was known mostly for his TV commercials. Given a shot at making his first feature by a struggling studio that had nothing to lose, Obayashi did what any aspiring auteur would do: He went to his 11-year-old daughter Chigumi for ideas. What they came up with is a tragi-comic festival of the uncanny about a posse of seven Japanese schoolgirls, a maiden aunt with heartbreaking secret, her freaky-ass white cat named Snowflake and the house of the title, an ooky-spooky hallucination out of gothic myth and Japanese folklore, jazzed by an animated, ADD-afflicted spirit like something from the minds of Tex Avery and Busby Berkeley on crack. Though: No summary really does House justice, and every little thing about it demands attention, from the schoolgirls themselves—precocious archetypes who go by the nicknames Gorgeous, Melody, Fantasy, Prof, Sweet, Mac and Kung Fu—to the anything-goes flourishes of gimmick and technique, which evoke everything from silent film to children’s shows, classic surrealist cinema to Italian giallo. Obayashi crams every frame with a surplus of mad ideas, as if his background in 30-second spots demanded he never let the screen remain calm for an instant. House suggests that the nitrous-oxide hyperdrive of Japanese pop culture—as vivid now as ever—is a brilliantly imagined, if not in fact transcendental brand of therapy. —Steve Dollar


17. House Party

house_party_poster2.jpg Year: 1990
Director: Reginald Hudlin
Stars: Kid ‘n Play, Full Force, Robin Harris, Martin Lawrence, Tisha Campbell, A.J. Johnson
Rotten Tomatoes Score: 93%
Rating: R
Runtime: 100 minutes

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Originally meant as a vehicle for DJ Jazzy Jeff and the Fresh Prince, this high school romp follows two best friends (hip-hop duo Kid ’n Play) as they get ready to throw an epic house party. Featuring a cast filled with up-and-coming actors and hip-hop stars, the audience gets to see if, between his no-nonsense father (the late Robin Harris) and his dimwitted bullies (Full Force), Kid can survive the night. Between Hudlin’s keen direction and a hip-hop drenched soundtrack, the film is filled with infectious energy and originality that captures the life of Black American teens in the late 1980s and early 1990s. —Adreon Patterson


18. A Mighty Wind


a_mighty_wind_poster.jpg Year: 2003
Director: Christopher Guest
Stars: Christopher Guest, Eugene Levy, Michael McKean, Catherine O’Hara
Genre: Comedy
Rotten Tomatoes Score: 92%
Rating: PG-13
Runtime: 91 minutes

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There’s a reason mockumentaries and musical subjects work so well together, evidenced by A Mighty Wind. Detailing the folk and bluegrass artists who worked with music producer Irving Steinbloom, the film follows Mitch & Mickey, The Folksmen and The New Main Street Singers as they reunite to put on a tribute concert following Steinbloom’s passing. Not only are the songs created for the film toe-tapping good fun, but seeing Guest, McKean and Shearer reunite as band mates after working together on This is Spinal Tap and watching Levy and O’Hara work their magic together once again made the film a classic as soon as it hit theaters. —Amanda Wicks


19. Metropolitan


Metropolitan_movie_poster.jpg
Year: 1990
Director: Whit Stillman
Stars: Carolyn Farina, Edward Clements, Chris Eigeman, Taylor Nichols, Allison Parisi, Dylan Hundley
Rotten Tomatoes Score: 93%
Rating: PG-13
Runtime: 98 minutes

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There have been nearly as many “next Woody Allens” in film as there have been “next Michael Jordans” in basketball or “next Bob Dylans” in music, but sometimes the moniker fits. In Whit Stillman’s debut, he staked his claim as the Woody of the upper-class WASPy NYC set and won a whole army of loyal followers. For good reason, too—seldom has any director, regardless of experience, so deftly juggled dialogue that could so easily have delved into too-clever-by-half-isms, or trained such a sympathetic eye on a sometimes questionable nostalgia for the end of an age. Most of all, though, seeing Metropolitan just makes you feel smart and witty and somehow elevated. Not bad for the price of a movie ticket.—Michael Dunaway


20. Back to School

movie poster back to school.jpg
Year: 1986
Director: Alan Metter
Stars: Rodney Dangerfield, Sally Kellerman, Keith Gordon, Burt Young, Robert Downey Jr., Paxton Whitehead
Rotten Tomatoes Score: 86%
Rating: PG-13
Runtime: 96 minutes

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Rodney Dangerfield, an ideal populist buffoon, graduates from one of four leads in Caddyshack to the star of the show in Back to School. It’s an almost perfect vehicle for Dangerfield’s bluster, which worked so well not just because of his thorough disregard for society’s arbitrary rules but also because of the core of sadness that clearly lurked within. That hint of pathos, along with Dangerfield’s decades-honed schtick, elevates Back to School above most ‘80s college comedies.—Garrett Martin


21. Down By Law

down_by_law_poster.jpg
Year: 1986
Director: Jim Jarmusch
Stars: Tom Waits, John Lurie, Roberto Benigni, Ellen Barkin
Rotten Tomatoes Score: 87%
Rating: R
Runtime: 107 minutes

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What makes Down By Law the quintessential Jarmusch film is in the deliberate exclusion of a sequence most other directors would have turned into their calling card. Two innocent inmates (John Lurie and Tom Waits) are joined by a third prisoner (Roberto Benigni), who is guilty but has a pretty airtight argument for self-defense. While playing cards, they discuss various exciting prison break scenes in film history, which motivates Benigni’s character to mention that he has a foolproof plan of escape. After a scene that references such cinematic moments, Jarmusch directly cuts to the prisoners already running away from prison, having cut the escape sequence all together. Jarmusch succinctly demonstrates that he isn’t interested in action but is far more fascinated by the individual quirks and mannerisms of his characters, while the dialogue that references such other prison break films expresses how deeply American mainstream pop culture has defined a big part of his personality.—Oktay Ege Kozak


22. American Splendor

american-splendor.jpg Year: 2003
Directors: Robert Pulcini, Shari Springer Berman
Stars: Paul Giamatti, Hope Davis, Judah Friedlander, James Urbaniak
Rotten Tomatoes Score: 94%
Rating: R
Runtime: 100 minutes

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Harvey Pekar’s “American Splendor” books are fascinating: Pekar believed that even the most mundane and seemingly uncomplicated lives were worth documenting. American Splendor showcases this theory by combining real footage of Pekar, fictionalized versions of characters from his life—maintaining both stylized caricatures and naturalistic drama—and even animated segments pulled from the comics to create a cohesive whole that presents an ordinary life as a fascinating experience. —Ross Bonaime


23. Stranger Than Paradise

stranger_than_paradise_poster.jpg Year: 1984
Director: Jim Jarmusch
Stars: John Lurie, Eszter Balint, Richard Edson
Rotten Tomatoes Score: 96%
Rating: R
Runtime: 90 minutes

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Jarmusch has fashioned a wildly idiosyncratic, stylish and coherent body of work. In the early ’80s, right out of film school, Jarmusch inadvertently helped define the American independent movement when his second feature, Stranger Than Paradise, found an audience of people who enjoyed its hip-but-relaxed pace, deadpan humor and apparent awareness of world cinema. The film is stylistically simple, with even fewer shots than the film he made during school, Permanent Vacation, and it seemed to satisfy a hunger for movies that eschew Hollywood formula. That hunger didn’t go unnoticed by the industry, which has since created specialized subsidiaries of major studios, festivals like Sundance and cable channels that champion “independent” filmmakers.—Robert Davis


24. A Hard Day’s Night

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Year: 1964
Director: Richard Lester
Stars: John Lennon, Paul McCartney, George Harrison, Ringo Starr, Wilfrid Brambell
Rotten Tomatoes Score: 98%
Rating: G
Runtime: 87 minutes

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That opening chord of “A Hard Day’s Night” is iconic on its own, but when it’s paired with scenes of the Fab Four gleefully outrunning a crowd of screaming fans? Forget about it. The first Beatles movie—a mockumentary filmed at the height of Beatlemania—also happens to be their best; it’s funny, silly, weirdly melancholy at times (it’s hard not to see the foreshadowing when Ringo temporarily quits the band after feeling unappreciated) and full of some fantastic early performances. It manages to poke fun at the fame machine from the inside, and we always get the sense that no one found it funnier than John, Paul, George and Ringo.—Bonnie Stiernberg


25. City Lights

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Year: 1931
Director: Charles Chaplin
Stars: Charles Chaplin, Virginia Cherrill, Harry Myers, Florence Lee
Rotten Tomatoes Score: 98%
Rating: G
Runtime: 90 minutes

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In his later years, Charlie Chaplin was known for bringing pathos into his comedy whenever he had the opportunity. City Lights is the movie where he earns every bit of it. While its structure resembles Chaplin’s usual picaresque format, there’s more of a deliberate purpose as the tramp tries to help a poor, blind flower girl, played adorably by Virginia Cherrill. Harry Myers also deserves a mention for his performance as the millionaire who’s generous when he’s drunk and can’t remember his good deeds when he’s sober. —Jeremy Mathews


26. Time Bandits

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Year: 1981
Director: Terry Gilliam
Stars: John Cleese, Sean Connery, Shelley Duvall, Michael Palin, Katherine Helmond, Ian Holm
Rotten Tomatoes Score: 89%
Rating: PG
Runtime: 110 minutes

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The first in Terry Gilliam’s “Trilogy of Imagination,” Time Bandits breathes with the unfettered glee of cinematic magic. Told through the eyes of Kevin, a neglected 11 year-old (Craig Warnock), the film details a literal battle between Good and Evil, between God (Ralph Richardson) and the Devil (David Warner)—though they’re never explicitly referred to as such. What Gilliam accomplishes, as Kevin meets such luminaries as Robin Hood (John Cleese), Napoleon (Ian Holm) and an irrepressibly charming King Agamemnon (Sean Connery, of course), is the perfect ode to imagination, wherein a kid’s bedroom musings gain the seriousness and weight of world-shaking war. Like a much weirder step-cousin to Bill & Ted, Time Bandits employs nostalgia and pseudo-history in equal measure to capture, with boundless invention, what it feels like be 11 again.


27. The Gold Rush

chaplin_gold_rush_poster.jpg Year: 1925
Director: Charlie Chaplin
Stars: Charlie Chaplin, Mack Swain, Tom Murray, Georgia Hale
Rotten Tomatoes Score: 100%
Rating: NR
Runtime: 82 minutes

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The Klondike gold rush made the perfect setting for Charles Chaplin’s tramp to run wild. Chaplin took all the motifs he could find from adventure novels, melodramas and other stories of the northern frontier, tossed them in a blender and served up a collection of what would become his most famous scenes. He finds humor in peril—with a suspenseful teetering cabin scene, as well as starvation (when he famously makes a meal of his boot) and of course finds time to show off with his dancing roll scene. However, no one has succeeded in finding any humor in the atrocious voiceover Chaplin added to the 1942 rerelease. Be sure to watch the original version. For a more serious take on the Klondike hardships, see Clarence Brown’s The Trail of ’98 (1928).


28. The Player

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Year: 1992
Director: Robert Altman
Stars: Tim Robbins, Greta Scaachi, Fred Ward, Whoopi Goldberg
Rotten Tomatoes Score: 98%
Rating: R
Runtime: 124 minutes

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Robert Altman’s cameo-heavy Hollywood satire was rapturously received in 1992, and along with the next year’s Short Cuts it represents his late-career peak. Structured a bit like a film noir, albeit in the shallow, pampered world of movie executives, The Player’s mockery of the business gradually grows warmer until it seems to embrace the schmaltz and insincerity of Hollywood. It’s smart satire with a wicked bite and a couple of great performances from Robbins and Goldberg, and a bonus Burt Reynolds cameo for all you Gator fans.—Garrett Martin


29. A Christmas Story

A_Christmas_Story_film_poster.jpg Year: 1983
Directors: Bob Clark
Stars: Peter Billingsley, Darren McGavin, Melinda Dillon, Ian Petrella, Scotty Schwartz, R.D. Robb
Rotten Tomatoes Score: 89%
Rating: PG
Runtime: 93 minutes

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To wring something as genuinely warm and heartfelt as it is hilarious from a central theme of rampant consumerism is a rare thing. To supplant Christmas Day TV scheduling previously reserved only for classics like It’s a Wonderful Life and Miracle on 34th Street is quite another. Director Bob Clark assembles a pool of onscreen talent who were clearly born to inhabit Jean Shepherd’s treasured story of childhood amidst Major Awards, first swear words, cynical Mall Santas, and—of course—the ruminations on what it truly means to shoot your eye out. —Scott Wold


30. The Ruling Class

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Year: 1972
Director: Peter Medak
Stars: Pete O’Toole
Rotten Tomatoes Score: 83%
Rating: PG
Runtime: 154 minutes

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Peter O’Toole is electrifying in this bitter satire of British social status and the treatment of mental health. The Ruling Class frequently switches tones with no warning—this the kind of movie where characters will occasionally break out into absurd songs despite not being a musical, but that also ends with a bleak final passage that is way more of a horror film than anything else. It’s not particularly subtle in its critique of capitalism and class structure, but satire doesn’t have to be subtle to be effective. O’Toole was nominated for an Oscar for this one, and it’s obvious why when you watch it.—Garrett Martin


31. Man Bites Dog

man-bites-dog-movie-poster.jpg Year: 1992
Directors: Rémy Belvaux, André Bonzel, Benoît Poelvoorde
Stars: Rémy Belvaux, Benoît Poelvoorde, Andre Bonzel
Rotten Tomatoes Score: 100%
Rating: NC-17
Runtime: 97 minutes

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An undeniable forebear to Behind the Mask: The Rise of Leslie Vernon, Man Bites Dog won the International Critics’ Prize at the 1992 Cannes Film Festival, only to receive an NC-17 rating upon its US release, banned in Sweden altogether. One can understand the squeamishness: Man Bites Dog unflinchingly portrays serial murder in its graphic banality, victims ranging from children to the elderly to a gang-raped woman whose corpse is later photographed with her entrails spilling all over the table on which she was violated, the perpetrators lying in drunken post-revelry, heaped on the floor. Filmed as a mockumentary, Man Bites Dog goes to distressing lengths to portray the exigencies of murder as basely as possible, incorporating the reluctance of the crew filming such horrors to offer the audience a reflection of the ways they were probably reacting. The fascinated sorrow expressed by the documentary film’s director (Rémy Belvaux) as he realizes what making a documentary film about a serial killer actually means, becoming more and more complicit with the killings as the film goes on, explicitly points to our willingness as bystanders to stomach the horrors displayed. Still, we react viscerally while the film explores conceptual themes of true crime as pop culture commodity and reality TV as detrimental mitigation of truth, ultimately indicting viewers apt to enjoy this movie while simultaneously catering to them. Benoit (Benoît Poelvoorde), the subject of the faux film, is of course an incredibly intelligent societal outcast beset by xenophobia and misogyny, offering up countless neuroses to explore behind his psychopathy and serial murder, which he treats as a legitimate job. But Man Bites Dog is more about the ways in which we consume a movie like Man Bites Dog, concerned less about the flagrant killing it indulges for laughs than it is the laughs themselves, implying that the real blame for such well-known horror falls at our feet, in which each day we take big, basic steps to normalize the violence and hate that constantly surrounds us. —Dom Sinacola


32. Singin’ in the Rain

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Year: 1952
Directors: Stanley Donen, Gene Kelly
Stars: Gene Kelly, Debbie Reynolds, Donald O’Connor, Jean Hagen, Rita Moreno
Rotten Tomatoes Score: 100%
Rating: G
Runtime: 103 minutes

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The most legendary of Hollywood musicals, Singin’ in the Rain is a warm, beautiful, feather-light look at Hollywood on the cusp of the talkie revolution, with timeless performances from Gene Kelly, Debbie Reynolds and Donald O’Connor. Musicals can be an acquired taste in the year 2020, but this is one of those legit classics that pretty much anybody interested in the movies should see at some point in their life. It’s a charming, romantic trifle that’s made with perfect precision.—Garrett Martin


33. Young Adult


young adult movie poster.jpg Year: 2011
Director: Jason Reitman
Stars: Charlize Theron, Patton Oswalt, Patrick Wilson, Elizabeth Reaser, Jill Eikenberry, Mary Beth Hurt
Rotten Tomatoes Score: 80%
Rating: R
Runtime: 94 minutes

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Four years after Juno Jason Reitman and Diablo Cody reteamed for the smarter, funnier, and all around less annoying Young Adult. Charlize Theron clearly savors the chance to play the kind of disastrous midlife crisis typically reserved only for men, as a formerly successful young adult novelist struggling with alcoholism, depression and writer’s block. Patton Oswalt delivers the kind of tragicomic turn he excels at as the the bullied nerd Theron used to look down at in high school. Young Adult explores how paralyzing life can be when you lose sight of a future and regret everything in your past, in a poignant and darkly hilarious fashion.—Garrett Martin


34. Wedding Crashers

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Year: 2005
Director: David Dobkin
Stars: Owen Wilson, Vince Vaughan, Christopher Walken, Rachel McAdams, Isla Fisher, Jane Seymour
Rotten Tomatoes Score: 75%
Rating: R
Runtime: 119 minutes

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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


35. Casa de Mi Padre

casa de mi padre.jpg Year: 2012
Director: Matt Piedmont
Stars: Will Ferrell, Diego Luna, Gael García Bernal, Efren Ramirez, Adrian Martinez, Nick Offerman, Pedro Armendáriz Jr.
Rotten Tomatoes Score: 41%
Rating: R
Runtime: 84 minutes

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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


36. The Brothers Solomon


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Year: 2007
Director: Bob Odenkirk
Stars: Will Forte, Will Arnett, Chi McBride, Malin Akerman, Kristen Wiig, Lee Majors
Rotten Tomatoes Score: 16%
Rating: R
Runtime: 93 minutes

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You might be wondering how a movie written by Will Forte, directed by Bob Odenkirk and starring Forte and Will Arnett developed a rep as a catastrophic failure. Well, it kind of was, at least at the box office: it’s one of the few widely released films I can think of that didn’t even crack a million dollars its first weekend, and it didn’t even make a million total during its short time in theaters. Okay, and critics hated it, too, but critics have hated a lot of hilarious comedies. And although The Brothers Solomon is too inconsistent to be genuinely hilarious, it’s still a movie that will make you laugh hard and often if you’re on the same comedic wavelength as Forte. Forte has certain stylistic tics—a love for music, a weird way with language, a fascination with cringe-inducing awkwardness from characters that often have sincere and good intentions, the courage to then take those characters into dark and depressing territory as those intentions turn sour—and they are all as present in The Brothers Solomon as they are in his beloved TV show The Last Man on Earth. The Brothers Solomon is far from perfect, but it’s a vital part of Forte’s oeuvre, and a weird footnote to comedy god Bob Odenkirk’s multifaceted career.—Garrett Martin