The 50 Best Comedies on HBO Max Right Now (June 2020)

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The 50 Best Comedies on HBO Max Right Now (June 2020)

Can a streaming service have too much content?

Probably not, but HBO Max is determined to find out. Warner’s new streamer launched a couple of weeks ago with 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’ve been able to strip it down to the 50 funniest, and 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 50 funniest movies on HBO Max today.

1. Raising Arizona

raising-arizona-movie-poster.jpg Year: 1987
Directors: Ethan Coen, Joel Coen
Stars: Nicolas Cage, Holly Hunter, John Goodman, William Forsythe, Francis McDormand
Rotten Tomatoes Score: 91%
Rating: PG-13
Runtime: 95 minutes

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Understated dramatic performances are all well and good, but it takes pinpoint control on behalf of both directors and cast to deliver the sustained overstated performances found throughout Raising Arizona. From its opening courtship sequence to the struggles of H.I. (Nicholas Cage) and Ed (Holly Hunter) to form a family by borrowing an “extra” from a family with a surplus to the final battle with the Lone Biker of the Apocalypse, the Coen brothers’ film remains an immensely beguiling and quotable farcical fable. —Michael Burgin


2. A Fish Called Wanda

movie poster fish called wanda.jpg Year: 1988
Director: Charles Crichton
Stars: Jamie Lee Curtis, John Cleese, Kevin Kline, Michael Palin
Rotten Tomatoes Score: 94%
Rating: R
Runtime: 98 minutes

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This ensemble piece shows what can happen when four skilled comic actors (John Cleese, fellow Monty Python alum Michael Palin, Kevin Kline and Jamie Lee Curtis) are given a script (written by Cleese) that puts them all on equal footing. The result is a tour-de-force of crisply delivered, character-driven comedy that, while tough on old ladies, fish and terriers, continues to reward new and returning viewers. (The film also broke through the Academy’s normal bias against comedies, winning Kevin Kline a richly deserved Best Supporting Actor for his role as Otto.) —Michael Burgin



3. What About Bob

what about bob poster.jpg Year: 1991
Director: Frank Oz
Stars: Bill Murray, Richard Dreyfuss, Julia Hagerty, Kathryn Erbe
Rotten Tomatoes Score: 84%
Rating: PG
Runtime: 99 minutes

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Despite a great co-directorial debut with 1990’s Quick Change and memorable cameos in movies like Little Shops of Horrors, Bill Murray’s career took a critical dive after 1984’s Ghostbusters. He didn’t even take a major role between 1984 and 1988. So when What About Bob? came out in 1991, critics had long been talking about the Murray slump, and there was legitimate reason to think his career was fading away. What About Bob? is no Groundhog Day, but Murray’s fantastic as the phobia-riddled patient of a pompous psychiatrist played by Richard Dreyfuss (who is maybe too believable as an arrogant blowhard who barely tolerates his family.) It’s a classic Murray role but also an atypical one: Bob isn’t a sarcastic know-it-all, but a human puppy dog unaware of the drama and turmoil that follows in his wake. —Garrett Martin


4. 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



5. Bridesmaids

bridesmaids.jpg Year: 2016
Director: Paul Feig
Stars: Kristen Schaal, Maya Rudolph, Melissa McCarthy, Wendi McLendon-Covey, Ellie Kemper
Rotten Tomatoes Score: 90%
Rating: R
Runtime: 125 minutes

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Unlike The Hangover, which was basically a long comedy sketch, Bridesmaids is actually a movie. This is always the big question when it comes to comedies: Should you aspire to make a full cinematic experience and risk coming up short (Wedding Crashers) or do you simply shoot for non-stop emotionless laughs and achieve wild success at a less transcendent achievement (Anchorman)? Bridesmaids is a thoroughly hilarious, full-bodied story thanks to the brilliance of Kristen Wiig, and it has staying power in the pantheon of less aspirational film comedy. —Ryan Carey


6. The Philadelphia Story

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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



7. Planes Trains and Automobiles

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Year: 1987
Director: John Hughes
Stars: Steve Martin, John Candy, William Windom, Michael McKean, Edie McLurg
Rotten Tomatoes Score: 91%
Rating: R
Runtime: 92 minutes

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Anyone who’s ever endured holiday traffic on their way home for Thanksgiving can relate to this John Hughes tale—although hopefully you’ve never had to endure the sheer number of transportation mishaps (not to mention some accidental spooning) Neal Page and Del Griffith go through. Planes, Trains and Automobiles pits a petulant Steve Martin (Neal) against the usually mirthful John Candy (Del) as they travel home for the holidays. Weather and time are stacked up against them, so they end up traveling together with some disastrous results. Of course, nothing goes according to plan as Thanksgiving gets closer and closer. —Bonnie Stiernberg and Pete Mercer


8. Gremlins 2

gremlins-2-movie-poster.jpg Year: 1990
Director: Joe Dante
Stars: Zack Galligan, Phoebe Cates, John Glover, Robert Prosky
Rotten Tomatoes Score: 69% (nice)
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



9. 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


10. Adam’s Rib

adams-rib-movie-poster.jpg Year: 1949
Director: George Cukor
Stars: Spencer Tracy, Katharine Hepburn, Judy Holliday
Rotten Tomatoes Score: 100%
Rating: NR
Runtime: 101 minutes

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George Cukor’s Adam’s Rib is a curio of a time when misogyny wasn’t so much a fault as a societal given, which may be why the dynamic between married lawyers Adam Bonner (Spencer Tracy) and Amanda Bonner (Katharine Hepburn, whose character thankfully wasn’t named Eve) feels at once well-balanced and hilariously unreal. A prototypical “war of the sexes” comedy in which each side represents the status quo for his or her respective gender, Adam’s Rib transcends its dumbest Mars-vs-Venus trappings by portraying Tracy’s Bonner as a stuffy turd too caught up in his derision of women to do anything about the fact that a famous musician lothario (David Wayne) is getting mighty close to cuckolding him, were Amanda a dunce susceptible to shameless advances. She’s not, and not once does Hepburn—perfectly cast—give any impression that she’ll fall for it, being clearly the smartest person in any room and fully aware of what kind of effect her extra-marital flirting has on her wussy husband.

The plot is simple: A woman (Judy Holliday) shoots and injures her cheating husband (Tom Ewell) after catching him in the act, so District Attorney Adam must represent the prosecution (cheating asshole) while Amanda, energized by her husband’s blindness regarding a woman’s helplessness when it comes to adultery, takes up the defense. The trial goes as one might expect, with Hepburn’s charisma holding the attention of every scene, but the real surprise in Cukor’s film comes within its final moments, when the rocky marital fall-out between our leads ends in an almost nihilistic bit wherein Adam reveals he can be just as emotionally manipulative as he expects all women are. Which may be screenwriters Ruth Gordon and Garson Kanin’s funniest joke: Adam’s Rib is about how men and women are equal only in how equally terrible they can be to each other. —Dom Sinacola



11. School of Rock

school_of_rock_poster.jpg
Year: 2003
Director: Richard Linklater
Stars: Jack Black, Joan Cusack,
Rotten Tomatoes Score: 91%
Rating: PG-13
Runtime: 110 minutes

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School of Rock gets plenty of comic mileage of the fact that Jack Black’s character, Dewey Finn, isn’t nearly as book smart as his students: “You’re gonna have to use your head, and your brain, and your mind, too,” he tells them. But it’s Dewey who uses his head, brain and mind as he becomes musical mentor, creator of lesson plans and manipulator of an inflexible educational system. (With school music programs being slashed at schools nationwide, School of Rock was ahead of its time.)

School of Rock doesn’t go overboard on the sentimental aspects—it establishes that young guitarist Zach has a controlling, overbearing father without beating the audience over the head with it. And while it advocates giving children a means of self-expression and catharsis, it doesn’t elevate rock music into something more than it should be.—Curt Holman


12. 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



13. Punch-Drunk Love

punch-drunk-love.jpg Year: 2002
Director: Paul Thomas Anderson
Stars: Adam Sandler, Emily Watson, Philip Seymour Hoffman, Luis Guzman
Rotten Tomatoes Score: 79%
Rating: R
Runtime: 95 minutes

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It may be hard to recall now that we’ve all rallied around his talent—allowing him to transcend the stigma of his Netflix deal while he still profits ludicrously off it—but there was once a time when the world doubted Adam Sandler. Long before the Safdies or even Noah Baumbach got their time getting tight with the Sandman, we have P.T. Anderson to thank for inspiring such hope. Compared to the scope of There Will Be Blood, or the melancholy of Boogie Nights, or the inexorable fascination at the heart of The Master, or the obsession and obfuscation of Phantom Thread, Punch-Drunk Love—a breath of fresh, Technicolor air after the weight of Magnolia—comes off like something of a lark for Anderson, setting the stage for the kind of incisive comic chops the director would later epitomize, and complicate, with Inherent Vice. A simple love story between a squirmy milquetoast (Sandler) on the verge and the woman (Emily Watson) who yanks him back to life, Punch-Drunk Love is as confounding as it is a delight, an expression of unmitigated, sputtering passion—sad and febrile and, most importantly, optimistic about what anyone is truly capable of doing. This might be as sincere as Anderson gets. —Dom Sinacola


14. 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



15. Elf

elf_poster.jpg
Year: 2003
Directors: Jon Favreau
Stars: Will Ferrell, Zooey Deschanel, James Caan, Mary Steenburgen, Bob Newhart, Ed Asner
Rotten Tomatoes Score: 84%
Rating: PG
Runtime: 107 minutes

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In a sense, making Christmas “funny” can be as easy as responding to something meant to be sincere and joyful with cynicism and darkness. Is there any comedic Christmas character that embodies a genuine love of Christmas? Thankfully, we have Will Ferrell’s fearlessly committed performance as the titular elf to answer this question with a resounding yes. Nothing represents Christmas cheer better than Will Ferrell in yellow tights, a green parka and cone-shaped cap. He wrings a ton of comedy out of responding to everything with wide-eyed, childlike wonder. Arguably our generation’s classic Christmas movie, watching Buddy the Elf makes you laugh, makes you smile and, to paraphrase from the Grinch, makes your heart grow three sizes bigger. Even if the movie devolves into a formulaic, race-against-the-clock flick in the last 30 minutes, its myriad gifts outweigh its problems. From endlessly quotable nuggets like “cotton-headed ninnymuggins”; the hysterical fruit spray scene; Zooey Deschanel showcasing her pre-She & Him singing chops; Mr. Narhwal and the arctic puppets (a band name if I ever heard one); to, finally, Ferrell’s infectious enthusiasm, Elf is instant holiday merriment. —Greg Smith & Jeremy Medina


16. Harold and Maude

harold-and-maude-movie-poster.jpg Year: 1971
Director: Hal Ashby
Stars: Ruth Gordon, Bud Cort, Cyril Cusack, Vivian Pickles
Rotten Tomatoes Score: 84%
Rating: PG
Runtime: 92 minutes

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The original Daily Variety review begins, “‘Harold and Maude’ has all the fun and gaiety of a burning orphanage.” History has been kinder. Though it may be dark, Harold and Maude is certainly a romantic comedy: Young Harold (Bud Cort) and 79-year-old Maude (Ruth Gordon) do find love, their courting wickedly funny as Harold finds increasingly more gruesome ways to scare off the suitors sent by his mother. Still, Hal Ashby’s masterpiece is unlike any other film of its ilk, before or after its 1971 release, and Gordon is brilliant as the manic pixie dream septuagenarian. Just don’t go in expecting a happily ever after. —Josh Jackson



17. Bringing Up Baby

bringing_up_baby_poster.jpg
Year: 1938
Director: Howard Hawks
Stars: Katharine Hepburn, Cary Grant, Charles Ruggles, May Robson
Rotten Tomatoes Score: 93%
Rating: NR
Runtime: 102 minutes

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The textbook example of a screwball comedy, Bringing Up Baby finds Cary Grant’s hilariously uptight paleontologist Dr. David Huxley struggling to keep his life together when the flirtatious agent of chaos that is Katherine Hepburn’s Susan Vance comes crashing into his life. Add in shenanigans involving a baby leopard, a collapsing brontosaurus skeleton and some deftly executed pre-MPAA sexual innuendos and you have not only one of the best romantic comedies of all time but one of the funniest American movies ever made. —Mark Rozeman


18. Something Wild

something_wild_poster.jpg
Year: 1986
Director: Jonathan Demme
Stars: Melanie Griffith, Jeff Daniels, Ray Liotta, Tracey Walter, Jack Gilpin
Rotten Tomatoes Score:
Rating: R
Runtime: 113 minutes

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Something Wild offers the odd-couple pairing of Charles Driggs (Jeff Daniels), a vice-president of a banking company living a comfortable existence in a Long Island suburb, and Audrey Hankel (Melanie Griffith), a free-spirited woman seemingly without attachments, but also with a lot of money at her disposal to fund her devil-may-care ways. At first introducing herself to Charles as Lulu, Audrey basically ropes this yuppie into following her on a bizarre road trip throughout a good part of the East Coast—an adventure that, true to genre form, encompasses everything from screwball comedy to violent thriller, with the tone often shifting on a dime. Certainly, Demme’s film lives up to its title just in the all-over-the-place story it weaves. But the film is more than just the sum of its deliberately disparate parts—especially because neither of these two characters can be easily pinned down as types. The first time we see Charles in the film, he’s walking away from a diner having not paid for his meal—an act he later justifies as his way of rebelling within the system. Whether that is in fact true or not, it’s nevertheless clear that he does have certain unruly impulses in him just itching to pop out—which naturally catches the eye of someone like Audrey, who has made such unruliness her life’s mantra. But Audrey isn’t simply the kind of character who would later become known as the “Manic Pixie Dream Girl.” Both Audrey and especially Charles do learn new things about themselves during this odyssey—but it’s not as simple as Audrey learning the dangers of her unfettered lifestyle and Charles becoming more of a bad-ass by embracing that same lifestyle. Instead of being about self-improvement, Something Wild is more about self-awareness: a realization of how complex human beings can be. —Kenji Fujishima



19. 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


20. A Hard Day’s Night

hard_days_night_poster.jpg
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



21. In Bruges

in bruges poster.jpg
Year: 2008
Director: Martin McDonagh
Stars: Colin Ferrell, Brendan Gleeson, Ralph Fiennes
Rotten Tomatoes Score: 84%
Rating: R
Runtime: 107 minutes

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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


22. City Lights

city_lights_poster.jpg
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



23. Pretty in Pink

pretty_in_pink_poster.jpg
Year: 1986
Director: Howard Deutch
Stars: Molly Ringwald, Andrew McCarthy, Jon Cryer, James Spader, Harry Dean Stanton
Rotten Tomatoes Score: 77%
Rating: PG-13
Runtime: 96 minutes

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Let’s ignore the fact that she ends up with the wrong guy in the end (Team Duckie for life!) and examine what makes Pretty in Pink’s Andie so impossibly cool: She works in a record store and has killer taste in music. Her outfits are daring and incredible. She brushes off insults from evil richie-rich Steff (James Spader) like they ain’t no thang. She supports her deadbeat dad and essentially serves as head of their household. But most importantly, she’s the picture of courage, staying true to herself the whole way through and never changing to please Blane and his wealthy friends—and if there’s any single movie character teen girls should be modeling themselves after as they attempt to swim the treacherous waters of high school without drowning, she’s the one. —Bonnie Stiernberg


24. A Christmas Story

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Year: 1983
Director: Bob Clark
Stars: Darren McGavin, Peter Billingsley, Melinda Dillon, Ian Petrella
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



25. When Harry Met Sally

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Year: 1989
Director: Rob Reiner
Stars: Billy Crystal, Meg Ryan, Carrie Fisher, Bruno Kirby
Rotten Tomatoes Score: 90%
Rating: R
Runtime: 96 minutes

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Easily the most beloved romantic comedy of its decade, the story of Harry (Billy Crystal), Sally (Meg Ryan) and their 12-year journey to couple-hood boasts a solid script by Nora Ephron that feeds and feeds off of the unexpected chemistry between its leads. (And with each new generation of lovers watching the diner scene for the first time, another woman laughs and another man sits silently, wondering what’s so funny.) —Michael Burgin


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. Babe: Pig in the City

babe-pig-in-the-city-movie-poster.jpg Year: 1998
Director: George Miller
Stars: James Cromwell, Elizabeth Daily, Magda Szubanski, Mickey Rooney, Mary Stein
Rotten Tomatoes Score: 65%
Rating: G
Runtime: 90 minutes

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Three franchises mostly define George Miller’s almost five-decade career: Mad Max, Happy Feet and Babe—the latter comprised by the two films Miller wrote about the talking pig who thinks he’s a sheepdog. Miller has kept such a distinct visual language throughout these 50-some years, we can draw a direct aesthetic line between Fury Road’s lavish colors depicting the grotesque beauty of a post-apocalyptic hellscape, and Babe: Pig in the City’s old-school fairy-tale world, equally enchanting and deadly. It’s is a textbook example of solid sequel-making: Instead of blindly recreating the charming family drama of Babe, following the titular pig hell-bent on defying his social place in his world, Miller dials the story’s fantasy to 11 to take us to an awe-inspiring metropolitan city that’s a hodgepodge of the most beautiful and recognizable urban spots in the world. Pushing human characters even more to the background, Miller’s film tells of Babe’s latest exploit leading a group of plucky and downtrodden animals in their quests for freedom and dignity. Like so many classic children’s entertainments, in Pig in the City, horrors lurk around every corner but the possibilities of life’s wonders similarly shine. —Oktay Ege Kozak


28. Good Boys

good_boys_poster.jpg
Year: 2019
Director: Gene Stupnitsky
Stars: Jacob Tremblay, Keith L. Williams, Brady Noon, Will Forte, Lil Rel Howery, Retta
Rotten Tomatoes Score: 80%
Rating: R
Runtime: 95 minutes

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Good Boys manages to stand on its own two tiny feet independently from Superbad in how much the dialogue and behavior of the kids ring true. In many ways, the “R” rating feels natural, relatable even: This was the time we all experimented with adult language. What the film’s script gets so painfully right is how we used the words without understanding them. One of the first jokes in the film focuses on how the Beanbag Boys know the word “cum” while having no idea how to pronounce it. They puff out their chests claiming to know everything there is to know about sex, but think of Thor’s parents’ sex toys as weapons and an unusually smelly necklace. The cursing and adult material isn’t just put into the tweens’ mouths for simple shock value; it’s essential to grounding these characters no matter how bonkers their hijinks become.

Meanwhile, the thematic glue that holds Good Boys together is that balance between the value of such close friendships and the importance of gracefully taking the next steps into adulthood. The tight chemistry and the impeccable timing among the young actors, as well as writers Lee Eisenberg and Gene Stupnitsky’s emphasis on capturing the awkward but charmingly determined behavior of boys within this age group, keeps the film’s otherwise episodic structure moving. Stupnitsky, who comes from TV comedy and directs his first feature here, brings his expertise from the small screen to create pacing that lends to an improvisational atmosphere, though Daniel Gabbe’s editing occasionally veers toward the erratic. Still, Good Boys manages to find that happy medium between outrageous and heartstring-pulling.—Oktay Ege Kozak



29. The Nice Guys

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Year: 2016
Directors: Shane Black
Stars: Russell Crowe, Ryan Gosling, Angourie Rice, Margaret Qualley, Keith David
Rotten Tomatoes Score: 92%
Rating: R
Runtime: 116 minutes

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Good performances can polish average movies with just enough elbow grease they end up looking like gems. Think Jennifer Lawrence in Silver Linings Playbook, or Alan Rickman in Robin Hood: Prince of Thieves. Every advance that Shane Black’s The Nice Guys takes toward quality is made on the strengths of Russell Crowe and Ryan Gosling. Black is as quick with action scenes as with punchlines. The Nice Guys is funny. It’s exciting. If you find yourself growing tired of wordplay, Black will turn things around and slide in some Three Stooges slapstick. If you get tired of that, he’ll set off a gun or throw a few punches, though it is impossible to imagine anybody finding the clownish sight of Gosling tumbling off of balconies or crashing through plate glass tiresome. Gosling and Crowe are a great pair, so great that their team-up should justify funding for a buddy picture series where Holland and Jackson undertake jobs that spiral out of hand and above their pay grades. Crowe plays it straight and grumpy, and you half expect him to declare that he’s too old for this shit at any given moment. Gosling, on the other hand, shapes Holland through boozy tomfoolery and pratfalls. They’re a standout odd couple, but Black’s films are defined by great odd couples as much as they are by great scripting. In The Nice Guys, he leaves it up to Gosling and Crowe to use the former to fill in the gaps left behind by the lack of the latter.—Andy Crump


30. Arthur

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Year: 1981
Director: Steve Gordon
Stars: Dudley Moore, Liza Minnelli, John Gielgud, Geraldine Fitzgerald
Rotten Tomatoes Score: 88%
Rating: PG
Runtime: 99 minutes

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One of the rare comedies to receive a fair amount of Oscar attention, the original Arthur remains a treat. Dudley Moore’s turn as an immature, alcoholic billionaire was his best work outside of his partnership with Peter Cook, and his romance with Liza Minnelli feels surprisingly natural. John Gielgud also won his only Oscar for his role as Arthur’s paternalistic butler. Steve Gordon’s script balances laughs with loneliness, desperation, and a somewhat realistic class consciousness, but it’s the performances of its three leads that make Arthur truly special—along with Christopher Cross’s chintzy, goofball theme song.—Garrett Martin



31. 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


32. All of Me

all_of_me_poster.jpg Year: 1984
Director: Carl Reiner
Stars: Steve Martin, Lily Tomlin, Victoria Tennant, Madolyn Smith Osbourne
Rotten Tomatoes Score: 88%
Rating: PG
Runtime: 93 minutes

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People couldn’t get enough of body swap comedies in the ‘80s, but All of Me stands alongside Big as the best of the bunch for a few reasons. First off is because it stars two of the greatest comedians of all time, Steve Martin and Lily Tomlin, when they were at the peak of their powers. Secondly the concept isn’t as straight-forward as a man and a woman trading bodies; Tomlin’s spirit takes over half of Martin’s body, and the tension as they try to coexist while each having control of one of his two sides leads to some great physical comedy from Martin and bantering between the two. Finally, Carl Reiner is a comedy genius, and knows how to set things up and time them out for maximum impact. It’s good.—Garrett Martin



33. In a World


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Year: 2013
Director: Lake Bell
Stars: Lake Bell, Fred Melamed, Rob Corddry, Michaela Watkins, Ken Marino
Rotten Tomatoes Score: 92%
Rating: R
Runtime: 91 minutes

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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


34. Hairspray

hairspray 1988 movie poster.jpg Year: 1988
Director: John Waters
Stars: Divine, Ricki Lake, Jerry Stiller, Colleen Fitzpatrick, Sonny Bono, Ruth Brown
Rotten Tomatoes Score: 98%
Rating: PG
Runtime: 92 minutes

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There’s a reason John Waters’ subversive throwback to American Bandstand and the fight for racial integration has since spawned a Broadway show, a popular film remake and a live TV musical: The most “accessible” film of the legendary queer director’s wide-ranging career may not be as unsettling as the decade’s other leer at postwar Americana (Blue Velvet), but it nonetheless manages to smuggle a range of radical ideas about race, gender and the importance of teen culture past the censors in Tracy Turnblad’s “flamboyant flip.” Set in Baltimore in 1962, Hairspray follows Tracy (Ricki Lake) as her determination to appear on The Corny Collins Show becomes a quest to de-segregate the city’s most beloved cultural institutions, aided by her best friend, Penny (Leslie Ann Powers); her boyfriend, Seaweed (Clayton Prince); Seaweed’s mother, Motormouth Maybelle (Ruth Brown); heartthrob Link Larkin (Michael St. Gerard); and (ultimately, reluctantly) her overbearing mother, Edna (Divine). But it’s not simply a paean to interracial cooperation, or a piece of bubblegum nostalgia for the heyday of rock ‘n’ roll: Befitting Waters’ bomb-throwing sensibilities, the film’s denouement raises the specter of white supremacist terror, and with it the unseemly truth that it’s often supported by the most “respectable” among us. In this sense, if Hairspray is a throwback, it’s one that refuses to forget the nation’s blemishes—a camp-inflected, brightly colored, broadly funny knife into the heart of the system, sealed with a matinee kiss. —Matt Brennan



35. 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


36. 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



37. CB4

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Year: 1993
Director: Tamra Davis
Stars: Chris Rock, Allen Payne, Deezer D, Chris Elliott, Phil Hartman
Rotten Tomatoes Score: 55%
Rating: R
Runtime: 88 minutes

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CB4 isn’t the best rap satire movie of 1993. That would go to Fear of a Black Hat. It is the best rap satire movie of 1993 on HBO Max, though, and that still counts for something. The central joke in CB4 is that Chris Rock’s NWA-parodying gangsta rapper is actually a well-behaved kid from the suburbs who creates fake criminal personas for him and his group. It might go for the obvious punchline too often, but at its best CB4 is a smart satire of how America and the entertainment industry views black performers and the stereotypes they often force them into. Also, hey, it’s got Chris Rock, Phil Hartman and Chris Elliott in it, so you shouldn’t have any doubt that it’ll be funny.—Garrett Martin


38. Rock ‘n’ Roll High School

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Year: 1979
Director: Allan Arkush
Stars: P.J. Soles, Vincent Van Patten, Clint Howard, Mary Woronov, the Ramones
Rotten Tomatoes Score: 81%
Rating: PG
Runtime: 94 minutes

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This might be known as “that Ramones movie,” but it’s P.J. Soles’s show. As Riff Randell, the biggest Ramones fan at Vince Lombardi High, the Carrie and Halloween actress gives us one of the best on-screen depictions of what it means to be a passionate fan of anything, but especially rock ‘n’ roll. Riff’s enthusiasm is infectious and her love for the Ramones updates the archetype of the teenage girl swooning over ‘50s and ‘60s pop stars for the late ‘70s, just as the Ramones revived bubblegum pop through the dirty lens of that rotting decade. You don’t have to like the Ramones to like this movie—you just have to like rebellion and rock ‘n’ roll and the wholesale destruction of confining institutions like the American high school.—Garrett Martin



39. Tropic Thunder

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Year: 2008
Director: Ben Stiller
Stars: Ben Stiller, Jack Black, Robert Downey Jr., Steve Coogan, Danny McBride
Rotten Tomatoes Score: 82%
Rating: R
Runtime: 107 minutes

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Ben Stiller’s parody of Hollywood obliviousness maybe hasn’t aged that well—the visual of a white man in black face is so instantly jarring that any comment it might be trying to make about the racism of the entertainment industry can easily get overlooked, as proved by all the times social media has tried to “cancel” Robert Downey Jr. over this role. It’s one of those movies that’s hard to forget, though—I saw it once, in the theater, almost a decade ago, and will often find myself remembering parts of it without at first even remembering what movie those moments are from. The great cast (including Steve Coogan, Danny McBride, Bill Hader and Tom Cruise in what is easily his best comedic role) is a big reason why.—Garrett Martin


40. Notting Hill

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Year: 1999
Director: Roger Michell
Stars: Julia Roberts, Hugh Grant, Richard McCabe, Rhys Ifans, Emma Chambers
Rotten Tomatoes Score: 83%
Rating: PG-13
Runtime: 124 minutes

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Like most good romantic comedies, everything about Notting Hill is an absolute dream: Oh, you’re a world-famous American actress, wealthy and beloved by millions? Neat. And you’re staying in one of the most beautiful neighborhoods in London (one of the most beautiful cities in the world)? Super cool. But oh no! You collide with a guy in the street, and he spills orange juice all over you! Life is ruined! But wait a second. He’s an adorable independent bookstore owner with a group of quirky friends (including a hilarious Rhys Ifans and a pre-Downton Abbey Hugh Bonneville) and a penchant for spitting out screenwriter Richard Curtis’ (Four Weddings and a Funeral, Love Actually) charming one-liners and the face of Hugh Grant, and this is your meet-cute. Anna (Julia Roberts) may “just be a girl, standing in front of a boy, asking him to love her” … but she’s a damn lucky girl. —Bonnie Stiernberg



41. Amélie

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Year: 2001
Director: Jean-Pierre Jeunet
Stars: Audrey Tautou, Mathieu Kassovitz, Serge Merlin, Rufus
Rotten Tomatoes Score: 88%
Rating: R
Runtime: 121 minutes

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Delicate and delicious, Amélie is an easily, exceedingly lovable little French trifle. With the face of an angel, the heart of a child and the haircut of a Parisian pixie, Amélie Poulain (Audrey Tautou) sweeps us clean off our feet while Tautou launches herself into the American consciousness as the do-gooding 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. Her fantastical adventures—in the name of idealized, even cinematic, coupling—unfold in flights of magical realism, Jean-Pierre Jeunet holding up love itself as both realistically magical and magically realistic. —Nick Marino


42. 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



43. Hail, Caesar!

hail-caesar.jpg Year: 2016
Directors: Ethan Coen, Joel Coen
Stars: George Clooney, Tilda Swinton, Josh Brolin, Ralph Fiennes, Jonah Hill, Alden Ehrenreich, Christopher Lambert, Channing Tatum, Scarlett Johansson
Rotten Tomatoes Score: 86%
Rating: PG-13
Runtime: 106 minutes

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The period zaniness of Joel and Ethan Coen’s Hail, Caesar! is an ode to old Hollywood—and much more—as only they can do, tracing the efforts of James Brolin’s studio scandal fixer through a parade of 1950s soundstages, back lots and actors. His latest potential headline concerns the abduction of a Biblically epic movie star—George Clooney having a helluva good time doing his best Chuck Heston/Kirk Douglas amalgam—by what turns out to be a tea sandwich-serving think tank of communists. Other subplots have Scarlett Johansson’s starlet plotting out her unwed motherhood in the public eye and the screen makeover of an unsophisticated cowboy by Ralph Fiennes’ debonairly enunciating director, Laurence Laurentz. There are dueling gossip columnist twins (Tilda Swinton pulling double duty), a hapless film editor (Frances McDormand) and scattered movies-within-the-movie, which even pauses midway through for a thoroughly enchanting—and cheeky—Gene Kelly-styled song-and-dance number starring Channing Tatum as a heavily made-up matinee star with controversial extracurricular activities. Most of the main characters/performances take blatant inspiration from Hollywood legends of yore, and the cast seems to have as much fun as the Coens. Hail, Caesar! is by no means their best work, but it’s characteristically gorgeous, spiritedly acted and rife with political, religious and creative (sub)text for moviegoers as thoughtful and dorky as Joel and Ethan themselves. —Amanda Schurr


44. Stakeout

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Year: 1987
Director: John Badham
Stars: Richard Dreyfuss, Emilio Estevez, Madeleine Stowe, Aidan Quinn, Forest Whitaker
Rotten Tomatoes Score: 88%
Rating: R
Runtime: 117 minutes

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There might be a bit of a disconnect between Stakeout’s action scenes and its low-stakes, character-driven humor, as Richard Ebert pointed out in his review, but you can’t deny that Dreyfuss and Estevez have a weird, unexpected chemistry as a pair of cops on a lengthy stakeout. Dreyfuss has a long history of being a fussy ham, but that tendency works in his favor in this movie, and he actually kind of reins it in a bit here. The ‘80s was the era of the buddy cop comedy, and Stakeout was one of the best. It’s relatively forgotten today, but it was one of the bigger hits of 1987, and prompted a deeply unloved sequel that followed six years later. Skip that one but feel free to add this to your queue.—Garrett Martin



45. Stuber

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Year: 2019
Director: Michael Dowse
Stars: Kumail Nanjiani, Dave Bautista, Iko Uwais, Betty Gilpin, Natalie Morales
Rotten Tomatoes Score: 41%
Rating: R
Runtime: 105 minutes

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A good buddy comedy hinges greatly on its stars, and that might be more true with Stuber than any of them. Kumail Nanjiani and Dave Bautista are great together as the normal, everyday Uber driver and the action hero super cop, and their chemistry elevates what would otherwise be a rather by-the-numbers affair. The big question about Stuber, of course, is will Marvel slip in a winking reference for the super Stuber stans whenever the Guardians and the Galaxy and the Eternals hang out?—Garrett Martin


46. Josie and the Pussycasts

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Year: 2001
Directors: Harry Elfont, Deborah Kaplan
Stars: Rachael Leigh Cook, Rosario Dawson, Tara Reid, Parker Posey, Alan Cumming
Rotten Tomatoes Score: 53%
Rating: PG-13
Runtime: 99 minutes

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Josie and the Pussycats isn’t the disaster many thought it was when it came out, but it’s also not quite the brilliant, subversive satire that many today have tried to argue. It’s an occasionally funny, occasionally audacious parody of pop culture that criticizes the corporate vacuousness of the entertainment industry, but lightly, and only to the extent that that same industry would let a thoroughly corporate product like this criticize it. Is it better than most disposable turn-of-the-century teen comedies? Of course. Is it a fun way to kill 100 minutes? Yeah, especially if you’re old enough to be nostalgic for that era and get the movie’s pop cultural references. Is it some brilliant lost classic waiting to be rediscovered? Not quite. It’s a slick, silly film smart enough to update an old Archie comic into an irreverent, self-referential comedy, and that’s more than good enough.—Garrett Martin



47. Analyze This

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Year: 1999
Director: Harold Ramis
Stars: Robert De Niro, Billy Crystal, Lisa Kudrow, Joe Viterelli, Chazz Palminteri
Rotten Tomatoes Score: 69%
Rating: R
Runtime: 110 minutes

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A few months after The Sopranos debuted, the great Harold Ramis tackled the same basic concept—a mob boss starts doing therapy—with a much lighter touch. Robert De Niro plays the mobster, in full Godfather mode, with Billy Crystal as his bemused analyst. Analyse This is far from Ramis’s best movie—this is the same guy who directed Groundhog Day, Caddyshack and National Lampoon’s Vacation, after all—but it somehow wound up as his most successful, at least at the box office. It also lit fire to De Niro’s second career as an unlikely comedy star, which, uh, thanks, Analyze This? It has some solid jokes, and De Niro and Crystal do have a bit of chemistry together.—Garrett Martin


48. American Pie

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Year: 1999
Director: Paul Weitz
Stars: Jason Biggs, Mena Suvari, Alyson Hannigan, Chris Klein, Eugene Levy
Rotten Tomatoes Score: 61%
Rating: R
Runtime: 96 minutes

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The original American Pie is a cut above the typical raunchy teen sex comedy for two reasons. First is the cast. The cast members that have charisma have a ton of it, including Jason Biggs and Seann William Scott in career-defining roles, and Alyson Hannigan as the surprisingly experienced band geek. Ringers like Eugene Levy and Jennifer Coolidge do the comedic heavy-lifting when needed. (SCTV legend Levy basically had a second or third career popping up in all the sequels to this thing.) On top of that, it’s surprisingly sweet for a movie about getting laid, especially considering at one point Scott’s character Stifler downs a beer full of semen. It was a gross-out comedy that your parents could enjoy. A lot of it probably plays horribly today, of course—even in ‘99, setting up a webcam so your friends could ogle a naked classmate crossed the line from joke to sexual harassment. So maybe tread lightly with this one.—Garrett Martin



49. Dodgeball: A True Underdog Story

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Year: 2004
Director: Rawson Marshall Thurber
Stars: Vince Vaughn, Christine Taylor, Ben Stiller, Rip Torn, Stephen Root, Justin Long
Rotten Tomatoes Score: 70%
Rating: PG-13
Runtime: 98 minutes

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This idiotic sports romp from the height of Vince Vaughn’s reign over Hollywood comedy is a favorite of adolescent dudes of all ages. Is it dumb? Absolutely. Is it funny? Sometimes. Ben Stiller amps up his unlikable side to 11, while Stephen Root and Rip Torn put in the effort to make it work. They’re two great character actors who excel at either comedy or drama, and they keep Dodgeball humming along.—Garrett Martin


50. Schizopolis

schizopolis.jpg Year: 1996
Director: Steven Soderbergh
Stars: Steven Soderbergh, Dave Jensen, Betsy Brantley, Eddie Jemison
Rotten Tomatoes Score: 61%
Rating: R
Runtime: 97 minutes

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Everything and nothing at all, Schizopolis came about in the midst of a prolific period for Steven Soderbergh—though one could say that for practically any movie he’s made throughout his career. Released the same year as Gray’s Anatomy, and on the heels of King of the Hill and The Underneath, one an award-winning bildungsroman and the latter a remake of a Robert Siodmak noir, Schizopolis puts something of a cap on the notion of Soderbergh as auteur. Here he seems capable of making any kind of movie he wants to make—this time a largely improvised experimental comedy shot on a quick-and-dirty microbudget, pretty much between breakfast and dinner. And, as further testament to Soderbergh’s weird pandextrousness, Schizopolis feels inextricably of its time, mapping in broad, absurd strokes the way meaningful communication has become a lost privilege of a technologically advancing society. As Soderbergh himself (who also stars) states in a prelude to the actual film: “In the event that you find certain sequences or ideas confusing, please bear in mind that this is your fault, not ours.” As a director in full control of even his most tossed-off films, he’s probably right. —Dom Sinacola

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