Now that we all must have HBO Max to watch Hollywood’s latest blockbusters, it’s time to dig deep into its large catalog of library titles to see what else the service has to offer. And after the few years we all just experienced, what could be more appropriate than a great comedy? Luckily, HBO has quite a few to choose from. There are new films, of course, but they have a lot to offer when it comes to library titles, particularly from the ‘80s and ‘90s. Here are some of the best chances you have for a hilarious night in. And this is just at the moment, too; more titles are arriving all the time.
For more recommendations, check out our list of the best comedies on Netflix, Hulu, and Prime Video, or browse our picks for the best movies on HBO.
Editor’s note: This article was updated March 2023 to include The Last Word.
13 Going on 30 (2004)
Run Time: 1 hr 38 min | Director: Gary Winick
Cast: Jennifer Garner, Mark Ruffalo, Judy Greer, Andy Serkis, Kathy Baker, Phil Reeves
Rom-coms had a bad rap for a long time, but if there’s one modern entry just about everybody seems to love, it’s 13 Going on 30. No doubt, a big part of that comes down to the fact that Gary Winick‘s just-shy-of-saccharine-sweet romance boasts one of the most likable ensembles of all time, includingJennifer Garnerand Mark Ruffalo as the darn cutest rom-com duo of the 21st century, and supporting players like everybody’s BFF Judy Greer and a Thriller-dancing Andy Serkis. But the film also indulges a pure fantasy about the lives we wish we had and learning not to take things for granted with the tale of 13-year-old girl who wakes up as her dream 30-year-old self and realizes she might just have the wrong priorities. Garner’s fish-out-of-water performance is giddy and gleeful on a level with Will Ferrell in Elf and Tom Hanks in Big, and her chemistry with Ruffalo is a through-the-roof treat. It’s one of the best feel-good movies of the 21st century and joy to watch from start to finish. — Haleigh Foutch
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The Last Word (2017)
Run Time: 1 hr 48 min | Director: Mark Pellington
Cast: Shirley MacLaine, Amanda Seyfried, AnnJewel Lee Dixon
The Last Word is a delightful Shirley MacLaine (Steel Magnolias) vehicle that both reminds us how amazing she is and how precious life can be. This feel-good comedy centers around successful businesswoman Harriet (Shirley MacLaine), who hires a journalist named Anne (Amanda Seyfried) to write her obituary while she’s still alive. Over the course of the story, the two grow close and change each other’s perspective for the better. MacLaine and Seyfried bounce off one another so well and are the perfect duo to deliver this film’s message about living out your dreams, being kind to your fellow man, and understanding how we affect the world around us. – Tauri Miller
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Jennifer’s Body (2009)
Run Time: 1 hr 42 min | Director: Karyn Kusama
Cast: Megan Fox, Amanda Seyfried, Adam Brody, Johnny Simmons, J.K. Simmons
Megan Fox and Amanda Seyfried (The Dropout) co-star in the clever dark comedy Jennifer’s Body from prolific writer Diablo Cody (Juno). Although wildly underappreciated upon release, Jennifer’s Body crafts an original story that subverted many expectations within the horror genre, allowing director Karyn Kusama to explore themes of sexuality, femininity, and bodily autonomy. Utilizing the demonic metaphor, Jennifer’s Body plays expectations through an unexplored queer romance and an allegory of female friendship. Brilliantly written and featuring award-worthy performances, Jennifer’s Body rightfully found itself in cult classic territory and has been gaining popularity ever since. – Yael Tygiel
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Horrible Bosses (2011)
Run Time: 1 hr 46 min | Director: Seth Gordon
Cast: Jason Bateman, Charlie Day, Jason Sudeikis, Jamie Foxx, Jennifer Aniston, Colin Farrell
Boasting an A-list comedy cast led by Jason Bateman, Charlie Day, andJason Sudeikis;Horrible Bossesfollows three best friends who all have been burnt out by their jobs and in particular their demanding (and sometimes dangerous) bosses. The three then decide to take matters into their own hands, quitting their jobs, and consulting with a mysterious criminal (Jamie Foxx) to help guide them in their plot to murder their bosses and shenanigans ensue. Horrible Bosses plays as both a pitch-black comedy and a populist studio comedy, the characters in the film are doing despicable things but the fact that almost all of them are played by charismatic actors and actresses makes it easier to root for the three burnt-out heroes. There’s also a scene-stealing Jennifer Anistonas Day’s boss, a sex-crazed dentist. So there is plenty of fun to be had, just maybe not for the whole family. – Nate Richard
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Garden State (2004)
Run Time: 1 hr 42 min | Director: Zack Braff
Cast: Zack Braff, Natalie Portman, Steve Zahn, Peter Saarsgard, Ian Holm
Remember when the “mainstream actor returning to their childhood hometown” subgenre of indie comedies felt fresh? Garden State had many imitators, but there’s still a lot of charm inZack Braff’s directorial debut. Braff doesn’t use the film just to boost his ego; he’s entirely comfortable being vulnerable and pathetic, delivering one of his better performances.Natalie Portmanhas rarely been more charming, and the film features one of the last great performances from the legendaryIan Holmas Braff’s father. If nothing else, Garden State is a nostalgic trip into early 2000s music. – Liam Gaughan
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50 First Dates (2004)
Run Time: 1 hr 39 min | Director: Peter Segal
Cast: Adam Sandler, Drew Barrymore, Rob Schneider, Sean Astin, and Dan Aykroyd
As far as Adam Sandler romcoms go, 50 First Dates is pretty great. Released in 2004, the film takes place in Hawaii and follows a veterinarian (Sandler) who crosses paths with a lovely young woman (Drew Barrymore) and has a pleasant day. But when he goes to follow up and ask her on a date the next day, she doesn’t remember who he is. As it turns out, she suffers from short-term memory loss, and her memory resets every day, so he spends the rest of the film winning her over day after day to try and strike up a relationship. It’s honestly extremely sweet, and Barrymore and Sandler have great chemistry. – Adam Chitwood
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We’re the Millers (2013)
Run Time: 1 hr 50 min | Director: Rawson Marshall Thurber
Cast: Jason Sudeikis, Jennifer Aniston, Emma Roberts, Will Poulter
We’re the Millers is a raunchy family comedy from director Rawson Marshall Thurber and writers Bob Fisher, Steve Faber, and Sean Anders. Jason Sudeikis (Ted Lasso) takes center stage as a slacker drug dealer tasked with transporting a large shipment of weed from Mexico across the border. Accompanying him on the criminal journey is a fake family he’s pulled together, hiring the local teens to pretend to be children of him and Rose (Jennifer Aniston), a stripper. Highlighted by a stellar cast, including Emma Roberts, Will Poulter, and Kathryn Hahn (WandaVision), and an uproariously ridiculous plot, We’re the Miller is unsurprisingly entertaining yet unexpectedly full of heart. – Yael Tygiel
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Father of the Bride (2022)
Run Time: 1 hr 57 min | Director: Gary Alazraki
Cast: Andy Garcia, Gloria Estefan, Adria Arjona, Diego Boneta
Andy Garcia (Ocean’s Eleven) and Gloria Estefan star in a hilarious modern update to the Father of the Bride film from 1991, which was a retelling of the 1950s version, based on the original novel from 1949. This latest iteration sees Garcia and Estefan comically attempting to hide the strain in their relationship, as well as their impending divorce, while they plan the wedding for their daughter (Adria Arjona). Adding to the Father of the Bride hijinks are the new in-laws who have traditions of their own, building opportunities for uncomfortably relatable comedy based on old-school family expectations. Father of the Bride is a much-needed update of the amusing comedy. – Yael Tygiel
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Let Them All Talk (2020)
Run Time: 1 hr 53 min | Director: Steven Soderbergh
Cast: Meryl Streep, Gemma Chan, Dianne Wiest, Candice Bergen
Three incredible powerhouses, Meryl Streep, Dianne Wiest, and Candice Bergen, enchantingly play Alice, Susan, and Roberta, respectively, in Steven Soderbergh’s Let Them All Talk. Let Them All Talk follows these three lifelong buddies as they head out on a cruise together to rekindle their bond – and hopefully heal old wounds. As Alice (Streep) attempts to work on her latest book, her nephew (Lucas Hedges) and her literary agent (Gemma Chan) join the trip, attempting to uncover details about her latest novel. With a clever script from first-time screenwriter Deborah Eisenberg, Let Them All Talk delicately explores complex themes like friendship, forgiveness, and staying connected through life changes. – Yael Tygiel
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French Dispatch (2021)
Run Time: 1 hr 47 min | Director: Wes Anderson
Cast: Benicio Del Toro, Adrien Brody, Tilda Swinton
Wes Anderson’s undeniably recognizable yet unique style, both aesthetically and script-wise, is commendable in the very Wes Anderson production, The French Dispatch. Bursting with huge celebrity names, including many of Anderson’s frequent collaborators like Adrien Brody (Succession) and Tilda Swinton (Avengers: Endgame), The French Dispatch is a fictional story set in a fictional French city, presenting on screen a collection of tales published in The French Dispatch Magazine. Anderson’s artistry with color and scenery, and his accumulation of talent without overwhelming audiences, is a testament to his dexterity in cinema, placing The French Dispatch impeccably beside his previous films. – Yael Tygiel
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The Heat (2013)
Run Time: 1 hr 57 min | Director: Paul Feig
Cast: Sandra Bullock, Melissa McCarthy, Michael McDonald
Uproarious director Paul Feig brings the humor to The Heat, a buddy cop comedy starring Sandra Bullock(The Lost City) and Melissa McCarthy(Nine Perfect Stranger) as an odd couple forced to team up to take down a drug lord. Bursting with physical comedy, at which both Bullock and McCarthy excel, The Heat is an underrated delight. Bullock’s uptight FBI agent feels like a culmination of her characters from Miss Congeniality 2 and The Proposal, while McCarthy’s loud and lewd Boston cop is a natural progression from her multitude of beloved over-the-top characters. Although the script from writer Katie Dippold is overly simple, the premise is cute and nonetheless enjoyable. – Yael Tygiel
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My Cousin Vinny (1992)
Run Time: 1 hr 59 min | Director: Jonathan Lynn
Cast: Joe Pesci, Ralph Macchio, Marisa Tomei
My Cousin Vinny is just so charming, so funny, so effortlessly smart. It deftly combines a couple of my favorite genres — the jargon-filled courtroom procedural and the screwball fish-out-of-water comedy — resulting in the kind of film it feels like they don’t make anymore. After two New Yorkers (Ralph Macchio and Mitchell Whitfield) are caught in the wrong place at the wrong time, getting arrested for the murder of an Alabama convenience store clerk, they call upon the service of Macchio’s cousin Vinny — a peerless Joe Pesci having the time of his life. Vinny is a lawyer, yes, but one who, like, just passed the bar and is used to small-stakes cases in Brooklyn, not straight up murder trials in such a different state. Watching Pesci jump through all the legal hoops with his unending, mildly grating form of charisma is entertainment of the highest caliber. And don’t get me started on the powerhouse that is Marisa Tomei’s performance. She won the Oscar for this thing (sigh, remember when the Oscars cared about comedy?), and her sparring/loving with Pesci is a two-hander for the ages. — Gregory Lawrence
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Tampopo (1985)
Run Time: 1 hr 54 min | Director: Juzo Itami
Cast: Tsutomu Yamazaki, Nobuko Miyamoto, Kōji Yakusho, Ken Watanabe, Rikiya Yasuoka
Anyone who enjoys eating food (in other words, everyone) absolutely must check out this 1985 gem from Japan which celebrates the act of eating in pretty much every way you can think of. Tampopo surrounds a central story of a woman striving to perfect her ramen recipe (aided by a young, dashing Ken Watanabe) with brief vignettes all centered around delicious, glorious food. It’s like if Kentucky Fried Movie really were about Kentucky Fried Chicken. The film offers a little bit of everything: thrills, cute kids, sex, gangsters… but above all, it’s hilarious. Just don’t try to watch it on an empty stomach.
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A Hard Day’s Night (1964)
Run Time: 1 hr 30 min | Director: Richard Lester
Cast: Paul McCartney, Ringo Starr, George Harrison, John Lennon, Wilfrid Brambell
The Beatles. What couldn’t they do? It should be enough that they got to be the best rock band ever. But no, it turns out they were really funny too. Richard Lester’s A Hard Day’s Night makes this clear, offering each of the Beatles (but especially Ringo) their own showcases to aver their personalities, acting skills, and comedy chops. Meanwhile, the film is filled with a ton of great songs to go with all the still-effective comedy bits. Lester and the band would team up again a year later for the broader Help!but this one is the gold standard rock and roll film for a reason.
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Safety Last! (1923)
Run Time: 1 hr 13 min | Director: Fred C. Newmeyer and Sam Taylor
Cast: Harold Lloyd, Mildred Davis, Bill Strother, Noah Young
You’re undoubtedly familiar with Charlie Chaplin and probably know a bit about Buster Keaton as well. Thanks to HBO Max, you can also become acquainted with another esteemed voice from the silent era, Harold Lloyd. Safety Last! offers a perfect place to start thanks to its iconic climax in which Lloyd hangs from the minute hand of a ticking clock. If you haven’t seen it, you’ve definitely seen something ripping it off. And even though the film is almost 100 years old, you’ll still marvel at how they pulled off the effect. But it’s not all daring clocktower stunts – the rest of the film is great as well. The plot focuses on a guy trying to make enough money in the big city to finally propose to his girlfriend, a pursuit that gets him into all kinds of trouble for our benefit. Lloyd has a unique everyman quality about him that is hard to dislike.
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The Hangover (2009)
Run Time: 1 hr 36 min | Director: Todd Phillips
Cast: Bradley Cooper, Ed Helms, Zach Galifianakis, Justin Bartha, Heather Graham, Ken Jeong, Rob Riggle, Mike Epps, Mike Tyson
The Hangoveris perhaps the most famous R-rated comedy to come out in their era of rebirth. The film follows three friends Phil (Bradley Cooper), Stu (Ed Helms), and Doug (Justin Bartha) who alongside Doug’s neurotic brother-in-law to be Alan (Zach Galifianakis) travel to Las Vegas for a bachelor party. Unfortunately the next morning they wake up horribly hungover with no recollection of the night before and worst of all Doug is missing. From drug-dealers, a tiger, Mike Tyson singing Phil Collins songs, a missing tooth, and the lost baby of a stripper, The Hangover is a celebration of debauchery in the City of Sin. – Nate Richard
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Shiva Baby (2020)
Run Time: 1 hr 18 min | Director: Emma Seligmann
Cast: Rachel Sennott, Molly Gordon, Polly Draper, Fred Melamed, Danny Deferrari, Jackie Hoffman
Shiva Baby follows Danielle (Rachel Sennott), a Jewish college senior who is secretly living a double-life as a sugar baby to Max (Danny Deferrari) after a break-up with her ex-girlfriend Maya (Molly Gordon). Her life begins to fall part when she is forced to attend a Shiva alongside her parents with Maya in attendance and to make matters even worse, Max is also there and is revealed to have a wife and kid. While Shiva Baby may sound like something more akin to newer teen comedies such as Booksmart, the way filmmaker Emma Seligmann directs Shiva Baby is insanely stressful and echos the Safdie Brothers style. – Nate Richard
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Wedding Crashers (2005)
Run Time: 1 hr 59 min | Director: David Dobkin
Cast: Owen Wilson, Vince Vaughn, Christopher Walken, Rachel McAdams, Isla Fisher, Jane Seymour, Bradley Cooper
Wedding Crashers is one of the main films that truly revitalized the R-rated studio comedy in a time when most comedies were made with a PG-13 rating in mind. Raunchy, vulgar, and while some of it has aged a bit poorly, that doesn’t preventWedding Crashers from being a modern comedy classic. Owen Wilson and Vince Vaughn star as John and Jeremy, two divorce mediators who crash weddings to have sex with all the love-hungry women. The two find their biggest opportunity yet when crashing the wedding of the daughter of the U.S. Secretary of the Treasury, where they meet the Secretary’s other daughters. Jeremy falls for the unhinged but lovable Gloria (Isla Fisher) while John sets his sights on the maid of honor Claire (Rachel McAdams). The two end up accompanying the family to a reunion on the family’s extravagant compound in Maryland. – Nate Richard
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