4 excellent HBO Max comedies to watch this weekend (July 24-26)

Lucas Gouveia/How-To GeekCredit: Lucas Gouveia/How-To Geek Published Jul 24, 2026, 1:00 PM EDT Derek Malcolm has been covering the worlds of tech and entertainment for more than two decades. Before coming to How-To Geek in 2025, Derek was a contributing editor and writer for the A/V and Home Theater section at Digital Trends, where he wrangled and wrote everything from what to watch on Netflix to reviews, explainers, and guides on the latest Bluetooth speakers, turntables, projectors, and other A/V gear. Based in Toronto, Derek graduated from Humber College's Journalism program in 1999, after which he started covering the worlds of music, movies, TV, and celebrity for publications such as TV Guide, Hello! magazine, and Inside Entertainment. He then got the bug for covering tech and gadgets in 2006, when he served as editor-in-chief of Canadian tech magazine Connected for more than a decade. An avid skier, when all the snow's gone Derek can be found at home spinning vinyl with his daughter or cheering on his favorite F1 team, McLaren. Sign in to your How-To Geek account For more than five decades, HBO/HBO Max has mastered the serious business of fire-breathing dragons, drug warfare, and gangsters sleeping with the fishes. But when you scroll past all that brooding, though, you'll find the service is also quietly stacked with all kinds of comedies, and right now, U.S. subscribers have four of them right at their fingertips for a weekend full of laughs. After a quick scour, I've pulled a handful for you, including a pink-clad legal underdog (who has a new series on Prime Video), a pair of moronic professional wedding guests, a mouthy mercenary who can't die, and my top pick, a mockumentary about a band that goes to 11. 4 Legally Blonde Elle Woods conquers Harvard law It's crazy, but Legally Blonde turned 25 this month, in a year when its pop culture legacy grew exponentially with the addition of its prequel series, Elle, which just premiered on Prime Video this month. The original 2001 box office hit, based on Amanda Brown's novel of the same name, was groundbreaking for stomping on the "dumb blonde" trope, and celebrated femininity as a strength instead of a weakness. Reese Witherspoon, in a Golden Globe-nominated role, stars as Elle Woods, a California college girl who's been dumped by her Harvard-bound boyfriend, Warner (Matthew Davis), for not being serious enough. To win him back, Elle sets her mind to getting into Harvard Law, where she discovers not only that Warner is a jackass, but that she's a formidable legal mind, landing a spot in defending a fitness mogul (Ali Larter) in her murder trial. The cast is absolutely stacked, too, and includes Selma Blair as Marner's equally-jerky girlfriend Vivian, Victor Garber as shady law Professor Callahan, Luke Wilson as kind-hearted attorney Emmett, and Jennifer Coolidge's as scene-stealing manicurist Paulette. Legally Blonde Release Date July 13, 2001 Runtime 96 minutes Cast Luke Wilson Emmetten Richmond Reese Witherspoon Elle Woods Selma Blair Vivian Kensington Matthew Davis Warner Huntington III Director Robert Luketic Writers Karen McCullah, Kirsten Smith Producers Marc Platt, Ric Kidney Main Genre Comedy 3 Wedding Crashers A Vince Vaughn and Owen Wilson classic comedy Another defining comedy of the 2000s, Wedding Crashers just passed its 20th anniversary amidst renewed chatter from its stars about a long-rumored sequel. And I, for one, am here for any resurgence of the lost art of the mid-budget R-rated comedies (think Old School, Superbad) that once ruled the box office. The dynamic duo of Owen Wilson and Vince Vaughn star as John and Jeremy, a pair of divorce mediators jaded by failed marriages, who frequently crash weddings for the free booze and endless assortment of bridesmaids for no-strings romance. But the womanizing pair get more than they bargain for when they attend "the wedding event of the year," hosted by Treasury Secretary William Cleary (Christopher Walken), and John falls hard for his daughter, Claire (Rachel McAdams). Jeremy, on the other hand, is saddled with Claire's psychotic "stage-five clinger" sister, Gloria (the hilarious Isla Fisher). Will Ferrell makes a legendary cameo and Bradley Cooper is dementedly creepy as Claire's unhinged boyfriend, Sack. Wedding Crashers Release Date July 13, 2005 Runtime 119 minutes Cast Owen Wilson John Beckwith Christopher Walken Secretary Cleary Rachel McAdams Claire Cleary Director David Dobkin Writers Steve Faber, Bob Fisher Producers Andrew Panay, Peter Abrams, Robert L. Levy Budget $40 Million Studio(s) New Line Cinema Distributor(s) New Line Cinema Executive Producer(s) Cale Boyter, Guy Riedel, Richard Brener, Toby Emmerich 2 Deadpool 2 Maximum effort, zero respect for the fourth wall The middle chapter of Ryan Reynolds’ excellent Deadpool trilogy, Deadpool 2 sits between the 2016 original—the one that proved an f-bomb slinging superhero could carry a blockbuster—and 2024's epic Deadpool & Wolverine, which finally merged the iconic Merc with a Mouth into the MCU. After finally running down Francis in the first instalment, Deadpool 2 finds the unkillable mercenary Wade Wilson (Ryan Reynolds) reeling from the death of his fiancée Vanessa (Morena Baccarin) and reluctantly protecting Russell (Julian Dennison), a volatile young mutant hunted by Cable (Josh Brolin), a time-traveling soldier on a kind of Terminator-style mission. Quiz 8 Questions · Test Your KnowledgeName that iconic comedy movieTrivia challenge From fake rockumentaries to time loops — can you identify these classic comedies from a single clue? Cult ClassicsCharactersPlot CluesQuotesDirectors Begin A bumbling TV news anchor in San Diego loses his job after a disastrous on-air incident, then must win back his career — and the woman he loves. What movie is this? ATalladega NightsBBlades of GloryCAnchormanDBruce Almighty Correct! Anchorman: The Legend of Ron Burgundy (2004) launched Will Ferrell's big-screen comedy career and gave us the unforgettable Ron Burgundy. The film became a cult classic and spawned a 2013 sequel. Not quite — the answer is Anchorman (2004). Will Ferrell plays Ron Burgundy, a pompous 1970s TV newsman whose world is turned upside down when Veronica Corningstone, played by Christina Applegate, joins his team. Continue Which film features the iconic line: 'I'm not even supposed to be here today!'? AClerksBOffice SpaceCMallratsDDogma Correct! Clerks (1994) is Kevin Smith's debut film, shot in black and white on a shoestring budget of around $27,000. Dante Hicks delivers that classic line repeatedly throughout the day he wasn't supposed to work. Not quite — that line belongs to Clerks (1994), director Kevin Smith's debut feature. Dante Hicks, who works at a convenience store on his day off, repeats the phrase like a mantra throughout his increasingly chaotic shift. Continue A hapless office worker discovers his life is literally a television show watched by millions, and begins to question everything around him. Which comedy-drama is this? AEdTVBThe Truman ShowCGroundhog DayDLiar Liar Correct! The Truman Show (1998) stars Jim Carrey as Truman Burbank, a man who has unknowingly lived his entire life on a giant TV set. Directed by Peter Weir, the film was both a critical and commercial hit. That's not it — the answer is The Truman Show (1998). Jim Carrey plays Truman Burbank, whose entire existence has been broadcast live since birth. EdTV came out just a year later with a similar premise but far less impact. Continue This mockumentary follows a fictional heavy metal band on a disastrous US tour, featuring an amp that 'goes to eleven.' Which film is it? AWalk Hard: The Dewey Cox StoryBSchool of RockCAlmost FamousDThis Is Spinal Tap Correct! This Is Spinal Tap (1984) was directed by Rob Reiner and largely improvised by its cast. It essentially invented the mockumentary genre and remains one of the most quoted comedies ever made. Not quite — the answer is This Is Spinal Tap (1984). Rob Reiner directed this pitch-perfect parody of rock excess, and the 'goes to eleven' scene became one of cinema's most beloved comic moments. Continue In which comedy does a man relive the same day over and over again while stuck in a small town covering a weather event he despises? A50 First DatesBGroundhog DayCThe Invention of LyingDClick Correct! Groundhog Day (1993) stars Bill Murray as cynical weatherman Phil Connors, trapped in Punxsutawney, Pennsylvania. Directed by Harold Ramis, the film has since become a philosophical touchstone about self-improvement. Not quite — the answer is Groundhog Day (1993). Bill Murray plays Phil Connors, a grumpy TV weatherman stuck in a time loop in Punxsutawney. The concept was so culturally impactful that 'Groundhog Day' is now a common phrase. Continue An airline flight descends into chaos when food poisoning strikes the crew, leaving a nervous wreck of a former pilot as the only person who can land the plane. Name that movie. AHot Shots!BFletchCAirplane!DTop Secret! Correct! Airplane! (1980) was directed by the Zucker-Abrahams-Zucker team and is widely considered one of the funniest films ever made. It relentlessly parodies disaster films and packs in more jokes per minute than almost any other comedy. Not quite — the answer is Airplane! (1980). This classic spoof was written and directed by Jerry Zucker, Jim Abrahams, and David Zucker. It launched Leslie Nielsen's second career as a deadpan comedy icon. Continue Which film includes the line: 'We're on a mission from God,' spoken by two brothers reuniting a blues band to save an orphanage? AWayne's WorldBThe Blues BrothersCSpaceballsDAnimal House Correct! The Blues Brothers (1980) stars John Belushi and Dan Aykroyd as Jake and Elwood Blues. Directed by John Landis, the film features an all-star musical cast and one of the most elaborate car chase sequences in comedy history. Not quite — that line is from The Blues Brothers (1980). John Belushi and Dan Aykroyd play Jake and Elwood, who use their divine mission as justification for a spectacular trail of mayhem across Chicago. Continue A group of medieval English knights embark on a ridiculous quest, battling killer rabbits and taunting Frenchmen along the way. What is this film? AErik the VikingBMonty Python and the Holy GrailCTime BanditsDJabberwocky Correct! Monty Python and the Holy Grail (1975) was made on a tiny budget with coconut shells standing in for horses. It remains one of the most quoted comedies in history and launched the Monty Python troupe to international fame. Not quite — the answer is Monty Python and the Holy Grail (1975). Made by the legendary British comedy group, the film parodies Arthurian legend with absurdist brilliance. Jabberwocky was also a Terry Gilliam medieval comedy, which makes it a sneaky wrong answer! See My Score Challenge CompleteYour Score / 8 Thanks for playing! Try Again Wade's answer is X-Force, a hilariously doomed super team whose skydiving debut is an all-time great comic book movie gag. Director David Leitch (Atomic Blonde, Bullet Train) keeps the action as sharp as the fourth-wall breaks. Deadpool 2 Release Date May 15, 2018 Runtime 120 minutes Cast Ryan Reynolds Wade Wilson / Deadpool / Juggernaut (voice) Director David Leitch Writers Rob Liefeld, Fabian Nicieza, Rhett Reese, Paul Wernick Producers Lauren Shuler Donner, Ryan Reynolds, Simon Kinberg Prequel(s) Deadpool Sequel(s) Deadpool & Wolverine Franchise(s) Deadpool, Marvel Main Genre Action Budget $110 million Studio(s) Marvel Entertainment, TSG Entertainment, Kinberg Genre, Maximum Effort, The Donners' Company Distributor(s) 20th Century Fox Executive Producer(s) Aditya Sood, Ethan Smith, Jonathon Komack Martin, Kelly McCormick, Paul Wernick, Rhett Reese, Stan Lee 1 This is Spinal Tap The greatest mockumentary this side of Cleveland They sang songs about women with big bottoms, their drummers kept dying in freak accidents, and, of course, their amps went to 11 (one louder than 10), but none of that prevented the Library of Congress' National Film Registry from adding This is Spinal Tap to its listing. The late Rob Reiner's 1984 directorial debut is the blueprint for every mockumentary that came after it—no Spinal Tap, no A Mighty Wind or The Office—and is a must-watch comedy. Reiner plays documentarian Marty DiBergi, who's tagging along with "one of England's loudest bands" on their American tour, as David St. Hubbins (Michael McKean), Nigel Tufnel (Christopher Guest), and Derek Smalls (Harry Shearer) combat canceled gigs, an album cover too offensive to print, and a disastrous tiny Stonehenge stage prop. With dialogue that was largely improvised, it's a classic that keeps getting better with age (unlike the band). This is Spinal Tap Release Date March 2, 1984 Runtime 82 minutes Cast Christopher Guest Nigel Tufnel Michael McKean David St. Hubbins Harry Shearer Derek Smalls Director Rob Reiner Writers Christopher Guest, Harry Shearer, Michael McKean, Rob Reiner Producers Karen Murphy Main Genre Comedy Get your laugh on this weekend How ever your weekend shapes up, some laughs should always be on the agenda, and hopefully at least one of these four movies will provide them. If you're looking for more suggestions, however, How-To Geek's other streaming guides can line up your next watch. Subscription with ads Yes, $10.99/month Simultaneous streams 2 or 4 HBO Max is a subscription-based streaming service offering content from HBO, Warner Bros., DC, and more. In 2025, the service re-branded itself as HBO Max after having previously cut "HBO" from its name. Live TV Live sports available in Standard and Premium plans Price Starting at $10.99/month or $109.99/year