7 Best Grown-up Comedy Movies On Max (HBO Max)

Staff & contributors

Looking for a chuckle? Kids will laugh at anything, but a good adult-friendly comedy can be harder to come by. From laugh-out-loud misadventures to inky black humor, here are the best grown-up comedies to stream right now.

, 2011

It might seem like a no-brainer that trying to make a comedy movie featuring a character with cancer is not a great idea. And while there may be a good share of failed attempts in that category, 50/50 is not one of them. And then it might come as a surprise that this subtle attempt at cancer comedy comes courtesy of Superbad creators Seth Rogen and Evan Goldberg. It also stars indie cutie Joseph Gordon-Levitt as the young and fit Adam Lerner, who works as a writer for public radio before learning that he has malignant tumors all along his spine. Between his overbearing mum (Anjelica Huston), slightly obnoxious but good-hearted bestie (Seth Rogen), self-help groups, and his therapist (played by Anna Kendrick), he struggles to find a way of acquiescing to his 50/50 chance of survival. Similarly, 50/50 strikes a delicate balance between the bromance gags, the date-movie elements, and the grave subject matter at its heart. It manages to mine humor, pathos, and simple honesty from a dark situation, and is not afraid to “go there”. The result is truly compassionate comedy.

Genre: Comedy, Drama

Actor: Adrian Glynn McMorran, Amitai Marmorstein, Andrea Brooks, Andrew Airlie, Anjelica Huston, Anna Kendrick, Beatrice King, Brent Sheppard, Bryce Dallas Howard, Cameron K. Smith, Chilton Crane, Christopher De-Schuster, D.C. Douglas, Daniel Bacon, Donna Yamamoto, Jason Vaisvila, Jessica Parker Kennedy, Jonathan Levine, Joseph Gordon-Levitt, Laura Bertram, Lauren Miller, Luisa D'Oliveira, Marie Avgeropoulos, Matt Frewer, Matty Finochio, P. Lynn Johnson, Peter Kelamis, Philip Baker Hall, Sarah Smyth, Serge Houde, Seth Rogen, Stephanie Belding, Stephen Colbert, Sugar Lyn Beard, Tom MacNeill, Veena Sood, Will Reiser, William 'Big Sleeps' Stewart, Yee Jee Tso

Director: Jonathan Levine

Rating: R

This drama was the first feature written and directed by an out Black lesbian, Cheryl Dunye, and it is an absolute joy: a cheeky faux-documentary that ingeniously blends lesbian dating life with a historical dive into Black actors in 30s Hollywood.

Dunye plays Cheryl, a self-effacing version of herself, an aspiring director working at a video store who begins to research an actress known as the Watermelon Woman for a documentary. The more Cheryl dives into her research, the more she sees parallels between her subject and her own relationship. 

As incisive as it is funny, The Watermelon Woman shares some common ground with other major indie debuts of the era like Spike Lee’s She’s Gotta Have It and funnily enough Kevin Smith’s Clerks, but Dunye’s style is wholly her own and a dazzling treat to experience.

 

Genre: Comedy, Drama, Romance

Actor: Brian Freeman, Camille Paglia, Cheryl Clarke, Cheryl Dunye, David Rakoff, Guinevere Turner, Irene Dunye, Lisa Marie Bronson, Sarah Schulman

Director: Cheryl Dunye

The Square is a peculiar movie about a respected contemporary art museum curator as he goes through a few very specific events. He loses his wallet, his children fight, the art he oversees is does not make sense to an interviewer... Each one of these events would usually require a precise response but all they do is bring out his insecurities and his illusions about life. These reactions lead him to very unusual situations. A thought-provoking and incredibly intelligent film that's just a treat to watch. If you liked Force Majeure by the same director, The Square is even better!

Genre: Drama

Actor: Anna-Stina Malmborg, Annica Liljeblad, Christopher Læssø, Christopher Laesso, Claes Bang, Daniel Hallberg, Denise Wessman, Dominic West, Elijandro Edouard, Elisabeth Moss, Emelie Beckius, Geica Pruteanu, Jan Lindwall, Johan Jonason, John Nordling, Julia Sporre, Lilianne Mardon, Linda Anborg, Lise Stephenson Engström, Lise Stephenson Engström, Madeleine Barwén Trollvik, Marina Schiptjenko, Martin Sooder, Moa Enqvist Stefansdotter, Nicki Dar, Pauline Hansson, Peter Vitanen, Sarah Giercksky, Sofie Hamilton, Stefan Godicke, Terry Notary

Director: Ruben Östlund

Rating: R

"Imagine a nightmare when you had to relive your adolescence," says Cecilia Aldarondo at the beginning of her third film, You Were My First Boyfriend. Indeed, the scene recalls a teen prom that could easily be yours (if you were one of the unpopular girls): neon lights, prettier dresses that are never yours, disapproving looks, and the impression that everyone around you is having the time of their lives, while you sit awkwardly in a corner. This image sets the tone for a self-exploration in documentary form that relies on a simple, yet imaginative premise, what if you could re-enact the formative events from back then, but do so today, by directing actors to step in for your past selves. Aldarondo approaches the topic sincerely and with curiosity. Not a pang of nostalgia there, but the heartfelt doc manages to reflect on the pasts that shape us in a witty way to promote self-acceptance and, ultimately, healing.

Genre: Documentary, Drama

Actor: Cecilia Aldarondo, Gabriel Kristal, Laura Gallegos, Melissa Baker, Sarah Baker Butterfield

Director: Cecilia Aldarondo

Rating: PG

If you're a fan of musical theater of any kind, Topsy-Turvy pays tribute to that notoriously tricky art form with a stunning attention to detail and a dedication to telling its story without any unnecessary drama whatsoever. It's hard not to get swept up in the humor, entertainment, and simple joy found in the writing process and in rehearsals of entire scenes. Come for the Oscar-winning costumes and makeup, stay for the wonderfully old-timey musical numbers, the brilliantly grounded performance from Jim Broadbent, and the sense of satisfaction of just watching everything finally come together to thunderous applause.

Genre: Comedy, Drama, History, Music

Actor: Adam Searles, Akemi Otani, Alison Steadman, Allan Corduner, Andy Serkis, Angela Curran, Anna Francolini, Ashley Artus, Ashley Jensen, Bríd Brennan, Cathy Sara, Charles Simon, David Neville, Debbie Chazen, Dexter Fletcher, Dorothy Atkinson, Eiji Kusuhara, Eleanor David, Eve Pearce, Francis Lee, Gary Yershon, Gemma Page, Geoffrey Hutchings, Heather Craney, Jim Broadbent, John Warnaby, Jonathan Aris, Julia Rayner, Julian Bleach, Kacey Ainsworth, Kate Doherty, Katrin Cartlidge, Keeley Gainey, Kenneth Hadley, Kevin McKidd, Lavinia Bertram, Lesley Manville, Lorraine Brunning, Louise Gold, Mark Benton, Martin Savage, Mary Roscoe, Matt Bardock, Matthew Mills, Mia Soteriou, Michael Simkins, Michelle Chadwick, Monica Dolan, Naoko Mori, Nicholas Boulton, Nicholas Woodeson, Nick Bartlett, Paul Barnhill, Paul Rider, Richard Attlee, Richard Coyle, Roger Heathcott, Ron Cook, Rosie Cavaliero, Sam Kelly, Sarah Howe, Shirley Henderson, Sophie Duval, Stefan Bednarczyk, Steve Speirs, Sukie Smith, Teresa Gallagher, Theresa Watson, Timothy Spall, Togo Igawa, Vincent Franklin, Wendy Nottingham

Director: Mike Leigh

By all appearances, Eliza and Louis have a charming marriage. They’re casual and good-humored in the morning and full of passion in the evening. So when Eliza finds a love note addressed to her husband one day, naturally, she freaks out. She enlists the help of her eccentric family and sets off to Manhattan, where they all try to get to the bottom of the affair; what follows is an endearingly awkward adventure around town.

Though the film often meanders both in plot and dialogue, the expert ensemble keeps things compelling with their convincing chemistry and wry, visual humor. Coupled with lush images of ‘90s New York and brilliantly droll writing, The Daytrippers is a joyride of a film, as unassuming as it is enthralling. 

Genre: Comedy, Drama, Family, Mystery

Actor: Adam Davidson, Amy Stiller, Anne Meara, Campbell Scott, Carol Locatell, Douglas McGrath, Hope Davis, Liev Schreiber, Marc Grapey, Marcia Gay Harden, Marcia Haufrecht, Parker Posey, Pat McNamara, Paul Herman, Peter Askin, Stanley Tucci, Stephanie Venditto

Director: Greg Mottola

Rating: R

, 2017

This fun drama is about a 90-year-old who’s still searching for answers to life’s existential questions. Lucky smokes, drinks, and is pretty angry (a not-so-chill atheist); but he’s still around.

Harry Dean Stanton, in what feels like an extension to his character Lucky, passed away a year after the film premiered in 2017. This was the last role of the legendary Alien and The Godfather actor.

Genre: Drama

Actor: Ana Mercedes, Barry Shabaka Henley, Bertila Damas, Beth Grant, David Lynch, Ed Begley Jr., Harry Dean Stanton, Hugo Armstrong, James Darren, Ron Livingston, Tom Skerritt, Yvonne Huff

Director: John Carroll Lynch

Rating: Not Rated