935 Best Comedy Movies to Watch (Page 19)

Need a chuckle? We know comedy gold can be hard to come by, so we’ve scoured the depths of the streaming landscape to dig it out. From dark humor to laugh-out-loud misadventures, these are the best comedies to stream now.

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271. The Watermelon Woman, 1996

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

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272. The Squid and the Whale, 2005

Director Noah Baumbach’s autobiographical film is a strikingly realistic take on divorce and the turmoil it sets on an already-dysfunctional family. Bernard (Jeff Daniels) is a selfish decadent writer who’s splitting with his unfaithful wife Joan (Laura Linney). Their two sons, Walt (Jesse Eisenberg) and Frank (Owen Kline), are taking different sides that reflect their personality. This separation only reinforces their insecurities as they quickly fall into depression and grow away from their friends. The parents, however, find unconventional lovers just as quickly, Bernard with a student of his, and Jane with her son’s tennis coach. The Squid and the Whale is a funny, emotional, and gripping story that finds a perfect balance in tone despite dealing with bitter divorce and troubled adolescence.

Genre: Comedy, Drama

Actor: Adam Rose, Alexandra Daddario, Andrew Kaempfer, Anna Paquin, Bobby Shue, Britta Phillips, David Benger, Dean Wareham, Eli Gelb, Elizabeth Meriwether, Emma Straub, Greta Kline, Halley Feiffer, James Hamilton, Jeff Daniels, Jesse Eisenberg, Jo Yang, Ken Leung, Laura Linney, Maryann Plunkett, Michael Countryman, Michael Santiago, Nico Baumbach, Owen Kline, Peggy Gormley, Peter Newman, William Baldwin

Director: Noah Baumbach

Rating: R

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273. The Sisters Brothers, 2018

This is a star-packed movie about two brother assassins played by John C. Reilly and Joaquin Phoenix, and starring Jake Gyllenhaal. You might have read the book of the same name, and it is always hard to make a great film out of a great book but the brilliant director of A Prophet Jacques Audiard has done it (again). He is aided by a superb darkly comic script and fantastic acting from the entire cast. Audiard is French, but his take on the American Western is filled with epic violence but also witty dialogue, brotherly love, and male camaraderie.Genre: Adventure, Comedy, Drama, Western
Actor: Aidan O'Hare, Aldo Maland, Allison Tolman, Andrew Litvack, Carol Kane, Creed Bratton, David Gasman, Diego Llano, Duncan Lacroix, Eric Colvin, Frédéric Siuen, Hugo Dillon, Ian Reddington, Jake Gyllenhaal, Jean-Marc Bellu, Joaquin Phoenix, Jochen Hägele, Jóhannes Haukur Jóhannesson, John C. Reilly, Kelda Holmes, Lenuta Bala, Lexie Benbow-Hart, Nick Cornwall, Patrice Cossonneau, Philip Rosch, Raymond Waring, Rebecca Root, Richard Brake, Riz Ahmed, Rutger Hauer, Sean Duggan, Theo Exarchopoulos, Trevor Allan Davies
Director: Jacques Audiard
Rating: R

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274. The Return of the Living Dead, 1985

Perfect for Halloween marathons with friends, The Return of the Living Dead treads the now well-worn template of zombie apocalypse movies with outstanding practical effects and a refreshingly unserious attitude. What the film might lack in terms of character writing or deeper themes, it more than makes up for with a relentless forward momentum. There isn't any grand mission to be accomplished when these morticians collide with a group of young punks, other than understanding what drives the undead creatures outside in order to survive the night. As a result, this is a movie that lives firmly in the moment, with thrills aplenty and its greatest moments found in the freaked-out reactions of its ensemble cast. The late James Karen, with his hilariously exaggerated hollering and whimpering, only nearly steals the show from the film's wonderful animatronics and disgusting prosthetic makeup. It's a great zombie movie for the reluctant horror newbie.

Genre: Comedy, Drama, Horror

Actor: Allan Trautman, Beverly Randolph, Brian Peck, Cathleen Cordell, Cherry Davis, Clu Gulager, David Bond, Don Calfa, Drew Deighan, James Dalesandro, James Karen, Jewel Shepard, John Durbin, John Philbin, Jonathan Terry, JR, Linnea Quigley, Mark Venturini, Michael Crabtree, Miguel A. Núñez, Miguel A. Núñez, Jr., Robert Craighead, Thom Mathews

Director: Dan O'Bannon

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275. The Outlaws, 2022

The Outlaws is an enjoyable BBC miniseries that centers on the lives and misadventures of seven lawbreakers sentenced to 120 hours of community service. The felons can’t be more different from each other, but as they gather every day to serve, they slowly bond in the process. It’s a bit like The Breakfast Club and The Good Place in that sense, although subplots of crime and heist make it a dash more thrilling.

The characters may appear as caricatures at first ("Everyone's a type," as one of them puts it), but don't be fooled: they're all nicely fleshed out with every episode, and each back story adds a new depth to the series. Stephen Merchant (co-creator of The Office UK) stars in, writes, and directs the series.

Genre: Comedy, Crime, Drama

Actor: Charles Babalola, Christopher Walken, Clare Perkins, Darren Boyd, Eleanor Tomlinson, Gamba Cole, Jessica Gunning, Rhianne Barreto, Stephen Merchant

Rating: TV-MA

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276. The Guard, 2011

The Guard played by Brendan Gleeson is a new character in cinema that appeals to the funny bone inside all of us. A character like this can make any movie lovable. It also features Don Cheadle playing an FBI agent who is in town to solve a crime under Gleeson's jurisdiction. An overall great movie with great writing. Please note, for those who have a hard time understanding different accents, subtitles are advised.

Genre: Action, Comedy, Crime, Mystery, Thriller

Actor: Brendan Gleeson, Conor Moloney, Darren Healy, David Pearse, David Wilmot, Dominique McElligott, Don Cheadle, Fionnula Flanagan, Gary Lydon, John Patrick Beirne, Katarina Čas, Laura Hitchings, Laurence Kinlan, Liam Cunningham, Liam O'Conghaile, Mark O'Halloran, Mark Strong, Mícheál Óg Lane, Owen Sharpe, Paraic Nialand, Pat Shortt, Ronan Collins, Rory Keenan, Sarah Greene, Wale Ojo

Director: John Michael McDonagh

Rating: R

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277. The Great Buster: A Celebration, 2018

In his last film, American Serb film historian Peter Bogdanovich celebrates silver screen legend Buster Keaton. The subject alone is compelling to watch. It would be easy to pull clips from Keaton’s works, dig through the headlines, pull in some celebrity interviews, and call it a day. However, in Bogdanovich’s hands, this documentary handles Keaton with respect. Instead of focusing on the scandals, Bogdanovich focuses on Keaton’s brilliant work. Instead of reciting facts, Bogdanovich highlights how his bits influenced film today. Excellent editing - cuts, structure, and scoring - helps us glide through Keaton’s work. The film truly understands Keaton’s life and exactly why he’s brilliant. Comprehensive yet very focused, this documentary honestly feels better than film school.

Genre: Comedy, Documentary, Drama

Actor: Ben Mankiewicz, Bill Hader, Bill Irwin, Buster Keaton, Carl Reiner, Cybill Shepherd, Dick Van Dyke, Eleanor Keaton, French Stewart, James Karen, Johnny Knoxville, Jon Watts, Leonard Maltin, Mel Brooks, Nick Kroll, Norman Lloyd, Orson Welles, Paul Dooley, Peter Bogdanovich, Quentin Tarantino, Richard Lewis, Tom Holland, Werner Herzog

Director: Peter Bogdanovich

Rating: Not Rated

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278. The Grand Seduction, 2013

The Grand Seduction, a remake of 2003 French-Canadian film La Grande Séduction (2003), is a lighthearted comedy about the residents of the small fishing village of Tickle Head, Newfoudland attempting to convince a young doctor to become its long-term caregiver in order to secure a contract for a new petrochemical facility. Desperate to guide the town out of its impoverished conditions and lack of employment opportunities, the citizens band together to pull ever bit out of deceit and chicanery out of their hats (in often laugh-out-loud fashion) in order to sway the young doctor Paul (Taylor Kitsch) into believing that Tickle Head is where he belongs. It’s a lighthearted and funny story, despite undeniably familiar shades of The Shipping News, Doc Hollywood and Funny Farm. Brendan Gleeson is particularly good as the new mayor of town and Paul’s head “seducer”. He gives the film that extra bit of humanity and wry humor that lifts it above the familiar plot points and into “notable recommendation” territory.Genre: Comedy
Actor: Brendan Gleeson, Cathy Jones, Gordon Pinsent, Janelle Hickey, Kevin Lewis, Lawrence Barry, Liane Balaban, Margaret Killingbeck, Mark Critch, Mary Walsh, Matt Watts, Michael Therriault, Natalia Hennelly, Percy Hynes White, Pete Soucy, Peter Keleghan, Sean Panting, Steve O'Connell, Taylor Kitsch
Director: Don McKellar
Rating: PG-13

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279. The Change, 2023

Initially, The Change’s premise might seem as eccentric as its kooky characters, but this comedy series set in ancient woods makes a compelling case for itself over six short episodes. When Linda (writer Bridget Christie) is diagnosed as menopausal, it triggers a flash of clarity: she’s tired of being reduced to “wife” and “mother.” Depressed by all her ledgers recording every second she’s spent doing unappreciated housework, Linda decides to reclaim a few thousand minutes, and takes off on her motorbike to the Forest of Dean to look for the time capsule of cherished belongings she hid there as a child following her mother’s death.

Because this motivation is only explained later, the show has a somewhat perplexing beginning, but a couple of episodes in, it finds its footing. The Change makes sharp punchlines out of boorish man-children — and, although it has varying success getting laughs out of its more bigoted characters, it does decenter them and dole out acceptance to the overlooked, making it refreshingly divergent from “topical” comedies’ usual flippancy. The spiritual link it draws between its apparently unrelated focuses — menopause and the natural environment — adds to its originality and empathy, making this a comedy of untypical thoughtfulness.

Genre: Comedy, Drama

Actor: Bridget Christie, Monica Dolan

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280. Teenage Bounty Hunters, 2020

With the deluge of hyper-stylized teen shows everywhere (but especially on Netflix), Teenage Bounty Hunters comes as a refreshing and welcome surprise. Sisters Blair and Sterling, played by Anjelica Bette Fellini and Maddie Phillips respectively, strike the perfect balance between spiky and endearing, creating a chemistry that’s rare to see among TV siblings. There’s friction but also love all around.

Their interactions alone make the series thoroughly enjoyable, but their coming-of-age hijinks and comedic timing, especially around their reluctant mentor Bowser (Kadeem Hardison), make it an absolute must-watch. If you enjoyed Booksmart but wished it was more action-packed, you'll surely love this show.

Genre: Action & Adventure, Comedy, Drama

Actor: Anjelica Bette Fellini, Charity Cervantes, Devon Hales, Eric Graise, Kadeem Hardison, Mackenzie Astin, Maddie Phillips, Method Man, Myles Evans, Shirley Rumierk, Spencer House, Virginia Williams, Wynn Everett

Rating: TV-MA

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281. Swarm, 2023

Created by Janine Nabers and Donald Glover (Atlanta), Swarm is a dark and bloody deep dive into fan culture. It follows Dre (Dominique Fishback), a young woman whose obsession with a Beyoncé stand-in takes a dark turn after the unexpected death of a loved one.

Artful, daring, and legitimately scary, Swarm is one of the bolder shows to come to streaming in a while. It doesn’t hold back, not with the commentary nor with the blood, which can be too much for some viewers, but if you were thrilled by films like Misery and The King of Comedy, then this mind-blowing take on celebrity mania will certainly have you hooked.

Genre: Comedy, Crime, Drama, Horror

Actor: Dominique Fishback

Rating: TV-MA

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282. Such Brave Girls, 2023

In an early scene in Such Brave Girls, Josie (Kat Sadler) compares herself and her sister Billie (Lizzie Davidson) to a more attractive woman. “She’s live, love, laugh,” she says, “We’re death, silence, hate.” At this point, you’d think Sadler, who is also the creator and writer of the show, and Davidson, who is Sadler’s real-life sister, are the types to indulge in their sadness and romanticize their dysfunction. Though that happens to some degree, Sadler is self-aware enough to steer clear of wallow territory and offer something insightful about mental health and the ways we cope (or fail to, anyway). Parents who dismiss depression are called out, as are social workers and supposed experts who stereotype people with the illness. But weirdly enough, the show is never downright cynical. Josie is sweet enough to cut through the darkness, as are her ignorant and selfish though ultimately well-meaning family members. You’ll probably recall Broad City and Fleabag while watching Such Brave Girls because of its unapologetic approach to both sex and suicide, but maybe more than those two shows, Such Brave Girls is willing to root its themes deeper into reality. It almost never brings up mental health without contextualizing it in the family’s low-income state, making it one of the most relatable and urgent shows you can watch right now.Genre: Comedy, Drama
Actor: Freddie Meredith, Kat Sadler, Lizzie Davidson, Louise Brealey, Paul Bazel
Rating: TV-MA

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283. Slacker, 1991

The walk-and-talk roots of the Before Trilogy are traceable to this low-budget cult movie from writer-director Richard Linklater, which came five years before our first introduction to Celine and Jesse. Rather than follow a single, winding conversation, though, Slacker hops from character to character every few minutes, and we never meet them again. In fact, we rarely even learn their names, which makes the credits a particular pleasure to watch as it identifies cast members with wry monikers like “Dostoyevsky wannabe,” “Ultimate loser,” and “Scooby Doo philosopher.”

Shot in Linklater’s adopted hometown of Austin, Texas, the movie captures the city’s uniquely alternative vibe — or, as one character succinctly puts it, “This town has always had its share of crazies.” Conversations range from the spaced-out to the flat-out paranoid, a fair amount of the movie’s ragtag band being partial to conspiracy theories, from the well-worn (JFK's death) or the more bizarre (the real meaning behind The Smurfs). With its freewheeling approach to narrative, Slacker shares the lovable weirdness of its characters, as attested to by its enduring status as a cult classic.

Genre: Comedy, Drama

Actor: Athina Rachel Tsangari, Bob Boyd, Charles Gunning, Clark Walker, D. Montgomery, Deborah Pastor, Kim Krizan, Mark James, Richard Linklater, Robert Jacks, Tommy Pallotta

Director: Richard Linklater

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284. Sherman’s Showcase, 2020

Reminding us that there's so much more to American sketch comedy than Saturday Night Live, Sherman's Showcase transports us into a bizarre variety show run by an egomaniacal host, where all the laws of space and time seem to be broken. It's all ultimately very silly, but the jokes that this mock-variety series pulls out of nowhere are so funny because of how unexpected they are—lampooning every niche of the entertainment industry with pure confidence in every line. But even if you don't get the humor here, Sherman's Showcase remains a delight to watch just because of the imagination poured into the performances. There are dancers aplenty and novelty songs done in countless styles that stand strong on their own as great music.

Genre: Comedy, Music

Actor: Bashir Salahuddin

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285. Rushmore, 1998

If it weren’t for his knack for writing, Max Fischer (Jason Schwartzman) would never have gotten into a prep school like Rushmore. But his art secures him a scholarship, and what he lacks in smarts and money, he makes up for in school pride. As he flunks more and more of his academics, however, he is eventually kicked out, and it’s outside the halls of his beloved Rushmore, stripped of all titles and insignia, where he learns to be his true self.

As the film’s comedic and emotional core, Schwartzman is a revelation as the ambitious and sharp-tongued Max. Equally captivating is Bill Murray’s deadpan but lovable turn as Max’s millionaire friend, Herman Blume. It’s a role so fitting, in fact, that the poor-rich-man character will follow Murray well into his career, long after the curtains close on Mr. Blume. Meanwhile, Wes Anderson will go on to do more colorful and stylized pictures than Rushmore, but thanks to its unbeatable wit and down-to-earth charm, the film remains to be one of the auteur’s most delightful and hilarious works to date.

Genre: Comedy, Drama

Actor: Alexis Bledel, Andrew Wilson, Antoni Scarano, Bill Murray, Brandon Trost, Brian Cox, Brian Tenenbaum, Connie Nielsen, Dipak Pallana, Ed Geldart, Eric Chase Anderson, George Farish, Jason Schwartzman, Jason Trost, Kim Terry, Kumar Pallana, Lucille Sadikin, Luke Wilson, Marietta Marich, Mason Gamble, Morgan Redmond, Olivia Williams, Paul Schiff, Sara Tanaka, Seymour Cassel, Stephen Dignan, Stephen McCole, Wallace Wolodarsky

Director: Wes Anderson

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