121 Best Dark Comedies Movies to Watch (Page 6)

Staff & contributors

This is an inexplicably and philosophically dark comedy.

Its protagonist, Larry, is a lackluster professor at a dull university. Then his life starts to unravel: his wife decides to leave him for one of his more successful colleagues; his unemployed brother moves in to stay on his couch.

So Larry ventures on a quest for meaning and clarity within his Jewish community.

All Cohen Brothers fans will appreciate the movie's aesthetics and comedic strength. The protagonist’s struggle will resonate with anyone who has had a religious upbringing: guilt is a big theme here.

I felt like I had to rewatch it to understand it. But I also enjoyed that weird sense of not understanding everything that's going on. Much like life itself.

The film rightfully earned itself two nominations for the Oscars, including Best Picture.

Genre: Comedy, Drama

Actor: Aaron Wolff, Adam Arkin, Alan Mandell, Allen Lewis Rickman, Amanda Day, Amy Landecker, Brent Braunschweig, Claudia Wilkens, Fred Melamed, Fyvush Finkel, George Wyner, James Cada, Jessica McManus, Joel Thingvall, Katherine Borowitz, Landyn Banx, Michael Lerner, Michael Stuhlbarg, Peter Breitmayer, Punnavith Koy, Raye Birk, Richard Kind, Sari Lennick, Scott Thompson Baker, Simon Helberg, Stephen Park, Steve Park, Tim Russell, Tyson Bidner, Yelena Shmulenson

Director: Ethan Coen, Joel Coen

Rating: R

Elisabeth Moss is in it. Calling The One I Love a romantic-comedy, looking it up, or trusting anyone else about it -- especially my review, will ruin this film for you. Just watch it. If one's penchant is typically opposed to titles with 'love' in them, then it's for you. Just hit 'play', or 'start', or whatever. The initial wtf-ness that attracted me to it is compelled further by excellent acting. And Elisabeth Moss is in it.

Genre: Comedy, Drama, Romance

Actor: Charlie McDowell, Elisabeth Moss, Jennifer Spriggs, Kiana Cason, Mark Duplass, Marlee Matlin, Mary Steenburgen, Mel Eslyn, Sean O'Malley, Ted Danson

Director: Charlie McDowell

Rating: R

In this office comedy of errors, Javier Bardem plays Blanco, the titular boss, but whether he is actually good is what the movie wryly examines.

As head of a small manufacturing company, Blanco treats his employees intimately, going so far as make their problems his own. He believes this is why his company is nominated for an excellence certification, but as he waits for the possible award, cracks start to appear in his “work is family” facade as everything that could go wrong, starts going wrong. The Good Boss is an anxiety fest for Blanco to be sure, but a winning tragicomedy for us all.

Genre: Comedy, Drama

Actor: Almudena Amor, Celso Bugallo, Daniel Chamorro, Fernando Albizu, Francesc Orella, Javier Bardem, Manolo Solo, Mara Guil, María de Nati, Nao Albet, Óscar de la Fuente, Rafa Castejón, Sonia Almarcha, Tarik Rmili, Yaël Belicha

Director: Fernando León de Aranoa

Rating: Not Rated

Lee Holloway (Maggie Gyllenhaal) is compassionate and diminutive, but her social awkwardness hinders her as she attempts to navigate young adulthood. After recently being hospitalized for self-harm, Lee is determined to prove she is capable of autonomously taking care of herself. She begins working as a secretary for E. Edward Grey (James Spader), a meticulous attorney.

It’s not long before both Lee and Edward realize they’re attracted to one another’s opposite natures: Lee’s obedience and Edward’s dominance. They begin a mutually consensual BDSM relationship, with both experiencing a sexual and emotional awakening. 

The premise may sound familiar: 50 Shades of Grey is widely acknowledged as, at the very least, owing its title to Secretary. But while 50 Shades of Grey portrays an unhealthy, toxic, and superficial idea of a BDSM affair, Secretary maintains that consent must be at the core of any relationship. And ultimately for Lee and Edward, BDSM becomes a way for them to communicate and overcome their individual pain, and unite stronger as a vulnerable, loving whole.

Genre: Comedy, Drama, Romance

Actor: Alison Tatlock, Amy Locane, Christina Gray, David Wiater, Diane McGee, Erin Cressida Wilson, Ezra Buzzington, Herbert Russell, James Spader, Jeremy Davies, Jessica Tuck, Julene Renee, Kyle Colerider-Krugh, Lacey Kohl, Lauren Cohn, Lesley Ann Warren, Lily Knight, Maggie Gyllenhaal, Mary Joy, Michael Mantell, Osgood Perkins, Oz Perkins, Patrick Bauchau, Sabrina Grdevich, Shannon Convery, Stephen McHattie, Steven Fierberg, Steven Shainberg

Director: Steven Shainberg

Rating: R

A young Steve Buscemi leads this wry farce about a calamitous film set where nothing goes right. The sardonic script skewers the ins and outs of low budget film production and the various personalities on set from belligerent directors, pretentious cinematographers, and egotistic actors. 

A playful three-act structure and trips into dream sequences keep things light, while a strong supporting cast, including a cheeky appearance by Peter Dinklage and the fantastic Catherine Keener, gives the film the backbone it needs. 

Genre: Comedy, Drama

Actor: Catherine Keener, Danielle von Zerneck, Dermot Mulroney, Hilary Gilford, James Le Gros, Kevin Corrigan, Lori Tan Chinn, Matthew Grace, Norman Fields, Peter Dinklage, Rica Martens, Robert Wightman, Steve Buscemi, Tom Jarmusch

Director: Tom DiCillo

Rating: R

Ray Romano and Chris O'Dowd (Bridesmaids) star in this dark comedy-thriller about a gangster who attempts a career as a Hollywood producer. It’s based on the novel that the 1995 John Travolta and Danny DeVito movie by the same name was also based on *catches breath*.

There is something undeniably funny about people in crime who try to reform themselves in Hollywood, the same thing that Bill Hader perfected in Barry. The switch from real to fake and back is equally as well-executed in Get Shorty.

Genre: Thriller

Actor: Carolyn Dodd, Chris O'Dowd, Chris O'Dowd, Goya Robles, Lidia Porto, Lucy Walters, Megan Stevenson, Ray Romano, Sean Bridgers

Director: Allen Coulter, Emin Hüseynov

Rating: TV-MA

A Korean police comedy built on a premise so dumb it's brilliant: a group of bumbling cops who are so bad at their job that they accidentally start an amazing fried chicken restaurant while undercover. All of the suspense and excitement that should be going into their actual mission is spent on this new job that actually begins to give them coordination and a greater sense of purpose. There may not be much of a deeper meaning to be found here, but the characters are lovable enough—and the filmmaking sharp enough—to get you invested in their personal happiness, and to get you to appreciate how strong editing and performances can make even the smallest throwaway line spit-take hilarious.

Genre: Action, Comedy, Crime, Family

Actor: Gong Myeong, Gong Myoung, Han Jun-woo, Heo Joon-seok, Honey Lee, Jang Jin-hee, Jeong Jae-kwang, Ji Chan, Jin Sun-kyu, Jung Won-chang, Kim Eui-sung, Kim Ji-young, Kim Jong-soo, Kim Kang-hyun, Lee Dong-hwi, Lee Ha-nee, Lee Joong-ok, Lee Jung-ok, Na Chul, Oh Jung-se, Ryu Seung-ryong, Shin Ha-kyun, Shin Shin-ae, Song Young-gyu, Tae Won-seok, Yang Hyun-min, Yoo Je-yoon

Director: Lee Byeong-heon, Lee Byoung-heon

Rating: Not Rated

It can be very frustrating to watch something, hoping that the show, play, or film would be worth watching, and find yourself feeling worse after the experience. Most of us end up just changing the channel, leaving the theater, or finding something else to watch, but instead of doing any of this, Yannick depicts the titular audience member interrupting the show with a gun. You can already imagine how tense the situation is, but Quentin Dupieux infuses a comedic, meta touch in the way Yannick questions and holds the audience hostage, as his conversations with them and the cast reveal the different expectations we have from art.

Genre: Comedy, Drama

Actor: Agnès Hurstel, Blanche Gardin, Caroline Piette, Charlotte Laemmel, Félix Bossuet, Jean-Paul Solal, Laurent Nicolas, Mustapha Abourachid, Pio Marmaï, Raphaël Quenard, Sava Lolov, Sébastien Chassagne, Stéphane Pezerat

Director: Quentin Dupieux

Thunder Road is both a single-shot 13 minute short and a 91-minute feature-film expanding the story. Both are excellent and award-winning, but I really recommend the full experience!

Jim Cummings (above) is the director, writer, and main actor of this dark comedy. He plays a police officer having the worst day of his life as he tries to sing Bruce Springsteen’s Thunder Road at his mother’s funeral.

This sight is funny, and so is most of the story. But it’s also cringe-inducing, and because the main character is so sincere in his decline, will make you feel guilty about laughing so much. 

Genre: Comedy, Drama

Actor: Ammie Masterson, Bill Wise, Chelsea Edmundson, Chris Doubek, Frank Mosley, István Mihály, Jacqueline Doke, Jim Cummings, Jocelyn DeBoer, Jordan Ray Fox, Kendal Farr, Macon Blair, Marshall Allman, Nican Robinson, Tristan Riggs

Director: Jim Cummings

Rating: N/A

Amongst the google searches for this one you'll find "Is Slotherhouse a real film?" and that says a lot. When the first poster and trailer dropped, I suspected it the work of AI, but now that the film is out on streaming, we should be glad it exists. A ludicrous horror-comedy that hits all the right notes in gore, cringe, and puns, Slotherhouse is quintessential fun cinema. It may be set in a college where internalized misogyny is completely off the charts as young women bruise and batter each other's egos in service of the queen bee Brianna (Sydney Craven) and may attempt just a tiny bit of character development to keep the ball rolling, but honestly, who cares? It's a film that completely leans into the absurd, the over the top, the ridiculous, and it does it surprisingly well.

Genre: Comedy, Horror, Thriller

Actor: Andrew Horton, Annamaria Serda, Bianca Beckles-Rose, Bradley Fowler, Cady Lanigan, Grace Patterson, Jelena Rakočević, Juliana Sada, Kelly Lynn Reiter, Lisa Ambalavanar, Milica Vrzić, Olivia Rouyre, Stefan Kapičić, Sydney Craven, Tiana Upcheva, Tiff Stevenson

Director: Matthew Goodhue

Rating: PG-13

When Mikey Saber’s porn career takes a dip in California, he returns to an estranged wife in Texas, where he meets new and old friends alike and attempts to rebuild his life through a couple of odd jobs. Though Mikey eventually earns his keep, his vanity and eagerness to succeed at all costs threaten to get the best of him.

All this happens against a vibrant backdrop of local sights, beautifully lit and framed by director Sean Baker (The Florida Project, Tangerine). Quaint, naturalistic, and ever-so-subtly political, Red Rocket is another great entry into Baker’s impressions of the vexed American Dream.

Genre: Comedy, Drama

Actor: Bree Elrod, Ethan Darbone, Karren Karagulian, Shih-Ching Tsou, Simon Rex, Suzanna Son

Director: Sean Baker

This artistic Australian coming-of-age drama stars Eliza Scanlen (Little Women, Sharp Objects) as Milla, a teen from a dysfunctional family. The father is a psychologist and the mother suffers from depression, so he medicates her under the table. Meanwhile, Milla, a 16 year old, starts dating a charismatic almost-homeless 24 year old drug dealer. Unusual circumstances make the family tolerate the relationship in this story where every character feels like the main one. 

If you're looking for something different, you will love Babyteeth. Something happens to Milla in the 10 minute mark that descriptions and reviews online all mention - but is definitely a spoiler. Just know that it's not all romance and coming-of-age, there is slow-burning darkness to this movie. 

Genre: Comedy, Drama, Romance

Actor: Andrea Demetriades, Arka Das, Ben Mendelsohn, Charles Grounds, Eliza Scanlen, Emily Barclay, Essie Davis, Eugene Gilfedder, Georgina Symes, Jaga Yap, Justin Smith, Michelle Lotters, Priscilla Doueihy, Quentin Yung, Renee Billing, Toby Wallace, Zack Grech

Director: Shannon Murphy

Rating: MA-17, Not Rated