53 Best Dark Comedies Movies to Watch On Itunes (Page 3)

After receiving virtually unlimited funding from a wealthy businessman, Lola (played by the always excellent Penelope Cruz) sets out to mount an ambitious adaptation of a bestselling novel. To make her vision work, she employs renowned actors Ivan Torres (Oscar Martinez) and Felix Rivero (Antonio Banderas), knowing full well that their opposite philosophies in art and life will clash. What follows is a series of preps and rehearsals that play out like social experiments in their twistedness, which all in all speak to the outrageousness of film, art, and life itself.

In this Spanish dark comedy, no one is spared from satire—from the idiosyncratic auteur down to the sell-out actor, all are parodied in equal measure, each of their egos broken down in great and hilarious detail.

Genre: Comedy, Drama

Actor: Ana Belén, Antonio Banderas, Daniel Chamorro, Irene Escolar, Isabel García Lorca, José Luis Gómez, Juan Grandinetti, Ken Appledorn, Manolo Solo, María Guinea, Mary Ruiz, Melina Matthews, Mónica Bardem, Nagore Aranburu, Oscar Martinez, Penélope Cruz, Pilar Bergés, Pilar Castro, Sue Flack

Director: Gastón Duprat, Mariano Cohn

Rating: R

The Banshees of Inisherin is an Irish dark comedy film that begins with the breakup of longtime friends Pádraic (Colin Farrell) and Colm (Brendan Gleeson). Averse to the sudden split, Pádraic tries to repair their relationship, but instead of achieving goodwill, he inadvertently sets off even more unrest in their little town of Inisherin. Set in 1923 against the backdrop of the Irish Civil War, the film doubles as a fable about the consequences of war. 

The last time Farrell and Gleeson were together was in the expert thriller In Bruges, and their reunion in The Banshees of Inisherin shows how powerful and chemistry-filled their pairing is. Theirs is a knockout turn, but it's also far from the only good thing in the movie. Packed with gorgeously lush images of rural Ireland, strong performances from an all-Irish cast, and a whipsmart script from writer-director Martin McDonagh, The Banshees of Inisherin is an impactful watch that will give you lots to unpack long after the credits roll. 

Genre: Comedy, Drama

Actor: Aaron Monaghan, Barry Keoghan, Brendan Gleeson, Bríd Ní Neachtain, Colin Farrell, David Pearse, Gary Lydon, Jon Kenny, Kerry Condon, Pat Shortt, Sheila Flitton

Director: Martin McDonagh

Rating: R

Of the many violence-inflected black comedies that Pulp Fiction spawned, Grosse Pointe Blank ranks among the best. Though it’s patently inspired by Tarantino’s magnum opus — John Cusack plays a sardonic, amoral hitman, and the film features bursts of stylized violence and a retro soundtrack — it never feels derivative. The film finds its own identity as a quirky romcom when Cusack’s character, Martin Blank, returns to his hometown for a 10-year high-school reunion on the advice of his terrified therapist (Alan Arkin).

Martin is experiencing professional disillusionment as part of the quarter-life crisis that often takes hold when one realizes it’s been a whole decade since high school. His profession puts a darkly comic spin on that convention, but the film doesn’t treat that element entirely flippantly. Unlike Martin — and so many of the film’s Pulp Fiction-inspired brethren — Grosse Pointe Blank isn’t nihilistic, but quite sincerely romantic. Its hybrid nature and surprising heart come to the fore in Martin’s renewed relationship with the girlfriend he jilted at prom: Debi (Minnie Driver), now a ska-loving radio DJ. Cusack and Driver have sparkling chemistry, which makes the sincerity with which their characters grapple with the possibility of a second chance at happiness all the more absorbing to watch.

Genre: Action, Comedy, Drama, Romance, Thriller

Actor: Alan Arkin, Ann Cusack, Barbara Harris, Belita Moreno, Benny Urquidez, Bill Cusack, Bobby Bass, Carlos Jacott, Dan Aykroyd, David Barrett, Doug Dearth, Hank Azaria, Jenna Elfman, Jeremy Piven, Joan Cusack, John Cusack, K. Todd Freeman, Michael Cudlitz, Minnie Driver, Mitchell Ryan, Steve Pink

Director: George Armitage

If you like any of the following: Irish accents, Woody Harrelson, Pulp Fiction, or dark comedy;  then this is the movie for you. This mix of violence, mafia, existential talk, and painfully comical situations might not be for everyone, but it has every component to make its target audience very pleased. And given how chaotic and crazy it can get, it should be enjoyed one take at a time, focusing on each delightful scene rather than the overall plot. Directed by Martin McDonagh, Seven Psychopaths makes a perfect comeback after In Bruges, without veering very much from it (consequently if you like this movie make sure you check out In Bruges too).

Genre: Comedy, Crime

Actor: Abbie Cornish, Amanda Warren, Brendan Sexton III, Christian Barillas, Christine Marzano, Christopher Gehrman, Christopher Walken, Colin Farrell, Crispin Glover, Frank Alvarez, Gabourey Sidibe, Harry Dean Stanton, Helena Mattsson, James Landry Hébert, John Bishop, Johnny Bolton, Joseph Lyle Taylor, Kevin Corrigan, Kiran Deol, Linda Bright Clay, Long Nguyen, Martin McDonagh, Michael Pitt, Michael Stuhlbarg, Olga Kurylenko, Patrick O'Connor, Richard Wharton, Ronnie Gene Blevins, Sam Rockwell, Samantha Cutaran, Tai Chan Ngo, Tom Waits, Woody Harrelson, Zeljko Ivanek

Director: Martin McDonagh

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

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

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

Welcome to the Dollhouse tells the story of Dawn, an unpopular seventh-grader mercilessly bullied at school and ignored at home. Her day-to-day is painful to watch; her classmates make fun of her, her teachers never believe her, and her parents punish her, blatantly favoring her other siblings over her. But all this she puts up with, as if going through the murky in-between stage that is adolescence isn't confusing enough. Dawn finds no respite elsewhere, except perhaps in her friend Ralphy (another target of bullying) and her crush, the high schooler Steve.  

A Sundance jury winner back in '96, Welcome to the Dollhouse is as darkly funny as it is grim. It takes on a deadpan approach in handling its more serious topics; it doesn't make fun of them so much as it shines them in a new and blinding light. It's difficult to look away from this frank and well-balanced film; a sure good watch for anyone curious to know what it's really like to be a teenage loner.

Genre: Comedy, Drama

Actor: Angela Pietropinto, Bill Buell, Brendan Sexton III, Christina Brucato, Christina Vidal, Daria Kalinina, Elizabeth Martin, Eric Mabius, Heather Matarazzo, Ken Leung, Matthew Faber, Molly Howe, Rica Martens, Richard Gould, Siri Howard, Stacey Moseley, Teddy Coluca, Telly Pontidis, Victoria Davis, Will Lyman

Director: Todd Solondz

Rating: R

In The Kid Detective, Adam Brody stars as Abe Applebaum, a once-beloved child prodigy turned pathetic P.I. stuck in the glory days of his past. At 32 years old, he’s still solving petty mysteries and coasting on his parents’ money, but things start to change when he is finally dealt with a real, adult case: a murder that confounds even the local police. As Abe uncovers more details about the case, he also unwittingly finds a connection to his traumatic past and begins a long-overdue coming-of-age journey. 

Released during the first year of the pandemic, The Kid Detective understandably flew under the radar when it first came out, garnering sufficient critical praise but not enough fanfare. It will no doubt find a second life among film lovers, though; it’s too smart and riveting to go unnoticed. Most impressive is how director Evan Morgan, in his feature debut, deftly balances multiple genres in a movie that often feels as if Wes Anderson's The Royal Tenenbaums, Roman Polanski's Chinatown, and modern stoner humor were somehow rolled into one. The gags consistently amuse, the drawn-out mysteries pay off, and the human element persists throughout. Adam Brody, himself a kid celebrity back in the day, expertly carries this delightful and sobering film. 

Genre: Comedy, Drama, Mystery

Actor: Adam Brody, Alan Catlin, Alicia Brand, Amalia Williamson, Avery Esteves, Barbara Rajnovich, Bethanie Ho, Brent Skagford, Bruce McFee, Dallas Edwards, David Rosser, Deborah Tennant, Devin Myler, Giovanna Moore, Isaac Kragten, Jake Bell-Webster, Jesse Noah Gruman, Jonathan Whittaker, Kaitlyn Chalmers-Rizzato, Kaleb Horn, Kevin Hoffman, Kira Gelineau, Lisa Truong, Marcia Bennett, Marcus Zane, Marlaina Andre, Maurice Dean Wint, Peter MacNeill, Sarah Sutherland, Sharon Crandall, Sophia Webster, Sophie Nélisse, Sophie Nélisse, Steve Gagne, Tracy Rowland, Tyler Duke, Tzi Ma, Wayne St-George, Wendy Crewson

Director: Evan Morgan

Rating: R

Before “burnout,” “bullshit jobs,” and “quiet quitting” became part of our everyday lexicon, there was a film in the ‘90s that prophesied the rise of these workplace problems. Office Space follows three co-workers who, having had enough of their dreary low-paying jobs, fight back against their company via an embezzlement scheme. 

Office Space makes the most out of its indie budget as it mostly takes place in the cramped quarters of a company, effectively bottling us into the cubicled windowless world of the characters. But the real beauty of the film is in the details, from its quick zingers and thoughtful takes on the essence of work down to its elaborate “planning to plan” scheme in the background and the employees’ forced politeness singing happy birthday to their boss. Modern viewers will notice that Office Space sits right in between the dystopian thriller Severance and the beloved sitcom The Office—a dark comedy that highlights the necessity of humanity in everyday work. 

Genre: Comedy, Drama

Actor: Ajay Naidu, Alexandra Wentworth, Ali Wentworth, Barbara George-Reiss, Cassie Townsend, Charissa Allen, David Herman, Diedrich Bader, Gabriel Folse, Gary Cole, Greg Pitts, Heath Young, Jack Betts, Jackie Belvin, Jennifer Aniston, Jennifer Jane Emerson, Jesse De Luna, Joe Bays, John C. McGinley, Josh Bond, Justin Possenti, K. Todd Lytle, Kinna McInroe, Kyle Scott Jackson, Linda Wakeman, Michael McShane, Mike Judge, Orlando Jones, Paul Willson, R.C. Keene, Richard Riehle, Ron Livingston, Rupert Reyes, Samantha Inoue Harte, Spencer Kayden, Stephen Root, Todd Duffey, Tom Schuster

Director: Mike Judge

Rating: R