35 Best Dark Comedies Movies to Watch On Cineplex Canada (Page 2)

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

There’s a lot to think about in Dream Scenario, which posits the possibility of collectively seeing the same real man in your dreams. Norwegian filmmaker Kristoffer Borgli drops the painfully ordinary Paul (Cage) in an extraordinary reality to show us how easily one can spiral into insanity, how dangerous groupthink can be, how fickle cancel culture is, and how anything can happen to anyone, even to someone as unsuspecting as Paul. But Borgli doesn’t just experiment with ideas here, he also expertly plays with sounds and transitions, sometimes even cutting a scene before someone is done talking, to capture the skittish and unreliable language of dreams. More impressively, he takes into account how this phenomenon would play in our real, profit-oriented world. The capitalistic urge to make Paul an advertising tool, for instance, or to create tech that makes it possible for others to appear in dreams too, is both uncanny and depressingly realistic. Some might feel that Borgli is biting off more than he can chew but there’s a balance and ease to Dream Scenario that makes it feel inevitable. That’s thanks to Borgli’s brilliant direction but also, in no small part, to Cage’s inspired performance as a pathetic but harmless loser.

Genre: Comedy, Fantasy, Horror, Science Fiction

Actor: Agape Mngomezulu, Al Warren, Amber Midthunder, Ben Caldwell, Conrad Coates, David Klein, Domenic Di Rosa, Dylan Baker, Dylan Gelula, James Collins, Jennifer Wigmore, Jeremy Levick, Jessica Clement, Jim Armstrong, Jordan Raf, Josh Richards, Julianne Nicholson, Kaleb Horn, Kate Berlant, Krista Bridges, Lily Bird, Lily Gao, Liz Adjei, Maev Beaty, Marc Coppola, Marnie McPhail, Michael Cera, Nicholas Braun, Nicolas Cage, Nicole Leroux, Nneka Elliott, Noah Centineo, Noah Lamanna, Philip van Martin, Ramona Gilmour-Darling, Richard Jutras, Sofia Banzhaf, Star Slade, Stephen R. Hart, Tim Meadows, Will Corno

Director: Kristoffer Borgli

Rating: R

Among the sea of class satires released in the last year, Triangle of Sadness is one of the better ones. Directed by Ruben Östlund (The Square, Force Majeure), the film follows an ultra-rich group of people who get stranded on an island after their luxury cruise ship sinks. The social pyramid that has long favored them suddenly turns upside down when a crew member (a glowing Dolly de Leon) effectively runs the group of sheltered castaways.

Triangle of Sadness may not be as sharp as Östlund’s previous work, and it may not add anything particularly new to the saturated discussions of social class, but it remains a darkly humorous and engaging watch, masterfully helmed by a strong script and ensemble.

Genre: Comedy, Drama

Actor: Alex Schulman, Alicia Eriksson, Amanda Schulman, Amanda Walker, Arvin Kananian, Beata Borelius, Camilla Läckberg, Carolina Gynning, Charlbi Dean, Christina Saliba, Dolly de Leon, Emma Warg, Fredrik Quinones, Fredrik Wikingsson, Hanna Oldenburg, Harris Dickinson, Hedda Rehnberg, Henrik Dorsin, Iris Berben, Jean-Christophe Folly, Karin Myrenberg, Linda Anborg, Malte Gårdinger, Nana Manu, Oliver Ford Davies, Ralph Schicha, Shaniaz Hama Ali, Stefan Godicke, Sunnyi Melles, Vicki Berlin, Woody Harrelson, Zlatko Burić

Director: Ruben Östlund

Rating: R

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

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

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, Charissa Allen, David Herman, Diedrich Bader, Gabriel Folse, Gary Cole, Greg Pitts, Jack Betts, Jackie Belvin, Jennifer Aniston, Jennifer Jane Emerson, Jesse De Luna, Joe Bays, John C. McGinley, Kinna McInroe, Kyle Scott Jackson, Michael McShane, Mike Judge, Orlando Jones, Paul Willson, Richard Riehle, Ron Livingston, Rupert Reyes, Spencer Kayden, Stephen Root, Todd Duffey, Tom Schuster

Director: Mike Judge

Rating: R