136 Best Dark Comedies Movies to Watch (Page 2)

Robert Downey Jr's triumphant return to film, this movie is a satirical take on film noir and detective movies in general. The screen chemistry between Gay Perry the private eye, played by Val Kilmer, and Downey Jr's robber turned actor, Harry Lockhart, is hysterical, and the film's tongue in cheek nature is witty, smart, and delivers. Directed by the man who directed Lethal Weapon, the action is top notch, the laughs are pretty much constant, and the mystery is compelling. It's mind boggling that nobody saw this when it came out.

Genre: Action, Comedy, Crime, Mystery, Thriller

Actor: Ali Hillis, Angela Lindvall, Ariel Winter, Ben Hernandez Bray, Bill McAdams Jr., Brendan Fehily, Brian Simpson, Cole S. McKay, Corbin Bernsen, Daniel Browning Smith, Dash Mihok, David Newsom, Evan Parke, Harrison Young, Indio Falconer Downey, Jake McKinnon, Joe Keyes, Josh Richman, Judie Aronson, Kathy Lamkin, Larry Miller, Laurence Fishburne, Lela Edgar, Martha Hackett, Michelle Monaghan, Nancy Fish, Robert Downey Jr., Rockmond Dunbar, Saida Pagan, Shannyn Sossamon, Stephanie Pearson, Tanja Reichert, Teresa Maria Herrera, Val Kilmer, Vincent Laresca, Wiley M. Pickett

Director: Shane Black

Rating: R

Will Ferrell plays a well organized IRS agent named Harold Crick who seems to have figured out everything in his life to the dot. Little does he know his life is being run by someone else, a nervous and morbid novelist, famous for ending her works with the death of the main character. As the nature of his life and eventual doom, he decides to lay back and enjoy the ride, breaking all his ingrained and boring habits. While this film is recommended for everyone, Will Ferrel fans, especially, need to watch this to see Will's acting variety.

Genre: Comedy, Drama, Fantasy, Romance

Actor: Andrew Rothenberg, Bob Papenbrook, Bradley Mott, Bruce Jarchow, Celeste Pechous, Cheryl Lynn Bruce, Christian Stolte, Danny McCarthy, Danny Rhodes, Denise Hughes, Dustin Hoffman, Eli Goodman, Emma Thompson, Frank Caeti, Guy Massey, Jarrett Sleeper, John M. Watson Sr., John Mohrlein, Julia Heron, Keith Kupferer, Kristin Chenoweth, Larry Neumann Jr., Linara Washington, Linda Hunt, Maggie Gyllenhaal, Marc Forster, Martha Espinoza, Mike McColl, Nadirah Bost, Nathan Adloff, Ora Jones, Peggy Roeder, Peter Grosz, Queen Latifah, Ray Kurut, Ricardo Gutierrez, Ricky Adams, Sandra Marquez, Sia A. Moody, T.J. Jagodowski, Tab Baker, Tim Krueger, Tom Hulce, Tonray Ho, Tony Hale, Will Clinger, Will Ferrell, William Dick

Director: Marc Forster

Rating: PG-13

An early gem from Finnish maestro Aki Kaurismäki, Drifting Clouds is a deceptively simple story. The aftermath of job losses for wife Ilona (Kati Outinen) and husband Lauri (Kari Väänänen) holds a series of misfortunes, all of them tests to their marital bond. But this is only the beginning: as with Kaurismäki's endearing use of flat irony and detached performances by regular actors of his, things can only get worse before they get better. Humanism has always shined through the director's films, and this first part of a "Finland" trilogy makes no exception to the rule: the fact that labor and closeness are the two main themes (and are equally important for one's survival) already elevates the absurdist comedy to something way more caring, engaged, and ultimately, tender.

Genre: Comedy, Drama

Actor: Aarre Karén, Antti Reini, Clas-Ove Bruun, Elina Salo, Esko Nikkari, Kaija Pakarinen, Kari Väänänen, Kati Outinen, Markku Peltola, Mato Valtonen, Matti Onnismaa, Ona Kamu, Outi Mäenpää, Pentti Auer, Rose-Marie Precht, Sakari Kuosmanen, Silu Seppälä, Sulevi Peltola, Tero Jartti, Vesa Mäkelä

Director: Aki Kaurismäki

Martin Scorsese — plus screenwriter Paul Schrader, editor Thelma Schoonmaker, and cinematographer Robert Richardson — reimagine nocturnal New York City as an eternally flaming circle of hell in this darkly funny fever dream. Frank Pierce (Nicolas Cage) is an insomniac paramedic who’s haunted by the ghosts of all the lives he couldn’t save and is on a nightmarish run of losing every patient he tries to help. There’s no respite for him anywhere; he’s so burnt out he begs to be fired, but the city is so desperate they won’t let him leave their tired ranks of medics, who are mostly jaded, sometimes sadistic, and yet still addicted to the euphoric high of saving a life.

As Frank is pushed ever closer to breaking point, the film takes on the hallucinatory qualities of his perspective, the cinematography growing feverish and the editing powered by a wild, manic energy. What stops the movie from feeling like a spiral into actual hell is the strange light that keeps Frank returning to work — the perpetual need for redemption and grace that prevents him from becoming cold to his job but makes his sanity fragile. In typical Scorsese-Schrader style, this is a raw, visceral, and very human search for grace in an unsparing urban hellscape.

Genre: Drama, Horror, Thriller

Actor: Afemo Omilami, Aida Turturro, Aleks Shaklin, Andy Davoli, Antone Pagán, Arthur J. Nascarella, Bernie Friedman, Betty Miller, Brian Smyj, Bronson Dudley, Catrina Ganey, Charis Michelsen, Cliff Curtis, Craig muMs Grant, Cullen O. Johnson, David Zayas, Ed Jupp Jr., Floyd Resnick, Frank Ciornei, Fuschia!, Graciela Lecube, Jack O'Connell, James Hanlon, Jesse Malin, John Goodman, John Heffernan, Jon Abrahams, Joseph P. Reidy, Judy Reyes, Julyana Soelistyo, Larry Fessenden, Leonid Citer, Lia Yang, Marc Anthony, Mark Giordano, Martin Scorsese, Mary Beth Hurt, Mary Diveny, Marylouise Burke, Matthew Maher, Melissa Marsala, Michael Carbonaro, Michael Kenneth Williams, Michael Mulheren, Mtume Gant, Nestor Serrano, Nicolas Cage, Omar Scroggins, Patricia Arquette, Phyllis Somerville, Queen Latifah, Raymond Cassar, Richard Spore, Sonja Sohn, Sylva Kelegian, Terry Serpico, Theo Kogan, Tom Cappadona, Tom Riis Farrell, Tom Sizemore, Ving Rhames

Director: Martin Scorsese

Rating: R

Martin Scorsese had just spent a year prepping for The Last Temptation of Christ when Paramount Pictures unceremoniously pulled the plug on the movie just one month before production was due to start. After Hours was Scorsese’s way of exorcising all that disappointment and frustration, and you can feel it: this black comedy vibrates with manic intensity as it charts a night from hell in the life of Paul (Griffin Dunne), a somewhat scuzzy yuppie living in ‘80s New York City.

In keeping with its title — which suggests the movie is suspended in temporal limbo — After Hours feels like it takes place in some mythological hellscape, a demonic underworld in which everyone Paul meets has been sent forth with the express mission to make his life more miserable. Surreal coincidences pile up, deepening his paranoia and turning his simple goal of returning home into a labyrinthine quest for survival on the deserted, rain-soaked streets of SoHo. It’s the kind of celluloid nightmare that terrorizes and thrills you at the same time (a la the Safdie brothers’ best works, which draw inspiration from After Hours). Only a director of Scorsese’s caliber could turn profound professional disappointment into such a win as this.

Genre: Comedy, Drama, Thriller

Actor: Bronson Pinchot, Catherine O'Hara, Charles Scorsese, Cheech Marin, Clarence Felder, Dick Miller, Frank Aquilino, Griffin Dunne, Henry Judd Baker, John Heard, Larry Block, Linda Fiorentino, Margo Winkler, Martin Scorsese, Murray Moston, Paula Raflo, Robin Johnson, Rocco Sisto, Rockets Redglare, Rosanna Arquette, Stephen Lim, Teri Garr, Tommy Chong, Verna Bloom, Victor Argo, Victor Bumbalo, Victor Magnotta, Will Patton

Director: Martin Scorsese

Rating: R

Here’s a biopic that focuses on capturing the feel of the era it depicts, rather than all the facts — and is all the better for it. 24 Hour Party People takes the same punk approach to storytelling as its subjects did to music, playfully throwing off the dull constraints that often make based-on-a-true-story movies feel like uninspired celluloid translations of a Wikipedia page. 

In the film’s opening scene, Steve Coogan’s Tony Wilson breaks the fourth wall to address us directly and semi-spoil the movie’s ending. But it doesn’t matter, because the ride is so fun: we’re taken on an immersive trip through the heyday of the Manchester music scene: the births of Joy Division, New Order, the Happy Mondays, and Wilson’s Factory Records label and legendary Hacienda nightclub, an incubator for acid house and rave culture. The era’s hedonism is brought to life by the movie’s frenetic editing, documentary-style cinematography, and strobe-heavy visuals. For all its onscreen anarchy, though, the movie remarkably never feels loose or self-indulgent. Its irreverence is grounded by the ironic filter of the meta filmmaking, which frequently breaks the fourth wall to draw attention to its own conceits. A refreshing rejection of biopic tropes, but also a thrilling transportation into and evocation of the Madchester era.

Genre: Comedy, Drama, Music

Actor: Andy Serkis, Chris Coghill, Christopher Eccleston, Daniel Lestuzzi, Danny Cunningham, Darren Tighe, Dave Gorman, Elizabeth Kelly, Enzo Cilenti, Fiona Allen, Helen Schlesinger, John Simm, John Thomson, Kate Magowan, Keith Allen, Kenny Baker, Kieran O'Brien, Lennie James, Margi Clarke, Mark E. Smith, Martin Hancock, Naomi Radcliffe, Neil Bell, Paddy Considine, Paul Popplewell, Peter Gunn, Peter Kay, Ralf Little, Raymond Waring, Rob Brydon, Ron Cook, Rowetta, Sean Cernow, Sean Harris, Shirley Henderson, Simon Pegg, Smug Roberts, Steve Coogan, Toby Salaman, Tony Wilson

Director: Michael Winterbottom

Rating: R

The Fundamentals of Caring is an offbeat comedy/drama starring Paul Rudd as a man attempting to overcome his looming divorce by becoming the caretaker for a teenager with muscular dystrophy (Craig Roberts, Submarine). The two develop an unconventional relationship based largely on sarcasm and profanity, delivering many laugh-out-loud moments, while also slowly exposing the pain each is carrying inside.

Together, at Ben’s urging, they embark on a road trip across the western United States for Craig to see the world. It’s somewhat formulaic but fun and touching road movie that covers much familiar ground, but also offers a fine illustration of caregiving, personal growth, and emotional healing. Paul Rudd is as good ever, and Roberts is utterly superb. One of the best movies on the Netflix Originals catalog, and an undeniable winner, all-in-all.

Genre: Comedy, Drama

Actor: Alan Boell, Alex Huff, Ashley White, Bill Murphey, Bobby Cannavale, Craig Roberts, Donna Biscoe, Fred Weller, Frederick Weller, James Donadio, Jennifer Ehle, Julia Denton, Matt Mercurio, Megan Ferguson, Paul Rudd, Rob Burnett, Robert Walker Branchaud, Samantha Huskey, Selena Gomez, Walter Hendrix III

Director: Rob Burnett, Robert Meyer Burnett

Rating: Not Rated, TV-MA

The debut feature by Palestine’s most well-known director, Chronicle of a Disappearance is an unusual movie about the decades-long Israel-Palestine conflict in that it's closer to absurdist comedy than anything else. The only physical violence we see here are men cat-fighting in the street or arm-wrestling each other in cafes, and Israeli presence is limited to a couple of bumbling police officers. Chronicle is full of slapstick cinema touches — right down to the Buster Keaton-esque eyes of director Elia Suleiman, who appears here as a silent wanderer — and yet we feel the bitter reality of the occupation framing every deadpan gag. 

Structured as a series of vignettes, Chronicle’s loose form is both a way to depict the stagnation and dry repetition in which Palestinians are stuck and a wry metaphor for all this listlessness. Suleiman speaks plainly in some chapters — such as the one following a woman who is repeatedly turned down from renting an apartment in Jerusalem because she’s Arab — and more obliquely in others, forcing you to recall the movie’s setting to understand his often-understated commentary. A singular film from an utterly unique director, Chronicle of a Disappearance is both a portrait of a country’s erosion and a quietly defiant act of resistance.

Genre: Drama

Actor: Ali Suliman, Elia Suleiman, Fawaz Eilemi, Fuad Suleiman, Iaha Mouhamad, Jamel Daher, Juliet Mazzawi, Leonid Alexeenko, Nazira Suleiman, Ola Tabari, Ula Tabari

Director: Elia Suleiman

A healthy mix of despair and self-deprecation has always been Bo Burnham's signature, but Inside takes it to the next level. It's a deconstructed film, rather than a simple one-night special; a one-man-show that constantly undercuts itself. Even more so, it sabotages its own immersive qualities and explores the depths of self-loathing by turning oneself into comedy material. Some may say, it's a classic move, but the pandemic reality and Burnham's unkempt look predispose us to embrace all the cringe (YouTube reactions), quirkiness, (the sock puppet), and frightening angst (suicide jokes) he puts forward. Emotional rawness and a polished DIY look fits the Netflix bill, but as far as the content goes, this one goes straight to the world heritage lockdown archives.

Genre: Comedy, Drama

Actor: Bo Burnham

Director: Bo Burnham

Rating: R