23 Must-See Dark Comedy Movies on HBO Max: Laugh in the Dark

Suicide Squad (2016) brings together an ensemble of DC Comics most notorious supervillains, directed by David Ayer. The captivating plot follows a secret government agency, Task Force X, leading these anti-heroes on dangerous missions in exchange for leniency. The stellar cast, including Will Smith as Deadshot, Margot Robbie as an eccentric Harley Quinn, and Jared Letos controversial take on the Joker, breathe life into complex characters. The movies high-octane action sequences and stunning special effects engage viewers throughout. Behind-the-scenes efforts, like Robbie doing her own stunts and Letos immersive Joker portrayal, add authenticity. The film won an Oscar for Best Makeup and Hairstyling, showcasing its creative excellence. Its unforgettable soundtrack, featuring hits like Heathens by Twenty One Pilots, adds another layer of appeal. Watch Suicide Squad for its unique blend of dark humor, action, and character depth.

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The Player is a must-watch for anyone intrigued by the darker side of Hollywoods glittering facade. Directed by Robert Altman and based on Michael Tolkins novel, this 1992 satirical film noir offers an incisive critique of the film industry. Tim Robbins stars as Griffin Mill, a studio executive whose life spirals out of control after receiving death threats from a disgruntled writer. The film skillfully blends drama and dark humor, exposing the cutthroat nature of Hollywood with wit and gravitas. Notable for an unbroken 8-minute opening shot, the movie showcases Altman’s innovative direction. Stellar performances by Robbins, Greta Scacchi, and Fred Ward add depth and intrigue. Cameos by Hollywood stars like Bruce Willis and Julia Roberts further enhance its appeal. The film's accolades, including two Academy Award nominations and Best Director at Cannes, attest to its cinematic excellence. The Player is an essential viewing for its sharp storytelling, clever satire, and artistic brilliance.

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Get Shorty is an unmissable gem in the crime-comedy genre, seamlessly blending humor, satire, and thrilling elements. Directed by Barry Sonnenfeld and based on Elmore Leonards novel, this 1995 release tells the captivating story of a Miami mobster, brilliantly portrayed by John Travolta, who unexpectedly delves into the chaotic world of Hollywood. With a stellar cast featuring Gene Hackman, Rene Russo, and Danny DeVito, Get Shorty showcases sharp dialogue and intriguing characters. Travolta's standout performance as Chili Palmer earned him a Golden Globe, adding another reason to watch. The film's wit, humor, and insider look at Hollywood's underbelly, combined with a memorable soundtrack, make Get Shorty a must-see. It's a compelling tale of crime meeting cinema, delivering both laughs and thrills in equal measure. Don't miss out on this classic that masterfully captures the absurdity and allure of Tinseltown.

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Fargo (HBO) is an engaging black comedy crime film set against the chilling, snow-covered landscapes of North Dakota and expertly directed by the Coen Brothers. The movie showcases Frances McDormands Oscar-winning performance as Marge Gunderson, a sharp and endlessly resourceful pregnant police chief. The plot unravels the darkly humorous and desperate actions of Jerry Lundegaard, a hapless car salesman portrayed brilliantly by William H. Macy, who orchestrates a botched kidnapping. Steve Buscemi delivers a memorable turn as the frenetic crook, Carl Showalter. With Roger Deakins haunting cinematography enhancing the bleak and eerie atmosphere, the film stands as a testament to stellar storytelling and character development. Awarded two Academy Awards and featuring an evocative soundtrack by Carter Burwell, Fargo merges thought-provoking themes with dark humor, making it a must-watch that captivates from start to finish.

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Succession | Max is a must-watch TV series that captivates audiences with its intense exploration of a global media conglomerates power dynamics, family politics, and rivalries. The show follows the formidable Roy family as they navigate shifting loyalties and scheming alliances to control their empire. What sets Succession | Max apart is its brilliant storytelling combined with unparalleled production quality. The luxurious and imposing settings reflect the characters' immense wealth and influence. The show features commanding performances, notably Brian Cox as the ruthless patriarch Logan Roy, Jeremy Strong as the conflicted Kendall Roy, and Sarah Snook as the assertive Shiv Roy, adding depth and nuance to the narrative. With sharp and witty dialogue, the series keeps viewers engaged and entertained. Additionally, it draws inspiration from real-life media moguls, lending an air of authenticity. The compelling character arcs and gripping plot twists make Succession | Max an unmissable journey into the world of corporate power and family intrigue.

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The Visit (2015) is a gripping thriller produced by M. Night Shyamalan, centering on two siblings, Rebecca and Tyler, whose visit to their grandparents turns into a haunting ordeal. The films unique found-footage style adds a fresh twist to the classic horror genre, offering a mix of suspense, mystery, and well-timed humor. Olivia DeJonge and Ed Oxenbould lead an impressive cast, with standout performances by Deanna Dunagan and Peter McRobbie, whose characters disturbing behaviors build unrelenting tension. M. Night Shyamalans direction, coupled with Paul Cantelons eerie soundtrack, creates a compelling and atmospheric experience. The films commercial success, grossing over $100 million on a $5 million budget, underscores its wide appeal. For fans of psychological thrillers that keep you on the edge of your seat, The Visit is an excellent choice, blending chills with an engaging storyline and memorable performances.

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The Family (HBO) is a must-watch for fans of dark comedy and action thrillers. Directed by Luc Besson, this 2013 film stars Robert De Niro as Fred Blake, a former Mafia boss who enters the Witness Protection Program with his family, only to find that old habits die hard. Set in France, the movie masterfully blends humor and tension, offering an entertaining narrative driven by stellar performances from Michele Pfeiffer, Dianna Agron, and John DLeo. The screenplay, adapted from Tonino Benacquistas novel Malavita, delves into family dynamics against a backdrop of crime and vengeance. With its unique mix of action, comedy, and drama, coupled with Alexandre Desplats evocative soundtrack, The Family delivers a captivating cinematic experience. Whether youre drawn to gripping plots or nuanced character portrayals, this film provides a well-rounded entertainment package. Dont miss this intriguing exploration of life and loyalty within a Mafia family.

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Tie Me Up! Tie Me Down! is a provocative and darkly comedic Spanish film from celebrated auteur Pedro Almodóvar. Released in 1990, the film stars Antonio Banderas as Ricky, a psychiatric patient, and Victoria Abril as Marina, a former porn star turned B-movie actress. Rickys obsessive love for Marina leads him to kidnap her in a bid to win her heart, touching on themes of love, obsession, and control. Produced by Almodóvar's own company, El Deseo S.A., this film showcases his vibrant visual style and unconventional storytelling. Featuring excellent performances—especially from Banderas and Abril—and comedic relief by Loles León, it navigates controversial themes with wit and creativity. Despite initial controversy and an X rating in the United States, its daring approach and compelling narrative make it a must-watch. With an evocative soundtrack by Bernardo Bonezzi, Tie Me Up! Tie Me Down! is a unique and bold exploration of love's darker facets.

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American Splendor, released by HBO in 2003, is a unique biographical comedy-drama that delves into the life of Cleveland file clerk Harvey Pekar, the genius behind the American Splendor comic book series. Directed by Shari Springer Berman and Robert Pulcini, the film stands out by blending performances from actors, real-life footage, and animations from Pekars comics, creating a rich, multifaceted narrative. Paul Giamattis profound portrayal of Pekar, alongside Hope Davis and Judah Friedlander, brings humor and empathy to the screen. Winning the Grand Jury Prize at Sundance and earning an Academy Award nomination for Best Adapted Screenplay, the film highlights the extraordinary in the ordinary. Quotes like Ordinary life is pretty complex stuff reveal its deep philosophical undertones. Including iconic tracks from Marvin Gaye and OK Go, American Splendor is a film that transcends traditional storytelling, making it a must-watch for those who appreciate nuanced, innovative cinema.

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Bachelorette is a must-watch for comedy enthusiasts, blending humor with heartfelt moments under Leslye Headlands deft direction. The film, produced by comedy titans Will Ferrell and Adam McKay, takes viewers on a rollercoaster ride through a chaotic bachelorette party where past and present collide. With performances by Kirsten Dunst, Isla Fisher, Lizzy Caplan, and Rebel Wilson, the film boasts a stellar cast that delivers both laughs and emotional depth. Shot primarily in New York City and Los Angeles, the movie captures the vibrant energy of its urban settings. Notably, it marks Rebel Wilsons impressive Hollywood debut. The memorable quotes and eclectic soundtrack, featuring hits like Call Me Maybe and Wannabe, add to the films charm. Bachelorette offers a fresh take on friendships, redemption, and wild escapades, making it an engaging and entertaining watch.

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Deadpool is a groundbreaking addition to superhero cinema, blending humor, action, and romance in a way that sets it apart from its peers. Released in 2016 and directed by Tim Miller, the film stars Ryan Reynolds as Wade Wilson, a mercenary who becomes Deadpool after a rogue experiment grants him accelerated healing powers. With witty dialogue, dark humor, and a relentless quest for revenge, Deadpools unique personality brings a refreshing twist to the genre. Morena Baccarin, T.J. Miller, and Ed Skrein deliver strong performances that complement Reynolds iconic portrayal. The film's production journey, from comic to screen, is an inspiring tale of persistence, spearheaded by Reynolds himself. This movie's R-rated humor and action-packed sequences redefine the superhero narrative, making it a must-watch. Its record-breaking box office success, critical acclaim, and engaging soundtrack, including hits like X Gon' Give It to Ya by DMX, further solidify Deadpool as a cultural phenomenon.

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Head Office, a satirical comedy directed by Ken Finkleman, offers an amusing glimpse into the cutthroat world of corporate politics. This 1986 film showcases Judge Reinhold as Jack Issel, an ambitious executive grappling with office chaos and underhanded dealings, while Danny DeVito, Jane Seymour, and Rick Moranis deliver stellar performances as colorful corporate characters. TriStar Pictures' production captures the essence of office dynamics in a humorous yet insightful manner, making it a standout in '80s cinema. With its witty humor and sharp, relatable narrative, viewers are treated to both laughter and thought-provoking commentary on business ethics. Filmed at the iconic One Chase Manhattan Plaza, it adds authenticity to its setting. Whether you're a fan of satirical comedy, interested in corporate dynamics, or simply seeking engaging entertainment, Head Office promises to be a delightful watch.

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Eating Raoul is a dark comedy that masterfully skewers the culture of 1980s America with its sharp, satirical tone. Released in 1982, this cult classic follows the Blands, a couple who find a quirky and morbid way to escape their monotonous life by eliminating swingers and capitalizing on their demise. Directed by Paul Bartel, who also stars alongside Mary Woronov, the film delivers offbeat humor and a unique storyline that remains relevant and entertaining today. Eating Raoul is celebrated for its small budget charm, witty dialogue, and memorable performances by a talented cast, including Robert Beltran as the scheming Raoul. This film not only offers a glimpse into a peculiar narrative but also serves as a cultural critique that is both humorous and thought-provoking. Additionally, the jazz-infused soundtrack by Arlon Ober adds a light-hearted complement to this darkly comedic gem. Watch it for a timeless satire thats both quirky and engaging.

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Night on Earth, directed by Jim Jarmusch, is a 1991 film that takes viewers on a global journey through five compelling vignettes, each set in a different city on the same night. The movie masterfully explores human connections and cultural diversity through the interactions between taxi drivers and their passengers. With an international cast including Winona Ryder, Gena Rowlands, and Roberto Benigni, each story blends humor and melancholy, providing a rich tapestry of urban life. Critically acclaimed for its unique narrative style and the iconic cinematography of Frederick Elmes, the film offers a visual feast despite being predominantly shot in New York and Los Angeles. The soundtrack, composed by Tom Waits, adds an atmospheric touch that complements the film’s mood. Whether you're drawn to heartfelt storytelling, character-driven plots, or simply a fan of Jarmusch's unique directorial flair, Night on Earth is a cinematic experience not to be missed.

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The Ruling Class is a 1972 British black comedy that masterfully blends wit, satire, and dark humor to critique the British aristocracy. The plot centers around Jack Gurney, a paranoid schizophrenic nobleman who believes he is Jesus Christ, and his struggle for power within his family. Directed by Peter Medak and written by Peter Barnes, the film is lauded for its acerbic wit and scathing social commentary. Peter O'Toole's portrayal of Jack Gurney is both regal and disturbingly charming, a performance that earned him an Academy Award nomination. The film also features standout roles from Alastair Sim and Arthur Lowe. Notable for its surreal and absurd humor, The Ruling Class offers a unique and unforgettable cinematic experience. The film's score, composed by John Cameron, enhances its dark and surreal atmosphere, with the memorable inclusion of Dem Bones performed by the cast. For anyone interested in thought-provoking satire and exceptional performances, The Ruling Class is a must-watch.

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Life After Beth is a must-watch for its unique blend of horror and comedy, offering a fresh take on the zombie genre. Directed by Jeff Baena and showcased at the Sundance Film Festival before airing on HBO, this 2014 film masterfully explores themes of grief, love, and family with a humorous twist. The dynamic performances by Dane DeHaan, Aubrey Plaza, John C. Reilly, and Molly Shannon breathe life into a storyline that is both hilarious and heart-warming. DeHaan portrays a young man struggling to come to terms with his girlfriend’s death and her subsequent return as a zombie, while Plaza's eerie yet comedic portrayal of Beth adds depth and charm. Moreover, the film's clever dialogue, memorable quotes, and eclectic soundtrack enhance its appeal. With Jeff Baena's skilled direction and a compelling narrative, Life After Beth promises an entertaining and thought-provoking cinematic experience.

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Observe and Report (2009) is a compelling HBO dark comedy-drama that offers a unique twist on the mall-cop genre. Lead by the talented Seth Rogen as Ronnie Barnhardt, the delusional head of mall security, viewers are taken on a humorous yet dramatic ride as he contends with local cops over a mall inquiry. Directed by Jody Hill, the film blends awkward humor with unexpected depth, shining a light on the complexities of its characters. With standout performances from Anna Faris and Ray Liotta, and a memorable soundtrack, Observe and Report is a must-watch for those who appreciate dark comedies with a touch of emotional resonance.

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I, Tonya, a 2017 biographical sports black comedy-drama, offers a riveting portrayal of figure skater Tonya Hardings tumultuous life, from her challenging childhood to her infamous role in the 1994 Winter Olympics controversy. Directed by Craig Gillespie and penned by Steven Rogers, the film stands out with its mockumentary format, featuring gripping interviews and sensational performances by Margot Robbie as Tonya, Sebastian Stan as Jeff Gillooly, and Allison Janney, who earned an Academy Award for her role as Tonyas abrasive mother. The movie sheds light on the complexities of truth, ambition, and societal pressures, highlighted by compelling quotes like, America. They want someone to love, but they want someone to hate. The powerful soundtrack adds a nostalgic touch, further enhancing the film’s emotional depth. Whether you're a sports enthusiast or a fan of masterful storytelling, I, Tonya is a must-watch for its intense drama, dark humor, and thought-provoking narrative.

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Why You Should Watch Withnail and I Withnail and I, a British black comedy from 1987, is a cinematic gem revered for its dark humor and endearing eccentricity. Set in 1969, it follows Withnail and I, two out-of-work actors navigating the gritty yet comical undertones of life in London. Seeking respite, they venture into the countryside, only to grapple hilariously with their ineptitude. Authored by Bruce Robinson and partly autobiographical, the film shines with superb performances: Richard E. Grant's flamboyant Withnail, Paul McGann's more grounded I, and Richard Griffiths' lovable Uncle Monty. Grant's outrageous lines and the pair's chemistry forge humor and poignancy. Despite its lack of major accolades, its enduring cult status, ranked 29th in BFI's top British films, attests to its cultural significance. Its memorable quotes and evocative soundtrack featuring Jimi Hendrix add layers to the film’s allure. Withnail and I promises a humorous yet thoughtfully bleak exploration of friendship and desperation.

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Parasite, directed by Bong Joon-ho, is a masterful South Korean black comedy thriller that not only entertains but also offers a sharp social commentary on class disparity. The film intricately weaves the tale of the impoverished Kim family infiltrating the affluent Park household, posing as highly skilled professionals. Viewers are drawn in by the compelling performances of the cast, including Song Kang-ho and Choi Woo-shik. The movies production is meticulously detailed, with sets that vividly contrast the stark differences between the two families. Awarded the Palme dOr and four Oscars, including Best Picture, Parasite is a cinematic breakthrough, being the first non-English-language film to win the prestigious award. Its captivating storytelling, excellent use of visual symbols, and haunting score make it a must-watch for anyone interested in experiencing a film that is both intellectually stimulating and emotionally gripping.

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