20 Seriously Dark & Messed Up Comedy Movies, Ranked

20 Seriously Dark & Messed Up Comedy Movies, Ranked
Image credit: Hulu, Columbia Pictures, Eagle Pictures, Bleecker Street, Magnolia Pictures, Lionsgate, Lauren Films, Republic Pictures, TriStar Pictures, Sony Pictures, Drafthouse Films, PolyGram Filmed Entertainment, A24, Orion Pictures

For all the Tropic Thunder and In Bruges fans.

After you've watched all the big-name dark comedies out there, it might feel like you're out of good options, but that's not true; there are still plenty of darkly hilarious movies under the radar, waiting for you to hit play.

Warning: some of these movies are seriously messed up.

20. Death Becomes Her (1992)

Rotten Tomatoes score: 55%

Two rivals, an actress and an author, drink a magical potion that promises eternal youth, but they find themselves with a body that can't die but can still suffer damage, leading to a series of darkly comedic efforts to maintain their appearance and outdo each other, all while dealing with the consequences of their immortality.

19. Tucker & Dale vs Evil (2010)

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Rotten Tomatoes score: 85%

Tucker and Dale, two well-meaning hillbillies heading to their fixer-upper cabin for some vacation time, are mistaken for murderous backwoods killers by a group of preppy college students. When one of the students gets separated from her friends, the misunderstanding leads to a series of hilariously gruesome accidents that Tucker and Dale must navigate to prove their innocence.

18. Happy Death Day (2017)

Rotten Tomatoes score: 71%

A college student relives the day of her murder over and over again, in a loop that will end only when she discovers her killer's identity. With each repetition, she gets closer to unraveling the mystery surrounding her death, learning valuable lessons about herself and her relationships along the way.

17. Go (1999)

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Rotten Tomatoes score: 91%

The film unfolds in a non-linear narrative following the interconnected lives of several young Los Angelenos over the course of one day and night; a drug deal gone wrong ties together the diverse tales of a group of characters, exploring their decisions, mistakes, and the unpredictable consequences that follow.

16. Observe and Report (2009)

Rotten Tomatoes score: 51%

A delusional, bipolar mall security guard becomes obsessed with catching a flasher terrorizing the mall parking lot, but his quest for justice and recognition becomes increasingly unhinged, leading to a darkly comedic showdown that challenges his perceptions of heroism and reality.

15. The Guard (2011)

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Rotten Tomatoes score: 94%

An unorthodox Irish policeman with a confrontational personality is forced to team up with a straight-laced FBI agent to investigate an international drug-smuggling ring, leading to a culture clash and unconventional tactics in tackling crime on the west coast of Ireland.

14. The Art of Self-Defense (2019)

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Rotten Tomatoes score: 83%

After being brutally mugged, a meek accountant joins a local dojo to learn how to protect himself, but he finds himself drawn into a bizarre, masculine world led by an enigmatic sensei, leading to darkly comedic consequences as he delves deeper into the dojo's cult-like practices and violent undertones.

13. God Bless America (2011)

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Rotten Tomatoes score: 66%

Fed up with the crassness and cruelty of American culture, a middle-aged man and a teenage girl embark on a violent cross-country spree, targeting reality TV stars, bigots, and others they deem culturally detrimental, sparking a controversial debate on media influence and moral decay.

12. Tie Me Up! Tie Me Down! (1989)

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Rotten Tomatoes score: 69%

A recently released psychiatric patient kidnaps a porn star to convince her to marry him and prove that he's rehabilitated. Their unconventional relationship evolves, blending Stockholm syndrome and genuine affection, against a backdrop of quirky characters and unpredictable events.

11. Freeway (1996)

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Rotten Tomatoes score: 76%

A twisted take on "Little Red Riding Hood," this film follows a teenage girl with a rough background as she heads to her grandmother's house after her mother's arrest. On the way, she encounters a seemingly charming but ultimately predatory man, leading to a violent and darkly comedic confrontation that upends the classic fairy tale's themes.

10. I Love You to Death (1990)

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Rotten Tomatoes score: 58%

Joey Boca, a chronic womanizer, finds himself in a precarious situation when his long-suffering wife Rosalie, upon learning of his infidelity, decides to murder him with the help of her mother and a couple of inept hitmen, setting off a series of botched assassination attempts that are as comedic as they are futile, with Joey miraculously surviving each one.

9. To Die For (1995)

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Rotten Tomatoes score: 89%

Suzanne Stone, an ambitious television weatherwoman, dreams of becoming a famous news anchor but finds her marriage to Larry Maretto hindering her career path; she seduces a teenager to get rid of her husband, sparking a darkly comedic chain of events filled with manipulation, deceit, and ambition.

8. Death to Smoochy (2002)

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Rotten Tomatoes score: 42%

When Rainbow Randolph, the corrupt star of a children's TV show, is fired for accepting bribes, his replacement, Sheldon Mopes as the earnest and ethical Smoochy the Rhino, finds himself targeted in Randolph's vengeful and increasingly unhinged plot to reclaim his status, plunging both characters into the absurd underbelly of children's television.

7. Cheap Thrills (2013)

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Rotten Tomatoes score: 88%

A chance meeting at a bar between a struggling family man, Craig, and an old friend, Vince, turns into a night of escalating dares and twisted games when a wealthy couple offers them money for performing dangerous and degrading tasks, testing the limits of their morality and desperation.

6. Man Bites Dog (1992)

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Rotten Tomatoes score: 74%

A darkly satirical mockumentary that follows a charismatic but sociopathic serial killer, Ben, as he goes about his daily life of murder and mayhem, with a film crew documenting his philosophies on art, life, and death, becoming increasingly complicit in his brutal acts.

5. Throw Momma from the Train (1987)

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Rotten Tomatoes score: 64%

A frustrated writing student, Larry Donner, and an obnoxious fellow student, Owen Lift, become entangled in a murder plot against Owen's tyrannical mother, mistakenly believing they've entered a reciprocal arrangement inspired by Hitchcock's "Strangers on a Train," leading to a series of misunderstandings and comedic situations.

4. Very Bad Things (1998)

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Rotten Tomatoes score: 41%

A bachelor party in Las Vegas goes horribly wrong when the hired prostitute accidentally dies, and the group of friends decides to cover up the accident, resulting in a downward spiral of lies, betrayal, and murder as they desperately try to maintain normalcy in their lives.

3. The Death of Dick Long (2019)

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Rotten Tomatoes score: 75%

In a small Alabama town, the mysterious death of Dick Long triggers a desperate attempt by his bandmates Zeke and Earl to cover up their involvement, leading to a series of comedic yet dark missteps as the truth gradually unfolds, revealing bizarre circumstances.

2. Triangle of Sadness (2022)

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Rotten Tomatoes score: 72%

A satirical drama set aboard a luxury cruise for the ultra-rich, where a fashion model couple, Carl and Yaya, navigate through a social hierarchy turned upside down by a storm and subsequent shipwreck, ending up on a deserted island with survivors, challenging their relationships and societal roles.

1. Happiness (1998)

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Rotten Tomatoes score: 83%

In a disturbingly dark comedy, the lives of three sisters, Joy, Trish, and Helen, intertwine with those around them, revealing deep personal struggles; Joy faces love and job disappointments, Trish discovers her husband Bill's appalling secret, and Helen, a successful author, feels unfulfilled, leading each to confront their own version of "happiness" in a stark, suburban landscape.