52 Deliciously Dark Comedies You Should See Before You Die

These films are dark, depraved, and deeply hilarious.

1. Arsenic and Old Lace (1944)

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Written by: Julius J. Epstein and Philip G. Epstein
Directed by: Frank Capra
What it’s about: Mortimer Brewster (Cary Grant) must deal with his eccentric family, including his aunts Abby (Josephine Hull) and Martha (Jean Adair), who poison lonely bachelors with arsenic, and his homicidal brother Jonathan (Raymond Massey), whose face has been mangled by a drunk plastic surgeon.

2. Kind Hearts and Coronets (1949)

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Written by: Robert Hamer and John Dighton
Directed by: Robert Hamer
What it’s about: Louis Mazzini (Dennis Price) vows to avenge his mother after she is disowned by her aristocratic family, the D’Ascoynes. Louis begins to off members of the family, all played by Alec Guinness, one by one, until he finally becomes the duke — shortly before he’s charged and convicted of murder.

3. All About Eve (1950)

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Written by: Joseph L. Mankiewicz
Directed by: Joseph L. Mankiewicz
What it’s about: Broadway star Margo Channing (Bette Davis) has just turned 40 and worries about the future of her career. She meets Eve Harrington (Anne Baxter), who purports to be a fan, but turns out to be an incredibly ambitious actor who forces her way into Margo’s life and eventually becomes an even bigger success.

4. Dr. Strangelove or: How I Learned to Stop Worrying and Love the Bomb (1964)

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Written by: Stanley Kubrick, Peter George, and Terry Southern
Directed by: Stanley Kubrick
What it’s about: In the war room, President Merkin Muffley of the United States (Peter Sellers) and his advisers — including General Buck Turgidson (George C. Scott) and Dr. Strangelove (Sellers) — debate a first strike nuclear attack on the Soviet Union that will bring about a nuclear apocalypse.

5. Who’s Afraid of Virginia Woolf? (1966)

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Written by: Ernest Lehman
Directed by: Mike Nichols
What it’s about: Troubled older couple George (Richard Burton) and Martha (Elizabeth Taylor) invite over the young and more innocent Nick (George Segal) and Honey (Sandy Dennis) for late-night drinks. The more they all imbibe, the crueler and more violent their games get, culminating in a declaration of war.

6. Harold and Maude (1971)

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Written by: Colin Higgins
Directed by: Hal Ashby
What it’s about: Young, but death-obsessed Harold Chasen (Bud Cort) meets 79-year-old Maude (Ruth Gordon), who has a zest for life. They engage in a short-lived but passionate romance, as Maude gives Harold a new appreciation for the world around him and shows him how to make the most of his time on earth.

7. Network (1976)

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Written by: Paddy Chayefsky
Directed by: Sidney Lumet
What it’s about: After getting fired, TV anchor Howard Beale (Peter Finch) goes on the air and threatens to commit suicide. His impassioned rants and raves earn incredible ratings, prompting the network to look for similar programming, at which point, Diana Christensen (Faye Dunaway) greenlights a show with radical terrorists.

8. Brazil (1985)

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Written by: Terry Gilliam, Tom Stoppard, and Charles McKeown
Directed by: Terry Gilliam
What it’s about: In a dystopian future filled with useless machines and endless bureaucracy, government employee Sam Lowry (Jonathan Pryce) seeks to rescue suspected terrorist Jill Layton (Kim Greist), a woman he has seen in his recurring dreams. In doing so, he runs afoul of the dangerous totalitarian government.

9. After Hours (1985)

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Written by: Joseph Minion
Directed by: Martin Scorsese
What it’s about: Over the course of one night, Paul Hackett (Griffin Dunne) tries to get back to his apartment and faces a series of misadventures along the way, encountering the mysterious Marcy (Rosanna Arquette), her sculptor roommate Kiki (Linda Fiorentino), and burglars Neil and Pepe (Cheech and Chong).

10. Throw Momma From the Train (1987)

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Written by: Stu Silver
Directed by: Danny DeVito
What it’s about: In a modern take on Hitchcock’s Strangers on a Train, novelist Larry Donner (Billy Crystal) meets Owen Lift (Danny DeVito) on a train. Owen decides he will kill Larry’s ex-wife Margaret (Kate Mulgrew) in exchange for Larry killing Owen’s overbearing mother (Anne Ramsay).

11. Evil Dead II (1987)

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Written by: Sam Raimi and Scott Spiegel
Directed by: Sam Raimi
What it’s about: At an abandoned cabin in the woods, Ash Williams (Bruce Campbell) and his girlfriend Linda (Denise Bixler) are terrorized by a demonic force that possesses Linda, forcing Ash to kill her. In this sequel, Ash attempts to stop the evil work of the Necronomicon once and for all with his trademark flair.

12. Heathers (1988)

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Written by: Daniel Waters
Directed by: Michael Lehmann
What it’s about: Veronica Sawyer (Winona Ryder) has infiltrated the Heathers, the meanest, most popular clique in school. After she and her boyfriend J.D. (Christian Slater) accidentally kill Queen Bee Heather Chandler (Kim Walker), they go to extreme measures to right high school’s wrongs.

13. The War of the Roses (1989)

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Written by: Michael J. Leeson
Directed by: Danny DeVito
What it’s about: Married couple Oliver (Michael Douglas) and Barbara Rose (Kathleen Turner) go from blissfully happy to at each other’s throats, leading Barbara to throw Oliver out of the house. But he finds a loophole that will let him stay, so the two set about ruining each other’s lives and causing as much destruction as possible.

14. Misery (1990)

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Written by: William Goldman
Directed by: Rob Reiner
What it’s about: When novelist Paul Sheldon (James Caan) gets in a car accident after getting caught in a blizzard, he is rescued by Annie Wilkes (Kathy Bates). She claims to be his biggest fan but turns out to be dangerously psychotic, refusing to let Paul leave and horrifically abusing him when he tries.

15. Delicatessen (1991)

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Written by: Gilles Adrien, Marc Caro, and Jean-Pierre Jeunet
Directed by: Marc Caro and Jean-Pierre Jeunet
What it’s about: In post-apocalyptic France, landlord Clapet (Jean-Claude Dreyfus) doubles as a butcher, luring job seekers to his building and killing them to provide meat for his tenants. When his daughter Julie (Marie-Laure Dougnac) falls for Louison (Dominique Pinon), she drums up a rebellion to stop her father.

16. Man Bites Dog (1992)

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Written by: Rémy Belvaux, André Bonzel, Benoît Poelvoorde, and Vincent Tavier
Directed by: Rémy Belvaux, André Bonzel, and Benoît Poelvoorde
What it’s about: A crew of filmmakers are making a documentary about charming serial killer Ben (Benoît Poelvoorde), documenting the atrocities he commits without intervening. Eventually, the filmmakers are brought into Ben’s world and begin to participate in his heinous crimes.

17. Death Becomes Her (1992)

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Written by: Martin Donovan and David Koepp
Directed by: Robert Zemeckis
What it’s about: Bitter actresses and rivals Madeline Ashton (Meryl Streep) and Helen Sharp (Goldie Hawn) spar over Dr. Ernest Menville (Bruce Willis), who left Helen for Madeline. Both women discover a potion promising eternal youth — but only learn of the serious consequences when they’re trying to murder each other.

18. Serial Mom (1994)

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Written by: John Waters
Directed by: John Waters
What it’s about: Baltimore housewife Beverly Sutphin (Kathleen Turner) is secretly a serial killer, murdering anyone who commits even the slightest offense against her. The authorities eventually catch on, but Beverly’s trial turns into a circus where she manages to discredit every witness against her.

19. Happiness (1998)

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Written by: Todd Solondz
Directed by: Todd Solondz
What it’s about: Three sisters search for happiness — Trish (Cynthia Stevenson) is married to Bill Maplewood (Dylan Baker), a pedophile rapist; Helen (Lara Flynn Boyle) is obsessed with Allen (Philip Seymour Hoffman), a man making obscene calls; and Joy (Jane Adams) falls for one of her students (Jared Harris), who is also married.

20. To Die For (1995)

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Written by: Buck Henry
Directed by: Gus Van Sant
What it’s about: Ambitious Suzanne Stone (Nicole Kidman) is determined to become a news anchor. When her husband Larry (Matt Dillon) tries to get her to spend more time at home, she seduces a high school boy (Joaquin Phoenix) and convinces him and his friends to murder Larry.

21. Welcome to the Dollhouse (1995)

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Written by: Todd Solondz
Directed by: Todd Solondz
What it’s about: Awkward, unpopular Dawn Wiener (Heather Matarazzo) tries to survive the horrors of seventh grade, including a romance with a boy (Brendan Sexton III) who threatens to rape her, a younger sister (Daria Kalinina) who gets all the attention, and a cool older guy (Eric Mabius) she doesn’t have a chance with.

22. The Cable Guy (1996)

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Written by: Lou Holtz Jr.
Directed by: Ben Stiller
What it’s about: Steven Kovacs (Matthew Broderick) strikes up a friendship with his seemingly harmless cable guy, Ernie “Chip” Douglas (Jim Carrey). But Chip soon takes on more and more eccentric behavior, deliberately inserting himself in Steven’s life and ultimately trying to ruin all his relationships.

23. Freeway (1996)

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Written by: Matthew Bright
Directed by: Matthew Bright
What it’s about: In this loose adaptation of Little Red Riding Hood, troubled Vanessa Lutz (Reese Witherspoon) gets a ride to her grandmother’s house from guidance counselor Bob Wolverton (Kiefer Sutherland). Bob turns out to be a serial killer, but when Vanessa defends herself, everyone takes Bob’s side over hers.

24. Fargo (1996)

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Written by: Joel Coen and Ethan Coen
Directed by: Joel Coen and Ethan Coen
What it’s about: Police chief Marge Gunderson (Frances McDormand), who is very pregnant, pursues a grisly homicide case in Fargo, Minn., discovering that an unlikely suspect, car salesman Jerry Lundegaard (William H. Macy), is actually the man who set the crimes in motion.

25. The House of Yes (1997)

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Written by: Mark Waters
Directed by: Mark Waters
What it’s about: In this film based on the Wendy MacLeod play of the same name, Marty Pascal (Josh Hamilton) brings his fiancée Lesly (Tori Spelling) home to meet his family. Once there, she encounters his dangerously delusional twin sister Jackie-O (Parker Posey), with whom Marty has an inappropriate relationship.

26. Very Bad Things (1998)

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Written by: Peter Berg
Directed by: Peter Berg
What it’s about: A Vegas bachelor party for Kyle Fisher (Jon Favreau) goes from bad to worse when his friend Michael (Jeremy Piven) accidentally kills a prostitute, and another friend, Robert Boyd (Christian Slater), suggests they cover it up. Deaths pile up as the friends struggle to make it to Kyle’s wedding in one piece.

27. Slums of Beverly Hills (1998)

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Written by: Tamara Jenkins
Directed by: Tamara Jenkins
What it’s about: Vivian Abromowitz (Natasha Lyonne) moves with her family from cheap apartment to cheap apartment in Beverly Hills because her father Murray (Alan Arkin) can’t afford to pay rent. Newly endowed with breasts, Vivian embarks on a journey of sexual discovery with her neighbor Eliot (Kevin Corrigan).

28. Bride of Chucky (1998)

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Written by: Don Mancini
Directed by: Ronny Yu
What it’s about: Evil doll Chucky (Brad Dourif) is brought back to life by his ex-girlfriend Tiffany (Jennifer Tilly). Chucky ends up killing Tiffany, only to bring her back in doll form, and the two go on a killing spree to procure the Heart of Damballa, an amulet that will help them reclaim human bodies.

29. Ravenous (1999)

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Written by: Ted Griffin
Directed by: Antonia Bird
What it’s about: During the Mexican-American War, Captain John Boyd (Guy Pearce) encounters Colonel Ives (Robert Carlyle), who has taken to killing and eating men in order to absorb their strength. Boyd struggles to convince everyone of what Ives is doing, while Ives’ body count continues to rise.

30. Jawbreaker (1999)

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Written by: Darren Stein
Directed by: Darren Stein
What it’s about: A group of high school mean girls, led by Courtney Shayne (Rose McGowan), accidentally murder their friend Liz (Charlotte Ayana) when a prank goes wrong. When outcast Fern Mayo (Judy Greer) finds out, Courtney keeps her quiet by transforming her into hot exchange student Vylette.

31. Fight Club (1999)

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Written by: Jim Uhls
Directed by: David Fincher
What it’s about: The narrator (Edward Norton) is a listless, unhappy man who gets drawn into the world of fight clubs by Tyler Durden (Brad Pitt). As Tyler becomes more destructive, the narrator tries to thwart him, unaware that the two men are inextricably linked.

32. Election (1999)

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Written by: Alexander Payne and Jim Taylor
Directed by: Alexander Payne
What it’s about: High school teacher Jim McAllister (Matthew Broderick) tries to stop overzealous Tracy Flick (Reese Witherspoon) from becoming student body president. He convinces jock Paul Metzler (Chris Klein) to run, but is unprepared for Paul’s sister Tammy (Jessica Campbell), who’s also running for president out of revenge.

33. American Beauty (1999)

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Written by: Alan Ball
Directed by: Sam Mendes
What it’s about: Lester Burnham (Kevin Spacey) is unhappy with his life — his wife Carolyn (Annette Bening) is cheating on him, and his daughter Jane (Thora Birch) hates both her parents. Lester becomes obsessed with Jane’s best friend Angela (Mena Suvari) and buys weed from his neighbor Ricky (Wes Bentley).

34. Drop Dead Gorgeous (1999)

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Written by: Lona Williams
Directed by: Michael Patrick Jann
What it’s about: Amber Atkins (Kirsten Dunst) vies to win a beauty pageant against evil Becky Leeman (Denise Richards) in the small town of Mount Rose, Minn. There’s clear corruption in the form of Gladys Leeman (Kirstie Alley), head of the pageant and Becky’s mother — and then girls start dying horribly.

35. Chuck & Buck (2000)

Written by: Mike White
Directed by: Miguel Arteta
What it’s about: Buck O’Brien (Mike White) has a serious case of arrested development — he’s obsessed with the sexual experimentation he and his friend Chuck (Chris Weitz) did when they were 11. Buck makes an advance at Chuck (now Charlie), who rejects him, but Buck refuses to give up his obsessive quest.

36. American Psycho (2000)

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Written by: Mary Harron and Guinevere Turner
Directed by: Mary Harron
What it’s about: Wealthy investment banker Patrick Bateman (Christian Bale) lives a secret double life as a sadistic serial killer. As Patrick becomes increasingly unhinged, he tries to convince people about the horrors he’s inflicting, but no one will take him seriously.

37. Adaptation. (2002)

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Written by: Charlie Kaufman
Directed by: Spike Jonze
What it’s about: Charlie Kaufman (Nicolas Cage) struggles to adapt The Orchid Thief, a novel by Susan Orlean (Meryl Streep), while his twin brother Donald (Cage) suddenly becomes a successful screenwriter. Things turn violent when Charlie meets John Laroche (Chris Cooper), the protagonist of Susan’s novel.

38. Death to Smoochy (2002)

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Written by: Adam Resnick
Directed by: Danny DeVito
What it’s about: Rainbow Randolph Smiley (Robin Williams) is the host of a popular children’s show who gets busted for making deals with parents to get their kids on his show. When he’s replaced by the innocent Sheldon Mopes (Edward Norton), Randolph sets about destroying Sheldon and his character, Smoochy the Rhino.

39. The Rules of Attraction (2002)

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Written by: Roger Avary
Directed by: Roger Avary
What it’s about: At Camden College in New Hampshire, the students are more concerned with sex and drugs than with studying. Sean Bateman (James Van Der Beek) pines after Lauren Hynde (Shannyn Sossamon), while being pined after by bisexual Paul Denton (Ian Somerhalder).

40. The Good Girl (2002)

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Written by: Mike White
Directed by: Miguel Arteta
What it’s about: Justine Last (Jennifer Aniston) is stuck at a boring retail job and in a marriage with the clueless Phil (John C. Reilly). She begins an affair with Holden Worther (Jake Gyllenhaal), who has named himself after the protagonist of Catcher in the Rye, then tries to get rid of him when things get too intense.

41. Bad Santa (2003)

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Written by: Glenn Ficarra and John Requa
Directed by: Terry Zwigoff
What it’s about: Alcoholic and sex addict Willie T. Stokes (Billy Bob Thornton) poses as a mall Santa along with his accomplice Marcus (Tony Cox), who dons an elf costume, so that the two can disable the mall security system and rob the safe. Along the way, Willie scandalizes parents and mall employees with his foul language and bad behavior.

42. Shaun of the Dead (2004)

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Written by: Edgar Wright and Simon Pegg
Directed by: Edgar Wright
What it’s about: Aimless electronics shop employee Shaun (Simon Pegg) doesn’t seem to notice that the zombie apocalypse is happening all around him. Eventually he catches on and tries to survive, along with his friends, while also attempting to win back his recent ex-girlfriend Liz (Kate Ashfield).

43. Art School Confidential (2006)

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Written by: Daniel Clowes
Directed by: Terry Zwigoff
What it’s about: Jerome (Max Minghella) follows his passion to art school, where he falls for art model Audrey (Sophia Myles). Meanwhile, the community is living in fear of a serial killer, the Swarthmore Strangler, and Jerome finds himself in a rivalry with undercover detective Jonah (Matt Keeslar).

44. Choke (2008)

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Written by: Clark Gregg
Directed by: Clark Gregg
What it’s about: Victor Mancini (Sam Rockwell) is a sex addict who works as a Colonial America reenactor and intentionally chokes at restaurants to con people into giving him money. While seeking care for his ill mother (Anjelica Huston), he develops real feelings for her doctor Paige Marshall (Kelly Macdonald).

45. World’s Greatest Dad (2009)

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Written by: Bobcat Goldthwait
Directed by: Bobcat Goldthwait
What it’s about: Single father Lance Clayton (Robin Williams) does his best to connect with his difficult teenage son Kyle (Daryl Sabara). After Kyle accidentally strangles himself during autoerotic asphyxiation, Lance writes a suicide note on his son’s behalf, and finds new popularity in death.

46. The Loved Ones (2009)

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Written by: Sean Byrne
Directed by: Sean Byrne
What it’s about: Awkward Lola Stone (Robin McLeavy) asks Brent (Xavier Samuels) to prom, but he turns her down. In retaliation, Lola and her twisted father (John Brumpton) kidnap Brent and brutally torture him so that Lola can have the prom night she always dreamed of.

47. Jennifer’s Body (2009)

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Written by: Diablo Cody
Directed by: Karyn Kusama
What it’s about: Needy Lesnicki (Amanda Seyfried) is best friends with the much more popular Jennifer Check (Megan Fox). But the two butt heads when Jennifer is sacrificed to a demon and then becomes possessed, viciously murdering and eating high school boys.

48. Four Lions (2010)

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Written by: Chris Morris, Jesse Armstrong, and Sam Bain
Directed by: Chris Morris
What it’s about: Omar (Riz Ahmed), Waj (Kayvan Novak), Barry (Nigel Lindsay), and Faisal (Adeel Akhtar) are four British Muslim men who aspire to be suicide bombers. Despite their convictions, they are terrible at being jihadists and mostly end up doing more harm to their cause than good.

49. Super (2010)

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Written by: James Gunn
Directed by: James Gunn
What it’s about: Short-order cook Frank Darbo (Rainn Wilson) decides to fight crime and takes on the superhero identity of The Crimson Bolt. He meets Libby (Ellen Page), who wants to be his sidekick, Boltie, but proves herself to be seriously unstable, and both end up way over their heads.

50. God Bless America (2011)

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Written by: Bobcat Goldthwait
Directed by: Bobcat Goldthwait
What it’s about: Miserable insurance salesman Frank Murdoch (Joel Murray) is fed up with the rudeness and cruelty of American pop culture. He teams up with disaffected teenager Roxy Harmon (Tara Lynne Barr), and the two go on a violent killing spree, culminating in the destruction of an American Idol-like reality show.

51. Killer Joe (2011)

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Written by: Tracy Letts
Directed by: William Friedkin
What it’s about: Drug dealer Chris Smith (Emile Hirsch) is deeply in debt, so he hires contract killer Joe Cooper (Matthew McConaughey) to murder his mother and collect the insurance money. Things get complicated when Joe begins sleeping with Chris’ little sister Dottie (Juno Temple) and threatens to take her away.

52. Cheap Thrills (2013)

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Written by: Trent Haaga and David Chirchirillo
Directed by: E.L. Katz
What it’s about: Desperate for money, Craig (Pat Healy) and his high school friend Vince (Ethan Embry) end up playing a sick game with twisted rich couple Colin (David Koechner) and Violet (Sara Paxton), who encourage the men to brutalize themselves for increasing monetary rewards.

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