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Home›Movies›Comedy›Dark Comedy Movies to Watch Alone on Plex

Tag Mix

Dark Comedy Movies to Watch Alone on Plex

50movies

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+ Slow Burn1976 + Atmospheric1855 + Gritty1522 + Bleak1468 + Disturbing1446 + Thought-Provoking1394 + Intense1361 + Emotional1273 + Book1191 + Dialogue-Heavy962 + 2020s + 2010s + 2000s + 90s + 80s + 70s + Under 2 Hours

The King of Comedy (1982) poster

The King of Comedy

1982Comedy · Drama1h 49m

Dark Disturbing Thought-Provoking Antihero Cops

The Sisters Brothers (2018) poster

The Sisters Brothers

2018Comedy · Drama2h 1m

Dark Emotional Hitman Friendship Gritty

Secretary (2002) poster

Secretary

2002Comedy · Drama1h 51m

Weird Dark Romantic Quotable Solo

The Voices (2014) poster

The Voices

2014Comedy · Crime1h 44m

Dark Weird Disturbing Serial Killer Campy

Super (2010) poster

Super

2010Action · Comedy1h 36m

Dark Funny Disturbing Weird Superheroes

August: Osage County (2013) poster

August: Osage County

2013Comedy · Drama2h 1m

Dark Emotional Intense Dysfunctional Family Ensemble Cast

Beau Is Afraid (2023) poster

Beau Is Afraid

2023Adventure · Comedy2h 59m

Dark Funny Weird Disturbing Dysfunctional Family

The Professor (2019) poster

The Professor

2019Comedy · Drama1h 30m

Funny Thought-Provoking Dark College Dialogue-Heavy

Buffalo '66 (1998) poster

Buffalo '66

1998Comedy · Drama1h 50m

Weird Dark Emotional Kidnapping Dysfunctional Family

Deconstructing Harry (1997) poster

Deconstructing Harry

1997Comedy · Drama1h 36m

Funny Dark New York Dialogue-Heavy Nonlinear

The Apprentice (2024) poster

The Apprentice

2024Comedy · Drama2h 2m

Dark Thought-Provoking Disturbing Political New York

Teeth (2008) poster

Teeth

2008Comedy · Horror1h 34m

Disturbing Dark Weird Gory Campy

The Exterminating Angel (1962) poster

The Exterminating Angel

1962Comedy · Drama1h 33m

Language: Spanish

Weird Thought-Provoking Dark Single Location Black & White

May (2003) poster

May

2003Comedy · Drama1h 33m

Disturbing Weird Dark Strong Female Lead Serial Killer

World's Greatest Dad (2009) poster

World's Greatest Dad

2009Comedy · Drama1h 39m

Dark Thought-Provoking Bleak Coming-of-Age High School

Religulous (2008) poster

Religulous

2008Comedy · Documentary1h 41m

Funny Thought-Provoking Dark Mockumentary Dialogue-Heavy

The Love Witch (2016) poster

The Love Witch

2016Comedy · Horror2h 1m

Weird Dark Funny Magic Retro

The Rules of Attraction (2002) poster

The Rules of Attraction

2002Comedy · Drama1h 50m

Dark Weird Disturbing Love Triangle College

Excision (2012) poster

Excision

2012Comedy · Drama1h 21m

Dark Disturbing Weird Dysfunctional Family Gory

Come to Daddy (2019) poster

Come to Daddy

2019Comedy · Horror1h 36m

Weird Disturbing Dark Dysfunctional Family Twist Ending

JCVD (2008) poster

JCVD

2008Action · Comedy1h 36m

Language: French

Thought-Provoking Dark Heist Europe Nonlinear

Mississippi Grind (2015) poster

Mississippi Grind

2015Comedy · Drama1h 48m

Bleak Dark Road Trip Friendship Gritty

Spun (2003) poster

Spun

2003Comedy · Crime1h 41m

Chaotic Dark Weird Fast-Paced Gritty

The Oranges (2011) poster

The Oranges

2011Comedy · Drama1h 30m

Dark Funny Dysfunctional Family Suburbs Dialogue-Heavy

Freeway (1996) poster

Freeway

1996Comedy · Crime1h 44m

Disturbing Dark Chaotic Serial Killer Dysfunctional Family

A Boy and His Dog (1975) poster

A Boy and His Dog

1975Comedy · Drama1h 31m

Weird Dark Bleak Animals Survival

He Was a Quiet Man (2007) poster

He Was a Quiet Man

2007Comedy · Drama1h 35m

Dark Weird Funny Thought-Provoking Antihero

Middle Men (2009) poster

Middle Men

2009Comedy · Crime1h 45m

Dark Chaotic Mafia Fast-Paced Gritty

Solitary Man (2009) poster

Solitary Man

2009Comedy · Drama1h 30m

Dark Thought-Provoking Dysfunctional Family Antihero Dialogue-Heavy

L'Âge d'or (1930) poster

L'Âge d'or

1930Comedy · Drama1h 3m

Language: French

Weird Thought-Provoking Dark Surreal Black & White

Buffet Froid (1979) poster

Buffet Froid

1979Comedy · Crime1h 33m

Language: French

Dark Weird Bleak Surreal Dialogue-Heavy

Swimming with Sharks (1994) poster

Swimming with Sharks

1994Comedy · Crime1h 33m

Dark Funny Intense Kidnapping Revenge

Cul-de-sac (1966) poster

Cul-de-sac

1966Comedy · Crime1h 52m

Dark Weird Funny Chaotic Island

Kontroll (2003) poster

Kontroll

2003Comedy · Crime1h 47m

Language: Hungarian

Dark Weird Funny Suspenseful Atmospheric

Zola (2021) poster

Zola

2021Comedy · Crime1h 26m

Chaotic Weird Dark Road Trip Stylish

Dinner in America (2020) poster

Dinner in America

2020Comedy · Romance1h 48m

Weird Dark Funny Suburbs Dialogue-Heavy

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