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Home›Movies›Comedy›Dark 2000s Comedy Movies on Plex

Tag Mix

Dark 2000s Comedy Movies on Plex

27movies

Comedy ×
Dark ×
2000s ×
On Plex ×

27movies

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+ Solo2944 + Intense1848 + Gritty1703 + Atmospheric1340 + Violent1323 + Slow Burn1321 + Disturbing1180 + Friends1124 + Book1092 + Suspenseful967 + Under 2 Hours

Secretary (2002) poster

Secretary

2002Comedy · Drama1h 51m

Weird Romantic Dark Quotable Solo

Bandits (2001) poster

Bandits

2001Comedy · Crime2h 3m

Funny Dark Feel-Good Heist Prison Break

Spread (2009) poster

Spread

2009Comedy · Romance1h 38m

Dark Los Angeles Stylish Date Night

Black Sheep (2006) poster

Black Sheep

2006Comedy · Horror1h 26m

Funny Weird Dark Chaotic Monsters

Teeth (2008) poster

Teeth

2008Comedy · Horror1h 34m

Disturbing Weird Dark Gory Campy

Sicko (2007) poster

Sicko

2007Comedy · Documentary2h 3m

Thought-Provoking Dark Mockumentary Friends True Story

Hatchet (2006) poster

Hatchet

2006Comedy · Horror1h 24m

Scary Dark Serial Killer Friendship Gory

May (2003) poster

May

2003Comedy · Drama1h 33m

Disturbing Weird Dark Serial Killer Strong Female Lead

Two for the Money (2005) poster

Two for the Money

2005Comedy · Crime2h 2m

Dark Intense Sports Dialogue-Heavy Friends

World's Greatest Dad (2009) poster

World's Greatest Dad

2009Comedy · Drama1h 39m

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

Religulous (2008) poster

Religulous

2008Comedy · Documentary1h 41m

Funny Thought-Provoking Dark Dialogue-Heavy Mockumentary

The Rules of Attraction (2002) poster

The Rules of Attraction

2002Comedy · Drama1h 50m

Dark Weird Disturbing Love Triangle College

JCVD (2008) poster

JCVD

2008Action · Comedy1h 36m

Language: French

Dark Thought-Provoking Heist Europe Gritty

Spun (2003) poster

Spun

2003Comedy · Crime1h 41m

Chaotic Dark Weird Fast-Paced Gritty

The Matador (2005) poster

The Matador

2005Action · Comedy1h 37m

Funny Weird Dark Hitman Dialogue-Heavy

Fido (2006) poster

Fido

2006Comedy · Drama1h 32m

Funny Weird Dark Zombies Suburbs

Leaves of Grass (2009) poster

Leaves of Grass

2009Comedy · Crime1h 44m

Funny Dark Weird Dysfunctional Family Road Trip

Death to Smoochy (2002) poster

Death to Smoochy

2002Comedy · Crime1h 49m

Funny Dark Weird Revenge Campy

Lesbian Vampire Killers (2009) poster

Lesbian Vampire Killers

2009Comedy · Horror1h 26m

Funny Dark Chaotic Weird Vampires

Beyond Re-Animator (2003) poster

Beyond Re-Animator

2003Comedy · Horror1h 35m

Weird Chaotic Dark Zombies Prison

Postal (2007) poster

Postal

2007Action · Comedy1h 40m

Chaotic Weird Dark Campy Violent

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

Kontroll (2003) poster

Kontroll

2003Comedy · Crime1h 47m

Language: Hungarian

Dark Weird Funny Suspenseful Gritty

War, Inc. (2008) poster

War, Inc.

2008Action · Adventure1h 46m

Chaotic Dark Hitman Political Violent

2001 Maniacs (2005) poster

2001 Maniacs

2005Comedy · Horror1h 27m

Funny Disturbing Dark Revenge Small Town