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Home›Movies›Comedy›Dark 2000s Comedy Movies to Watch Alone on Plex

Tag Mix

Dark 2000s Comedy Movies to Watch Alone on Plex

12movies

Comedy ×
Dark ×
Solo ×
2000s ×
On Plex ×

12movies

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+ Slow Burn1976 + Atmospheric1855 + Gritty1522 + Bleak1468 + Disturbing1446 + Thought-Provoking1394 + Intense1361 + Emotional1273 + Book1191 + Dialogue-Heavy962 + Under 2 Hours

Secretary (2002) poster

Secretary

2002Comedy · Drama1h 51m

Weird Romantic Dark Quotable Date Night

Teeth (2008) poster

Teeth

2008Comedy · Horror1h 34m

Disturbing Weird Dark Gory Campy

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 Dialogue-Heavy Mockumentary

The Rules of Attraction (2002) poster

The Rules of Attraction

2002Comedy · Drama1h 50m

Dark Disturbing Weird 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

Dark Chaotic Weird Fast-Paced Gritty

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

Thought-Provoking Dark Dysfunctional Family Antihero Dialogue-Heavy

Kontroll (2003) poster

Kontroll

2003Comedy · Crime1h 47m

Language: Hungarian

Dark Weird Funny Suspenseful Gritty