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Home›Movies›Comedy›Dark 2000s Comedy Movies

Tag Mix

Dark 2000s Comedy Movies

104movies

Comedy ×
Dark ×
2000s ×

104movies

Keep narrowing

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

Where to watch

On Tubi39 On Hoopla30 On Kanopy29 On Plex27 On The Roku Channel23 On Prime Video21

Charlie and the Chocolate Factory (2005) poster

Charlie and the Chocolate Factory

2005Adventure · Comedy1h 55m

Whimsical Funny Dark Weird London

Shaun of the Dead (2004) poster

Shaun of the Dead

2004Comedy · Horror1h 39m

Funny Dark Chaotic Survival Zombies

In Bruges (2008) poster

In Bruges

2008Comedy · Crime1h 48m

Dark Funny Thought-Provoking Hitman Europe

Burn After Reading (2008) poster

Burn After Reading

2008Comedy · Drama1h 36m

Dark Funny Chaotic Conspiracy Ensemble Cast

Lemony Snicket's A Series of Unfortunate Events (2004) poster

Lemony Snicket's A Series of Unfortunate Events

2004Adventure · Comedy1h 48m

Whimsical Funny Dark Stylish Visually Stunning

Jennifer's Body (2009) poster

Jennifer's Body

2009Comedy · Horror1h 47m

Dark Funny Weird Monsters High School

Idiocracy (2006) poster

Idiocracy

2006Adventure · Comedy1h 25m

Funny Thought-Provoking Dark Fish Out of Water Time Travel

Kiss Kiss Bang Bang (2005) poster

Kiss Kiss Bang Bang

2005Comedy · Crime1h 43m

Funny Dark Whodunit Cops Los Angeles

The Brothers Grimm (2005) poster

The Brothers Grimm

2005Action · Adventure1h 58m

Whimsical Weird Dark Con Artist Magic

Chicago (2002) poster

Chicago

2002Comedy · Crime1h 53m

Funny Dark Courtroom Prison Musical

The Break-Up (2006) poster

The Break-Up

2006Comedy · Romance1h 46m

Funny Dark Dialogue-Heavy Date Night Friends

Just Like Heaven (2005) poster

Just Like Heaven

2005Comedy · Fantasy1h 35m

Romantic Funny Dark Heartwarming Date Night

Bad Santa (2003) poster

Bad Santa

2003Comedy · Crime1h 32m

Dark Funny Gritty Friends Christmas

A Serious Man (2009) poster

A Serious Man

2009Comedy · Drama1h 46m

Dark Thought-Provoking Funny Dysfunctional Family Dialogue-Heavy

Trick 'r Treat (2007) poster

Trick 'r Treat

2007Comedy · Fantasy1h 22m

Creepy Funny Dark Serial Killer Monsters

The Whole Nine Yards (2000) poster

The Whole Nine Yards

2000Comedy · Crime1h 38m

Funny Dark Mafia Hitman Suburbs

Secretary (2002) poster

Secretary

2002Comedy · Drama1h 51m

Weird Dark Romantic Quotable Date Night

Death at a Funeral (2007) poster

Death at a Funeral

2007Comedy · Drama1h 31m

Funny Chaotic Dark Dysfunctional Family Ensemble Cast

Volver (2006) poster

Volver

2006Comedy · Drama2h 1m

Language: Spanish

Emotional Heartwarming Dark Dysfunctional Family Strong Female Lead

Smokin' Aces (2006) poster

Smokin' Aces

2006Action · Comedy1h 49m

Dark Chaotic Funny Mafia Hitman

Duplex (2003) poster

Duplex

2003Comedy1h 29m

Funny Dark Chaotic New York Friends

Intolerable Cruelty (2003) poster

Intolerable Cruelty

2003Comedy · Crime1h 40m

Funny Dark Romantic Hitman Con Artist

Ghost World (2001) poster

Ghost World

2001Comedy · Drama1h 51m

Weird Dark Thought-Provoking Friendship Coming-of-Age

Broken Flowers (2005) poster

Broken Flowers

2005Comedy · Drama1h 46m

Thought-Provoking Dark Road Trip Slow Burn Dialogue-Heavy

Confessions of a Dangerous Mind (2002) poster

Confessions of a Dangerous Mind

2002Comedy · Crime1h 53m

Weird Dark Thought-Provoking Spies Hitman

Bandits (2001) poster

Bandits

2001Comedy · Crime2h 3m

Funny Dark Feel-Good Heist Prison Break

The Weather Man (2005) poster

The Weather Man

2005Comedy · Drama1h 41m

Dark Bleak Thought-Provoking Dysfunctional Family New York

The Squid and the Whale (2005) poster

The Squid and the Whale

2005Comedy · Drama1h 21m

Thought-Provoking Emotional Dark Coming-of-Age Dysfunctional Family

11:14 (2004) poster

11:14

2004Comedy · Crime1h 26m

Chaotic Dark Suspenseful Cops Heist

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 Dark Weird Gory Campy

99 Francs (2007) poster

99 Francs

2007Comedy · Drama1h 44m

Language: French

Dark Chaotic Weird Antihero Paris

Adam's Apples (2005) poster

Adam's Apples

2005Comedy · Crime1h 35m

Language: Danish

Funny Dark Weird Smart Solo

Sicko (2007) poster

Sicko

2007Comedy · Documentary2h 3m

Thought-Provoking Dark Mockumentary Friends True Story

In the Loop (2009) poster

In the Loop

2009Comedy1h 46m

Funny Chaotic Dark Political Dialogue-Heavy

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