
Awkward Comedy movies
Cringe-powered, character-based humor: misreads, social discomfort, odd sincerity, and painfully funny situations.

71. The Darjeeling Limited
Adventure Drama Comedy Globetrotting Adventure Relationship Drama2007•1h 32min
United States
Director: Wes Anderson
Vibe
Three American brothers who have not spoken to each other in a year set off on a train voyage across India with a plan to find themselves and bond with each other -- to become brothers again like they used to be. Their "spiritual quest", however, veers rapidly off-course (due to events involving over-the-counter pain killers, Indian cough syrup, and pepper spray).
Themes
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72. My Sassy Girl
Drama Comedy Romance Romantic Comedy Awkward Comedy2001•2h 17min
South Korea
Director: Kwak Jae-yong
Vibe
A dweeby, mild-mannered man comes to the aid of a drunk young woman on a subway platform. Little does he know how much trouble he’s in for.
Themes
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73. Happy-Go-Lucky
Comedy Drama Awkward Comedy Coming-of-Age Drama2008•1h 58min
United Kingdom, United States
Director: Mike Leigh
Vibe
A look at a few chapters in the life of Poppy, a cheery, colorful, North London schoolteacher whose optimism tends to exasperate those around her.
Themes
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74. The Station Agent
Drama Comedy Relationship Drama Awkward Comedy2003•1h 28min
United States
Director: Tom McCarthy
Vibe
When his only friend dies, a man born with dwarfism moves to rural New Jersey to live a life of solitude, only to meet a chatty hot dog vendor and a woman dealing with her own personal loss.
Themes
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75. The Man Who Copied
Comedy Drama Romance Crime Awkward Comedy2003•2h 3min
Brazil
Director: Jorge Furtado
Vibe
A young photocopier operator becomes infatuated with his neighbor and, unable to afford anything from her shop, turns to shady schemes to make money.
Themes

76. Cashback
Drama Comedy Romance Bittersweet Romance Awkward Comedy2007•1h 42min
United Kingdom
Director: Sean Ellis
Vibe
After a painful breakup, Ben develops insomnia. To kill time, he starts working the late night shift at the local supermarket, where his artistic imagination runs wild.
Themes
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77. The Savages
Drama Comedy Family Drama Awkward Comedy2007•1h 54min
United States
Director: Tamara Jenkins
Vibe
A sister and brother face the realities of familial responsibility as they begin to care for their ailing father.
Themes
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78. The Squid and the Whale
Comedy Drama Coming-of-Age Drama Awkward Comedy2005•1h 21min
United States
Director: Noah Baumbach
Vibe
Based on the true childhood experiences of Noah Baumbach and his brother, The Squid and the Whale tells the touching story of two young boys dealing with their parents' divorce in Brooklyn in the 1980s.
Themes
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79. Transamerica
Drama Adventure Comedy Relationship Drama Awkward Comedy2005•1h 43min
United States
Director: Duncan Tucker
Vibe
A transgender woman takes an unexpected journey when she learns that she had a son, now a teenage runaway hustling on the streets of New York.
Themes
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Vibe
Brennan Huff and Dale Doback might be grown men. But that doesn't stop them from living at home and turning into jealous, competitive stepbrothers when their single parents marry. Brennan's constant competition with Dale strains his mom's marriage to Dale's dad, leaving everyone to wonder whether they'll ever see eye to eye.
