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

81. Charlie Bartlett
Comedy Drama Romance Awkward Comedy Coming-of-Age Drama2008•1h 37min
United States, Canada
Director: Jon Poll
Vibe
Awkward teenager Charlie Bartlett has trouble fitting in at a new high school. Charlie needs some friends fast, and decides that the best way to find them is to appoint himself the resident psychiatrist. He becomes one of the most popular guys in school by doling out advice and, occasionally, medication, to the student body.
Themes
Available on

82. Secondhand Lions
Family Comedy Parent-Child Family Awkward Comedy2003•1h 51min
United States
Director: Tim McCanlies
Vibe
The comedic adventures of an introverted boy left on the doorstep of a pair of reluctant, eccentric great-uncles, whose exotic remembrances stir the boy's spirit and re-ignite the men's lives.
Themes
Available on

83. Waitress
Drama Comedy Romance Romantic Comedy Awkward Comedy2007•1h 45min
United States
Director: Adrienne Shelly
Vibe
A small town waitress stuck in a lousy marriage finds love when an exciting out-of-towner enters her life.
Themes
Available on

85. Me and You and Everyone We Know
Comedy Drama Awkward Comedy Family Drama2005•1h 31min
United Kingdom, United States
Director: Miranda July
Vibe
Single dad Richard meets Christine, a starving artist who moonlights as a cabbie. They awkwardly attempt to start a romance, but Richard’s divorce has left him emotionally damaged. Meanwhile, Richard’s sons—one a teenager, the other 6-years-old—take part in clumsy experiments with the opposite sex.
Themes
Available on

86. Knocked Up
Comedy Romance Drama Romantic Comedy Awkward Comedy2007•2h 9min
United States
Director: Judd Apatow
Vibe
After a chance meeting and a night spent together, TV journalist Alison and unemployed Ben learn they’re going to be parents. Can they stay together when they have almost nothing in common?
Themes
Available on
Vibe
Young Nigel Slater has big culinary aspirations, even though all his mother knows how to make is toast. When his mother dies, relations grow strained between Nigel and his father, especially when he remarries a woman who wins his heart with a lemon meringue pie. Nigel enters culinary school, starts working in a pub, and finds himself competing with his stepmother - both in the kitchen and for his father's attention.
Themes
Available on

88. I'm a Cyborg, But That's OK
Drama Comedy Romance Psychological Drama Romantic Comedy2006•1h 45min
South Korea
Director: Park Chan-wook
Vibe
Young-goon, mentally deranged and frequently electro-charging herself with a transistor radio, has been admitted into a mental institution. Firmly believing herself to be a cyborg, she refuses to consume like a human being. Il-soon is another patient, who catches the eye of Young-goon and soon becomes a close friend. Il-soon is now confronted with the biggest task: to cure Young-goon's mental problem and have her eat real food.
Themes
Available on

90. Eagle vs Shark
Comedy Romance Romantic Comedy Awkward Comedy2007•1h 27min
New Zealand
Director: Taika Waititi
Vibe
Love blossoms for Lily over double Meaty Boy burgers at mid-day when uber-computer nerd Jarrod comes in and leaves with free extra large fries. After gatecrashing Jarrod's party and proving her skills on the game console, Lily goes down to Jarrod's home town with him so he can settle an old score with a past school bully.


