Awkward Comedy backdrop

Awkward Comedy movies

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

Charlie Bartlett

81. Charlie Bartlett

Comedy Drama Romance Awkward Comedy Coming-of-Age Drama
6.9

20081h 37min

United States, Canada

Director: Jon Poll

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

High school pressure, Drug addiction dynamics, Adolescent depression, Private school divide, Suicide attempt challenges, Psychiatrist role

Available on

Amazon Video
Apple TV
Google Play Movies
Data provided by JustWatch.Availability may vary by region.

Secondhand Lions

82. Secondhand Lions

Family Comedy Parent-Child Family Awkward Comedy
7.5

20031h 51min

United States

Director: Tim McCanlies

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

Wealth as lure, Deception and loyalty, Intergenerational mentorship, Coming of age pressure, Family isolation vs attachment, Legacy and memory

Available on

Amazon Video
Apple TV
Google Play Movies
Data provided by JustWatch.Availability may vary by region.

Waitress

83. Waitress

Drama Comedy Romance Romantic Comedy Awkward Comedy
7.0

20071h 45min

United States

Director: Adrienne Shelly

A small town waitress stuck in a lousy marriage finds love when an exciting out-of-towner enters her life.

Themes

Economic dependence and escape, Illicit relationship and consequences, Domestic abuse and autonomy, Female friendship and solidarity, Creative coping through work, Dream pursuit and risk

Available on

Amazon Video
Apple TV
Google Play Movies
Data provided by JustWatch.Availability may vary by region.

Son of Rambow

84. Son of Rambow

Comedy Awkward Comedy
7.0

20071h 36min

France, Germany

Director: Garth Jennings

Will is looking for an escape from his family when he encounters Lee, the school bully. Armed with a video camera and a copy of Rambo, Lee plans to make his own action-packed video epic.

Themes

Belonging under peer pressure, Religious conformity vs creativity, Identity within groups, Power dynamics among youths, Family rupture and independence, Collective art as escape

Available on

Amazon Video
Apple TV
Google Play Movies
Data provided by JustWatch.Availability may vary by region.

Me and You and Everyone We Know

85. Me and You and Everyone We Know

Comedy Drama Awkward Comedy Family Drama
7.2

20051h 31min

United Kingdom, United States

Director: Miranda July

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

Art gallery exposure, Playground boundary negotiation, Separation emotional strain, Hope chest symbolism, Shoe salesman vulnerability, Chat session ambiguity

Available on

Kanopy
Criterion Channel
Philo
Data provided by JustWatch.Availability may vary by region.

Knocked Up

86. Knocked Up

Comedy Romance Drama Romantic Comedy Awkward Comedy
6.9

20072h 9min

United States

Director: Judd Apatow

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

Deception and trust, Unplanned pregnancy, Partnership under stress, Responsibility and maturation, Work-life balance, Family dynamics

Available on

Amazon Video
Apple TV
Google Play Movies
Data provided by JustWatch.Availability may vary by region.

Toast

87. Toast

Drama Comedy History Family Family Drama
6.5

20101h 36min

United Kingdom

Director: S.J. Clarkson

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

Sexual awakening, Ambition and loyalty, Family dynamics under strain, Maternal influence through cooking, Remarriage and adjustment, Nostalgia and craft

Available on

Amazon Prime Video
Amazon Video
Hoopla
Data provided by JustWatch.Availability may vary by region.

I'm a Cyborg, But That's OK

88. I'm a Cyborg, But That's OK

Drama Comedy Romance Psychological Drama Romantic Comedy
6.9

20061h 45min

South Korea

Director: Park Chan-wook

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

Grandparent grandchild relationship, Delusions of cyborg identity, Institutional control and care, Trauma echoes across generations, Manipulation within care dynamics, Reliance on machines

Available on

Amazon Prime Video
Amazon Video
Apple TV
Data provided by JustWatch.Availability may vary by region.

Angel-A

89. Angel-A

Romance Comedy Drama Fantasy Romantic Comedy
7.0

20051h 31min

France

Director: Luc Besson

A beautiful and mysterious woman helps an inept scam artist get his game together... but is their meeting purely coincidence?

Themes

Performance under pressure, Trust and manipulation, Unlikely partnership, Romance vs deception, Ambition and control, Fate vs coincidence

Available on

Amazon Video
Apple TV
Google Play Movies
Data provided by JustWatch.Availability may vary by region.

Eagle vs Shark

90. Eagle vs Shark

Comedy Romance Romantic Comedy Awkward Comedy
6.7

20071h 27min

New Zealand

Director: Taika Waititi

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.

Themes

Loyalty under pressure, Loss and memory, Parent-child tension, Family dysfunction, Revenge versus relationship, Deception and truth

Available on

Amazon Video
Apple TV
Google Play Movies
Data provided by JustWatch.Availability may vary by region.