Awkward Comedy backdrop

Awkward Comedy movies

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

The Darjeeling Limited

71. The Darjeeling Limited

Adventure Drama Comedy Globetrotting Adventure Relationship Drama
7.2

20071h 32min

United States

Director: Wes Anderson

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

Dysfunctional family dynamics, Sibling relationship, Control vs autonomy, Journey as catalyst, Grief and displacement, Unspoken parental ties

Available on

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

My Sassy Girl

72. My Sassy Girl

Drama Comedy Romance Romantic Comedy Awkward Comedy
7.9

20012h 17min

South Korea

Director: Kwak Jae-yong

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

Parental pressure, Rules for happiness, Unconventional relationship dynamics, Public spaces as romance sites, Drinking as social catalyst, Transformation through adversity

Available on

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

Happy-Go-Lucky

73. Happy-Go-Lucky

Comedy Drama Awkward Comedy Coming-of-Age Drama
7.0

20081h 58min

United Kingdom, United States

Director: Mike Leigh

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

Optimism vs exasperation, Care for at-risk youth, Family expectations and choice, Romantic tension and boundaries, Bias and intolerance

Available on

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

The Station Agent

74. The Station Agent

Drama Comedy Relationship Drama Awkward Comedy
7.6

20031h 28min

United States

Director: Tom McCarthy

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

Loneliness vs connection, Vulnerability and care, Unlikely friendships, Outsider integration, Disruption of solitude, Routine as shelter

Available on

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

The Man Who Copied

75. The Man Who Copied

Comedy Drama Romance Crime Awkward Comedy
7.6

20032h 3min

Brazil

Director: Jorge Furtado

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

Deception as strategy, Romance under pressure, Crime as means to security, Material wealth obsession, Social climbing costs, Illusion versus reality


Cashback

76. Cashback

Drama Comedy Romance Bittersweet Romance Awkward Comedy
7.1

20071h 42min

United Kingdom

Director: Sean Ellis

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

Memory as catalyst, Insomnia as escape, Time freeze fantasy, Imagination vs reality, Romantic longing and obstacles, Art as coping

Available on

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

The Savages

77. The Savages

Drama Comedy Family Drama Awkward Comedy
7.1

20071h 54min

United States

Director: Tamara Jenkins

A sister and brother face the realities of familial responsibility as they begin to care for their ailing father.

Themes

Aging and memory, Sibling responsibility, Caregiving burden, Familial estrangement, Parental abuse legacy, Artistic ambition vs family duty

Available on

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

The Squid and the Whale

78. The Squid and the Whale

Comedy Drama Coming-of-Age Drama Awkward Comedy
7.3

20051h 21min

United States

Director: Noah Baumbach

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

Deception and betrayal, Divorce and custody, Parental conflict, Creative ambition vs family, Generational tension, Public success vs private life

Available on

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

Transamerica

79. Transamerica

Drama Adventure Comedy Relationship Drama Awkward Comedy
7.3

20051h 43min

United States

Director: Duncan Tucker

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

Parent child relationship, Gender identity conflict, Trauma from sexual abuse, Road trip resilience, New identity tension, Social stigma pressure

Available on

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

Step Brothers

80. Step Brothers

Comedy Awkward Comedy
6.9

20081h 38min

United States

Director: Adam McKay

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.

Themes

Becoming an adult, Childhood trauma, Stepbrother dynamics, Slacker identity, Class discrimination, Autonomy vs dependence

Available on

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