Awkward Comedy backdrop

Awkward Comedy movies

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

171. Cashback

Cashback
Drama Comedy Romance Bittersweet Romance Awkward Comedy
7.1
20071h 42minUnited Kingdom
Director: Sean Ellis

Overview

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.

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

I'm a Cyborg, But That's OK
Drama Comedy Romance Psychological Drama Romantic Comedy
6.9
20061h 45minSouth Korea
Director: Park Chan-wook

Overview

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.

173. Little Miss Sunshine

Little Miss Sunshine
Comedy Drama Family Drama Awkward Comedy
7.8
20061h 42minUnited States
Director: Valerie Faris

Overview

A family loaded with quirky, colorful characters piles into an old van and road trips to California for little Olive to compete in a beauty pageant.

Themes

Family pressure under failure, Dysfunctional family dynamics, Road-trip bonding under stress, Sibling relationships under strain, Pursuit of recognition vs care, Societal pageant judgment

Available on

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

174. It's a Boy Girl Thing

It's a Boy Girl Thing
Comedy Fantasy Romance Awkward Comedy Romantic Comedy
6.2
20061h 35minCanada, United States
Director: Nick Hurran

Overview

A visit to a natural history museum proves catastrophic for two high school rivals, an overachiever and a jock, when an ancient Aztec statue casts a spell that causes them to switch bodies and see exactly what it's like to walk in the other's shoes.

Themes

Appearance vs reality, Popularity vs scholarship, Role reversal among rivals, Empathy through shared experience, Competitive pressure and identity shifts, Rumor dynamics and social humiliation

Available on

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

175. She's the Man

She's the Man
Comedy Romance Romantic Comedy Awkward Comedy
6.4
20061h 45minUnited States
Director: Andy Fickman

Overview

Viola Hastings is in a real jam. Complications threaten her scheme to pose as her twin brother, Sebastian, and take his place at a new boarding school. She falls in love with her handsome roommate, Duke, who loves beautiful Olivia, who has fallen for Sebastian! As if that were not enough, Viola's twin returns from London ahead of schedule but has no idea that his sister has already replaced him on campus.

Themes

Deception in romance, Sports as social equalizer, Gender disguise, Romantic rivalry, Cross-dressing comedy device, Disguise-driven misperceptions

Available on

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

176. Angel-A

Angel-A
Romance Comedy Drama Fantasy Romantic Comedy
7.0
20051h 31minFrance
Director: Luc Besson

Overview

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.

177. The Family Stone

The Family Stone
Comedy Drama Romance Romantic Comedy Family Drama
6.3
20051h 43minUnited States
Director: Thomas Bezucha

Overview

An uptight, conservative businesswoman accompanies her boyfriend to his eccentric and outgoing family's annual Christmas celebration and finds that she's a fish out of water in their free-spirited way of life.

Themes

Big family dynamics, Holiday pressure, Christmas tradition clash, Engagement ring symbolism, Fish out of water, Connecticut context

Available on

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

178. Just Friends

Just Friends
Comedy Romance Romantic Comedy Awkward Comedy
6.2
20051h 34minGermany, United States
Director: Roger Kumble

Overview

While visiting his hometown during Christmas, a man comes face-to-face with his old high school crush whom he was best friends with – a woman whose rejection of him turned him into a ferocious womanizer.

Themes

Appearance vs authenticity, Friendship boundaries in love, Success as gatekeeping, Deception and reputation management, Hometown christmas romance

Available on

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

179. The Squid and the Whale

The Squid and the Whale
Comedy Drama Coming-of-Age Drama Awkward Comedy
7.3
20051h 21minUnited States
Director: Noah Baumbach

Overview

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.

180. Thumbsucker

Thumbsucker
Comedy Drama Coming-of-Age Drama Awkward Comedy
6.5
20051h 36minUnited States
Director: Mike Mills

Overview

Justin Cobb, a teenager in suburban Oregon, copes with his thumb-sucking problem, romance, and his diagnosis with ADHD and subsequent experience using Ritalin.

Themes

Adolescent autonomy and dependence, Academic ambition and deception, Family aging anxieties, Peer influence and risk-taking, Romance and boundary testing, Stimulant use and performance

Available on

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