Awkward Comedy backdrop

Awkward Comedy movies

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

Brad's Status

51. Brad's Status

Comedy Drama Relationship Drama Awkward Comedy
6.5

20171h 41min

United States

Director: Mike White

Although Brad has a satisfying career, a sweet wife and a comfortable life in suburban Sacramento, things aren't quite what he imagined during his college glory days. When he accompanies his musical prodigy son on a university tour, he can't help comparing his life with those of his four best college friends who seemingly have more wealthy and glamorous lives. But when circumstances force him to reconnect with his former friends, Brad begins to question whether he has really failed or if their lives are actually more flawed than they appear.

Themes

Parental expectations, Peer influence, Social comparison, Wealth gap pressure, Midlife discontent, Identity through achievement

Available on

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

Alibi.com

52. Alibi.com

Comedy Family Awkward Comedy Parent-Child Family
6.5

20171h 30min

France

Director: Philippe Lacheau

Greg founded a company called Alibi.com that creates any type of alibi. With his associate, Augustin, and Medhi his new employee, they devise unstoppable stratagems and stagings to cover their clients. But meeting Flo, a pretty blonde who hates men who lie, will complicate Greg's life, which begins by hiding the true nature of his activity. During the presentation to parents, Greg understands that Gérard, the father of Flo, is also one of their clients.

Themes

Trust under pressure, Deception in relationships, Romantic tension, Honesty vs secrecy, Professional boundaries blur, Business ethics under strain

Available on

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

Little Miss Sunshine

53. Little Miss Sunshine

Comedy Drama Family Drama Awkward Comedy
7.8

20061h 42min

United States

Director: Valerie Faris

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.

Mistress America

54. Mistress America

Comedy Awkward Comedy
6.7

20151h 24min

United States, Brazil

Director: Noah Baumbach

A college freshman cures her disappointment and loneliness by allowing herself to be pulled into the wacky schemes of her future stepsister.

Themes

Class inequality, Deception and perception, Ambition and dependence, Female friendship dynamics, Creative validation and risk, Urban aspiration and domestic security

Available on

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

The Wedding Ringer

55. The Wedding Ringer

Comedy Awkward Comedy
6.6

20151h 41min

United States

Director: Jeremy Garelick

Doug Harris is a loveable but socially awkward groom-to-be with a problem: he has no best man. With less than two weeks to go until he marries the girl of his dreams, Doug is referred to Jimmy Callahan, owner and CEO of Best Man, Inc., a company that provides flattering best men for socially challenged guys in need. What ensues is a hilarious wedding charade as they try to pull off the big con, and an unexpected budding bromance between Doug and his fake best man Jimmy.

Themes

Wedding ritual pressure, Genuine connection vs facade, Paid friendship manipulation, Loyalty under commercial terms, Social role performance, Approval dynamics in social circles

Available on

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

Amélie

56. Amélie

Comedy Romance Romantic Comedy Awkward Comedy
8.3

20012h 2min

France, Germany

Director: Jean-Pierre Jeunet

One day, the quirky waitress Amélie discovers in her apartment a hidden stash: an old box of childhood toys and little keepsakes that once belonged to a boy who used to live there. After returning the box deeply moves its owner, she decides to secretly interfere in other people’s lives in order to help them.

Themes

Small acts of joy, Acts of kindness, Urban interconnectedness, Loneliness and connection, Imagination as solace, Chance encounters, Self discovery through others

Available on

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

Obvious Child

57. Obvious Child

Comedy Romance Romantic Comedy Awkward Comedy
6.7

20141h 25min

United States

Director: Gillian Robespierre

An immature, newly unemployed comic must navigate the murky waters of adulthood after her fling with a graduate student results in an unplanned pregnancy.

Themes

Pregnancy decision under pressure, Autonomy versus dependence, Career versus personal life, Parental support and boundaries, Romantic connection and hesitation, Unemployment and self-direction

Available on

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

What If

58. What If

Drama Comedy Romance Romantic Comedy Awkward Comedy
6.8

20131h 38min

Canada, Ireland

Director: Michael Dowse

A young man meets a fun, unconventional girl at a party. As they talk, they realize they have a lot in common and decide to keep things as friends. It would all be fine—except over time it turns out to be much harder than they expected.

Themes

Friendship versus romance, Boundaries and desire, Distance and commitment, Social expectations in dating, Career versus relationship, Trust under ambiguity

Available on

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

Sleeping with Other People

59. Sleeping with Other People

Comedy Romance Romantic Comedy Awkward Comedy
6.5

20151h 40min

United States

Director: Leslye Headland

Jake and Lainey have known each other since college: on one awkward night, they lost their virginity. Twelve years later, they run into each other at a support group for sex addicts—and this time a friendship starts to form between them.

Themes

Loyalty under pressure, Commitment issues, Career vs romance, Friends to lovers, Deception and desire, Casual dating expectations

Available on

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

It's Kind of a Funny Story

60. It's Kind of a Funny Story

Comedy Drama Coming-of-Age Drama Awkward Comedy
7.1

20101h 42min

United States

Director: Anna Boden

A clinically depressed teenager gets a new start after he checks himself into an adult psychiatric ward.

Themes

Coming of age, Academic pressure, Mental health care, Creative aspiration, Psychiatric ward, Peer friendship dynamics

Available on

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