Movies Like Pink Skies Ahead

If you liked Pink Skies Ahead (2020), a comedy and drama movie directed by Kelly Oxford, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
John Mulaney: Kid Gorgeous at Radio City (2018)
★ 7.9/10Also comedy and tv movie
John Mulaney relays stories from his childhood and "SNL," eviscerates the value of college and laments getting older in this electric comedy special.
2
The Neighbor in the Window (2020)
★ 7.3/10Also drama and tv movie
A suburban wife finds herself and the security of her family threatened by another seemingly friendly neighborhood mom.
3
Teen Spirit (2011)
★ 5.9/10Also drama and comedy
Amber, a mean popular girl who gets electrocuted and dies, is not allowed to enter into heaven unless she helps the least popular girl in school become Prom Queen within a week, but things do not go as planned.
4
Bill Burr: Drop Dead Years (2025)
★ 7.2/10Also comedy and tv movie
In what might be his most personal and introspective hour yet, Bill offers hilarious takes on everything from male sadness to dating advice.
5
Welcome Home Roscoe Jenkins (2008)
★ 6/10Also comedy and drama
When a celebrated TV show host returns to his hometown in the South, his family is there to remind him that going home is no vacation!
6
Family Weekend (2013)
★ 6.3/10Also comedy and drama
A 16-year-old girl takes her parents hostage after they miss her big jump-roping competition.
7
Afterlife of the Party (2021)
★ 6.7/10Also comedy and drama
A social butterfly who dies during her birthday week is given a second chance to right her wrongs on Earth.
8
My Dinner with Hervé (2018)
★ 6.3/10Also drama and tv movie
An unlikely friendship evolves over one wild night in LA between a struggling journalist and actor Hervé Villechaize, the world's most famous gun-toting dwarf, resulting in life-changing consequences for both.
9
Hello (2022)
★ 6.3/10Also drama and tv movie
An emotionally unavailable flight attendant meets a potential love interest and later finds out that her "perfect guy" has ulterior motives. As the clock ticks down on New Year's Eve, she must fight to keep her…
10
Ricky Gervais: Mortality (2025)
★ 7/10Also comedy and tv movie
Ricky Gervais tackles life, death and the state of the world in a brutally honest special that spares no topic, even his own mortality.
11
Landline (2017)
★ 6.2/10Also comedy and drama
A teenager living with her sister and parents in Manhattan during the 1990s discovers that her father is having an affair.
12
My Own Love Song (2010)
★ 6.2/10Also comedy and drama
A wheelchair-bound singer and her best friend embark on a roadtrip to Memphis.
13
Psych: The Movie (2017)
★ 7.2/10Also comedy and tv movie
The ambitious friends come together during the holidays after a mystery assailant targets one of their own. A comedic thrill-ride follows, as the wild and unpredictable Psych team pursues the bad guys, justice … and…
14
Small Apartments (2012)
★ 5.9/10Also comedy and drama
When a clumsy deadbeat accidentally kills his landlord, he must do everything in his power to hide the body, only to find that the distractions of lust, the death of his beloved brother, and a crew of misfit characters…
15
On Becoming a Guinea Fowl (2024)
★ 7.5/10Also comedy and drama
On an empty road in the middle of the night, Shula stumbles across the body of her uncle. As funeral proceedings begin around them, she and her cousins bring to light the buried secrets of their middle-class Zambian…
16
Defendor (2009)
★ 6.4/10Also drama and comedy
A crooked cop, a mob boss and the young girl they abuse are the denizens of a city's criminal underworld. It's a world that ordinary Arthur Poppington doesn't understand and doesn't belong in, but is committed to…
17
Clear History (2013)
★ 6.1/10Also comedy and tv movie
Nathan Flomm, in order to avoid the humiliation of having missed out on a hugely successful business, assumes a new identity on Martha's Vineyard. He plots revenge when his former business partner moves to the same town.
18
Lady Windermere's Fan (1925)
★ 6.9/10Also comedy and drama
A society woman believes her husband is having an affair, a misconception which may have dire personal consequences for all involved.
19
SubUrbia (1997)
★ 6.2/10Also comedy and drama
A group of suburban teenagers try to support each other through the difficult task of becoming adults.
20
House of D (2004)
★ 6.3/10Also comedy and drama
In the present, artist Tom Warshaw recalls his traumatic coming of age. As a 13-year-old growing up in New York City in 1973, Tom hangs out with Pappass, a mentally disabled man. With Tom's mother battling depression…