Movies Like Living in Oblivion

If you liked Living in Oblivion (1995), a comedy movie directed by Tom DiCillo, 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
How High (2001)
★ 6.4/10Also comedy
Jamal and Silas, two ordinary guys who smoke something magical, pass their college entrance exams with flying colors and end up at Harvard. Ivy League ways are strange but Silas and Jamal take it in a stride -- until…
2
Die, Mommie, Die! (2003)
★ 6.6/10Also comedy
Angela Arden is a washed up, has-been singing star who is trapped in a hateful marriage to film producer Sol Sussman. In an attempt to escape her marriage so that she can be with a hunky layabout, she poisons her…
3
Seriously Single (2020)
★ 6.8/10Also comedy
While her free-living bestie urges her to embrace singlehood, a commitment-craving social media expert can't stop following the life of a former love.
4
Die Hart (2023)
★ 5.9/10Also comedy
Kevin Hart - playing a version of himself - is on a death-defying quest to become an action star. And with a little help from John Travolta, Nathalie Emmanuel, and Josh Hartnett - he just might pull it off.
5
Jackass Presents: Bad Grandpa (2013)
★ 6.2/10Also comedy
86-year-old Irving Zisman is on a journey across America with the most unlikely companion: his 8 year-old grandson, Billy.
6
The Last American Virgin (1982)
★ 6.6/10Also comedy
The friendship of a group of young friends struggling with teen sex, drugs, and work is jeopardized by a romantic interest which may turn pals into bitter rivals.
7
Cheap Thrills (2013)
★ 6.4/10Also comedy
Recently fired and facing eviction, a new dad has his life turned upside down when he meets a wealthy couple who offer a path to financial security... but at a price.
8
John Mulaney: Kid Gorgeous at Radio City (2018)
★ 7.9/10Also comedy
John Mulaney relays stories from his childhood and "SNL," eviscerates the value of college and laments getting older in this electric comedy special.
9
Hollywood Shuffle (1987)
★ 6.5/10Also comedy
Aspiring actor and hot-dog stand employee Bobby Taylor catches the ire of his grandmother for auditioning for a role in the regrettably titled exploitation film "Jivetime Jimmy's Revenge." When Tinseltown Studios casts…
10
Barely Legal (2003)
★ 5.9/10Also comedy
Teenager Deacon works at a video shop, and his buddies, Fred and Matt, sell the bootleg porno films he acquires. Deacon gets fired, but the pals have the bright idea of filming their own Internet porn flick in order to…
11
Death at a Funeral (2010)
★ 5.9/10Also comedy
Aaron's father's funeral is today at the family home, and everything goes wrong: the funeral home delivers the wrong body, his cousin accidentally drugs her fiancé, and Aaron's successful younger brother, Ryan, flies…
12
Ricky Gervais: Mortality (2025)
★ 7/10Also comedy
Ricky Gervais tackles life, death and the state of the world in a brutally honest special that spares no topic, even his own mortality.
13
The Super (1991)
★ 5.9/10Also comedy
Louie Kritski is a heartless landlord who has been so negligent in keeping up his ghetto apartment that he is threatened with jail time. The judge gives him another option -- he must live in his rat-infested hell hole…
14
Fist Fight (2017)
★ 6/10Also comedy
When one school teacher gets the other fired, he is challenged to an after-school fight.
15
Eenie Meanie (2025)
★ 6.3/10Also comedy
A former teenage getaway driver gets dragged back into her unsavory past when a former employer offers her a chance to save the life of her chronically unreliable ex-boyfriend.
16
Bill Burr: Drop Dead Years (2025)
★ 7.2/10Also comedy
In what might be his most personal and introspective hour yet, Bill offers hilarious takes on everything from male sadness to dating advice.
17
The Killer's Game (2024)
★ 6.4/10Also comedy
When top hitman Joe Flood is diagnosed with a terminal illness, he decides to take matters into his own hands – by taking a hit out on himself. But when the very hitmen he hired also target his ex-girlfriend, he must…
18
Bananas (1971)
★ 6.7/10Also comedy
When a bumbling New Yorker is dumped by his activist girlfriend, he travels to a tiny Latin American nation and becomes involved in its latest rebellion.
19
I Love My Dad (2022)
★ 5.9/10Also comedy
A hopelessly estranged father catfishes his son in an attempt to reconnect.
20
Moonwalkers (2015)
★ 6.1/10Also comedy
What if Apollo 11 never actually made it? What if, in reality, Stanley Kubrick secretly shot the famous images of the moon landing in a studio, working for the US administration? This is the premise of a totally…