Movies Like My Dinner With Oswald

If you liked My Dinner With Oswald (1997), a comedy movie directed by Paul Duane, 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
Duplex (2003)
★ 6.1/10Also comedy
When a young couple buys their dream home, they have no idea what the sweet little old lady upstairs is going to put them through!
2
Psycho Therapy: The Shallow Tale of a Writer Who Decided to Write About a Serial Killer (2025)
★ 6.8/10Also comedy
A struggling writer in the midst of a divorce befriends a retired serial killer who incidentally becomes his marriage counselor by day, and killing counselor for his next book by night.
3
They Cloned Tyrone (2023)
★ 6.5/10Also comedy
A series of eerie events thrusts an unlikely trio onto the trail of a nefarious government conspiracy lurking directly beneath their neighborhood.
4
Louis C.K.: Ridiculous (2026)
★ 6.1/10Also comedy
From a bee getting shot in New York City to paying strangers to take his aging father, Louis C.K. unleashes the ridiculous thoughts in his mind.
5
Driver's Ed (2026)
★ 6.9/10Also comedy
A group of teens hit the road in a stolen driver's ed car, racing against time to help a lovesick high school senior track down his college-freshman girlfriend and win her back.
6
Sextuplets (2019)
★ 6.2/10Also comedy
Father-to-be Alan is shocked to learn that he was born a sextuplet. With his newfound brother Russell riding shotgun, the duo sets out on a hilarious journey to reunite with their remaining long-lost siblings.
7
Fun with Dick and Jane (1977)
★ 6.6/10Also comedy
When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.
8
The Mouse That Roared (1959)
★ 6.4/10Also comedy
The Duchy of Grand Fenwick decides that the only way to get out of their economic woes is to declare war on the United States, lose and accept foreign aid. They send an invasion force (in chain mail, armed with bows…
9
Much Ado About Nothing (2013)
★ 6.8/10Also comedy
A modern retelling of Shakespeare's classic comedy about two pairs of lovers with different takes on romance and a way with words.
10
Qwerty (2012)
★ 6.4/10Also comedy
Before introverted word-nerd Zoe gains the courage to enter the National Scrabble Championship, she meets her emotional match in Marty, an irascible recluse. She finds him equally pitted against the opposing forces in…
11
Shane Gillis: Beautiful Dogs (2023)
★ 7/10Also comedy
In a rowdy stand-up set, Shane Gillis riffs on his girlfriend's Navy SEAL ex, touring George Washington's house and being bullied by an Australian Goth.
12
I Love My Dad (2022)
★ 5.9/10Also comedy
A hopelessly estranged father catfishes his son in an attempt to reconnect.
13
Manhattan Murder Mystery (1993)
★ 7.3/10Also comedy
A middle-aged couple suspects foul play when their neighbor's wife suddenly drops dead.
14
Amazon Women on the Moon (1987)
★ 5.9/10Also comedy
Centered on a television station which features a 1950s-style sci-fi movie interspersed with a series of wild commercials, wacky shorts and weird specials, this lampoon of contemporary life and pop culture skewers some…
15
Simpsley (2026)
★ 8.1/10Also comedy
When penniless con-artist Marge Bouvier is sent to Italy to convince wealthy sap Seymour Skinner to come home, she's tempted by the trappings of his affluent lifestyle. But there’s a big fat fly in the ointment…
16
The Bed Sitting Room (1969)
★ 5.9/10Also comedy
In the hazy aftermath of World War III, the fallout from a 'nuclear misunderstanding' is producing strange mutations amongst the survivors, and the noble Lord Fortnum finds himself transforming into a bed sitting room.
17
Analyze This (1999)
★ 6.5/10Also comedy
Countless wiseguy films are spoofed in this film that centers on the neuroses and angst of a powerful Mafia racketeer who suffers from panic attacks. When Paul Vitti needs help dealing with his role in the "family,"…
18
Spa Weekend (2026)
★ 6.5/10Also comedy
Four lifelong friends realize that somewhere between careers, relationships, families, and everyday responsibilities, they’ve forgotten how to take care of themselves and each other. Burned out and overdue for a break…
19
Yellow Mirror (2026)
★ 8.1/10Also comedy
A defective lamp reveals a heartbreaking truth about what Homer believes is reality, and an AI-powered tablet befriends and controls Maggie. The Simpsons struggle to find the light through two dark tales of the curious…
20
Hard to Die (1990)
★ 6/10Also comedy
While doing the inventory for a lingerie outlet in a high rise office building, five attractive women are terrorized by a series of bizarre killings. They suspect that the strange janitor, who witnessed another series…