Movies Like The Optimist

If you liked The Optimist (1938), a comedy movie directed by E.W. Emo, 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
American Dreamer (2022)
★ 6/10Also comedy
In this winsome comedy, an entitled Economics professor pursues a tactic to buy an ailing widow’s mansion for nothing, but he quickly realizes that his seemingly foolproof strategy won’t be as easy as he thought.
2
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.
3
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.
4
Cold Feet (2018)
★ 6.6/10Also comedy
Although he actually just wanted to steal money, the crook Denis finds himself in the position of caretaking for the stroke patient Raimund. When Raimund's granddaughter Charlotte turns up, Denis has enough of it and…
5
Brain Donors (1992)
★ 6.1/10Also comedy
Three manic idiots—a lawyer, a cab driver and a handyman—team up to run a ballet company to fulfil the will of a millionaire. Stooge-like antics result as the trio try to outwit the rich widow and her scheming big-shot…
6
Babes (2024)
★ 6/10Also comedy
After getting pregnant from a one-night stand, a single woman leans on her married best friend and mother of two to guide her through gestation and beyond.
7
Mr. Bones (2001)
★ 6/10Also comedy
A medicine man is sent looking for the son of his tribal king, and brings back an American golfer and a host of goons intent on keeping him in the golf tournament.
8
The Manny (2015)
★ 6.3/10Also comedy
Young industrialist Clemens Klina doesn't have time for his children and accidentally hires a man who actually came to him, seeking revenge, as a nanny for them.
9
Louis C.K.: Oh My God (2013)
★ 7.6/10Also comedy
Filmed at the Celebrity Theatre in Phoenix, AZ on February 15th and 16th, 2013, Oh My God is Louis C.K.'s fifth stand-up special, his first for HBO since 2007's Shameless, and his first since winning a Emmy Award for…
10
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.
11
The Goldfish (2019)
★ 6.5/10Also comedy
Oliver is a banker and portfolio manager and leads a life in the fast lane, which one day comes to an abrupt end, as he builds a self-inflicted accident on highway with 230 km / h and raced through a guardrail. When he…
12
Support Your Local Gunfighter (1971)
★ 6.6/10Also comedy
A con artist arrives in a mining town controlled by two competing companies. Both companies think he's a famous gunfighter and try to hire him to drive the other out of town.
13
Chris D'Elia: Man on Fire (2017)
★ 6.2/10Also comedy
Unbridled comic Chris D'Elia reconsiders his approach to major life events like marriage, not having kids and buying pants for your friends.
14
Thunderstruck (2012)
★ 6.2/10Also comedy
After NBA star Kevin Durant switches talent with 16 year old Brian, the teenager becomes the star of his high school team, but Durant starts struggling and eventually learns an important lesson.
15
Clear History (2013)
★ 6.1/10Also comedy
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.
16
Accident Man (2018)
★ 6.3/10Also comedy
Mike Fallon, the Accident Man, is a stone cold killer. When a loved one is murdered by his own crew, Fallon is forced to avenge the one person who actually meant something to him.
17
The Distinguished Gentleman (1992)
★ 6/10Also comedy
A Florida con man uses the recent death of the long time Congressman from his district, who he just happens to share a last name with, to get elected to his version of paradise, the U.S. Congress, where the money flows…
18
The Horse's Mouth (1958)
★ 6.7/10Also comedy
Gulley Jimson is a boorish aging artist recently released from prison. A swindler in search of his next art project, he hunkers down in the penthouse of would-be patrons the Beeders while they go on an extended…
19
Go West (1940)
★ 6.6/10Also comedy
A con man heading west to search for gold teams up with a pair of scheming brothers along the way. The trio soon find themselves in the middle of a feud between two rival families and two underhanded land developers.
20
Not My Day (2014)
★ 6.4/10Also comedy
When Banker Till (Axel Stein) is kidnapped during a bank robbery, he has the time of his life...