Movies Like Dumb Money

If you liked Dumb Money (2023), a history and comedy movie directed by Craig Gillespie, 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
The Wolf of Wall Street (2013)
★ 8/10Also drama and comedy
A New York stockbroker refuses to cooperate in a large securities fraud case involving corruption on Wall Street, corporate banking world and mob infiltration. Based on Jordan Belfort's autobiography.
2
Rogue Trader (1999)
★ 5.9/10Also drama and history
Rogue Trader tells the true story of Nick Leeson, an employee of Barings Bank who--after a successful trading run--ends up accumulating $1.4 billion in losses hidden in account #88888.
3
The Big Short (2015)
★ 7.4/10Also comedy and drama
The men who made millions from a global economic meltdown.
4
Digger (2026)
★ 7.5/10Also comedy and drama
The most powerful man in the world embarks on a frantic mission to prove he is humanity's savior before the disaster he's unleashed destroys everything.
5
Two for the Money (2005)
★ 6.1/10Also comedy and drama
A former college athlete joins forces with a sports consultant to handicap football games for high-rolling gamblers.
6
Not Okay (2022)
★ 6.2/10Also comedy and drama
An ambitious young woman, desperate for followers and fame, fakes a trip to Paris to up her social media presence. When a terrifying incident takes place in the real world and becomes part of her imaginary trip, her…
7
The Luckiest Man in America (2025)
★ 6.3/10Also drama and history
1984; Michael Larson, an unemployed ice-cream truck driver from Ohio, steps onto the game show "Press Your Luck" harboring a secret: the key to endless amounts of money. But his winning streak is threatened when the…
8
Playing God (2021)
★ 6/10Also comedy and drama
A brother and sister con-artist duo find themselves scamming a grieving billionaire by convincing him they can introduce him to God, face-to-face.
9
Once Upon a Time... in Hollywood (2019)
★ 7.4/10Also comedy and drama
Los Angeles, 1969. TV star Rick Dalton, a struggling actor specializing in westerns, and stuntman Cliff Booth, his best friend, try to survive in a constantly changing movie industry. Dalton is the neighbor of the…
10
American Fiction (2023)
★ 7.2/10Also comedy and drama
A novelist fed up with the establishment profiting from "Black" entertainment uses a pen name to write a book that propels him into the heart of hypocrisy and the madness he claims to disdain.
11
The Smashing Machine (2025)
★ 6.4/10Also drama and history
In the late 1990s, up-and-coming mixed martial artist Mark Kerr aspires to become the greatest fighter in the world. However, he must also battle his opioid dependence and a volatile relationship with his girlfriend…
12
Hustlers (2019)
★ 6.5/10Also drama and comedy
A crew of savvy former strip club employees band together to turn the tables on their Wall Street clients.
13
Dolemite Is My Name (2019)
★ 7/10Also drama and comedy
The story of Rudy Ray Moore, who created the iconic big screen pimp character Dolemite in the 1970s.
14
I Care a Lot (2021)
★ 6.6/10Also drama and comedy
A court-appointed legal guardian defrauds her older clients and traps them under her care. But her latest mark comes with some unexpected baggage.
15
A King in New York (1957)
★ 6.7/10Also comedy and drama
A recently-deposed "Estrovian" monarch seeks shelter in New York City, where he becomes an accidental television celebrity. Later, he's wrongly accused of being a Communist and gets caught up in subsequent HUAC hearings.
16
A Serious Man (2009)
★ 6.7/10Also comedy and drama
It is 1967, and Larry Gopnik, a physics professor at a quiet Midwestern university, has just been informed by his wife Judith that she is leaving him. He scrambles to find a semblance of meaning as he loses control of…
17
The Joneses (2010)
★ 6.2/10Also comedy and drama
A seemingly perfect family moves into a suburban neighborhood, but when it comes to the truth as to why they're living there, they don't exactly come clean with their neighbors.
18
Mainstream (2021)
★ 6.3/10Also comedy and drama
A young woman thinks she’s found a path to internet stardom when she starts making YouTube videos with a charismatic stranger – until the dark side of viral celebrity threatens to ruin them both.
19
Bad Education (2019)
★ 6.7/10Also drama and history
A superintendent of a school district works for the betterment of the student’s education when an embezzlement scheme is discovered, threatening to destroy everything.
20
The Disaster Artist (2017)
★ 7.1/10Also comedy and drama
An aspiring actor in Hollywood meets an enigmatic stranger by the name of Tommy Wiseau, the meeting leads the actor down a path nobody could have predicted; creating the worst movie ever made.