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3 movies like Dumb Money that you need to watch

Paul Dano in Dumb Money.
Sony Pictures

Two years ago, the GameStop short squeeze briefly put the power of Wall Street in the hands of regular investors as they outmaneuvered the hedge fund bros and the professional traders who placed millions of dollars into a bet that GameStop’s stock would fall. The new movie, Dumb Money, is director Craig Gillespie’s dramatization of these events. But there are at least three movies like Dumb Money that you may want to watch for a more complete picture of Wall Street shenanigans, as well as an illustration of how the system is rigged against the little guy.

Although there’s definitely drama in Dumb Money‘s depiction of the rise and fall of the GameStop stockholders, it’s also got a lot of laughs thanks to a fantastic cast that includes Paul Dano, Pete Davidson, Vincent D’Onofrio, America Ferrera, Nick Offerman, Anthony Ramos, Sebastian Stan, Shailene Woodley, Seth Rogen, Dane DeHaan, Clancy Brown, and more. This film may even be a contender during next year’s Academy Awards. But once you’ve seen Dumb Money in theaters, these are the three movies that you need to watch next.

Boiler Room (2000)

Vin Diesel in Boiler Room.
New Line Cinema

Boiler Room notably features Vin Diesel in one of his earliest film roles as Chris Varick, a talented seller at a chop shop brokerage firm, J.T. Marlin. However, the focus of this movie falls on Seth Davis (Giovanni Ribisi), a young man who is recruited to join the company by Greg Weinstein (Nicky Katt). Although Seth initially embraces his new job, he eventually realizes that the firm’s tactics are immoral and wrong.

Seth’s work at J.T. Marlin also puts a tremendous strain on his relationship with his father, Judge Marty Davis (Ron Rifkin). But if Seth is ever going to put things right and help recover the assets of his victims, then he needs his father’s help to do so.

Rent or buy Boiler Room on Google Play, Prime Video, YouTube, and Apple TV+.

The Wolf of Wall Street (2013)

Leonardo DiCaprio in The Wolf of Wall Street.

The Wolf of Wall Street‘s Jordan Belfort (Leonardo DiCaprio) is a lot like Boiler Room‘s Seth Davis, except without any moral qualms about what he’s doing. Director Martin Scorsese’s film doesn’t just show the ease with which Belfort swindles his clients with pump-and-dump stocks, it also revels in the excessive lifestyle that Belfort’s wealth affords him. Belfort’s life is a heady brew of women, alcohol, and as many drugs as he can get his hands on.

Like Dumb Money, this movie is based on a true story, and it’s not too long before Belfort’s outrageous activities draw the attention of FBI Agent Patrick Denham (Kyle Chandler). This movie also features Margot Robbie in her first breakout performance as Belfort’s mistress (and later, his second wife), Naomi Lapaglia. Even a decade before her role as Barbie, Robbie steals every scene that she’s in.

Watch The Wolf of Wall Street on Netflix and Paramount+.

The Big Short (2015)

The cast of The Big Short.

Robbie also has a notable cameo appearance in The Big Short, as director Adam McKay uses her to help explain some of the Wall Street concepts and jargon to the audience. Selena Gomez and the late Anthony Bourdain make similar cameos in the movie as well. In terms of tone, this film is closer to Dumb Money than the other two movies on this list. But instead of following armchair investors, The Big Short focuses on the professionals who saw the crash of 2008 coming and made sure that they profited from it at the expense of the nation.

Another thing that The Big Short has in common with Dumb Money is that it has an absolutely stacked cast including Christian Bale, Steve Carell, Ryan Gosling, Brad Pitt, Jeremy Strong, and Marisa Tomei. But all of these familiar faces may not keep you from feeling contempt for the real people that their characters were inspired by.

Watch The Big Short on Netflix.

Blair Marnell
Blair Marnell has been an entertainment journalist for over 15 years. His bylines have appeared in Wizard Magazine, Geek…
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