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There are plenty of great satirical movies like The Big Short that turn the dry procedures of finance and business into riveting cinematic entertainment. The Big Short uses self-aware humor and A-list cameos to explore the mistakes and misdeeds that led to the 2007 housing market crash. The script by Charles Randolph and director Adam McKay, based on financial journalist Michael Lewis’s book The Big Short: Inside the Doomsday Machine, won the Academy Award for Best Adapted Screenplay. The movie received nominations in four other Oscar categories, including Best Picture and Best Director for McKay. The Big Short won the Producers Guild Award for Best Picture as well.
The Big Short’s hilarious performances and award-winning script tackled a typically tiresome topic in a refreshingly engaging way. With fourth-wall-breaking and celebrity cameos, The Big Short found uniquely entertaining methods to explain complex financial terminologies like synthetic CDOs and subprime mortgages. From Moneyball to The Wolf of Wall Street, there are a bunch of other movies like The Big Short that use filmmaking tricks, masterful acting, and razor-sharp writing to turn business deals, economic disruptions, and financial transactions into captivating plot points.
10 Money Monster (2016)
One of many movies starring George Clooney and Julia Roberts together, Money Monster casts the former as a Jim Cramer-style TV financial expert while she plays the long-time director of his show. In a satirical blend of Network and The King of Comedy, a live taping of the show is hijacked by a gunman who lost his entire life savings on a bad stock tip. Like The Big Short, this movie explores the contrast between well-compensated financial gurus who tank the economy and the working-class people who are actually affected by it.
- Available to stream on Starz or rent on Apple TV
9 War Dogs (2016)
Directed by Todd Phillips before he tackled Joker, War Dogs tells the true but fictionalized tale of a pair of young, hungry arms dealers who were contracted by the U.S. Army to supply the Afghan National Army with $300 million’s worth of weapons. A modern riff on the fast-paced Goodfellas style of the criminal biopic, War Dogs stars Jonah Hill, Miles Teller, and Ana de Armas. Like The Big Short, this movie explores the corrupting power of money in an entertaining way. Once the gun runners are taken in by the allure of nine-figure government contracts, they get in over their heads and there’s no going back.
- Available to stream on Hulu
8 Boiler Room (2000)
In Boiler Room, a college dropout takes a job as a broker at a small-time investment firm and quickly gets drawn into the crooked financial industry. Boiler Room assembled a star-studded ensemble to lampoon the world of finance, much like The Big Short. Giovanni Ribisi leads a cast that includes Vin Diesel, Nia Long, Ben Affleck, and Jamie Kennedy. Boiler Room touches on a lot of the same themes as The Big Short, particularly the allure of wealth and the notion that enough is never enough.
- Available to rent on Apple TV
7 Vice (2018)
A biting biopic of former U.S. Vice President Dick Cheney, Vice is another political drama from The Big Short director Adam McKay, exhibiting his unique satirical style in an Oscar-caliber prestige drama. Vice continued McKay’s transition from Anchorman-style absurdist comedy into more serious true-life dramatizations. McKay reunited with two of The Big Short‘s actors for the cast of Vice: Christian Bale as Cheney and Steve Carell as Donald Rumsfeld. Vice shares The Big Short’s blend of big laughs and shocking historical revelations.
- Available to stream on The Roku Channel or rent on Prime Video
6 Wall Street (1987)
Oliver Stone offered his own politically charged take on the business of finance with Wall Street. The movie doesn’t just share The Big Short’s sly sense of satire; it also has its lucrative Hollywood star power. Charlie Sheen heads the cast of Wall Street as an eager young stockbroker who takes a job working for Michael Douglas’s character, an amoral corporate raider who lures him to the dark side of finance. Douglas won the Academy Award for Best Actor for his iconic turn as Gordon Gekko, and he reprised the role 23 years later in the sequel Wall Street: Money Never Sleeps.
- Available to stream on Hulu, Paramount+, and FuboTV
5 Glengarry Glen Ross (1992)
David Mamet adapted his own Pulitzer Prize-winning play into a screenplay for the movie adaptation of Glengarry Glen Ross. It’s about a group of real estate salesmen who have to step up their game when the corporate office sends in a motivational trainer to inform them that all but the top two among them will be fired. Like The Big Short, Glengarry Glen Ross has an all-star cast including screen legends like Al Pacino, Jack Lemmon, Ed Harris, and Alan Arkin. The story of Glengarry Glen Ross is a microcosm of the cutthroat capitalist system that The Big Short explored on a macro scale.
- Available to stream on Hulu and Plex
4 Moneyball (2011)
A lot of the talent that worked on The Big Short, both on-camera and off-camera, previously worked on Moneyball. Like The Big Short, this is an award-winning Brad Pitt movie that makes data a lot more riveting than it seems. Pitt stars as Billy Beane, the general manager of the Oakland Athletics, who uses a sabermetric analysis to determine the best baseball talent so that he can assemble a competitive team with his limited financial resources. Moneyball is even based on a nonfiction book by the same author as The Big Short, Michael Lewis.
- Available to stream on AMC+, Peacock, and DirecTV
3 The Founder (2016)
Like The Big Short, The Founder is a movie that takes dry subject matter – in this case, the origins of McDonald’s – and turn it into compelling drama. Michael Keaton stars as Ray Kroc, the unscrupulous businessman who stumbled upon a burger restaurant run by the McDonald brothers, played by Nick Offerman and John Carroll Lynch, and promised to turn it into a nationwide fast food franchise. At first, Kroc is committed to making the McDonald brothers’ dreams come true, but then his greed takes over.
- Available to stream on Netflix or rent on Apple TV
2 Office Space (1999)
Mike Judge’s cult classic Office Space offers a comedic deconstruction of corporate culture, much like The Big Short. Whereas The Big Short takes place in the 2000s, Office Space has a distinctly ‘90s sensibility. It revolves around a group of undervalued employees at a software company who become disillusioned with their mundane work and plot to rob the place through a series of micro-transactions. Office Space has a cast full of hilarious performers, led by Ron Livingston and an early-career Jennifer Aniston, and features Gary Cole in the role of the typical office manager, Bill Lumbergh, one of the best ‘90s comedy movie villains.
- Available to stream on HBO Max
1 The Wolf Of Wall Street (2013)
One of Martin Scorsese’s wildest movies, The Wolf of Wall Street is a biopic about unscrupulous stockbroker Jordan Belfort, who made himself rich by defrauding the working class, a role played brilliantly by Leonardo DiCaprio. Like The Big Short, this movie constantly breaks the fourth wall to explain financial terminology to the audience – and points out that it’s confusing by design to trick people out of their hard-earned pennies. The Wolf of Wall Street is a pitch-black comedy that offers the perfect intersection between the financial drama of The Big Short and the raunchy humor of The Hangover.
- Available to stream on Prime Video, Paramount+, and FuboTV
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