20 Money Movies We Bet You'll Love

It’s all about the Benjamins, baby!
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Pretty in Pink

John Hughes tells the story of a high school girl (Molly Ringwald, of course) who lives on the poor side of the tracks and has to choose between her best friend (Jon Cryer) and a rich classmate (Andrew McCarthy). Buy it here.
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Capitalism: A Love Story

Michael Moore explores the dark side of capitalism in his latest controversial documentary. Buy it here.
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Boiler Room

A college dropout (Giovanni Ribisi) joins a brokerage firm to appease his federal judge father-only to find out that the company he’s working for is not on the right side of the law. Buy it here.
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Envy

Ben Stiller plays a family man green with envy after his neighbor and best friend (Jack Black) makes millions off an absurd invention. Buy it here.
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It Could Happen to You

A cop (Nicolas Cage) stiffs a waitress (Bridget Fonda), but promises he’ll share his lottery ticket winnings with her if he hits big. Turns out he’s sitting on a $4 million jackpot. Reality check: This won’t ever happen to you, but the plot makes for a nice romantic comedy. Buy it here.
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Casino

Joe Pesci and Robert De Niro are at their gangster finest in this Martin Scorcese crime drama about two mobsters who work a Vegas casino. Sharon Stone stars as De Niro’s not-to-be-trusted wife. Buy it here.
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Jerry Maguire

"SHOW ME THE MONEY." Enough said. Buy it here.
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Dirty Work

Two slacker brothers (Norm MacDonald and Artie Lange) start a revenge-for-hire business to pay for their ailing father’s medical treatment. Buy it here.
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Friends with Money

A group of girlfriends-three with money, one who is making ends meet as a housecleaner (Jennifer Aniston)-survive the ups and downs of marriage, love and wealth. Buy it here.
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Dog Day Afternoon

On a hot day in Brooklyn, two unskilled criminals (Al Pacino and John Cazale) try to rob a bank and instead become the center of a media circus. Buy it here.
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Ghost

It’s first and foremost a love story, but this film features greed in a big and tragic way: Sam (Patrick Swayze) was murdered for money. Buy it here.
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Mr. Deeds

Adam Sandler stars as the title character, a small town man who inherits a corporate empire-and proves he’s not as naive as people think. Buy it here.
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Pretty Woman

This movie was originally going to be called $3,000; we’re glad the powers-that-be went with Pretty Woman. Buy it here.
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Rounders

Matt Damon plays a recovered gambler who returns to his old ways to help a friend (Edward Norton) pay off loan sharks. Buy it here.
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Money for Nothing

When an unemployed dockworker (John Cusack) finds $1.2 million in unmarked $100 bills, he decides to take the money and run. Unfortunately, it’s not that easy. Buy it here.
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Money Pit

This ’80s ditty stars Tom Hanks and Shelley Long as a couple that sinks money into a crumbling house. Buy it here.
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Overboard

A wealthy heiress (Goldie Hawn) loses her memory in an accident and a scraping-by handyman (Kurt Russell) with three rowdy sons claims she’s his wife. Buy it here.
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Small Time Crooks

Woody Allen writes, directs and stars in this comedy about an ex-con (Allen) whose get-rich-quick scheme pays off-in unexpected ways. Buy it here.
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Trading Places

An investor and con artist (Dan Ayckroyd and Eddie Murphy) are forced by a pair of billionaire brothers to swap lives. Buy it here.
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Wall Street

The mother of all money movies stars Michael Douglas as the ruthless and greedy Gordon Gekko. Douglas reprised his role for the sequel, in theaters now. Buy the original here. *FOR A SLIDESHOW OF OUR FAVORITE MOVIES FOR THE WORKING STIFF, CLICK HERE.*
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