Tax Season Film Fest: The Top 5 Financial True-Crime Movies

Leondardo DiCaprio, The Wolf of Wall Street/Paramount Pictures publicity photo [promotional image]

Just as it does every April, the deadline for U.S. citizens to file their income-tax returns is looming.

As always, the occasion turns the nation’s thoughts collectively to the good, the bad, and the ugly regarding finances — particularly in terms of what’s legal and what’s not when it comes to divvying up money between yourself, Uncle Sam, and any other number of other parties.

Related: December 11, 2008 — $65 Billion Fraudster Bernie Madoff Busted

So maybe you got your returns in early this year and you’re looking for a couple of flicks to relax with while waiting for a refund. Then again, perhaps you need a bit of motivation to get those numbers crunched and properly delivered to the IRS on time.

Either way, the following five films all depict what happened in real life to tax scammers and other financial fraudsters who imagined they could beat the system. They couldn’t. Watch, enjoy, and — above all — heed the warnings!

THE UNTOUCHABLES (1987)
Director: Brian De Palma
Cast: Kevin Costner, Robert De Niro, Charles Martin Smith

Bravura filmmaker Brian De Palma’s operatic take on Al Capone versus Federal Agent Elliot Ness during Prohibition-era Chicago is a classic for its sleek style, its larger-than-life performances, and screenwriter David Mamet’s Tommy-gun-impact storytelling and dialogue.

What goes often unmentioned, though, is that, for all its gunfights and chase scenes, The Untouchables pays serious attention to the manner in which Capone actually got taken down: by getting busted for tax evasion.

Related: Crime History — Al “Scarface” Capone Goes Down For Tax Evasion

Charles Martin Smith, who created an enduring “nerd” archetype as Terry the Toad in American Graffiti (1973), makes a lasting impact as Frank J. Wilson, the member of Ness’s Untouchables team who forsakes fists and bullets for even deadlier weapons: financial ledgers and the United States Treasury Department. [History]

WALL STREET (1987)
Director: Oliver Stone
Cast: Michael Douglas, Charlie Sheen, Martin Sheen

When anyone brings up the movie Wall Street, one phrase comes to mind: “Greed is good!”

It’s spoken by Michael Douglas as Gordon Gekko, a Manhattan-based “Master of the Universe” scammer of billions based on real-life ultra-’80s stock-market schemers who went to jail over staggering monetary figures, such as Ivan Boesky and Michael Milken.

Related: The Deadliest Decade — Pop Culture Highlights From 9 Totally ’80s Crimes

That endlessly quoted line, in fact, is based on a statement made by Boesky when he delivered a 1986 commencement address at (of all colleges) UC Berkeley, stating:

“Greed is all right, by the way. I want you to know that. I think greed is healthy. You can still be greedy and feel good about yourself.”

Director Oliver Stone followed up this landmark hit with a 2010 sequel that starts with Gekko getting out of jail, Wall Street: Money Never Sleeps. Unlike the original, that one did not make a killing. [Business Insider]

CATCH ME IF YOU CAN (2002)
Director: Steven Spielberg
Cast: Leonardo DiCaprio, Tom Hanks, Christopher Walken

Catch Me If You Can is a light-hearted true-crime story so mind-boggling it could only be true. Leonardo DiCaprio plays Frank Abagnale, Jr., a real-life master of disguise and manipulator of everyone he came across. He was such a successful con man that he amassed a fortune through embezzlement and forged checks without getting caught for decades.

Tom Hanks costars as Frank Hanratty, the FBI agent who chased Abagnale all over the world for years, and came to begrudgingly admire his target’s unprecedented skill as a con artist extraordinaire.

Related: How Black-ish Star Jenifer Lewis Is Trying To Bring Her Con Artist Ex To Justice

The movie ends with Hanratty finally nailing Abagnale and the two men warming to one another. In real life, Abagnale did his jail time, then went to work with Hanratty and other law-enforcement officers in preventing fraud and hunting down forgers.

Interestingly, what initially sent Abagnale off on his globe-trotting crime spree was resentment against the IRS, as his father’s own tax troubles had prevented him from getting a loan. [History vs. Hollywood]

AMERICAN HUSTLE (2013)
Director: David O. Russell
Cast: Bradley Cooper, Christian Bale, Jeremy Renner

In the late 1970s and early 1980s, the FBI launched an operation called ABSCAM in which agents disguised as Arab oil sheiks busted more than 30 political figures, including seven congressmen, who had been taking bribes. American Hustle fictionalizes its characters, but the basic elements of the ABSCAM sting remain true to the real deal.

Related: 9 Tactics Master Manipulators Use To Control Their Victims

Bradley Cooper stars as Richie DiMaso, an FBI agent based on Anthony Amoroso, who helped conceive and execute ABSCAM. Christian Bale plays Irving Rosenfeld, modeled on real-life con man Melvin Weinberg who cut a deal with the feds to work on ABSCAM. Jeremy Renner portrays Mayor Carmine Polito, the movie’s version of Angelo Errichetti, the popular mayor of Camden, New Jersey, who went down on ABSCAM charges. [Time]

THE WOLF OF WALL STREET (2013)
Director: Martin Scorsese
Cast: Leonardo DiCaprio, Jonah Hill, Margot Robie

New York City’s reigning cinema maestro Martin Scorsese pulls out all the stops and goes way, way, way over-the-top with The Wolf of Wall Street, an adaptation of a memoir by true-life “boiler room” fraud operator, penny-stock scam kingpin, and world-class tax evader Jordan Belfort.

In keeping with the fact-based excess and insanity, Leonardo DiCaprio plays Belfort like a rampaging bull market in human form, as he scarfs up everything in his path — mansions, luxury cars, yachts, international beauties — with utter abandon … and no regard for the fact that the financial schemes running the whole mad engine are completely illegal.

Related: Bateman Skincare Line, Inspired by American Psycho Is, Uh, Cruelty-Free

After it all came crashing down, Belfort did some time behind bars and had to pay restitution to the more than 1,500 clients he bilked. But, true to his self-anointed “wolf” status, Belfort bounced back and, since the movie, has been a hugely successful, always in-demand motivational speaker. [Slate]

Main photo: Leondardo DiCaprio, The Wolf of Wall Street/Paramount Pictures publicity photo [promotional image]

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