The Real Deal Movie List

“The difference between tax avoidance and tax evasion is: a) whatever the IRS says, b) a smart lawyer c) ten years in prison d) all of the above?” ~ Tax lawyer Avery Tolar (character played by Gene Hackman in the movie The Firm)

THE BLUES BROTHERS (1980)

The Blues Brothers have 11 days to save an orphanage that is about to be closed for non-payment of taxes. This financial reason allowed us, the audience, to enjoy the blues music and performances of John Belushi and James Brown.

HARRY’S WAR (1981)

As evidenced by the movie poster, this is a story of one man whose aunt’s heart attack after a confrontation with the IRS spurs him into a full-scale war against the institution. He soon finds media attention and no lack of supporters.

THE UNTOUCHABLES (1987)

We all know that Al Capone was done in by his unpaid taxes, but there is no better movie to explain how this was done than The Untouchables. Kevin Costner stars as Eliot Ness, a Treasury Department agent who finds a way to bring down the invincible Al Capone played by Robert de Niro. That handsome Brit actor called Sean Connery also stars.

DAVE (1993)

When a U.S. president goes into a coma, his double Dave takes over the official duties, only to wreak havoc on the ruthless way the governmental business is normally run. Dave is a gentle everyman who brings humanity and common sense to the White House, much to the dismay of his presidential staff and the amusement of audiences. When the time comes to balance the national budget, Dave uses his tax advisor to help cut down unreasonable expenditures.

THE FIRM (1993)

Before he began going on impossible missions, Tom Cruise embodied on screen the everyman—a nice, honest American who finds himself in exceptional situations. The Firm—the first and possibly the best book by John Grisham—was adapted for the screen to showcase Cruise’s “everyman” charm. He plays a tax lawyer who thinks he will be billing hours of doing tax documents for a conservative Mississippi law firm. That he does, except that soon he learns that his client is the Mafia and that doing a correct tax statement is the least of his problems.

THE SHAWSHANK REDEMPTION (1994)

The classic prison drama stars Tim Robbins as Alan Dufresne, a man wrongly accused and sentenced to life in prison. He survives years of hardship by becoming a tax advisor not only to prisoners but also to the wardens. His clever “creative accounting” eventually buys him his freedom through an elaborate scheme.

HAPPY GILMORE (1996)

Adam Sandler stars as Happy Gilmore, a happy-go-lucky hockey player who wants to save his grandma’s house, repossessed by back taxes. But instead of playing the scruffy game of hockey, he needs to play the gentleman’s game of golf—and win. A silly comedy but with a very real underlying premise. Short of winning the lottery (or in this case a golf championship), how could an ordinary guy like Happy come up with $270,000 of back taxes?

STAR WARS: EPISODE 1 – THE PHANTOM MENACE (1999)

Even though it was filmed some 20 years after the first movie in the series, this is, technically, Episode 1 in the saga of stories from a “galaxy far, far away.” An introductory scrawl explains that there is intergalactic conflict due to taxation of trade routes to outlaying star systems. Even in the outer reaches of the universe, taxes still have to be paid. The trade dispute results in the Trade Federation suspending all shipping to a small planet called Naboo, and we are off to meet young Anakin Skywalker, Obi Wan Kenobi, and Yoda. But it all starts with a tax dispute….

CATCH ME IF YOU CAN (2002)

Frank Abagnale Jr.’s family got destroyed when his father failed to pay taxes, their house was repossessed, and the parents divorced. Leonardo DiCaprio is a virtuoso of acting in the role of Frank, the human chameleon whose true story as a master of con started with an IRS fraud.

THE PRODUCERS (2005)

This classic comedy, which had two film editions and countless theater productions, tells the tale of an accountant and a flamboyant if a bit dishonest Broadway producer who realize that they can make more money producing a flop than a hit. All goes surprisingly well until the IRS gets involved.

THE TOURIST (2010)

Although this is mostly an action thriller and a love story, the root of the elaborate plot lies in tax evasion. Alexander Pearce is a British man wanted by his government for 774 million pounds in unpaid taxes. In order to evade the tax people (as well as Belarussian mafia to whom he owes a further two billion dollars), Alexander enlists the help of his lover Elise (Angelina Jolie). Elise embarks on a charade of a romance with a random tourist (Johnny Depp) in order to fool both the police and the gangsters.

ON THE BASIS OF SEX (2018)

The story of the early years of U.S. Supreme Court Justice Ruth Bader Ginsburg, who won a groundbreaking tax case. Fighting for gender equality, Ginsberg brought to court a case of a man who was unable to deduct caregiver costs because he was a man. Ginsberg successfully argued that this inequality of taxation was a sex discrimination case.

ROBIN HOOD (2018)

This is a version with a youthful and energetic cast—Taron Egerton, Jamie Foxx, and Jamie Dornan—but there are many other versions of the same tale (e.g., the 1991 version with Kevin Costner or even the 1976 version with Sean Connery). In each of them, the hero is the forest bandit Robin Hood, who steals from the rich to distribute the gains to the poor. One of the most “politically engaged” versions is the 2010 one starring Russell Crowe and directed by Ridley Scott. Against the background of the French attempt to invade England during the reign of King John the Lackland, a lot of conflict revolves around tax obligations, inheritance, and baronial resistance to fiscal obligations to the crown.

THE LAUNDROMAT (2019)

Director Steven Soderbergh uses many cinematic tricks and a stellar cast that includes Meryl Streep, Gary Oldman, and Antonio Banderas to make the Panama Papers scandal understandable within the scope of a two-hour movie. The numerous ways in which one could evade payment of taxes or make the profits evaporate into an offshore black hole are explained in a series of vignettes on an African tycoon, an American housewife, and a Chinese billionaire.