The Untouchables (1987):
Admittedly, Brian DePalma's tale of the Chicago underworld is historically inaccurate, melodramatic and filled with some of Robert DeNiro's most egregious scenery chewing. But David Mamet's script gets a few things right, namely that Al Capone's bootlegging empire wasn't brought down by bullets or business rivals, but rather by his failure to file his tax returns.
Oscar note: it was nominated for four Oscars and brought home one -- Sean Connery won for best supporting actor.
Moral of the Story: Don't bring a knife to a gun fight. And don't bring a gun to a forensic accountant fight.
Stranger Than Fiction (2006):
In this 2006 film, an IRS accountant played by Will Farrell hears a disembodied voice narrating his life. Upon further investigation, he realizes that the mystery speaker is actually a suicidal writer who has created him as a character in her latest book. Unfortunately, he is slated to die in the last chapter.
Moral of the Story: IRS agents are real people, too ... or are they?
Harry's War (1981):
Harry Johnson (Edward Herrmann) is a mild-mannered mailman until the IRS takes on his favorite aunt. When she dies of a heart attack in court, Harry declares war on the government -- and uses her extensive military surplus collection to quickly escalate his attacks.
Moral of the Story: When fighting the IRS, it helps to bring a tank.
The Adventures of Robin Hood (1938):
Sure, it's tough when your king's in jail, his brother is scheming to take over the country, and another noble stooge is arresting the locals for poaching, but the straw that breaks the camel's back is the onerous taxes that Prince John decides to levy on the country. No wonder that Robin Hood and his merry band are popular with the locals!
Oscar note: Nominated for four Oscars, it won three -- for best art direction, film editing and original score.
Moral of the Story: Tax increases + skilled archers = Occupy Sherwood Forest
Dinner for Schmucks (2010):
In between cringeworthy scenes of public humiliation, betrayal and flailing romance, this 2010 film offers an interesting look at the misfits who run the IRS. On the one side, hapless Barry Speck (Steve Carrell) crafts elaborate dioramas with mice; on the other, his arrogant boss Thurman Murch (Zach Galifianakis) attempts to use mind control on his employees and randomly threatens to audit his enemies.
Moral of the Story: On the dark side, if you underpay on your taxes, you'll have to pay interest. On the bright side, the IRS won't spank you.
Say Anything (1989):
In Cameron Crowe's classic, the path to teenaged love is filled with obstacles. But with the help of a boombox, a Peter Gabriel song and an IRS investigation that gets Ione Skye's disapproving father out of the way, John Cusack's Lloyd Dobler manages to get the girl.
Moral of the Story: If you want to keep your daughter away from deadbeats, be sure to pay your taxes -- and stay out of jail.
Slap Shot (1977):
The Charlestown Chiefs hockey team are on their way out, until a scheming manager and a trio of childlike hockey thugs transform the team. But even after they raise attendance and inspire fans, the owner still decides to fold the team, rather than sell it. The reason? She can take a hefty tax write off for a failed business.
Moral of the Story: "Old Time Hockey" is no match for newfangled accounting.
Johnny Tremain (1957):
A silversmith's apprentice who joins the American Revolution, Johnny Tremain falls in love, learns to shoot, listens to great patriots, and dumps tea into Boston Harbor. Along the way, the film gives a very Disney look at the birth of America.
Moral of the Story: Boston was a pretty boring place until taxation without representation riled up the locals!
The Blues Brothers (1980):
When a hefty pile of unpaid back taxes threatens the orphanage where they grew up, Jake and Elwood Blues hatch a scheme to raise money, reunite their friends, and create beautiful music.
Moral of the Story: There's nothing like the threat of the taxman to get the band back together.
More Article Galleries on DailyFinance
Advice for Recent College Grads
Prepare yourself for the "real world".View Course »