Former action movie star Wesley Snipes is the poster boy for tax cheats. He's so famous for trying to run rings around the IRS that you would expect other stars to learn from his example and make sure the bills are always paid. As is heavily evidenced from reading our list, nobody's learned a thing, even though Snipes was more harshly punished than perhaps anybody else.
Snipes is a guy who projects the image of a tough guy, and someone who isn't to be messed with. That's how he comes across in 'Demolition Man' and 'Blade,' and perhaps that's how he was hoping he'd come across to the IRS when they took him to court. Snipes hadn't just failed to pay his taxes, though - he'd knowingly supplied false information. That landed him with a three year stretch in prison, and an order to pay almost $18m in back taxes when he was released. His career has never picked up steam since his release, and so he'll likely never see that kind of money again.