3. Tim Allen, Drug Dealer
The Santa Claus used to roll with a different kind of white powder. While he was incubating his stand-up career, the Tim the Tool Man found some less than legal ways to make ends meet. Allen was caught with over a pound of cocaine in his trousers at an airport back in the '70s.
The drug-dealing comic proceeded to rat out everyone he knew, allowing him to whittle a potentially huge sentence down to just over two years. Aside from a 1997 DUI and some really shitty movies, this was the end of Allen's criminal side, though Wild Hogs should be considered obscene (and illegal) material.