6. Kevin Poulsen
Years active: 1980s
Hack job: Going by the name Dark Dante, Poulsen learned lock-picking en route to a spree of hack stunts that ranged from fixing radio station call-in contests to breaking into FBI databases. Poulsen's exploits landed him on Unsolved Mysteries, and after he was arrested and did his time, he got himself a spot as a senior editor at Wired magazine.
Total payout:Unclear, as some of his stuff was just for kicks, but dude got into a lot of stuff.
Punishment: 51 months in prison and $56,000 in restitution