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Rip Torn – Compared to most celebrities on this list, Torn didn’t spend a lot of time in jail. He was sentenced to four days for breaking into a bank while intoxicated. Apparently, he thought it was his home, and unfortunately for him, Rip was carrying a gun without a permit.
50 Cent – Before he became one of the best-known rappers in the world, 50 was involved in illegal activities. The police caught him with drugs and unregistered guns in his home, and the rapper was sentenced to six months in prison.