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I'm doing some research that I'd like your help with. This regards celebrities (oh no!)...

1) What musicians do you know the existence of have done time (former prison inmates preferred)?

2) What celebrities do you know the existence of have done time (former prison inmates preferred)?

doesnt look like you getting much help with this,may i ask why you are doing research on such a topic.

Hmm, well off the top of my head probably every single rapper out there, aside from Will Smith.

Willy Nelson got busted for marijuana possession back in 2006, according to the wiki.
Lil' Kim also served a year.

Those are the only two that come to mind immediately, though I have no idea why those two.