Cher
Cher is pretty unrecognizable here, right? That's because she is 13 in her mugshot! She was arrested in 1959 for "borrowing" a friend's car and driving it without a license in LA. She was always making her own rules.
50 Cent
50 Cent (aka Curtis Jackson) served some time in New York State Department of Correctional services back in 1994. He was only 19-years-old. He pleaded guilty to felony charges for selling hard drugs.