4. O.J. Simpson
Despite his famous records in San Francisco 49ers and running back for the Buffalo Bills, he had his career cut short in by public trial. In 1997, he was charged for being involved in a wrongful death and was ordered by a civil jury to pay $33,500,000 for damages. He was since charged for several other cases and finally got jailed for 33 years for assault, kidnapping, robbery, use of deadly weapons and criminal conspiracy. He is currently serving his sentence in jail. Indeed this man is by doubt one of the celebrities in jail who could have made bigger names had they not got their hands in crime.