In 1977, Bill Gates was taken into the slammer for driving without a license and running a stop sign. A year later, he received three speeding tickets in Seattle. Those tickets didn't dent his fortune though, which is estimated to be in the multi-billions.
Frank Sinatra
A young Frank Sinatra was caught and arrested doing something that's pretty normal by today's standards. In 1938, Sinatra was arrested in Hoboken, New Jersey for "seducing a woman." According to the complaint, Sinatra "did then and there have sexual intercourse with the said complainant, who was then and there a single female of good repute."