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."
Sinatra was released on $1,500 bail but was arrested one month later for the same crime but a different charge: adultery. Apparently, the woman was married. None of these "crimes" would stand up to the law in this generation!
Jay-Z
In 1999, Jay-Z climbing the music industry. He was very well-known, especially in the East Coast hip-hop scene. Apparently, no one was surprised when he was arrested for allegedly stabbing a record producer in New York City.