4. Ron Isley
The Isley Brothers singer was caught by the Internal Revenue Service for skipping on his taxes worth $3.1 million. Due to this, he was given a 25 month sentence in prison. Although, his attorney argued that due to some “unfortunate circumstances” like the death of his two accountants, Isley was not able to document and pay his taxes during the questionable years, still he was not given mercy by the judge. Mr. Biggs was set free in April 2010.