Bill Cosby – $400m

After having spent so many years under the spotlight for his career in comedy, Bill Cosby fell from good grace when he was convicted on multiple violation charges in 2018 and was moved to the general population of SCI Phoenix in January 2019. Despite this, he had already managed to acquire a gigantic fortune before his conviction estimated at around $400 million. He owned a house in Ellis Park, Pennsylvania, one in Massachusetts, and one in Los Angeles. Even though most of his awards and honors were taken back, he is still widely remembered for The Bill Cosby Show.