Bill Cosby: ~ Estimated $3.6 Million, Gulfstream IV
Bill Cosby rose to fame in the acting scene thanks to shows like The Bill Cosby Show, The Cosby Show, and Fat Albert and the Cosby Kids. He reportedly spent around $3.6 million to buy his private plane, which is a Gulfstream V. Despite all the success he had, he doesn’t really have a good reputation these days because of the numerous indecent assault allegations that were thrown at him. He received a three to ten-year sentence back in 2018 and has been in a state prison in Pennsylvania since September that same year.