Willie Nelson: ~ $25 Million
A bona fide country legend with the signature plaits and cowboy hat, Willie Nelson began his musical career with his first record album in 1962 and just 10 years later became so rich that he considered retiring! Since then he has released 69 albums with no retirement plan in action. At the moment, Nelson is said to be worth $25 million.
His net worth would have been much more, but in 1990, his assets were taken by the IRS, as he allegedly owned them $32 million in taxes, and after seizing his assets, Nelson had to pay them $16.7 million more! Willie started doing Pizza Hut and Taco Bell commercials to pay off his debts. Although he had to auction off his luxury tour bus for $80,000, he still owns his famous Luck, Texas ranch.