WILLIE NELSON – EST. $30 MILLION

The artist isn’t just one of music’s icons, but he is also one of the major figures in “outlaw country,” a subgenre developed back in the ’60s in response to the conservative Nashville sound. Throughout his career, Nelson is often highly regarded for his hit albums like Shotgun Willie, Stardust, and Red Headed Stranger. He went through quite a painful chapter in the 90s with his assets getting seized by the IRS for owing over $32 million. This led to The IRS Tapes: Who’ll Buy My Memories? The profits of which went to clear his debt.

Aside from making music, he also gets credit for appearing in films and has even done television work. Among the many titles he has worked on include The Electric Horseman, The Dukes of Hazzard, Austin Powers: The Spy Who Shagged Me, and Once Upon a Texas Train. In 1988, Nelson also tried his shot in writing, and has published his first autobiography.