Willie Nelson

Served in: U.S Air Force
Rank: E-1
Best Known For: The Highwaymen, The Electric Horseman
Est. Net Worth: $25 million

Willie Nelson is an outlaw country hero, and the Texas-native is also a proficient writer, poet, and activist. Nelson served in the Air Force briefly until a back injury forced him to resign. After his service, he picked music back up. He’d played the guitar and sang as a child, and he decided to become a musician full-time.

His brand of folk and outlaw country took off, and his albums topped the charts and sold millions. He also became an actor, appearing in The Electric Horseman in 1979. He also owns the business Willie Nelson Biodiesel, which pioneers vegetable oil as fuel.