Jason Lee – $20 million

Actor and voice actor Jason Lee is popularly recognized for his role in the hit comedy series My Name Is Earl, where he played the lead role. Since then, Jason’s star has continued to rise, and he went on to star in the Alvin and the Chipmunks movie series and rendered his voice talent to the character Syndrome in Disney’s The Incredibles. Interestingly, Jason made his first big break in professional skateboarding before retiring in 1995.

From his life as a professional skateboarder to a renowned actor, Jason led a rather unique career and earned paychecks that secured his home insurance. Even though he changed careers along the way, Jason managed to learn a lot from both areas and become really good at them. The actor honed his talent pretty well, so though he is retired, a lot of people still look up to him in this regard. Apparently, he left quite a legacy behind!