Clint Eastwood – $375 Million

Clint Eastwood is better known for his work as an award-winning film director, but he cemented his roots in Hollywood initially as an actor. Eastwood rose to prominence by appearing in Sergio Leone’s Man With No Name trilogy of movies in the ’60s. He then switched over to directing in the ’70s and his list of critically acclaimed films includes Million Dollar Baby, Invictus, American Sniper, and Sully. The 88-year-old is an FAA licensed private plane pilot, and he’s known to regularly fly his chopper to the studio just so that he avoids traffic.