Jay Leno | $450 Million

While his father had worked as an insurance salesman and his mother a homemaker, Jay Leno found his calling in the world of entertainment. Along with graduating from Emerson College as a speech therapy major, Leno started a comedy club there in 1973. By 1977, he landed his first appearance on The Tonight Show, where he performed a comedy routine. Suffice to say, that was just the first step he made towards stardom.

For a time, Leno landed a couple of acting gigs here and there for projects such as American Hot Wax, Good Times, and Collision Course. A few years later, he finally found his way back into the talk show scene, where he garnered widespread recognition for hosting The Tonight Show – talk about going full circle. This was then followed by his tenure on The Jay Leno Show. Nowadays, he spends most of his time on Jay Leno’s Garage, where he showcases some of his lovely rides.