Jay Leno – $450 Million

Jay Leno and Dr. Phil McGraw are both TV show hosts and producers, but their paths are quite different from one another. Jay’s career began as a featured standup comedian in The Tonight Show back in 1977 and was given side roles in other TV programs and movies such as Fun with Dick and Jane, Alice, and American Hot Wax. He was also often seen in The Late Night with David Letterman.

Jay became the main host of The Tonight Show then made a comeback with The Jay Leno Show. He still remains active with his being a standup comedian and has sold out up to 200 live shows already. He does return to the TV screen as a guest in his previous shows. Between Jay and Phil, the latter has more net worth as of this time, but Leno’s automobile investments are quite jaw-dropping.