Bob Newhart, 90 – $65 Million
Comedian Bob Newhart rose to fame back in the ’60s after his live album, The Button-Down Mind of Bob Newhart, became a huge hit. When he followed it up with a second live album, The Button-Down Mind Strikes Back!, he was met with another wave of success. He eventually started getting hired for various acting projects, and some of us might remember seeing him on The Bob Newhart Show, Catch-22, and The Librarian. He hasn’t gone into retirement yet, with his most recent role being on The Big Bang Theory.