Richard Chamberlain: ~ $20 Million

The blue-eyed poster boy of the 1960s, actor Richard Chamberlain, was a huge teen idol back in the day even, as he is remembered as Dr. Kildare from the TV show of the same name. Soon enough he was inundated with more acting offers such as in The Three Musketeers and The Bourne Identity.

Although he didn’t get much work in the 80s and later, Richard was smart with the money he had accumulated when he was acting. He chose to invest in real estate with his most expensive buy being in Hawaii. Richard had recently listed his oceanfront Maui manse for $19 million, and ultimately sold it for $13.8 million.