Billy Connolly – $20 Million

Billy Connolly started in the entertainment business in the 1960s. He first sang in the folk band The Humblebums and then began to perform on stage. He had a humble beginning by becoming a folk singer, along with the Scottish folk-rock band, The Humblebumbs. At the time, he was with his friends, Gerry Rafferty and Tam Harvey. In 1971, Billy decided to go solo. He also did stand-up comedy, and it was all a success, even earning him a number of awards.

Aside from being a musician and a comedian, he is also an actor who appeared in several film and TV projects, like Indecent Proposal, Muppet Treasure Island, The Boondock Saints, The Last Samurai, and Brave. At 77 years old, Bill is now retired and enjoying his $20-million net worth in his mansion in Florida, secured with the thought that he has something to pay for his mortgage.