Tony Bennett, 96 – $200 Million

Tony Bennett’s career in the music industry spans over fifty years. The American singer became a hit in the ’50s and ’60s from hugely popular singles and pop landmarks like I Left My Heart In San Francisco, The Shadow Of Your Smile, Stranger In Paradise, and Because Of You.

In the ’70s and ’80s, Bennett’s career began to flounder due to his issues with addiction. After getting his life back on track, he also managed to successfully re-launch his career. The Rags To Riches singer managed to rack up close to $200 million during his illustrious career. Bennett was recently diagnosed with Alzheimer’s disease and suffers from short-term memory loss.