Tony Bennett | Born 1926

Another icon on our list is Tony Bennett. The now 96-year-old crooner is famous for his traditional pop standards, big band, show tunes, and jazz songs. Outside of singing, the retired singer is also a renowned painter and has artworks that are on permanent public display in a number of institutions. They’re all under his birth name, Anthony Dominick Benedetto. Tony Bennett is just his professional name.

The hitmaker also made several investments, like founding the Frank Sinatra School of the Arts. However, in 2021, Bennett decided to leave the industry he loves. Before that, he continued to record, tour, and perform. He chose to retire due to the physical challenges that he had been experiencing. His final performance was held at Radio City Music Hall in August 2021.