Sidney Poitier – 91

Sidney Poitier was a trailblazer for African-American actors. His acting skills quickly made him an international star, as he went from theater to screen acting. Poitier’s most famous performance is in Lilies of the Field, for which he won an Academy Award. He was the first African-American to ever do so. While his skills as an actor were great, he also had other talents. After retiring from acting, he directed, recorded an album and became a diplomat. He received a British knighthood and a Presidential Medal of Freedom for his achievements. If anyone deserves to wind down and enjoy his $25 million net worth after retirement planning, it’s Sidney.