Billy Dee Williams – 83

Star Wars enthusiasts definitely recognize Billy Dee Williams, who had his rise to stardom for portraying Lando Carlrissian in the ‘Star Wars’ franchise. He is also set to reprise the role in the next installment of the franchise in 2019! Williams has appeared in several other iconic movies as well, but most notably next to ‘Star Wars’, Williams also had the opportunity to play Harvey Dent on 1989’s ‘Batman’. Despite his successful career, Williams’s personal life has some trials and tribulations, and literally at that, as he has faced many legal issues regarding domestic violence.