Billy Dee Williams – 84

Singer, actor, and artist Billy Dee Williams is perhaps known best for his Star Wars role, Lando Calrissian. Some of the notable films he’s appeared in include Brian’s Song, Mahogany, and Batman. As announced in August 2018, Billy Dee Williams is set to reprise his role on Star Wars: Episode IX. Williams underwent 52 counseling sessions in 1996 after a plea bargain, following his arrest for an alleged physical altercation with his then live-in girlfriend.

Before acting, he attended the New York National Academy of Fine Arts and Design, and he worked on some paintings in the late ’80s with some of them still on display at his BDW World Art online gallery.