BILLY DEE WILLIAMS – 83

Star Wars fans will instantly recognize Billy Dee Williams as Lando Calrissian in the 1980 installment The Empire Strikes Back. He also portrayed the infamous Harvey Dent in the 1989 Batman movie. However, only a handful knew that Williams started his career at Broadway during the mid-’40s, establishing his seven-decade stay in the industry. Williams will reprise his famous role as Lando in the upcoming Star Wars installment this year.

Because of all his hard work through all of those years that he has been in the industry, there is no doubt that there will be bad news regarding his financial status. However, behind the scenes, there is some bad news that surrounds him. Not because of his financial records but because of his love life. He had to hire lawyers twice for his two failed marriages, but he later landed a relationship that has been steady and happy since 1972.