Junior Bridgeman – 68

The National Basketball League (NBA) was already a thing during the ‘70s. Before we had the Michael Jordans or Kobe Bryants, stars like Junior Bridgeman were already popular on the scene. Bridgeman’s most considerable success came after he retired from the sport. He was reportedly earning more than $350K per year at the NBA, but this is nothing compared to the $600 million financial worth he’s accumulated as a businessman.

After his retirement, Bridgeman immediately capitalized on his business acumen and created a chain of fast-food restaurants. These days he manages two magazines, Ebony and Jet, which he acquired in 2020.

Simmons – 73

Richard Simmons dedicated his life to promoting a better life through exercise. Simmons became obese at a very young age, peaking at 268 pounds. Simmons did try losing weight and working out, but he noticed gyms prefer already slim customers, and he realized the need for a studio that would accommodate people with weight problems. He opened his studio named Anatomy Asylum, where he encouraged people to eat healthy instead of doing extreme diets and to workout in supportive environments. Simmons became famous and appeared on television quite often, but has withdrawn from the public since 2014 while his studio was closed in 2016.