Bobby Goldsboro – 81

Anyone who’s ever listened to hits like “Honey,” “Summer (The First Time),” and “Watching Scotty Grow” should know who Bobby Goldsboro is. The American pop and country singer and songwriter was one of those artists who left college to hone their musical talents.

And we probably wouldn’t even know his name if his efforts hadn’t paid off. Goldsboro’s 1968 single “Honey” remains the biggest hit of his career, as it became the largest-selling record in the world that year. But he’s also got several Top 40 hits on both “Billboard” and the county music chart and was still thriving in 2022.

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.