Nancy Sinatra – 80

The song, These Boots Are Made for Walking, from 1966 is Nancy Sinatra’s signature hit. It was this song that catapulted her into stardom. The daughter of the legendary music icon Frank Sinatra, Nancy began her career back in 1957. The 79-year-old Sinatra had a brief acting career too and appeared in the movie Speedway opposite Elvis Presley. She also co-starred with her father in Marriage on the Rocks. Nancy released her most recent album in 2013, but she hasn’t announced her retirement yet. She has two daughters who both received $1 million each as an inheritance from their late grandfather.

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.