Diana Ross – 77

Diana Ross had always dreamed of becoming a fashion designer before she even made it big in the music scene. She took on different classes pertaining to fashion from clothing design, to pattern making and tailoring, and everything in between. However, by the time she was 15 years old, Ross had joined the musical group Primettes, which was the sister group of the Primes. They were invited to audition for Motown Records, but they were too young to be signed up just yet. When they did, they changed their name to the Supremes.

Later on, their manager changed their name to Diana Ross and the Supremes. Ross found more success as a solo act. She later signed with RCA Records for a whopping $20 million for a seven-year contract, which was the highest at the time. To her credit, Ross has released several albums and hit singles that have helped increase her net worth considerably.