Diana Ross | $250 Million

Today, Diana Ross is one of the most well-known singers in the industry. Even so, she started her career like many celebrities – in square one. To help with her family’s home and personal loans, Diana once worked at a department store and as her neighborhood’s hairdresser. Her first stint in the music industry was with the all-girl group, The Primettes, which was later rebranded to The Supremes. Although they eventually parted ways, The Supremes is still considered one of the best-charting female groups in the business.

Following her departure from the group, Diana continued with her career as a solo artist. Since her debut album’s release, the singer has released many of today’s hit records, like Ain’t No Mountain High Enough, I’m Still Waiting, and Endless Love. Along the way, she also went into acting, with her most notable role being in 1972’s Lady Sings the Blues, where she earned an Oscar nomination and a Golden Globe Award.