BOBBIE GENTRY | 77, $100 MILLION

Being one of the first people to do something innovative is a great feeling, and that’s precisely what Bobbie Gentry did back in the days. She’s known for her ballsy move of putting a lot of investment in her work from scratch. Gentry composed and produced her own content, which is a common sight we see in today’s trends. She’s widely remembered for her hit song Ode to Billie Joe, which became one of the most popular songs during the late ’60s.

That title also paved the way for her to get a couple of awards, including a Grammy. Gentry listed 11 singles on the Billboard Hot 100 and 4 singles on the top 40 in the UK, respectively. Her album Fancy won her a Grammy nomination for Best Female Pop Vocal Performance. Since her retirement, her personal life became a mystery to her fans because of the lack of news about her.