R Kelly – Est. –$2 Million
After quitting high school, R. Kelly started performing as a subway musician. He got an opportunity to participate in Big Break, the talent show on TV.
He won prize money of $100,000. Kelly kicked start a career in professional singing and garnered a lot of praise and appreciation with 12 Play, his solo album. Bump N’ Grind, a single from the album, won six platinum certifications and broke several records.
Kelly’s unprecedented success over the years earned him the recognition he deserved and banking on his popularity. Though there has been some controversy surrounding him, his fame hasn’t faded away. He has accumulated a significant sum under his belt. However, Kelly’s net worth has come down to a negative 2 million now due to his struggles.