RuPaul was the only boy of his parents’ four children and eventually began wearing his sisters’ clothes and exploring cross-dressing, emulating stars like Diana Ross and Jane Fonda in his youth.

Following the success of his first album, RuPaul inked his first self-titled television slot. The VH1 talk show featured high-profile guests such as Diana Ross, Cher, and Mary J. Blige and ran for ...