RuPaul was born in San Diego, California. After several years as a drag performer in Atlanta in the 1980s, RuPaul came into the public eye in the early 1990s in New York City, performing under the name RuPaul Charles and later simply RuPaul.  He made many famous friends and even appeared in the music video for The B-52's video Love Shack. RuPaul later also filmed a video alongside Elton John.

One of RuPaul's most famous quotes is "We all came into this world naked; the rest of it is all drag." He has done acting and modeling as both a woman and a man (as evidenced in his biographical information as well as photographs on his web site.) Unlike most drag queens, who have a male name and a female name, and thus expect to have the appropriate gender-specific pronoun used for each, RuPaul seems to be comfortable with either "he" or "she".

Eventually he was signed to a modeling contract for MAC cosmetics, making him the first transvestite supermodel. He began releasing pop albums starting with Supermodel of the World which spawned the #1 dance hit Supermodel (You Betta Work). He landed a talk show on VH1, appropriately called The Rupaul Show where he interviewed celebrity guests and musical acts. Because his fanbase largely consisted of the gay community, he mostly performed at gay pride events and gay venues. He released a Christmas album entitled Ho, Ho, Ho and had guest appearances in many films including The Brady Bunch Movie.

RuPaul was nominated for an Emmy award when he appeared as a male, alongside Linda Hamilton in the made-for-TV Movie A Mother's Prayer. In the late 1990s he released his autobiography, Lettin' It All Hang Out. He has since faded into relative obscurity, taking bit roles (often as himself) in film and television.