James grew up in a "well-to-do" family in Saginaw, Michigan where he lived with his mother after his parents divorced. In the summer he would stay with his father in Fort Lauderdale, Florida until he moved to Fort Lauderdale for high school. After reading Andy Warhol’s book, The Warhol Sixties St. James moved to New York in 1984, where he studied performance art at New York University for two years before being absorbed into New York's club scene. St. James lived a celebutante lifestyle after becoming a close friend of nightlife icon and columnist Michael Musto.

St. James became a mentor of sorts to Michael Alig, although at first he and the other club personalities shunned the newcomer.Fenton Bailey, Randy Barbato; (1998) Format:Documentary The Shockumentary Undeterred, Alig soon created his own scene by gathering up other creative rejects of the nightlife world, copying St. James' flamboyant style with self-promotion and innovative themed parties. Alig eventually grew on St. James, and St. James morphed from celebutante to Club Kid while helping Alig create the new scene. Alig and St. James threw many parties together, eventually setting up the Disco 2000 club night at the New York City club The Limelight. St. James wrote several columns, most famously for the short lived New York City-based gay publication OutWeek during the magazine's two year life span from 1989-1991. St. James has appeared many times on television many along with the club kids on talk shows during the 1980s and 1990s, including The Jerry Springer Show, Geraldo, and The Joan Rivers Show.

As Alig got more into drugs, he infamously murdered his drug dealer roommate, Andre "Angel" Melendez. St. James' debut novel, Disco Bloodbath, documents the infamous rise to fame of Alig and the murder. To avoid having to testify against Alig or club owner Peter Gatien, St. James moved to Los Angeles, where he presently lives. A documentary and feature film both used the book as their basis.

St. James published a second book, Freak Show in 2007, winner of the American Library Association award for best young adult novel of the year . James curates art shows at the World of Wonder Gallery for the production company World of Wonder Productions, makers of both A Shockumentary (1998) and Party Monster (2003), and blogs regularly on World of Wonder's website, the WOW Report. In the 2000s St. James has made regular appearances on America's Next Top Model, cycles 5, 7, & 11 presenting contest skill challenges to the aspiring models.