Last week, influential hip-hop deejay Mister Cee resigned from New York radio station Hot 97 for fewer than 24 hours. Fabulously-named transgender vlogger Bimbo Winehouse had just published a recording of an encounter where Cee is apparently, as WorldStarHipHop thoughtfully described, “tricking for head & sex.” It wasn’t the first time Cee’s been in the news for seeking out transgender sex workers, so that part came as no surprise to anyone who’s kept up with his personal life in recent years. However, few listeners were prepared for the intensity and candor of Cee’s September 12 on-air conversation with program manager Ebro Darden. It was a watershed moment for both hip-hop and for one of the least visible segments of society: people who are attracted to transgender people.
By one measure, T-girl sites are the fourth most popular category of adult website, according to the authors of A Billion Wicked Thoughts. Most of the consumers of this material identify as straight men, and it’s often classified as a straight specialty genre. But despite a huge population with some level of sexual interest in trans people, it’s the rare person who discusses this interest openly. Among the rarest of all is someone involved in hip-hop willing to discuss their interest in trans women. The relationship between trans people and hip-hop is at the center of a volatile intersection of race, misogyny, and homophobia. I’ll try to contextualize hip-hop’s transphobia with a few examples from old school rap, showing what it was like back in the day for hip-hop artists of a certain age, like Cee, and what was at stake for him personally and professionally