In September 1999, he launched a multi-format "supersite" on the web site Rapstation.com. The site includes a TV and radio station with original programming, prominent hip hop DJs, celebrity interviews, free MP3 downloads (the first was contributed by multi-platinum rapper Coolio), downloadable ringtones by ToneThis, social commentary, current events, and regular features on turning rap careers into a viable living. Since 2000, he has been one of the most vocal supporters of peer-to-peer file sharing in the music industry.
Addressing the negative views associated with rap music, he co-wrote the essay book Fight the Power: Rap, Race, and Reality with Yusuf Jah. He argues that "music and art and culture is escapism, and escapism sometimes is healthy for people to get away from reality", but sometimes the distinction is blurred and that's when "things could lead a young mind in a direction." He also founded the record company Slam Jamz and acted as narrator in Kareem Adouard's short film Bling: Consequences and Repercussions, which examines the role of conflict diamonds in bling fashion. Despite Chuck D and Public Enemy's success, Chuck D claims that popularity or public approval was never a driving motivation behind their work. He is admittedly skeptical of celebrity status, revealing in a 1999 interview with BOMB Magazine that, "The key for the record companies is to just keep making more and more stars, and make the ones who actually challenge our way of life irrelevant. The creation of celebrity has clouded the minds of most people in America, Europe and Asia. It gets people off the path they need to be on as individuals."