Sly got his start in radio playing Top 40 hits at WJMM, a student-run station at James Madison Memorial High School. For long forgotten reasons, he disc jockeyed under the name Joel Connors. At the age of 18, Sly got his very first professional gig in radio doing overnights on weekends at Q106, a rock station at the time. Sly worked his way onto WSUP at the UW-Platteville. He spent more time in the studio than the classroom and soon began pursuing a career in radio full-time.

After stints in Oshkosh and at Madison’s famed album rock station 92.1 WMAD, Sly was hired to do overnights on WIBA-FM in 1985. He was the first to introduce The Beastie Boys to Madison listeners. In 1988, Sly moved to morning drive and soon began dominated the airwaves. It was there that Social Dilemma, Great Opening Lines and Vinyl from Hell were born.

Sly made the switch to talk radio in 1997 with shows on WTDY and WBGR. During that time he kept up his rock DJ cried by spinning records on WHLK “The Lake” and WWHG “The Hog”.

In 2016, Sly returned home to the mother ship 101.5 WIBA-FM.