Hillgrove's first job was as a disk jockey with WKJF (now KDKA-FM, known as "93.7 The Fan"), and in 1968, he joined WTAE-TV as the station's booth announcer. A year later, he swapped jobs with WTAE Radio announcer Del Taylor, wishing to get back into radio. In the mid-1960s, he served for a short period of time as "proprietor" (the name given to the host) of "The Place", a television show on WQED (Channel 13) that was a coffee-house style format.