Stern landed his first professional radio job while at Boston University, performing on-air skits, news casting and production duties at 1550 WNTN in Newton, Massachusetts from August to December 1975. He also hosted a show with three fellow students on WTBU, campus radio station, named "The King Schmaltz Bagel Hour" which was cancelled during its first broadcast for a sketch called "Godzilla Goes to Harlem". After his graduation, Stern landed some cover shifts in December 1976 at WRNW, a progressive rock station in Briarcliff Manor, New York where he was subsequently hired full-time working middays. He produced more creative commercials by calling the owners of businesses on the air, which he wrote "was mind-blowing to everyone there."