Shepherd began his radio career in Cincinnati, Ohio in 1948 as a broadcaster and later landed a late night show broadcast in Philadelphia, Pennsylvania. Jean got the nickname, Shep, when he was working at WOR radio in New York City.

At his overnight radio gig in New York City, Shep told stories, read some poetry and also organized stunts for fans who listened every night.

Jean Shepherd died on October 16, 1999 at age 78 in Sanibel, Florida and two weeks later this fitting tribute was aired in 2 parts.