Innate south side of Chicago, Illinois, Shepherd was raised in Hammond, Indiana where he graduated from Hammond High School around 1939. As the youth he worked for the brief period as a mailman within a steel-mill. He attended a University of Indiana. In the period of World War II he served in the U.S. Army Signal Corps.

Shepherd began his broadcast radio career in WSAI AM in Cincinnati, Ohio in 1948. He late got the tv show around Cincinnati called Rear Bumper. Within 1957 he was recommended as a replacement for the resigning Steve Allen on NBC's The Tonight Show. NBC executives sent Shepherd to New York to prepare for a position, however it were contractually attached to offer the position to Jack Paar first. NBC was certaaround Paar would survive for the role in prime period, however he accepted.

Shep, when he was known, settled within at WOR-AM radio New York City, New York on an overnight slot in which he delighted his fans by telling stories, reading poetry (especially a works of Robert W. Service), and organizing comedic listener stunts (notably the book, I, Libertine in 1956) until 1977. He was reputed to stand performed totally forswearing scripts. His unwritten narrative style was the precursor to it utilized by Spaulding Gray and Garrison Keillor.

Shepherd as well performed regulary at a old Village Limelight, & at various local colleges and universities. These shows were for instance broadcast hold up WOR-AM radio. Eight record albums of survive & studio performances of Shep were freed between 1955 and 1975.

Between 1976 and 1994 Shepherd became a film writer of note, producing many works for each TV & cinema. He too narrated numerous one works, a best known existence a holiday classic A Christmas Story. He performed prior to sold-out audiences at Carnegie Hall.

Shepherd wrote the series of humourous short stories just about growing higher in the Indiana steel towns, which were later assembled into books. Among the children were, In God We Trust, All Others Pay Cash and ''Wanda Hickey's Night of Golden Memories.'' A select few of victims situations were incorporated into his moving-picture show.

Marshall McLuhan characterized Shepherd as "the first radio novelist". Within a favorite bulletin, the American Radio Relay League described him as "a legend".

Shepherd was an amateur radio operator and his call sign was K2ORS. Whilst operating as an amateur, he was known to have a title Parker.

Shepherd improvised spoken word lyrics for the title track in jazz great Charles Mingus's 1957 album The Clown.