Radio
After his military service, Shepherd began his broadcast radio career in early 1945, on WJOB in Hammond, Indiana, later working at WTOD in Toledo, Ohio, in 1946. He began working in Cincinnati, Ohio, in January 1947 at WSAI, later also working at Cincinnati stations WCKY and WKRC the following year, before returning to WSAI in 1949. From 1951 to 1953, he had a late-night broadcast on KYW in Philadelphia, Pennsylvania, after which he returned to Cincinnati for several different shows on WLW-T and WLW. After starting on television there, he also returned to radio. "Shep", as he was known, left WLW radio in late summer of 1954 and settled in at WOR radio New York City on February 26, 1955, where he would remain until spring 1977. Beginning on an overnight slot in 1956, he delighted his fans by telling stories, reading poetry (especially the works of Robert W. Service), and organizing comedic listener stunts.
The most famous stunt was a hoax he created about a nonexistent book, I, Libertine, by a fake author "Frederick R. Ewing", in 1956. During a discussion on how easy it was to manipulate the best-seller lists based on demand, as well as sales, Shepherd suggested that his listeners visit bookstores and ask for a copy of I, Libertine, which led to booksellers attempting to order the book from their distributors. Fans of the show planted references to the book and author so widely that demand for the book led to claims of it being on The New York Times Best Seller list. Filling the demand, Theodore Sturgeon and Betty Ballantine wrote the long-awaited book to Shepherd's outline, with a cover designed by illustrator Frank Kelly Freas, published by Ballantine Books.
When he was about to be released by WOR in 1956 for lack of sponsors, he did a commercial for Sweetheart Soap, not a sponsor, and was immediately fired. His listeners besieged WOR with complaints, and when Sweetheart offered to sponsor him, he was reinstated. Eventually, he attracted more sponsors than he wanted – the commercials interrupted the flow of his monologues. Former WOR engineer, Frank Cernese, adds, "The commercials of that era were on 'ETs' – phonograph records about 14" in diameter. Three large turntables were available to play them in sequence. Shepherd preferred the engineer to watch and listen to his stories. That left little time to load the turntables and cue the appropriate cuts. That was when he started complaining about "too many commercials".
His last WOR broadcast was on April 1, 1977. His subsequent radio work consisted of short segments on several other stations, including crosstown WCBS, and occasional commentaries on NPR's All Things Considered.
In addition to his stories, his shows also contained humorous anecdotes and commentaries about the human condition, observations about New York City life, accounts of vacations in Maine, and travels throughout the world. One striking program recounted his participation in the March on Washington in August 1963, during which Martin Luther King Jr. gave his "I Have a Dream" speech, and another program that aired on November 25, 1963, covered the burial of assassinated President John F. Kennedy.
Throughout his radio career, he performed without scripts. His friend and WOR colleague Barry Farber marveled at how he could talk so long with so few notes. During a radio interview, Shepherd claimed that some shows took weeks to prepare, but this may have been in the planning rather than the writing of a script. On most of his Fourth of July broadcasts, he did read one of his most enduring and popular short stories, "Ludlow Kissel and the Dago Bomb that Struck Back", about a neighborhood drunk and his disastrous fireworks escapades. In the 1960s and 1970s, his WOR show ran from 11:15 pm to midnight, later changed to 10:15 pm to 11 pm, so his "Ludlow Kissel" reading was synchronized to many New Jersey and New York local town fireworks displays, which would typically reach their climax at 10 pm. It was possible, on one of those July 4 nights, to park one's car on a hilltop and watch several different pyrotechnic displays, accompanied by Shepherd's storytelling.
