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He was the grandmaster of the monologue. Without talking to listeners or interviewing guests, he would talk for sometimes as long as three and half hours with only an occasional commercial break. And it was usually fascinating.

Jean Shepherd started as a DJ in Cincinnati working at WCKY, WSAI and WKRC but preferred talk to playing records. After stints at WLW, Cincinnati and KYW, Philadelphia, he took the overnight job at WOR, New York and remained there for 22 years.

In the early 1960s, Shepherd moved to a 45 minute format on WOR. The show usually aired at 9:15, 10:15 or 11:15 pm. Some nights he would go into the studio with a scrap of paper with an idea on it or a newspaper article and launch into a story that was told in the first person. Other nights he would perform elaborate bits. His stories often revolved around his childhood, college or army experiences but they always had a point and always, like our literature teachers told us was necessary, had a beginning, a middle and an end.

Once, to prove to the sales staff that people listened to his program, he urged listeners to seek out a book called, “I Libertine.” The book didn’t exist but soon it was in heavy demand and ended up on The New York Times bestseller list. He eventually wrote the story and published the book.
Jean Shepherd may have influenced many of today’s talk hosts but none have come close to his unique brand of talent that graced the airwaves of the Northeast during those 22 years.