Shepherd began his broadcast radio career on WSAI-AM in Cincinnati, Ohio in 1948. From 1951 to 1953 he had a late-night broadcast on KYW-AM in Philadelphia, Pennsylvania, after which he returned to Cincinnati for a show on WLW. Shepherd settled in at WOR radio New York City, New York on an overnight slot in 1956, where he delighted his fans[3] by telling stories, reading poetry (especially the works of Robert W. Service), and organizing comedic listener stunts. He broadcast until he left WOR in 1977.
In addition to his stories, his shows also contained, among other things, humorous anecdotes and general commentaries about the human condition, observations about life in New York, accounts of vacations in Maine and travels throughout the world. Among the most striking of his programs was his account of his participation in the March on Washington in August 1963, during which Dr. Martin Luther King gave his "I Have a Dream" speech, and the program that aired on November 25, 1963—the day of President Kennedy's burial. However, his most scintillating programs remain his oftimes prophetic, bitingly humorous commentaries about ordinary life in America.
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