Shepherd had two children, a son Randall and a daughter Adrian, by his first wife, Joan Warner, but according to them, had virtually no contact with them after he divorced their mother. In fact, Jean Shepherd's last will and testament falsely stated that he had no children.
Shepherd helped John Cassavetes raise money to film Shadows (1959) by having John on his show as one of his rare guests in February 1957. Shep was so committed to the project that he loaned his assistant Ellen Paulos to Cassavetes to help with the film. The thankful Cassavetes expressed his thanks in the opening credits of the movie. A title reads: "Presented by Jean Shepherd's Night People." (The Night People were members of what the New York Times in the late 1950s called the "cult" of Shepherd listeners.) Shepherd also appears in a crowd sequence in the film, smoking a cigarette.
Subject of the song "Jean Shepherd" on the album "There Goes the Neighborhood" by Jim Testa.
The theme song used on his long-running radio show was "The Bahn Frei Polka" by Edouard Strauss. The particular version he used was recorded by Arthur Fiedler and the Boston Pops.
Twenty-five of his stories were published in "Playboy Magazine" from June 1964 through August 1981. After the publication in May 1973 of his short-story "Lost At C", only one more Shepherd story appeared in "Playboy", "A Fistful of Fig Newtons" in August 1981. Shepherd won four "Playboy" Writing Awards for Humor/Satire, for "Leopold Doppler and the Orpheum Gravy Boat Riot" (October 1965), "The Return of the Smiling Wimpy Doll" (December 1967), and "Wanda Hickey's Night of Golden Memories" (June 1969), all cited as First Place winners in their respective years (1965, '67 and '69), while "Ollie Hopnoodle's Haven of Bliss" (July 1968) won a Second Place award in 1968.
Was a licensed amateur (ham) radio operator with the call sign K2ORS. Following his death, another ham took over Jean's call sign to honour his memory.
Was named "Jazz Personality of the Year" for 1959 by "Metronome" Magazine.