Born in 1921 on the south side of Chicago, Illinois, Shepherd briefly lived in East Chicago, Indiana, and was raised in Hammond, Indiana, where he graduated from Hammond High School in 1939. The movie A Christmas Story is loosely based on his days growing up in Hammond's southeast side neighborhood of Hessville. As a youth he worked briefly as a mail carrier in a steel mill and earned his Amateur radio license (W9QWN) at age 16, sometimes claiming he was even younger. He sporadically attended Indiana University, but never graduated.
Television and films
Early in his career, Shepherd had a television program on WLW-TV in Cincinnati called Rear Bumper. He claimed that he was recommended to replace the resigning Steve Allen on NBC's Tonight Show. Shepherd was reportedly brought to New York City by NBC executives to prepare for the position, but they were contractually bound to first offer it to Jack Paar. The network was certain Paar would hold out for a role in prime time, but he accepted the late-night assignment. However, he did not assume the position permanently until Shepherd and Ernie Kovacs had co-hosted the show.  In late 1960 and early 1961, he did a weekly television show on WOR (channel 9) in New York, but it did not last long. Between 1971 and 1994, Shepherd became a screenwriter of note, writing and producing numerous works for both television and cinema, all based on his originally spoken and written stories. He was the writer and narrator of the show Jean Shepherd's America, produced by Boston Public Television station WGBH for PBS, in which he visited various American locales, and interviewed local people of interest. He used a somewhat similar format for the New Jersey Network TV show Shepherd's Pie. On many of the Public TV shows he wrote, directed and edited entire shows.  He also wrote and narrated many works, the most famous being the 1983 MGM feature film A Christmas Story, which is now considered a holiday classic. Shepherd narrates the film as the adult Ralph Parker, and also has a cameo role playing a man in line at the department store waiting for Santa Claus.  Ten years later, Shepherd and A Christmas Story director Bob Clark returned to the same working-class Cleveland street neighborhood to film a sequel, It Runs in the Family (later known as My Summer Story), released by MGM in 1994 and featuring an almost entirely different cast from the previous film.  PBS aired several television movies based on Shepherd stories, also featuring the Parker family. These included The Phantom of the Open Hearth (1976), which aired as part of the anthology series Visions; The Great American Fourth of July and Other Disasters (1982) and The Star-Crossed Romance of Josephine Cosnowski (1985), both as part of the anthology series American Playhouse; and Ollie Hopnoodle's Haven of Bliss (1988), a co-production with The Disney Channel. All were narrated by Shepherd but otherwise featured different casts.

Q: What was Jean's first TV show?
A: NBC's Tonight Show.

Q: What was his first movie?
A: unknown

Q: Was Jean an actor?
A: he wrote, directed and edited entire shows.
Was he successful at his career?
He also wrote and narrated many works,
He also wrote and narrated many works,