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According to Jason Zinoman, who chronicled David Letterman's life and career in his book "Letterman, The Last Giant of Late Night," the media star gravitated towards comedy as a child growing up in Indiana, listening to radio instead of TV, where he regularly heard comics like Jack Benny and sketch duo Bob and Ray. 

During his post-secondary days in the rebellious 1960s, Letterman used those comedic influences to demonstrate his penchant for insubordination when he joined local college radio station WBST in Muncie, Indiana. Frequently, he'd abandon the station's classical music format, opting to spin pop records and deliver fake news on-air. "It was like hiring a fox to guard the chicken coop," said one colleague about Letterman, who was fired twice. 

After graduation, Letterman landed a weekend weatherman spot on WLW-TV, where he would crack up viewers with lines like comparing hailstones to canned ham. But when the call went out for a full-time weatherman, Letterman was passed over and left his job. By this time, he was married to his first wife, Michelle Cook, and his decision to go into showbiz full-time proved to be a strain on their marriage after they moved to Los Angeles. The instability of life as an emerging stand-up comedian and Letterman's own insecurities not only resulted in the two divorcing in 1977, they also became the first of many black marks that would long taint his ego and personality.

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