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gained power from its rigorous formalism", as his biographer Jason Zinoman puts it, he was "a fascinatingly disgruntled eccentric trapped inside a more traditional talk show." The main competitor of the Late Show was NBC's The Tonight Show, which was hosted by Jay Leno for 22 years, but from June 1, 2009, to January 22, 2010, was hosted by Conan O'Brien.

In 19, the Late Show consistently gained higher ratings than The Tonight Show.

In 2000, he told an interviewer for Esquire that, while growing up, he admired his father's ability to tell jokes and be the life of the party.

Harry Joseph Letterman survived a heart attack at age 36, when David was a young boy.

The Late Show lost nearly half its audience during its competition with Leno, attracting 7.1 million viewers nightly in its 1993–94 season and about 3.8 million per night as of Leno's departure in 2009.

Other memorable moments included Letterman using a bullhorn to interrupt a live interview on The Today Show, announcing that he was the NBC News president and that he was not wearing any pants; walking across the hall to Studio 6B, at the time the news studio for WNBC-TV, and interrupting Al Roker's weather segments during Live at Five; and staging "elevator races", complete with commentary by NBC Sports' Bob Costas.

In one infamous appearance, in 1982, Andy Kaufman (who was already wearing a neck brace) appeared with professional wrestler Jerry Lawler, who slapped and knocked the comedian to the ground (though Lawler and Kaufman's friend Bob Zmuda later revealed that the event was staged).

Recognizing the more formal mood (and wider audience) of his new time slot and studio, Letterman eschewed his trademark blazer with khaki pants and white wrestling shoes wardrobe combination in favor of expensive shoes, tailored suits and light-colored socks. Paul Shaffer and the World's Most Dangerous Band followed Letterman to CBS, but they added a brass section and were rebranded the CBS Orchestra as a short monologue and a small band were mandated by Carson while Letterman occupied the slot.

Additionally, because of intellectual property disagreements, Letterman was unable to import many of his Late Night segments verbatim, but he sidestepped this problem by simply renaming them (the "Top Ten List" became the "Late Show Top Ten", "Viewer Mail" became the "CBS Mailbag", etc.) Time magazine stated that "Letterman's innovation ...