The show starred David Letterman.
Like other talk shows, the show featured at least two or three guests each night, usually including a comedian or musical guest. Letterman's show quickly established a reputation for being dangerous and unpredictable. A number of celebrities had even stated that they were afraid of appearing on the show. This reputation was born out of moments like Letterman's verbal sparring matches with Cher, Madonna (described by comedian Robin Williams as a "battle of wits with an unarmed woman"), and Shirley MacLaine. The show often featured quirky regular features, such as "Stupid Pet Tricks" and a facetious letter-answering segment on Fridays. Other memorable moments include Letterman using a bullhorn to interrupt the "Today Show" TV program (which was conducting a live interview at the time) to announce that he was not wearing any pants; interrupting the local news by walking into their studio; and the outrageous appearances by comedian Andy Kaufman. In one highly publicized appearance, Kaufman was slapped and knocked to the ground by professional wrestler Jerry Lawler. This performance was staged but appeared quite real. Another frequent guest was the cantankerous comic book creator Harvey Pekar, writer of American Splendor who got into frequent arguments with Letterman.
Letterman frequently used crew members in his comedy bits, so viewers got to know stage hands and writers as well as they did the host. Common contributors included bandleader Paul Shaffer, Chris Elliott, Calvert DeForest as Larry Bud Melman, announcer Bill Wendell, writer Adam Resnick, scenic designer Kathleen Ankers, stage manager Biff Henderson, producer Robert Morton, director Hal Gurnee, associate director Peter Fatovich, stage hand Al Maher, camera operator Baily Stortz and Jude Brennan.
In 1994, Letterman left NBC for a better deal with CBS, where he started "The Late Show with David Letterman". NBC had angered Letterman by breaking their promise from years earlier to give him the "Tonight Show" once Johnny Carson had retired. By the time Carson retired, the NBC executives had already given the show to Jay Leno. The "Late Night" time slot was then taken over by the show Late Night with Conan O'Brien.