Letterman Celebrates 30 Years in Late-Night TV As David Letterman and Howard Stern can attest, a 30-year anniversary celebration is a ripe opportunity to cringe at geeky haircuts. Letterman marked three decades in late-night TV on Wednesday on CBS by bringing Stern, one of his favorite guests, onto his "Late Show." They congratulated each other on age improving their looks. Then Letterman proved it, displaying a picture of them from when Stern first appeared on the then-NBC show in May 1984. Letterman had a bushy head of hair. Stern had a mustache. In this photo provided by CBS, Sirius radio personality Howard Stern throws money to the audience on the set of the "Late Show with David Letterman," Wednesday, Feb. 1, 2012 in New York. The money was set aside by Letterman to entice actor Brad Pitt to appear on the show. Letterman said about Stern's old picture: "It looks like a guy who was on to talk about a career of writing bad checks." Stern advised burning the picture but recalled how grateful he had been for the invite. "Back then, the fact that you asked me to be on a national television show was mind-blowing to me," he said. Letterman also brought some of his long-time employees onstage to present the "Top Ten Things Staffers Would Like to Say to Dave on his 30th Anniversary in Late Night." One of the cleanest, and most succinct, entries came from veteran executive producer Rob Burnett: "You're incompetent." The "Late Show with David Letterman" airs weeknights at 11:35 p.m. Eastern time.