David Letterman: Comedian, late night legend… and shrewd businessman? by Daniel Bukszpan @FortuneMagazine May 19, 2015, 1:26 PM EDT E-mail Tweet Facebook Google Plus Linkedin Share icons Whenever a television show with a few seasons under its belt goes off the air, there are always those who proclaim it “the end of an era,” even if it really isn’t. Well this time, it’s for real. On May 20, talk show host David Letterman will retire from CBS’s “The Late Show,” which he has hosted since 1993. He passes the torch and the time slot to comedian Stephen Colbert, formerly of Comedy Central’s “The Colbert Report,” but while no disrespect is intended to the very funny and intelligent successor, it just won’t be the same. The first episode of “Late Night with David Letterman” aired on NBC in 1982, and he’s been on the air ever since, surpassing Johnny Carson to become the longest-serving late-night talk show host in history. Most of today’s late night talk show hosts acknowledge him as a primary influence, to the extent that “Jimmy Kimmel Live,” which competes directly with Letterman’s time slot, is airing a repeat Wednesday night. “I have too much respect for Dave to do anything that would distract viewers from watching his final show,” Kimmel told The New York Times. Letterman has also shown that he knows his way around the boardroom. At his 2007 peak, Forbes reported that he was being paid $40 million a year, and both he and his film and television production company, Worldwide Pants, have been behind some major successes. But if the soon-to-be former host has plans to immerse himself in the business world, he didn’t say so in a recent interview with Rolling Stone. “What I’ve decided to do — and what I really want to do — is give myself over to my son and my wife,” he told the magazine. “My schedule is no longer a factor, so whatever they want, that’s what we’re going to do.” A spokesperson from Worldwide Pants told Fortune that it will continue as Letterman’s production company, but future developments lay past a horizon too distant for further specifics. In the meantime, here’s a look at a few of the business successes that both Letterman and his production company have been a part of.