He also got rich producing the TV sitcom “Everybody Loves Raymond”.
Raymond was, in some respects, another gift from CBS. They found a hot comic, Ray Romano, and showcased him on Letterman. When they offered Romano a sitcom, the arranged for Worldwide Pants, Letterman’s company, to produce it.
The show ran nine years (normally, five years worth of episodes is enough fir syndication). So, the profits generated through syndication were substantial—probably in the hundreds of millions of dollars. And Letterman got a share, although his involvement in the project was minimal.
Worldwide Pants has done relatively little in terms of pilot and program development since Romano’s show left the air—not what you’d expect from a production company that is serious about getting films produced or TV shows on the air.
Johnny Carson had a similar deal with NBC; his company was formed to produce the Tonight Show (he finally got a production deal after hosting the show for 20 years). NBC also steered Dick Clark’s blooper show to him, and they produced the hit sitcome Amen, and the film The Big Chill.
Carson was (arguably) a more successful producer than Letterman and he only dabbled in the trade. With Letterman’s retirement, the production company will become largely devoted to licensing clips/re-runs of his talk show.