When Letterman had Captain Beefheart on in his first year on air, it was actually as an interviewed guest. Don Van Vliet was promoting what woulds become his last album, 1982’s Ice Cream For Crow. Vliet comes out with a bottle of Perrier in a bag and immediately uses the bottle and the bag to mock Letterman’s lack of other guests—probably the whole reason he’s being interviewed at all.
Letterman is amused by a musician on Vliet’s new album listed as Richard “Midnight Hatsize” Snyder, which Beefheart tries, and fails, to explain. It goes about as well when he’s asked about the meaning of Ice Cream For Crow’s title—something about Reagan? They even throw to a clip, which is basically Beefheart and his band freaking out in the desert.
Letterman is polite about all this, flitting through topics such as Vliet’s work as an abstract painter and his pre-fame stint as a manager of a Kinney Shoes store. All of this was apparently not viewed as a disaster; Letterman brought Captain Beefheart back on the following year—though it was mainly to discuss his paintings.