Open Culture collected videos of the four times Hunter S. Thompson appeared on David Letterman, ranging from 1987 to 1997. I saw Thompson speak at live events a few times during this era, and he was usually mumbling and incoherent. He's much sharper and funnier in the videos.
In the clips here, you can see many of those appearances, first, at the top, from 1987, then below it, from 1988. Further up, see Letterman interview Thompson in an '87 episode inexplicably conducted in a Times Square hotel room. The show was "a strange beast," writes Vulture's Ramsey Ess. "For most of the episode it feels unruly, nerve-wracking, and a little dangerous," all adjectives Thompson could have trademarked. Just above, Thompson meets Letterman to discuss his just-published The Rum Diary, the novel he worked on for forty years, "a hard-bitten story," writes Kunzru, "of love, journalism and heavy drinking."
All of Thompson's appearances are unpredictable and slightly unnerving, and become more so in later years. "Thompson would become more dramatic and more twisted," writes Jason Nawara. "Whatever led up to the moment Thompson stepped on stage was probably far more astonishing (or terrifying) than anything caught on camera. Why is his hand bandaged? Why is he so paranoid? What is happening? When have you slept last, Hunter?" If late night television has become safe and boring, full of pandering patter largely devoid of true surprises, perhaps it is because Hunter S. Thompson has passed on. And perhaps, as Nawara seems to suggest, every generation gets the late-night TV it deserves.