“We were always friends before all of this happened. He has a way… he’s an unusual fellow. I’ve never met anyone quite like Jay. And I will say — and I’m happy to say — that I think he is the funniest guy I’ve ever known. Just flat out, if you go to see him do his nightclub act, just the funniest, the smartest, a wonderful observationist and very appealing as a comic.”
He continued, “Therefore, the fact that he is also maybe the most insecure person I have ever known… I could never reconcile that.”
Watch the full interview with Letterman on “Oprah’s Next Chapter” Sunday, Jan. 6, on OWN.