David Letterman Calls Jay Leno ‘Most Insecure Person I’ve Ever Known’

by | December 28, 2012 at 9:56 AM | Oprah's Next Chapter, The Late Show with David Letterman, The Tonight Show

David Letterman with Oprah Winfrey on 'Oprah's Next Chapter' (Photo: OWN)

David Letterman and Jay Leno’s 20-year rivalry is still a juicy topic of conversation.

Naturally, it came up when Dave sat down with his pal Oprah Winfrey for a revealing interview on an upcoming episode of “Oprah’s Next Chapter.”

“Jay and I were friends, we were always friends before all of this happened,” Letterman says, denying the long-running claims that their rivalry began when Leno was named the successor of “The Tonight Show” over Letterman when Johnny Carson retired in 1992. It’s true that the snub stung Dave and stoked the funnyman-feud, but Letterman says there’s more to it than that.

“He has a way … He’s an unusual fellow. I’ve never met anyone quite like Jay,” Letterman tells Winfrey. “And I will say, and I’m happy to say, that I think he’s the funniest guy I have ever known.”

“If you go to see him do his nightclub act, [he's] just the funniest, the smartest, a wonderful observationist, and very appealing as a comic,” the “Late Show” host continues.

But then comes the zinger, capping off the compliment with a cutting remark.

“Therefore, the fact that he is also maybe the most insecure person I have ever known … I could never reconcile that,” Letterman adds.

Oprah’s full interview with David Letterman airs Jan. 6, 2013, at 9/8c on OWN.