David Letterman calls Jay Leno completely insecure

For a guy who makes his living making people laugh, Jay Leno has been in some pretty high-profile beefs. Odds are pretty good that he didn’t spend this past Christmas Eve doing eggnog shooters with Conan O’Brien, who was briefly handed the reins to the The Tonight Show until Leno decided he wanted them back.

This Sunday, David Letterman weighs in on the man with the most famous chin in showbusiness. Leno and Letterman had a well-documented falling out when Johnny Carson announced he was retiring from NBC’s long-running The Tonight Show in the early ’90s.

Both comics were in the running for the job, with Letterman considered the favourite because his highly touted Late Night With David Letterman aired on NBC. Leno ultimately landed the gig, leading to a souring of the relationship. 

In an interview with Oprah Winfrey scheduled to run January 6 on Oprah’s Next Chapter, Letterman opens up on Leno, describing him as “the funniest guy I’ve ever known....a wonderful observationist and very appealing as a comic.”

He is however, less than complimentary about the off-stage Leno that America rarely gets to see. 

“He is also maybe the most insecure person I have ever known,” Letterman tells Winfrey. “I could never reconcile that.”

And if you think all that sounds good, just imagine what Winfrey will get out of O’Brien when she finally gets him on the couch for a future Oprah’s Next Chapter.

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