WATCH: David Letterman Says Jay Leno Is the "Most Insecure Person"

The funnyman explains his rivalry with the fellow late-night talk show host to Oprah Winfrey

David Letterman and Jay Leno have been longtime rivals, and that's no secret. The late-night hosts have been battling it out on dueling networks for decades, and they have held a seemingly mutual respect and distaste for one another during that time.

During a new interview with Oprah Winfrey on Oprah: The Next Chapter, Letterman opens up about what has kept their rivalry going so strong. Though Letterman criticizes Leno, he also offers him some very kind words.

"The rivalry -- Jay and I were friends. We were always friends before all of this happened," Letterman says. "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. Therefore, the fact that he is also maybe the most insecure person I have ever known, I could never reconcile that."

Letterman isn't the only one to open up about his anti-Leno sentiments in the past week. Jimmy Kimmel had less diplomatic things to say about his late night competition during a conference call discussing his new time slot.

"Jay Leno is not going to be able to stay on television forever, and obviously Jimmy Fallon is the heir apparent, and he’s doing a great job. So it makes sense people would talk like this," he said. "That said, you can never count Jay out. He seems to pop up just when you think he’s dead -- he comes alive and he’s got a hatchet."

The Leno hatred came to a forefront when he returned to his Tonight Show gig after he decided to take a stab at primetime in 2010. As a result, his replacement, Conan O'Brien, was pushed out of NBC -- but he quickly found a new home at TBS. Leno's reputation has never quite recovered, though the Tonight Show ratings have.

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