The Top 10 Moments from Oprah Winfrey’s Interview with David Letterman

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The Top 10 Moments from Oprah Winfrey’s Interview with David Letterman
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(Oprah Winfrey)

It's Top 10 List time!

But this time, "Late Show" host David Letterman isn't making the list. Instead, the late night veteran is the category as we take a look back at his recent sit-down with Oprah Winfrey, where he definitely did some squirming. Check out the Top 10 moments from Dave's "Next Chapter" interview with Oprah.

Number 10. Sex scandals aren't fun. On the 2009sex scandal that rocked his career and his marriage, Letterman said, "I hurt a lot of people. I have nobody to blame but myself. I'm not looking to blame anybody. I'm looking to find out why I behaved the way I behaved."

Number 9. A sex scandal may mean you'll end up sleeping on the couch. On "fixing" his marriage after the scandal blew up: "I'm still trying to fix it," he said, adding that he slept in a "variety of places" after telling his wife Regina Lasko about it. But he also revealed that his relationship with his wife has never been better.

Number 8. Retirement will be someone else's call. The 65-year old comic told Oprah that he and CBS president Les Moonves have an agreement: Moonves will call him when he wants him to step down. "When it's time for me to go, somebody else tell me," Letterman said. " Because I don't know when it's time to go."

Number 7. Depression is no joke. "You get on an elevator and the bottom drops out," Letterman said of his longtime struggle with depression. "You can't stand looking at the sunlight, you can't wait to get back in bed at night, you're shaking, you're shivering." Letterman said he had to "push through it" to work every day, calling his bout with depression "a sink hole."

Number 6. Dave is regular. After citing the fact that he has "a very low threshold of embarrassment" and inviting Oprah to join him and his psychiatrist to figure out why he has no problem embarrassing other people, Oprah asked Dave: "Do you see a psychiatrist regularly?"

"Is once a week regular?" he quipped.

Number 5. He has a heart. Oh his heart surgery 11 years ago, Letterman joked that he "loved everything about it." But then he revealed: "I was a hypochondriac, a hall of fame hypochondriac. So you go through heart surgery, that takes the edge off of hypochondria, necause now you really got something." He also added that everything good in his life came subsequent to his heart surgery, including the birth of his son Harry, "a therapeutic dose of an SSRI," and his wife.

Number 4. The joke was on him. Of Joaquin Phoenix's bizarre 2009 "Late Show" appearance --which was later revealed to be a hoax-- Letterman admitted he didn't know what to make of it. "I knew there was a joke, but I was not in on it," he said.

Number 3. It's not cool to make fun of kids. Letterman said he felt bad for almost making teen pop star Justin Bieber cry during an interview ("You forget they're 16," he said), and revealed the real reason he made a public apology to Sarah Palin's daughter, Willow, after an off-color joke about the 14-year old. "Sarah Palin was someone I wanted to continue to be able to make fun of," he said. "And I felt like if I don't apologize, if I don't sincerely express my regret, I will not be able to go forward making fun of her." He added that he also "felt bad for the 14 year old."

Number 2. His rivalry with Jay Leno isn't what people think. "I've never met anyone quite like Jay," Letterman said. "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."

And the number one moment from Dave's "Oprah's Next Chapter" interview: Oprah's explanation of her longtime "feud" with Letterman.

Oprah recounted an early "Late Show" appearance in which she humiliated by drunken audience members amid Letterman's baiting. "It felt so uncomfortable to me… I didn't want to have that experience again," she explained of her 16-year boycott of Letterman's show. While Dave said he didn't remember the episode, he apologized profusely and said,"I bet if I had the courage to look at that videotape it would sicken me."

"Oprah's Next Chapter" airs on Sundays at 9/8c on OWN.

More From This Contributor:

5 Surprising Oprah Winfrey Acting Roles

Jamie Foxx Talks Marriage With Oprah

Kerry Washington Makes Oprah Cry on 'Next Chapter'

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