Watch Letterman and Oprah Have a Long Talk

David Letterman has always been intensely shy - or at least, shy for a public figure - avoiding any and all interviews, publicity, and discussion of his personal life. He’s started to open up a little bit as he’s nearing retirement, beginning with an appearance on Alec Baldwin’s podcast last year and now, in a long interview on Oprah Winfrey’s TV show Oprah’s Next Chapter, which aired yesterday. Here’s a clip of Letterman discussing his retirement, explaining that he has a deal worked out with CBS President Les Moonves where Moonves decides when he retires, no questions asked. Hit the jump for the rest of Letterman and Oprah’s conversation, which touches, in detail, on pretty much everything Letterman-related you’d want to know about, including his rivalry with Leno, losing the The Tonight Show gig, his feud with Oprah, the time he thought he made Justin Bieber cry, the sex scandal, and other personal life stuff.

Letterman talks about his rivalry with Jay Leno.

Letterman and Oprah settle their feud.

Letterman explains about how he lost the Tonight Show job.

Letterman tells Oprah about apologizing to Justin Bieber after he thought he made him cry.

Letterman talks about how he hates being embarrassed.

Letterman divulges about his struggle with depression.

Letterman talks about that sex scandal thing.

Letterman shares how he saved his marriage.

Letterman tells his heart surgery experience.

Watch Letterman and Oprah Have a Long Talk