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Sitting down with Rolling Stone for a rare interview, David Letterman opened up on his two-step process of alienating and courting some of his most famous guest-emies—towering pop culture figures like Madonna, Oprah, and Richard Simmons—as well as his own plans for retirement. ("I would like to go beyond [my contracted] 2010, not much beyond," he told them.) He was also asked to weigh in on the curious scheduling shift going on at his old network NBC, where top ratings-getter Jay Leno is being forcibly vacated to make room for new The Tonight Show host Conan O'Brien, and his Late Night successor, Jimmy Fallon. No one is more confused about the changes than Letterman:

"Unless I'm misunderstanding something, I don't know why, after the job Jay has done for them, why they would relinquish that," Letterman said, adding, "I have to believe he was not happy about it."

Letterman speculated whether "that's actually what's going to happen," while acknowledging NBC might be too far down the road to retreat. [...] Letterman, who called O'Brien "a very funny guy," was asked about facing him as the new "Tonight" host. A cautious Letterman said he couldn't predict the outcome. "It will be weird to see Conan at 11:30, don't you think? Which is not to say he can't succeed, but, no, I don't know what the competition will be like. I hope we're able to do OK."

The late night landscape is hardly recognizable from the one Letterman originally landed his comedy spaceship upon back in the early '80s, lowering its pod doors to release fantastical alien life forms like Larry "Bud" Melman upon America's unwitting insomniacs. Today's audiences have since grown utterly inured to the sight of Conan's masturbating bears and copulating manatees. Pitting these veterans against one another might therefore inspire a competitive Letterman to reach even deeper into his bag of absurdist-stunt-comedy tricks—perhaps with a heavily hyped round of "Will the Former V.P. Candidate In A Bikini Float?" Time will tell.