David Letterman Finally Gets His Oprah Moment

After six years of pining from afar, David Letterman finally sat down with Oprah Winfrey, as the 22nd season of The Oprah Winfrey Show kicked off in New York City yesterday afternoon. It started out exactly as affectionately as you might think: Dave read a Top Ten list of reasons he loves Oprah (No. 8: “She helped me start my wildly popular ‘D’ magazine�), Oprah giggled a bit too hysterically at it, and once the silliness ended, they got all real and talked about Dave’s heart surgery, his son, and his love of his Montana ranch. We’d have bet anything Oprah would have had Dave in tears at some point, and we certainly would have bet she’d have asked him about 9/11, since that’s pretty much why she’s in town this week, but Dave remained, as Oprah put it, “interview-phobic� to the end.

We’ve always thought that Letterman was a terrific interviewer, at least compared to, say, Jay Leno, but has he mastered the art to the point he can control a chat while he’s being interviewed, by Oprah no less? More likely, Oprah wanted to stay within her long-suffering guest’s comfort zone. Plus, Dave didn’t get the whole hour, because you can’t do a show from New York without a duet between Lisa Marie Presley and a recording of her father, we guess.

At least Dave’s famed Oprah Log — a journal he kept on his show to document his long-running quest for an Oprah invite; representative entry: “Oprah did not call� — made one last appearance. And Winfrey did ask Letterman one question we’ve been wondering about all these years. If he wanted to be on Oprah’s show so badly, how come he didn’t just call up and volunteer? “I wanted to be asked, Oprah,� Dave answered. He was laughing, but it was clear he wasn’t joking. —Joe DeLessio