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| Paul McCartney, Ringo Starr and David Letterman (Photo: Jay Johnson/Worldwide Pants) |
There was a standing offer of $500 from Dave to anyone who booked a Beatle on the show. In 1989, Morty (Robert "Morty" Morton, the show’s executive producer) booked Ringo Starr and went to Dave to collect his money. Dave told him, "Ringo doesn’t count."
I really wanted to book Paul McCartney — and actually had a connection. My first four years on the show, my girlfriend and I were sharing a two-story duplex apartment on Morton Street with another friend and his girlfriend, Louise Eastman, who was Paul’s niece. I’d also become somewhat close to Paul’s daughters, Stella and Mary — and subsequently became friendly with Paul. But one night at dinner I had also witnessed a woman we were eating with ask Paul for a picture, and he had very gracefully declined, telling her, "Either you are a friend or a fan. You decide, dear, but you can’t be both." I loved Paul, and being a kid from a small town in Vermont, I couldn’t help but be in awe any time I was in his presence. And Paul was every bit as personable and warm as he appears in interviews. Quick with a story or a song (which always made everyone just stop cold — because this was, instantly, the coolest moment of everyone’s life), he was very eager to talk music or anything else.
So, ambivalently, I decided I was going to try to book Paul — but I didn’t want to ask him directly. I wanted to remain "a friend." So instead I struck up a "professional" relationship with his affable publicist, Geoff Baker. And I’ll cut to the chase here — it never happened. But I did get a cool story out of it. While in London, we were staying at a Sheraton in Knightsbridge. I had arranged to meet up with Stella and Mary, and they told me to meet them at the Hyde Park Hotel, which was across the street. So I was waiting in the lobby, and Morty — who, by coincidence, was staying in the same swanky hotel — came in and saw me, and gave me a look like "What the f*ck are you doing in here?"
I said I was meeting a couple of friends and left it at that. We talked for a couple of minutes — and then all a sudden Morty’s face turned sheet-white: "Holy f*ck, look at that …" And out of the elevator came Yoko Ono, Sean Lennon, Ringo Starr, George Harrison, and Paul McCartney with Stella and Mary. Stella and Mary waved to me. I waved back, and then from Paul came the hearty hello: "Dan the Man!" Morty looked at me like I was from Mars. And then I got to introduce Morty to Paul — and we both got to meet Yoko and all the remaining Beatles. And I realize there’s basically no way to write this story without it sounding like a complete brag, but it was definitely one of the coolest moments in my career. And in the end, I may have never booked Paul, but, for that moment, I was perfectly content to be more friend than fan.
Source: http://grantland.com/features/my-letterman-years/