Here’s what I see. Some of it might be projection, but I don’t think that it is.
Madonna is sincerely attracted to David Letterman, and I think that attraction has a lot to do with how they, in their respective ways, are innocents. I think there’s something really sweet about it. She’s also clearly angry with him because he’s made jokes at her expense and it seems that the jokes have hurt her feelings. She’s angry, but it doesn’t mean that she doesn’t still like him. She doesn’t seem to have a fully integrated opinion, except that she likes him.
I love everything she says with her eyes. In a lot of ways, the whole interview seems like one big flirt. It’s not acrimonious. There’s no way that he could be pulling on that list underneath her that way if it were acrimonious.
Dave, for his part, seems to get some of this, sort of, and like it, sort of, but to mainly have no idea what to do with her. He doesn’t seem able to register that she might find him romantically interesting–which I think she really does.
She’s so feline and poised. There’s a million things I could say about that persona, and about this interaction. Maybe literally a million. But it seems to me that the interview isn’t purely show business–or isn’t even mainly show business. It seems to me, that at bottom Madonna feels very personally engaged with Dave, very safe with him, and very affectionate. It carries over in their other interviews, too.
She seems over the years to have really watched him and thought about him.
The 2009 interview, where they end up in the pizza place, is kind of heartbreaking to me. She seems to still feel open with him, but she seems to think it’s a shame that he has evolved in some of the ways he has. She looks at him as though he’s lost some of what was initially so great, and as though she view his growing bitterness as a choice.
But that’s what I like. I like that [in 1994] she’s being so outrageous but that it seems to me to be coming from this totally pure interest to be in relationship with him (in the broader sense, not simply that she wants to date him–though not *not* that, either). I just love it. It’s like those videos where a cat and a duck are totally taken with each other–only it’s between these two moguls who, in their ways, are such masters of personality and moment. Watching it makes me feel really good.