I have watched it 3 times. And it gets better and better. Like Airplane. There’s always some new amazingness that reveals itself with each viewing.

Awkward but not super intense, both of them refusing to give, confrontational but not ugly – he asked what he wanted to ask, she replied the way she wanted to reply, and it was compelling the whole way through.

Wintour is not the most articulate person, and she can seem humourless, and she is indeed a judgy bitch, but better this than someone who’s begging you to love her. She knows what you think of her, she knows what people have been saying about her for years, and for the most part, Anna Wintour doesn’t give a sh-t.


She’s capable of smiling with her teeth.

It looks like it hurts her to do so but she can do it.

Anyway, if you haven’t already, the video is below. There are 2 segments. Watch both. My favourite part right now, because it always changes, is when Letterman presses her on the issue if it’s possible to be fashionable at a reduced income and you can actually see her sneer about having to go to Macy’s in Queens (Queens!) for a charity event next month.

Love her so much.

Photos from Wenn.com