One of Dar Williams most popular songs, this one explores competition, fear, jealousy and envy. In our 2010 interview with Dar Williams, the singer/songwriter explained: "They say the difference between envy and jealousy is envy is when you wish you had something somebody else had, and jealousy is when you wish they didn't have it. And so I've certainly felt envy for certain things. But I'm lucky, because I've been shown a lot of gracious behavior. And it's kind of a social contract that I'm not going to be a total pissant in return. So your life is better if you allow yourself to feel envious, but you don't allow yourself to feel out and out competitive, because that's almost like saying, 'I wish that person didn't –' It's more like, 'I wish I were – ' You know, somebody said, 'Wow, Ani DiFranco got to meet Bruce Springsteen. I wish I could meet Bruce Springsteen.' And I don't really have a great need to meet Bruce Springsteen, but I love the way that she said, 'I would do that really well, if I could do that.' But she was happy for Ani, she was happy for that moment.
And I think that's the way this community of women works. If you're doing your job right, you're not going to be like anybody else, and you're going to get the opportunities that other people don't get and vice versa. And you'll drive yourself crazy comparing too much. But 'As Cool As I Am' is basically saying I'm not going to be in a position of allowing myself to feel competitive with women because that is a black hole. And it's being in a relationship with a person who encourages you to do things competitively, that this person is really rejecting. Life is hard enough: you are going to feel envious, you are going to say, 'Oh, why not me, what's wrong with me?' So if you're in a relationship with some schmuck who's encouraging that avenue of thinking when there's so many opportunities to go down that avenue without that schmuck, ya gotta cut him loose. That's schmuck behavior."