When did you discover jazz?
By hearing people like Nat King Cole, Peggy Lee and Andy Williams. My folks liked to drive across the country to visit the grandparents. We'd be out in the desert, all the windows down, eating Velveeta cheese, with these guys on the radio. It wasn't full-on jazz, but a lot of it was really swinging.
What was your big breakthrough?
Dropping out of graduate school. I'd been studying philosophy at the University of Chicago. I hadn't been doing well because I was sitting in with jazz musicians at night – it's hard to read Heidegger, but it's especially hard if you're half asleep. So I said to myself, "I've got nothing to lose – I'm living in a $100-a-month room, so I should really go after music."
Each of your nine albums has been nominated for a Grammy. Are awards important?
Grammy nominations are certainly pleasant, but you can forget about them and lead a perfectly happy life – provided you have the approval of the musicians you work with.
Why do some people find jazz difficult to get into?
Because the demands of the intellect are a part of the jazz idiom: the ability to pay attention, and work out puzzles as you're hearing them. But it's a shame that people think jazz is relentlessly challenging, or that it's trying to be a club they can't join. I certainly don't think of jazz that way; at my shows, I really do try to play both to those who get the inside jokes, and those who wish they could.
Do you suffer for your art?
If you start to dwell on your pain, the amount of pain will increase. I consider myself very fortunate. I have a beautiful wife who supports my work, and is raising our daughter when I'm out on the road. This year, I'll be away for 200 nights; my wife is providing an incredible example to our daughter of how strong a woman can be.
What one song would work as the soundtrack to your life?
Carole King's So Far Away. We recorded it for my latest album, 1619 Broadway; that recording really touched on my feelings of loss, of missing my family and wanting to be home.
Which other artists do you most admire?
[Saxophonist and composer] Wayne Shorter represents to me not only the spearpoint-tip of the cutting edge of acoustic music in jazz, but the stories he tells through his compositions point quite profoundly to fundamental experiences of the psyche, heart and intellect. As [Rainer Maria] Rilke would say, he's "living the questions". Those questions are what art is made of.