What brought you to Atlanta in the first place? I had made a friend who was from Atlanta. We kind of became a singer-­songwriter duo at Berklee and both decided to withdraw, the plan being I would live with him in Atlanta and start a life and career down there. We had a falling-out, but I still ended up down there. I was far enough along into that lineage that there was nowhere else to go but back home into the world of "I told you so" at my parents' house. At the same time, I had had a real connection with the city, and I knew I wasn't done figuring that place out, so I stayed there.

What made you connect to it? I was connecting with the unbelievable open-­mindedness and friendliness - it sounds like a cliché, but it's a good cliché to have. For the first time in my life, I was playing shows at venues and making friends with people who were there. Where I was from in Connecticut, as a musical springboard, there's nothing. In Atlanta, people would just go out and get a beer and whatever was on was on. They would actively participate in watching shows. If somebody's girlfriend dragged him or her out to go see a show and they liked it, they were hooked. They were like, "See ya next week." I'd never seen anything like it.

What is your earliest memory of the city? Shawn Mullins. I can't think of Atlanta­ without thinking of Shawn Mullins. He was such a huge inspiration for me. The day I landed in Atlanta, the radio was playing his song "Lullaby" on a show called "Locals Only" on [radio station] 99X. Now, you are coming down to Atlanta to play ­music for a living, and you hear this guy with that song, and it's local? You want to pack up and go - leave before your boxes get there. From the very get-go, it was a challenge. Then, once I met him, I learned so much about how to be cool from him.

Like what? People who get famous in Atlanta are held to a certain standard of genuineness by their friends and fans. I don't know anyone in Atlanta who has lost their head if, when they became successful, they stayed in Atlanta. Once you leave Atlanta, everybody assumes you've lost your mind. Everyone assumes you have given up your heart. I could sell millions of records, and as long as I live in Atlanta, there's no dissent. If you go to New York, all the local musicians think you are a traitor. There's a little bit of a Shawshank Redemption-type thing with the local musicians in Atlanta. There is such a support. Even when there are people who are 10 times better than you, you still buddy up with them and find out how they got where they're at. There's better communication among artists there than anywhere else.

Atlanta has a long tradition of attracting celebrities as well - Elton John, Diddy, Whitney Houston, you. Why do you think that is? Because it has no metahipster awareness of itself. It's a very simple approach to living your life. For instance, if you're at Hartsfield-Jackson International Airport, and you're taking the escalator up to the gate … the dog-eat-dog world knows that the left side is for walking up and the right side is for chilling. But in Atlanta, the left side is for chilling out and the right side is for chilling out.

Besides the escalators, where was your favorite place to chill out? It's funny, because I didn't spend a lot of time there when I was there. But knowing who I am now, I would probably hang out in Little Five Points more. The only time I was in Little Five Points was when I was going to see a show at Variety Playhouse or doing my best imitation of a good first date. That was about it. I was also 21 when I first got there, so I never really considered myself a part of the culture. The combination of my age and how much I was into playing music and getting that going, I never really became a part of the recreational culture of Atlanta. Now I seize that in my life, and I would be hanging out in Little Five Points.

Where were you hanging out? What I most remember about Atlanta, which is still very special to me, is the drive I would do at least three times a week, from Duluth to Decatur to go to Eddie's Attic to play a show. I was on the standby list with Eddie; if somebody had car trouble in Chattanooga, Eddie would call me and say, "Wanna play for a half hour? An hour?" There was always this mood of complete excitement and complete vitality, getting into the car and preparing myself to go play. It was a very long drive down Clairmont Road to get to Eddie's Attic - you go straight for four miles past a bunch of lights.