The singer's early days in small clubs were like "getting paid to hang out with my friends. It was all about fellowship and community."

You immortalized Bethesda’s old Twist & Shout club in a song. But what’s the first one you think of when you remember Washington clubs?

Oh, gosh—of course there’s Food for Thought. It was this fabulous vegetarian restaurant in Dupont Circle that was known for its chili. Every kind of person of any color, any stripe, any orientation would go there, and it was pass the hat for the music.

When I was in my late twenties, my friend Jeff Deitchman had a longstanding night there, and my friend Reuben Musgrave and I went down to see him. Then Reuben got a gig there and let me sing a song on his set, and he introduced me to Bobby Ferrando, the owner. [Ferrando’s son, Dante, owns the Black Cat.] It was all word of mouth—friends helping friends.

So I got this gig on Friday nights from 6 until midnight. I’d play in half-hour sets and pass the hat—actually, it was a basket. I’d recognize people, and I wouldn’t pass them the basket because I didn’t want them to feel like they had to give again.

I lived in a group house in DC. My rent was probably $400, and I used to make the rent in an evening there. Well, maybe two evenings. People were extraordinarily generous. They really listened, and they made you feel welcome.

Food for Thought was a real important place for me. It helped me pay my rent and justify what I was doing, and I made a lot of friends.

What came before Food for Thought?

My first open-mike night was at the Red Fox Inn in Bethesda. I took off a year between high school and college, and I worked the cash register at Brentano’s in Chevy Chase and as a waitress at the Foundry in Georgetown. I wasn’t old enough to be a cocktail waitress, so I worked the oyster bar and cut my hands up. Anyway, I became best friends with a girl who also worked at Brentano’s, and she dragged me to the Red Fox Inn.

But I only played there once because then I discovered Nanny O’Briens in Cleveland Park. In those days, it was called Gallagher’s Pub. I think I made more friends there than anywhere else, and Sunday nights became a real gathering place. You’d listen to your friends and wait your turn.

In the beginning I was so nervous, I couldn’t even say anything—I’d just play. And then after a while I sort of timidly asked the host if I could audition for a job. He said, “Well, the owner’s right there.” And Jenny Gallagher said, “All right, I’ll hire you.”

I played Tuesday and Thursday nights in the summer and got $40 per night, and it was the greatest gig I ever had. I got asked to host the open-mike night eventually, and that was so much fun.

What made it so great?

You were background music, but you’d throw in an original here and there and nobody would notice, went the joke—and they didn’t. So you’d be working on being a better guitar player or trying out something you’d just learned.

I had a day job being an administrative assistant at a foundation in Dupont Circle, and I had this great job on the side—hosting an open mike and getting paid to hang out with all of my friends. It was like being the camp counselor. It was all about fellowship and community. It sounds corny, but it really was the place where everybody knew your name.

It’s something I miss—something that is so precious. When you play festivals, that’s a version of what I’m talking about—you get to visit with old friends. But usually when you’re out on the road, you’re traveling at night in your own pod. You become really close with the people you’re traveling with, but you don’t really meet anyone new. There’s a reason people get lonely and homesick on the road.