Brett Dennen’s rise from San Francisco singer/songwriter to organic pop star has been slow and steady, but in the past year the 29-year old redheaded guitarist has emerged as perhaps the most visible heir to Jack Johnson’s cool, breezy kingdom. His most recent album, 2008’s Hope for the Hopeless, debuted at 41 on the Billboard charts and helped score Dennen a young, vibrant fanbase outside his jam and roots-rock core. The album’s infectious track “San Francisco” is even featured in regular rotation on Taxi TV on the back of every New York cab. After a busy summer playing festivals, touring with O.A.R. and recording with his childhood hero Natalie Merchant, Dennen will spend most of the fall on the road with his new pals Grace Potter & the Nocturnals. Below, the singer/songwriter discussing his upcoming tour with the Nocturnals, his new jam-friendly backing band and why he spends his free time practicing fire dancing.

Let’s start by talking about your upcoming tour with Grace Potter & the Nocturnals. It seems like a perfect fit: you both grew out of the jamband scene, but have managed to capture a wider, roots-rock audience. How did you first meet?

Well, we met briefly back in, oh gosh, 2004 maybe? I think we were both playing High Sierra. We’ve known a lot of people in each others’ bands and so we’ve known of each other, but we’ve never hung out, really. But then we re-met, I think, actually at this year’s Bonnaroo. We got together and said, “Hey” and how excited we are to be touring with each other and kind of reacquainted ourselves a little bit.

Obviously a tour like this one lends itself to collaborations. Do you foresee a lot of sit-ins on your upcoming trek?

Oh, I can’t wait. We’ve got time to figure it out but I’m trying to figure out what songs she might want to do during my set with me and which songs I could do with her during her set—it could be a lot of fun, we could get a big band sound going up onstage. It could be a lot of fun. I mean, I’ve heard her and I’ve seen her show and just been like “Oh my gosh” and just been overwhelmed by the power of her performance—but I don’t have any of her albums, and I’m not a fan of her music yet. So, for me, it’s gonna be a big opportunity to fall in love with the music. It’s one of those things where I’ve heard her at festivals a lot and I’ve seen her, but I don’t own any of her albums—but I still feel really comfortable with her. So now I have the best chance to really get to know her music and just listen to it every night and see her rock out to it.

You also debuted a new backing band earlier this year that features a number of musicians and Relix readers are likely familiar with. Can you walk us through how you put this band together?

I have Ron Johnson on the bass from Karl Denson’s Tiny Universe, I have Randy Schwartz—who’s been playing with me for a while—on the drums, I have Ryan Jalbert from The Motet playing guitar and I have Jon Solo playing keyboard.

I just sort of met them over time. The keyboard player I just hired him randomly to do one gig with me in New York a TV show—I think it was Good Morning America, he came recommended by somebody and I liked him so much that I asked him to come back and be on tour with me. Ron Johnson, I got him off a really good recommendation of the ALO guys who I used to play with and then there is Ryan Jalbert—I was just auditioning for a guitar player and Ryan came and auditioned and I liked him and asked him to go on tour. It is good. We have been playing together since January. It is a bigger band, a bigger sound and a bigger vibe.

Speaking of this bigger band vibe, how did you approach the recording of Hope for the Hopeless? Did you write this songs in the studio, road test them or work on them in another fashion?

I wrote 40 or 41 songs and, with the help of my manager and people from my label, narrowed the list down to 20. Then I chose about 15 songs from that list myself. When it came time to record, I chose really exceptional musicians to record with. We didn’t even rehearse at all—we just met in the studio, they listened to the demos and made their own chord charts and I played the song live for them. I also played a few tracks by well known musicians that I felt captured the vibe I was going for. For instance, on “San Francisco” I played Joni Mitchell’s Court & Spark album. We’d do a run through as a band and right around the 3rd or 4th take we’d love it.

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