Singer Dawn Oberg
Dawn Oberg: She's really high maintenance—but totally worth it.

Bay Area musician Dawn Oberg is a true revelation. She has two excellent albums under her belt and a popular regular gig at San Francisco’s Rite Spot Cafe. Her latest record, Rye, is a triumphant collection of razor-sharp piano pop that’s brilliant and bracing. Her substantial wit, musical sophistication, and jazzy phrasing remind me of a more sardonic Carole King—a painfully honest, verbally dexterous, and fearless songwriter with a whopping gift for pop song construction. Chew on these sample lyrics from the song "Gentleman and a Scholar":

"He’s a gentleman and a scholar, unfailingly kind and polite
Not a pompous know-it-aller
Though I must say he’s usually right
He taught me how to drive a stick
Without once acting like a prick
In general he just doesn’t tick me off
And that’s not a thing at which I tend to scoff."

And at age 46, Oberg's going out on tour for the first time ever! And she insists she won’t be sleeping on any floors. Oberg plays the Atlantis Lounge at Mississippi Pizza Wednesday night, so please, get out there and give her some proper encouragement.

Culturephile: Wait. You’ve never toured before?
Dawn Oberg: I’ve never toured before. This is my first tour ever, just me, going out on the road. I’m excited and nervous about it and I’m writing this blog called “That’s How I Roll: What Happens When a 46-year-old High Maintenance Hussy Goes on Tour For the First Time.” I’m starting off the blog with the collective wisdom of my friends who’ve been on tour; they’ve all been very generous with their advice. It gives me things to think about.

In a way, it’s going to be like one big long gig. It’s like going to a gig in Oakland, but it takes a lot longer to drive there—and you’re doing it day after day. Just me, my car, and my keyboard. All me.

I hope in the future to take a band, but I’m too old to tour like the kids do it. Fortunately, Priceline is a high-maintenance person’s best friend, in terms of like hotels and stuff. You can get a pretty nice hotel room for not that much money. It’s not sustainable of course, unless I start making a lot of money. I’ll be lucky if I break even, I know that. I’m prepared to take a loss. 

This sounds like a real vision quest! A very personal journey of self-discovery. Is that the sort of thing you’ll be writing about in your blog?
I don’t know yet. I’m just gonna see how it goes. I'm probably not going to have a lot of time to type since I’ll be driving so much. I hope to get some lyric writing done. I’m just going to see what comes up.

Are you taking your own food? Do you have bothersome food allergies that need to be addressed?
I try to be gluten-free most of the time, but I’m not strict about it. I like a good salad. I have an espresso maker right by my bed—I’m kind of high maintenance that way, and it’s going to be a challenge. But I’m sure things have improved a lot [for the touring musician] in the last 20 years.

What's your biggest anxiety about the trip?
Getting to a gig and finding out it’s been cancelled. Or getting a flat tire.

Do you have Triple A?
No, I don’t. I suppose I should get it.Dawn Oberg       Mississippi Pizza           April 3 @ 9 pm

So you’re coming in cold to these gigs. You’ve not been here before. Do you have a strategy to win 'em over?
I’m concerned about that, but I've already had to do it so much anyway. I lived in Nashville for 15 years, and that prepared me for every manner of humiliation that you can possibly imagine. It’s like Willie Nelson says, “Nashville is the roughest.” I ain’t no Willie, but I’m ready enough.

[The song "Panties"] is a song about being a completely ignored musician in Nashville. I really wasn’t trying to get famous in Nashville. If music row would have liked my songs I would have wondered what I was doing wrong.

You've been doing music for quite a while, though. 
I was classically trained as a kid. I went to Berklee College of Music. I was a kid in the 70s so 70s pop stuff is an influence. I had a Barry Manilow songbook and Billy Joel sheet music. Yeah, I was a dork. I listened to Air Supply.

Music was always there, but I didn’t get serious about songwriting till I was in my 30s. Before that I just wrote these obnoxious country drinking songs with my old band. Our album was called You Drank My Backwash

What band was that?
Honky Tonk Happy Hour. You’ve never heard of them, I promise. Massively immature songs fronted by me. But right after that I was doing jazz, trying to find my pop voice, a better voice that said more serious, beautiful things. But it took a little bit. It was a gradual process.

Did you act more country when you sang country?
Not really. I drank a lot, though. But the stuff I do now I can’t have a drop or I’ll mess up. It’s too difficult.

What music inspired you to get serious about doing your own thing?
I was learning standards from the Great American Songbook, Cole Porter, Sammy Cahn, Irving Berlin, Harold Arlen, Jimmy Van Heusen. Those guys are on a whole other level than stuff you hear now. Lyrically and harmonically. It’s a lot more involved and complicated. R&B was a big influence too, so I started putting gospel chords on everything. Gospel chords are different than anything in pop or jazz.

What kind of piano do you bring on tour?
It’s a Kurzweil keyboard they don’t make them anymore. I needed something portable, pianos are just too heavy. I know that Ben Folds, even before he was famous, would take a grand piano on tour with him and have people help him with it, but to me, that just sounds like the height of masochism. But he did it, and he rocked it.

How long is the tour?
A month. It's Oregon, Seattle, Utah, Minnesota, Chicago, Cambridge, New York, Austin, and Los Angeles.

And you’re driving the whole way? By yourself? Good lord! If you get tired, please pull over and sleep. It’s worrisome to think about you driving around all by yourself. You have to stick to a tour schedule, and the next thing you know, you drive off the road never to be heard from again. So don’t push it too hard. Sleep when you need to.
I appreciate the concern. Thank you.

For more on Portland arts and culture, sign up for our weekly On The Town newsletter, subscribe to our RSS feed, and follow us on Twitter @aarondavidscott. Visit our Arts & Entertainment Calendar for our editors’ event picks.