When singer and rapper Dessa came through town in 2011 and played the Beachland Tavern, she didn't have her full ensemble with her.
"I just wasn't in a position to tour with another female vocalist," she admits via phone from her Minneapolis home. "I think people who did come last time and come this time will see the difference when I perform those same songs with [guest vocalist] Aby Wolf. It just has a bigger dynamic with the two female voices harmonizing."
A true wordsmith in the old-fashioned sense of the word, Dessa has built her band like she's built her audience — slowly but surely. Her music benefits from the foundation of language skills that she developed early in her life. As a result, she comes off as something like an urban Ani DiFranco. Her lyrics about self-empowerment get a good boost from the talented jazz and R&B players in her band.
"I was initially interested in the language artists as a writer," says Dessa, who has an undergraduate degree in philosophy. "I always liked writing, but I didn't have any talent for long form fiction. I was in college and I took a class on creative non-fiction. It's an incredible genre with a dry-sounding name. That genre title is devoid of excitement. I took a class on the personal essay, and I was floored by that. I don't know that you could call yourself a writer if you wrote short, funny essays about real life. To me that was professionally anecdotal. And yet my mind was blown."
She says she suddenly realized she wanted to be an essayist but at the same time she "didn't know how someone would go about doing that professionally." So she did the next best thing and took up spoken word. Through that scene she met the major underground hip-hop players in town, even dating rapper P.O.S. for a short time. Yoni, an MC affiliated with the Minneapolis Doomtree collective, met her at a spoken word event and invited her to audition for a group he was putting together. She was initially skeptical.
"I wasn't sure I would be a good fit for that role," she says. "He said, 'Why don't you come over and just try to rhyme over beats.' I thought he might be creepy, but I texted a friend and they told me he was okay. I went over there and did it. I wouldn't have impressed anyone that first day."
And yet she stuck with it. Before long, Yoni formally asked her to join the collective.
"I was asked at midnight on a Tuesday," she says. "I think it was Tuesday. It was too late to call anyone. I was in their living room and if you can feel like a princess surrounded by cigarette butts and empty beer cans, then that's how I felt. I was so happy. I called my mom. And she was like 'What's a Doomtree?' Her first piece of advice was 'Watch out for cocaine.' I was like, 'These guys can't afford any cocaine.'"
In the hip-hop tradition of putting out unofficial albums, she and her Doomtree pals released a series of EPs dubbed False Hopes.
"That was only five songs long," she says. "It was the first music I recorded and didn't have the pressure of a full-length. I was not as terrified as I would have been if it were 12 songs. I didn't have distribution or anything like that. It took me a long time to pull together a full-length album. I didn't know much about the industry side of it but I knew how to promote shows."
Eventually, she made her full-length debut with 2010's A Badly Broken Code, an autobiographical album of rag-tag hip-hop on which she alternates between spoken word diatribes and heady raps.
"I went on tour after A Badly Broken Code and then came home and started working with a live band," she says. "I like the ability to change the live show from the recorded stuff. These band guys were not hip-hop players. A lot of them were crackerjack technicians so they were really, really good musicians. Every once in a while they would add a couple of beats and change the key, just in the chorus. All of a sudden, the songs sounded more and more different from the record in in interesting ways. It's not like we're trying to be the Roots, but we're doing different stuff. We go on tour and the songs are really different."
Because she so completely rearranged the songs from A Badly Broken Code, she decided to re-record some of them for her follow-up album, 2011's Castor, the Twin.
"People liked the different versions and I captured the rearrangements, which sounded like chamber pop," she says. "They have rap and chamber pop together. There's strings and stand-up bass. There's a classically trained guitarist. It's a more delicate album with lyrics that push things forward."
She's even taken the band into the studio to record her forthcoming album, due out in March, which is when she'll give it a good push with an appearance at the South by Southwest music festival.
"There are moments of total self-doubt and frustration and moments of unfettered conceit where I'm on top of the world and no one can touch me," she says of the ongoing recording process for the new album. "I'm working just past my areas of expertise. I know intellectually when I say that out loud that it's a good thing. That's what you're supposed to do, but it feels scary and frustrating."