ALINA SIMONE Her enthusiastic cover of “Y.M.C.A.” is pretty excellent.

ALINA SIMONE probably won't be releasing an album of comedy songs anytime soon. "I hate funny songs! I really hate funny songs," the Brooklyn-based musician says—despite having many friends who are either comedians (Eugene Mirman, who like Simone is a child of Russian immigrants, is an old childhood friend) or successful comic songwriters. "I still cannot bring myself to like a funny song," Simone says. "It's black licorice—it just doesn't work for me. It's a candy that tastes bad."

It's a surprise, then, that Simone's first book, You Must Go and Win, is so funny. The collection of humorous essays recounts her trials as a struggling young artist and musician, and was written as something of a release valve after the long promotion period for her 2008 album, Everyone Is Crying Out to Me, Beware. That album was a collection of Russian-language covers of songs by Siberian cult folk-punker Yanka Dyagileva, who drowned mysteriously in 1991. Yanka's recordings were circulated via bootleg tapes—a method known as magnitizdat, the audiotape equivalent of samizdat—and Simone was given a cassette of Yanka's music by some buskers while she was walking around the Russian neighborhood of Brooklyn's Brighton Beach.

"It really surprised me, how interested people were," Simone says of the reception to Everyone Is Crying. "I think that it was because of the human interest story behind her. It was because Yanka's life story and maybe my life story sort of fit together in a nice package for the journalists: the fact that I left the Soviet Union, my parents were political refugees, and so there's a tie-in there in terms of her being kind of an anarchist."

But sharing Yanka's life and work took its toll on Simone. "That was really, really, harrowingly dark material—even for me!" she says. "She killed herself when she was 24, she had a very tragic life, and her songs are very heavy. I spent a year and a half not just singing these songs, but talking about her life again and again and again in interviews, and explaining who she was. I did feel like I needed a completely different creative outlet."

Still, it was something of a shock when Simone, who'd never contemplated being a writer, was approached to put a book together. "My editor discovered me on Pandora," she says. "He had it tuned to the PJ Harvey channel and my music came up, and as a result I ended up getting this bizarre email out of the blue, asking if I'd be interested in writing a book. I really thought potentially he had a major screw loose!" she laughs.

While she'll be reading passages from You Must Go and Win at her upcoming (free!) Portland solo show, she'll also be playing songs from her fantastic new record, Make Your Own Danger, which runs the gamut from fiery rock (the title track, and "Beautiful Machine") to haunting, wintry folk ("In the House of Baba Yaga"). "I was living a really peripatetic life when I recorded it," Simone says. "I was traveling and touring a lot, and I really missed New York, so there are definitely some songs on there that are about the city. My philosophy for this record was really the opposite of the Yanka record, which I wanted to all be of a piece. I just decided I wanted 11 really good songs, and I didn't care whether they all went together. I just wanted each song to stand out and really shine."