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She’s studied jazz and taught jazz, and when it came time to record her debut album, Olivia Flanigan worked with musicians she knows from Chicago’s jazz scene.

But Girl, due March 26 via Flood Music, reflects a different aspect of Flanigan’s musical interests.

“It goes back to the sound I had in my head before I ever went to college,” the singer-songwriter says.

Pressed further to name artists from her formative years who make up that sound, Flanigan cites Fiona Apple and Regina Spektor, adding, “I like original stuff that’s authentic.” And authenticity was what Flanigan hoped to capture in recording Girl by allowing her backing musicians to put their personal stamps on her original material.

“I picked those guys because I like their playing, so it was a lot of them bringing their sound to the music,” Flanigan explains. “I didn’t give them a ton of guidance, other than giving them demos. I didn’t write specific parts for them. It really came together quickly because they are live musicians, they are improvisers, and they are guys who are really good at being in the moment.” 

Flanigan recently took a few moments to discuss some significant music-related firsts in her life and career.

Her first favorite artist:
Olivia Flanigan:Ben Kweller. He was one of my favorites from a very young age. There’s something really relatable in his songwriting and the way he sings. He sounds honest, and it’s not overly poetic. … He was this young kid who was writing this stuff that young kids think about, and I was a young kid. It meant something to me.”

Her first concert:
Flanigan: “I come from a family of musicians, so there was never a lack of concert-going. In terms of big acts, I remember going to see The White Stripes. I remember we went to the Aragon here in Chicago, and I think I was 13. It was a great show.”

Her first instrument:
Flanigan: “The first instrument I played was flute; my mom’s a flute player. She taught privately, so I took a few flute lessons with her. But it just wasn’t going to work with the mother-daughter dynamic, so I ended up stopping playing flute after a year or two and switched to clarinet, which is what I played all through school.”

The first words that come to mind when describing her experience teaching jazz in Ecuador in 2017-18:
Flanigan: “I think it was anxiety-inducing. It was really exciting learning the language. That was my favorite part about being in Ecuador: the challenge of learning a new language. … It was really exciting to understand a culture. When you live there for a year, it’s different from going for a week, so it was cool to be a little bit more involved with the culture.”

The first song written for Girl.
Flanigan: “I think it was ‘Sorry,’ the final track on the album. I wrote that when I came back from Ecuador. I had been in a relationship before I went there, and during that time in Ecuador, I was doing some reflection. When you’re completely removed from your entire life, you’re able to reflect in a very different way. I think during that time I realized I had made a lot of mistakes in that relationship, and [the song] was me apologizing to that person, really sure that it was really going to work out.”

The backstory on the album’s first single, “Mannequin.”
Flanigan: “That one I wrote after I had been out listening to music [with other musician friends]. You know, there are just some people who you think are never being themselves; they’re trying to impress everyone else. … I just felt that way about [this guy I knew who was there].”

Her first impression of co-producer Dan Pierson:
Flanigan: “Dan and I went to the University of Illinois Urbana-Champaign, and we both were in the jazz studies department. He and I started the same year, but I was a sophomore who’d transferred from somewhere else. He was a super-talented guy [when we met] — a lot of people come into music school, and they’re flailing around. I remember he could already play, and he became a friend of mine right away … and he’s remained a friend through the years.

“He’s an amazing pianist, but he also got into recording. He’s developed that as being his thing. He’s connected with the jazz circle in Chicago but also with singer-songwriter people as well. I knew he did great work and I loved what he did, so I wanted him to do my album. I trust his musicianship and vision.”

— Introduction and interview by Chris M. Junior

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