Spotlight of the Week: Jenn Leo

Jenn Leo is a musician based in Milwaukee who primarily covers female singer-songwriters. She performs both solo and with duo Ben & Jenn.

ME: How did you get involved with Wisconsin Music Ventures?

JENN: Well, I met Allison when she was establishing a community handbell choir in Wauwatosa, so we had a few rehearsals and then COVID hit. When she said she was starting Wisconsin Music Ventures it sounded like something that I would find useful; before I joined I actually did some of the educational sessions. She knew I was trying to get into more proper format, and I didn’t have the EPK for the Green Room so she suggested the Backstage Pass program.

ME: Awesome! That said, I’d love to hear more about your duo Ben & Jenn!

JENN: We’ve been playing together for about two and a half years; we got acquainted just before COVID and started rehearsing, and then we just started playing out. Ben Schmidt is a very good fingerstyle guitar player and I’m a rhythm guitar player, so there’s that. I’m more of a singer; I’ve been singing in various forms since I was like four. Recently I’ve been getting more into the stuff that’s popular versus classical and musical theatre stuff that I used to do. Ben’s an untrained singer but he’s learning a lot and he’s getting more comfortable with different things so we’re kind of learning together what we’re good at.

ME: Is it originals and covers?

JENN: We’re trying to figure out how to create originals together without it getting cranky. He’s written a number of songs and he’s got a particular way that he likes to work while I’ve written very few songs, but I tend to do a lot of lyrics and with a more haphazard approach, so we’re trying to negotiate that at this point. I’ve helped with a few words here and there on a couple songs he’s written but that’s about it as far as originals for us.

ME: Thank you for sharing that!

JENN: As far as our instrumentation, we try to be kind of rootsy in our sound. Ben’s a huge fan of Iron Maiden and punk, and I tend to lean more into singer-songwriters, so negotiating that is fun and interesting. Sometimes he’ll send me something and I’ll be like “what am I listening for?” and that’s kind of his reaction to things I send to him too. But we hope that other people appreciate what we do.

ME: Well that always makes it fun and unique!

ME: That kind of touches on my next question, which is what your biggest influences are?

JENN: For me personally, it’s probably 85 percent female songwriters or at least female-led stuff. My heroines are Kate Bush, who I’ll probably never see in concert because she doesn’t tour; when I was in London she was having lunch at the Hard Rock Cafe but I was too chicken to go get an autograph or anything. Another one is Jane Siberry, who’s a Canadian singer-songwriter; I’ve seen her several times and got to talk to her in Chicago three years ago when she was playing solo at Oldtown School of Folk Music. She was very kind. Dar Williams is another; I got to do a songwriting workshop with her like a month ago in Stoughton. Then there’s Ani DiFranco; I waited outside her bus until 2AM a couple years ago and she signed my book. I got to see her play in a barn in Iowa a few months ago.

ME: That’s awesome. Sounds like an eclectic mix!

JENN: They all hit different things. I’ve been leaning more into of the women’s stuff as an adult because when I was a kid, pretty much everything I had access to for free was men. That’s what I grew up with but I’ve been trying to even it out.

ME: My last question for you is, what are you working on now?

JENN: I’m figuring out how to write songs. For some people it just falls out of their brain but it’s a work in progress. I have a lot of bits and pieces of keyboards and guitars and things that I want to start experimenting with. I want to mess a bit more with the production and recording of things and seeing where that can lead in terms of creating music. Covers are a lot of just doing what somebody else wrote correctly (laughs) so I’m breaking out of that in a way that I’m comfortable with. It’s been a struggle but I’m trying to get there and see what I’m capable of. I don’t have any solo gigs lined up right now but the duo has one at Mary’s Caddyshack at the end of January.

Visit Jenn Leo’s Facebook page here.

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