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Jessi Lynn became a Wisconsin country star after Nashville said no
The long way home
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Credit:Josh Janke

Months after Jessi Lynn moved to Nashville in 2000 to fulfill her country music dream, a vice president of a major record label took her to dinner and told her this:

She was too old, too fat, too dated-looking and too hardheaded to make it as a country music artist.

Then he added something else.

"He thought I had huge potential as a hit songwriter and that's where his interest was in working with me," recalls Lynn.

Her pride wounded, Lynn, now 31, never followed up on his offer. She wasn't ready to let go of her quest to be the next Reba McEntire or Wynonna Judd.

Country-star dreams were Jessi Lynn's escape from a vagabond youth shaped by her father's migrant work. It was her cure for the chronic asthma that kept her in hospitals as a kid.

And it was a dream too strong to be crushed by the meanness of Nashville, even if Nashville refused to nurture it.

In 2005, Lynn accidentally stumbled onto a path that led to success as a music artist. She came back to Wisconsin, the setting for the last chapter of her itinerant childhood, ending up in Madison.

She recorded her second album, You Ain't Seen Nothing Like This, with Jake Johnson at Paradyme Productions. She booked some local shows. In 2006, she won a Madison Area Music Award for Americana album of the year.

She joined the roster of Trackside Charities bands and played a series of big-production shows at regional stock-car racetracks, alongside prominent country acts like Emerson Drive.

The momentum hasn't stopped in 2009.

"I'm playing four to five shows a week now and I'm not even searching for them," says Lynn, who lives in Madison.

In the weeks ahead, she will be performing with Atlanta recording artist Sarah Peacock. She is traveling to Texas to do a series of shows with Beth Kille, the former Madison resident and Clear Blue Betty vocalist who is now based in Houston. The two have formed a duo called Dirt and Sunshine.

For now, Jessi Lynn has deferred reaching for a Nashville star.

"I haven't gone back because I recognize that this is a blessing," says Lynn.

"I have to go with this."

Rootless youth

Jessi Lynn was angry at her parents for moving from Montana to Washington state in 1984, when her father lost his job.

"I remember leaving my friends and being so upset about that," she says.

Years spent moving didn't end there. Her mother separated from her father in 1990. Jessi and her three siblings moved to her mother's home state of Wisconsin, only to return to Richland, Wash., when her parents reconciled nine months later.

"Moving back, I thought, was going to be great," says Lynn. "But I was an outcast with old friends because of the changes that had happened to me during puberty. No one knew who I was or something. It was awful, and the rejection was crippling."

She responded with anger and rebellion. "I ended up being taken out of school and home-schooled until ninth grade."

If Lynn's early years weren't grounded in any one place, neither were they bound by any one cultural influence.

She describes her mother as a hippie who "dedicated her life to Jesus." Musically, she remembers hearing Christian music playing from her mother's upstairs bedroom. Downstairs in the basement, her brother played death metal on his electric guitar.

Then her older sister started bringing home country music records. Her first concert was an Eddie Rabbitt show. After seeing Reba McEntire perform, Lynn says she was hooked.

"It was a 'show,' not just a concert where they stand behind a microphone and sing," says Lynn. "She danced and had a bunch of wardrobe changes. She entertained at her concerts." Lynn was in awe.

"Once I found country music, I was obsessed," recalls Lynn. "I mowed lawns and saved up money to buy a guitar. Every dollar went to that - concert tickets, CDs, magazines, anything I could get my hands on."

In 1994 Lynn's mother once again separated from her father and moved her family to the tiny Sauk County village of LaValle, population 326.

Lynn was 16 and enrolled at Reedsburg High. She graduated in 1996 and began bartending in Wisconsin Dells on her 18th birthday.

She was saving her money again - this time for a move to Nashville.

Hello, Music City

It was raining on the day in 2000 when Lynn packed all her possessions into her red Chevy S10 and departed for Nashville.

"The blue tarp holding all my belongings in place kept coming off, and I kept having to pull over to fix it," she recalls.

She drove to Kentucky to pick up her roommate, who was relocating from Branson, Mo. They were late to meet their apartment manager in Music City and sopping wet when they arrived after dark.

"We had no furniture," says Lynn. "I slept on an air mattress."

To earn money, Lynn once again tended bar. She spent her days making connections in songwriting circles.

"I came there wanting to be the next Reba or the next Barbara Mandrell. I thought I would show up, do some showcases, get a record deal by the time I was 23 and retire at 27."

She found out the real Nashville is not the place she'd read about.

"The music executives in Nashville have wives and jobs," says Lynn. "They're not out at clubs looking for talent. They want someone they can mold to fit their own plans."

Nashville, says Lynn, "kicked my butt pretty good."

Three years in Tennessee had an unintended consequence. Lynn says she got caught up in the drinking culture of the Nashville bar scene and returned north in 2003 to clean up her act. She moved in with her sister, a pastor in Minneapolis. For the next two years, Lynn became a personal trainer and put her music on hold.

Then in 2005 she returned to Nashville, this time with a new goal - to forge a career as a country music songwriter. She made a brief return trip to Wisconsin that year to record an album in Madison.

"I had worked with Jake Johnson on my first CD [2002's Just Me and My Guitar]. He had his own studio now, and I wanted him to record the new album."

Lynn credits that record, and more specifically the Madison Area Music Awards, with jump-starting her success as a Wisconsin-based country music performer.

"Jake was there to accept my award for me, and he made me sound like the biggest rock star that ever lived," she says. "My schedule just blew up from there. So I stopped everything and said, 'If this is the way that has been given to me right now, I'm going to stay in Wisconsin and see this through.'"

Madison, it turned out, was Jessi Lynn's music city.

Wisconsin star

Geography hasn't been the only unexpected dimension of Jessi Lynn's music career so far. She hasn't entirely forged a stereotypical country music audience.

Not that fairs, summer festivals and other Americana venues haven't been core to her tour schedule, but somewhere along the way, Jessi Lynn won over a sizable lesbian following.

The first night I interviewed Lynn for this story, we talked backstage at Club 5, the LGBT nightclub near the Beltline at Fish Hatchery Road.

We sat on stools in the glare of globe lights that framed makeup mirrors while a karaoke singer crooned Barry Gibbs' lines from "Staying Alive."

"A few years ago a friend of mine asked me to play a women's dance here," says Lynn. "They treat me very well."

As for her own sexual orientation, Lynn says she doesn't identify as anything. "The labels and all of that should just be gone."

Paradyme's Jake Johnson has become one of Lynn's most vocal fans.

"She's come a long way - from a way-too-green dreamy kid to an amazing songwriter and performer, and a professional studio vocalist," says Johnson.

"I've always liked her approach," he says. "It's about the song first. She never dwells on complexities of chords or song structure, or even exact melody, which holds up so many songwriters. If the song has meaning, those other things fall into place."

Lynn says she hasn't given up on Nashville for good, but for now, all of what she wanted out of country music is being realized in Wisconsin.

"I think because I was so sick with asthma growing up and never really had many friends because we moved around a lot, I just wanted to be somebody," she says.

"I hated being overlooked in every situation. I couldn't go to certain people's houses or do normal things because of my asthma, and my mother had such strong ties to me with keeping me alive, I guess I just wanted to be my own person and find my independence."

Now, Jessi Lynn says she is poised to ride more unexpected roads to success.

"I hope no one will be surprised if I come out with a rock record."

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