A career in music was always in the cards for Amy Helm. She found inspiration from her late father Levon Helm, the legendary drummer of The Band, from her mother, singer-songwriter Libby Titus, and from her stepfather, Steely Dan’s Donald Fagen.

AMY HELM
With: Connor Kennedy
When: p.m. May 14
Where: City Winery, 1200 W. Randolph
Tickets: $20-$28
Info: citywinery.com

“Music was always just what I could do from a very young age,” Helm says. “It’s what I loved to do and what came easiest for me.”

But fears and insecurities would often get in the way, Helm admits. So it was years before she was able to venture down her own path. Her parents split up when she was six. She lived with her mom in New York City where she studied jazz vocals with Dr. Aaron Bell (Duke Ellington’s bass player), who taught music at her high school.

“He was a huge, huge influence on me,” Helm recalls. “Studying with him for four years was something that really connected me with my singing. I think what I learned here carried me through my 20s and 30s when I was finding my way.”

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When it was time for college, she headed to the University of Wisconsin where she studied psychology, a subject she says interested her “probably because I had gotten really good at figuring out what the hell was going on as I grew up,” adding with a laugh, “It was a colorful childhood.”

It wasn’t until her late 20s, when Helm began singing in her father’s blues band (Levon Helm and the Barn Burners) that music began to take on new meaning for her.

“I was green and I didn’t’ feel ready and I didn’t quite know how to deal with the fact that every time I came on stage I was under the spotlight of ‘daughter of’,” Helm recalls. “Anytime I had insecurities about that my dad would point me in the right direction to just sing better and better each night.”

Amy Helm | PHOTO COPYRIGHT JANA LEO

Helm has developed into a deeply soulful, expressive singer-songwriter with a writing style that draws deeply from American musical traditions. She spent more than a decade as a supporting musician (in her father’s band and as a member of the roots band Ollabelle) before testing the waters as a solo artist. She says recording her first album, 2015’s “Didn’t It Rain,” was an “organic next step.”

“I spent a long time in the embrace of Ollabelle and my dad’s bands and I learned so much and got stronger in so many ways,” she says. “I felt ready to challenge myself to see what it would be like to actually have to sing an entire 90 minutes of music standing on the front lines.”

Those first shows as a front woman were a bit nerve-wracking, she admits with a laugh.

“I just remember making this one girl in the audience my point of focus, and she was into the music so that was a good thing. It’s gotten a lot easier now but I’m still learning quite a bit.”

Midway through working on the album, Helm’s world was thrown into emotional chaos. Not only did her father pass away in 2012 but also her marriage fell apart and her second child was born. It was a transformative time for Helm who decided to go back into the studio and rework the songs.

“I thought the album was finished but after going out on the road and performing the songs, I realized the songs sounded so much stronger than when I first recorded them. I wanted to get it right.”

Helm is currently working on a batch of new songs and hopes to be in the studio recording by the end of summer. Some of these songs will make the set list at City Winery, where she fronts a band that includes Cindy Cashdollar (steel guitar, dobro), Mark Marshall (guitar), Moses Patrou (drums) and Jacob Silver (bass).

Helm now lives in Woodstock, New York, with her sons ages 5 and 9. Her father’s music legacy hovers over her in this town where he established the now legendary Midnight Ramble concerts and his recording studio known as The Barn.

“My dad was a role model to so many musicians because he was a working man’s musician. Rock star status was irrelevant to him. I’m committed to trying to continue to respect his legacy. To create work for musicians. To create great music for people. To keep his legacy vibrant and alive.”

Mary Houlihan is a local freelance writer.