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The most charismatic and sustainable artists go against the grain, and Lili K. is the best kind of outsider.

Though only 23, she has cultivated a performance style and work ethic that rivals artistic peers years older than her. Going to Columbia College Chicago was one method of instilling a drive in the jazz vocalist. But Lili (born Lili Kryzanek) also slowly worked toward her career from a young age. Whether she was training in a performing arts high school or sneaking into jam sessions as an underage undergraduate, each step has been a calculated (and successful) move toward the release of her own music. Her debut album, “Ruby,” was recently released.

It is not every day that you meet a millennial so enamored of a genre of music from the past. But Lili’s love is driven less by curiosity, more by passion. She speaks frankly about her skills, describing her high school experiences around powerhouse vocalists. She dedicated herself to jazz, which would eventually open her up to a unique community of like-minded creatives.

Lili is an artist driven by choices, both smart and practical. She came to Chicago to study at Columbia even though she was accepted into the University of Miami’s prestigious Frost School of Music. A high school instructor was disappointed in the choice, but Lili stuck to her guns and in the end won artistically. She cites a friend who went to the school, who described the experience as sheltered from the true, diverse jazz world. “You can get some cool education and learn some awesome things, but I feel like the people … that’s what’s more important,” Lili said.

She cites one “people experience” she gained moving to Chicago. Like many college students in the city, Lili obtained a fake ID. But rather than get wasted at a local sports bar, Lili sneaked into jazz clubs like the Velvet Lounge, where she sat in on jam sessions. It was there she fully immersed herself in the local scene, finding close friends and future members of her band including her keyboardist, William Kurk. “It was just about immersing yourself in learning and throwing yourself at what the big guys who were regulars at jam sessions were doing,” Lili said.

And Lili’s music, a study of vocal jazz stylings of the past with a fresh, relatable sense of the present, is rooted in her life of learning. “It’s crazy to be with adults now who know what they’re doing,” said Lili. “Especially with improvisation. Watching someone solo and really understanding how musicians work with one another when performing. It’s just really awesome to sit there and listen and learn.”

After that, Lili surprisingly found herself immersed in the Chicago rap scene, before breaking out as a solo artist. Guest appearances and collaborations with artists such as Chance the Rapper and Vic Mensa introduced audiences to Lili’s talents. “It would work, but it wasn’t my band. So I really wanted to get something solid,” she said. Her band members include Kurk as well as other rising talents from the local jazz scene.

But now, with the release of “Ruby,” Lili is eager to share with the world her sound and vision. Backed by the Lili K. Band, “Ruby” is a culmination of years of writing.

Most of the songs on the album were previously composed but never recorded.

Lily also produced the record, and each song sounds as if you are in the room with her and the band. “I didn’t want it to be perfect. I wanted it to have that throwback sound, to have its flaws, to have talking in the background.” That throwback sound is exemplified on lead singles “Tommy” and “I Don’t Want You No More.” The latter’s black-and-white video, featuring her sweet, happy backing band, is straightforward and charming, much like Lili herself.

Julious is a freelance writer.

onthetown@tribpub.com

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When: 7:30 p.m. Saturday

Where: Bottom Lounge, 1375 W. Lake St.

Tickets: $10 (17+), 312-666-6755 or bottomlounge.com