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words • Jake Krez

photos • Keeley Parenteau

Chicago’s a city long known for both its unique musical diversity as well as its ability  to innovate from them. It’s never too hard to spot an artist that’s spent time here. For classically-trained jazz musician Lili K arriving on the cusp of the local Chicago creative renaissance that would span nearly a decade, the city has been a huge part of her growth over the years. But to truly break through both with herself and the world at large, it took getting away . Her long-awaited return came last month in the form of her first album since 2015, the eclectically free-spirited and aptly-named, Songs with Friends.

With nearly a decade in the game, the Milwaukee native has scouted the top and bottom end of what the music industry has to offer. Having built a name and an extensive catalogue over the last five years, she’s checked most of the boxes possible for an independent act. Now, four years removed from her last release, Ruby, the multifaceted vocalist is primed for what many might consider a comeback. Being forgotten is easy. It happens everyday. Persevering, meanwhile, is often harder to do. With Songs With Friends in the world, she isn’t worried about any of that. Lili’s just now starting to have fun with it.

In a story for the Sun-Times in 2013, I referred to Lili as “jazz with a nose ring” and she lived up to the billing with her jazz fusion project, Metal Petals alongside Peter CottonTale and features on Chance The Rapper’s now-iconic Acid Rap. Possessing a wide, classical range in her voice she quickly caught on with the growing wave of independent music in Chicago and rode it to some of the biggest stages in the country.

The ride, however, isn’t always as glamorous from within. Once you’ve seen behind the curtain, you know it’s just Dr. Oz back there with some levers. Jadedness is a real concern and at times when the hustle overpowers self-care, mental health can find a way to come calling in a hurry.

“For the first time ever I feel like I’m in the right mental place to release music and talk about vulnerability where I’m not ashamed of it or I don’t feel like it makes me weak anymore,” Lili said over drinks near the Brown Line in Ravenswood last month. “I had to leave Chicago for a bit, I had to just really cleanse everything and work on really addressing my past traumas, doing that allowed me to fall back in love with the process of creating and making music and using it as therapy.”


After breaking onto the national scene as the first voice heard on Acid Rap (“Even better than I was the last time….ooh…ooh…ooh”) Lili parlayed her experiences into an array of opportunities over the next couple of years. In today’s music climate, making it is relative. By 2015, many would assume Lili was there, wherever ‘there’ is. On the cover of the biggest websites, with a team in tow and stages calling, she seemed primed for something big on the horizon. And then, she largely went quiet.

“I pretty much stopped everything and decided I needed to be alone and figure my life out. Because I wasn’t happy with myself, I didn’t love music anymore, I didn’t know who I was, I didn’t trust anyone and I just felt like my guard was up and I was unhappy,” Lili explained. “You wake up and you’re like ‘when did I go off my path?’ Or ‘why did I think this was the right path?’ You don’t really know what happened or what the exact moment was, but you know some shit’s wrong. And the root of it was just within me.”

Musicians today are more insulated yet more accessible than ever before. Criticism is readily available from the comfort of one’s room. There’s no really getting away from the whole mechanism. By the end of that year, Lili was beginning to feel the weight of it all on her shoulders, and it was affecting her work. Simultaneously, it seemed each step forward took increasingly more from her creative control, resulting in a sort of loss of identity.

Across the music landscape and especially in Chicago, things were drastically different after 2016. Shit, the world was different after 2016. By the beginning of the next year Chicago’s talent pool began a certain divide as did the country at large. For Lili, frustration grew from the duality of being featured on some of the biggest records to come out of Chicago without earning the recognition she felt she was due. It’s a fair feeling, and one that strained relationships in her periphery that may not have if she was of the opposite sex. Regardless, she persevered, crafting a team of her own and releasing several projects.

In 2015 she we the first independent artist featured on ABC Chicago’s Windy City Live, a stage that has become a benchmark for local talent and became the first Tidal Rising artist featured on the platform while also headlining a stage at Made In America. To put it lightly, things were rolling leading into the next year. A new album in the works, a mechanism of her creation working for her, from the outside it seemed she had everything she’d worked for.

Songs with Friends came about as a practice in healing through expression over the course of four years as she found herself. With a renewed confidence, she was determined to stand on her own, but needed some familiar faces to help her assert herself once again. As she explains it, her career to this point has largely found her associated with a male figure: a significant other, manager, producer or others. It was a point that repeatedly emerged as a theme during her time away. Having ended her longtime relationship with fellow local talent ShowYouSuck amicably before heading back north, she found herself truly on her own for the first time and decided to create music on her own terms for the first time in years.

” I feel like a lot of my career has been me being tied to a man. Which is very frustrating when you feel like you’ve done so much work as an individual,” explained Lili. “I did so many things that I’m so proud of and it was frustrating to always be this person’s girlfriend, this person’s collaborator. And a lot of that really took a toll on my view of myself and my self worth and I had to become comfortable with being alone and secure in myself.”

Regardless, or perhaps because of it, Lili decided to tap some of her closest collaborators to take the small steps back into the scene. Pairing collaborations on her terms, she turned to trusted colleagues and friends for this reintroduction EP. The process that took her in vastly different creative directions that helped bridge the gap to an eventual album and open up the possibility of what her sound could be. On the project itself, the single “Big Bang” with local duo Air Credits finds her flirting with futuristic hip-hop motifs, “Will You Still Call?” with The O’My’s places two of the city’s most memorable and soulful voices side by side and “Right Here” sees her grooving with fellow Milwaukee native Klassik, returning to her roots almost literally.

“I just wanted to work with people I’ve always liked and admired and have always been kind to me in the industry. Which you know, a lot of times you see the worst sides of people when you work with them,” said Lili. “It sucks because it ruins a lot of what you thought was a good friendship. It’s been cool to just reach out to people who I know and trust. It’s real, it’s fuckin real.”

Between trips to California to unwind, Iceland to explore and Milwaukee to regroup, Lili has dedicated herself to writing, learning and evolving both herself and her art. The disposition is evident throughout. She finally feels like she’s enjoying the music again as she did when we first met, and its appropriately being done so with those she’s known and grown with.

It’s been four years since the world truly got to enjoy Lili K. Four years of searching, learning, understanding and moving forward has culminated with Songs With Friends. It’s a new sound, a new look, a new Lili.

“My music is completely different,” Lili explained. “The EP is fun, its a reintroduction. I’ve been gone for four years I’m sorry but I’m back.”

End image for Lili K Feature - hand in photo

In many ways, Lili’s musical journey over the last eight years is reflective of what many experience in their 20s. Working through relationships with others and one’s self is something that takes a lot without the added pressure of creating publicly. For her part, Lili has utilized those lessons and newfound understandings into a renewed confidence that has permeated her new content on Songs With Friends as well as her upcoming full-length return slated some time before 2020. Today, she smiles more, laughs more and genuinely appears to be on the other side of the position she found herself years ago. To ask her, she wouldn’t change a thing. Going through it has made returning even sweeter. As difficult as the journey may have been the sentiment she espoused so many years ago holds true with her latest: she’s even better than she was the last time.

“I had to get to the bottom of a lot of that shit and doing that allowed me to fall back in love with the process of creating and making music and using it as that therapy instead of this thing I don’t want to do anymore,” Lili said with a smile on her face. “Because whats the point of any of this if you’re not enjoying life? Really, whats the point if you’re not enjoying things or doing things that help people or give back. Like, what’s the point if positivity is not coming out of it?”

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