Chicago Latin soul musician Lester Rey still remembers the emotions he felt just seconds before taking the stage at Citlalin Gallery and Theater in Pilsen on a freezing night in January 2016.
“Definitely butterflies,” Rey cheekily recalled seven years later. “I was scared. I didn’t know how the night was going to turn out.”
That concert, which commemorated the release of his debut EP Blue Lion, was the first time he had presented his music to the world in such an open fashion. Even with a background in event curation, Rey couldn’t help but feel nervous.
“I hadn’t really curated a lot of events around my music at this point in my life,” Rey said. “I did curate shows in college—cultural shows, talent shows—even church, I was curating church services and sermons.”
But despite his reservations, Rey, donning a suit, wide-brim hat, and with a vintage microphone he bought specifically for that show, performed in front of a packed venue. Rey said his nerves dissipated once he took the stage.
“I wasn’t a stranger to performing, so once I got to the mic, I was like, ‘I know what I need to do,’” Rey said. “I was just so excited that it was music that I had written, that had come from the depths of my creativity and my mind.”
Rey was born in Humboldt Park and spent the first chunk of his childhood on the North Side. He spent his high school years bouncing between the suburbs and the city. However, it is Pilsen that Rey has come to identify as his home, both physically and creatively. Rey currently lives there, just houses down from his parents.
“It’s rooted in family,” Rey said. “A lot of our friends—muralists, graphic designers, DJs—they all live around here as well, whether in Pilsen, McKinley [Park], or Little Village.”
Rey’s musical journey began not in a packed venue in Pilsen, but in a Pentecostal church on North Ashland Avenue where he started playing a “child-sized” set of congas in the church band at the age of five. Though he wasn’t mic’d up for the churchgoers to hear, his bandmates gave him tips on how to improve. Later, when he was sixteen years old, Rey even learned production skills from another church member. Rey said playing in the church shaped his instincts as a musician.
“It was predominantly Puerto Rican; very Caribbean energy,” Rey said. “Salsa, merengue, heavy repetition [and] call-and-response. People were also part of the experience, so the energy was always at ten.”
Church was not only an integral part of Rey’s musical development, but of his spiritual upbringing as well. Before he wanted to be a musician, he wanted to be a pastor. When his pastor was away on missionary work, Rey was called upon to handle sermons at his church.
“I studied a lot of religion, a lot of theology,” he said. “I was undecided for my first couple years in community college, but I was always drawn toward philosophy and religious courses.”
But after a series of experiences Rey had as a young adult, he started to reject the religious teachings he was raised upon.
He said that at nineteen, he was forced to marry a woman he thought had gotten pregnant, threatened with being stripped of his positions as Sunday school teacher and worship leader if he didn’t. Three years later, he divorced her after finding out the baby was not his. That same year, he also tried marijuana and alcohol for the first time.
“I’m just trying new things at this age,” Rey said. “One of those things is choosing a new major, community leadership and civic engagement, focusing on social justice… I just started to see less and less of a reason to believe in the Christian version of God.”
At twenty-two, Rey enrolled at Northern Illinois University (NIU). On top of his coursework, he became heavily involved in NIU’s jazz studies program, where he sang with their jazz ensemble and played in their Afro-Cuban ensemble. Rey said his experiences playing in NIU’s jazz program were vital to his growth and development beyond the church music of his youth.
“I took a deeper dive into the catalogs of salsa musicians in more of a Latin jazz sense,” Rey said. “I was learning all these names [and] catalogs, and getting a richer, deeper knowledge and appreciation for the music that I had heard as a kid, but didn’t have the vocabulary to speak intelligently on.”
Rey graduated from NIU in 2014 and eventually moved back to Chicago, where he started performing with local salsa bands. Two years later, he released his debut EP Blue Lion, whose title pays tribute both to Chicago’s blues scene and the town in Puerto Rico where his parents grew up. Rey said that embracing a center-stage role was a crucial part of his experience creating that project.
“[Performing] with salsa bands, I would be the one singing lead, but I was singing cover songs that had been written thirty [or] forty years ago,” he said. “This was the first time that it was like, ‘Okay, I created a whole body of work and I’m sharing this.’”
Since Blue Lion, Rey has spent the last seven years releasing eight more EPs and making a name for himself not just within Chicago’s Latin music scene, but in the city’s music scene as a whole.
Of every project in Rey’s catalog, perhaps the most immediate and impactful is his most recent release, 2023’s Strawberry Moon.
Released on June 2 to coincide with the actual Strawberry Moon (the first full moon of summer) on June 3, Rey’s latest effort is an irresistible six-song, nineteen-minute joyride, packed with infectious dance rhythms and charismatic vocal performances.
Rey regards Strawberry Moon as a compilation of songs that document a chapter in his life, rather than a specific conceptual piece. Despite this, he insists the lyrics and sounds on the record are in close accordance with the EP’s title.
“I read that Indigenous communities found the strawberry to be a very meaningful fruit, in the sense that the seeds were exposed on the outside of the fruit, which to them [was] a sign of vulnerability,” he said. “I remember being inspired by that and thinking, ‘Well, there’s vulnerability in this music, there’s vulnerability in putting this new sound out, which is a very big departure from my Blue Lion sound.’”
Strawberry Moon opens up with “Azota,” a highlight. With thick, grumbling basslines and driving, off-kilter production, it sets a brisk pace for the rest of the EP.
The following track, “Chi Tea,” which contains a feature from Chicago hip-hop artist Heavy Crownz, is a feel-good party jam that emphasizes Rey’s light, melodic vocal work.
“Everything gonna be aight, we gonna be just fine,” Rey proclaims on the song, as his vocals stretch over punchy synths and emphatic bass hits.
Perhaps the biggest highlight on the project, however, is the closing cut, “Jardin.” The gentle guitar strumming and patient drumwork create a gorgeous soundscape for Rey’s vocals to flow freely.
Lyrics in “Jardin” cover concepts such as self-love.
“[It’s] very much reminding myself I don’t need to wait for my flowers,” Rey said. “I have so many flowers in my own garden that I can give you flowers… It’s this idea of being more patient.”
Rey said the reception to Strawberry Moon has been more “global” than other projects he has released. “Azota” was featured on the NBC show World Of Dance, and all six tracks have been featured on playlists outside of Chicago. The project has also received coverage from outlets such as Vocalo radio.
All the while, Rey is giving himself his flowers while looking towards the future. He plans to release his debut album in 2024—but right now he’s taking some time to enjoy it for himself.
“The album’s not mixed and mastered… it’s not ready for release,” Rey said. “But I’m sitting with it, I’m enjoying it, I’m blasting it in my car. I created an album for myself at this moment… In 2024, it’ll be for everyone else.”
Ryan Rosenberger is a Chicago-based music journalist who has been covering the scene since 2018. His work can be found in The Columbia Chronicle, These Days Mag, The Weekly, and more.