South Side hip-hop artist Kayo was never much of a student, so it may come as a surprise that the Auburn Gresham-based MC, who dropped out during his junior year of high school, got his musical start by writing a rap for a school project when he was in the fourth grade.
“The choices were to write an essay, do a documentary, or to write a rap about the subject,” Kayo said. “It seemed like the easiest [option] would be to write some rhymes. I did it, I got an A on the assignment, and my teacher was like, ‘dude, you are really, really good at this.’”
Kayo’s music career was off and running soon after that. He bought his first mic and started recording in the 8th grade, eventually recording his Southside Blue Hearts project at Classick Studios in 2016. After releasing a myriad of projects under a few different stage names, he finally rebranded as Kayo in 2019.
But his real coming out party wasn’t until 2023 where he released not one, but two projects, including his highly acclaimed album It Was Fun While It Lasted, which cemented his status as one of the torchbearers of Chicago’s newest generation of hip-hop artists.
Kayo, Now twenty-five years old, has moved upwards of twenty times during his life, bouncing between neighborhoods such as Washington Heights, Hyde Park, and Chicago Heights, in the southwest suburbs.
Despite all of the moving around, it is the Auburn Gresham neighborhood that has Kayo’s heart.
“I’m learning the best versions of myself here,” he said. “It’s where my heart is, it’s where most of my charity efforts will more than likely be in that time when I’m coming back to give back and shit, Auburn Gresham is definitely top of the list.”
Auburn Gresham is where Kayo currently lives and works and where he serves as a program director at St. Sabina Catholic Church, under the tutelage of its pastor, Rev. Father Michael Pfleger.
Kayo regards Plfeger as one of his biggest mentors.
“He literally has helped in every aspect of my life,” Kayo said. “I was engaged—I’m not anymore—he was instrumental in [working through] that. My work, my music, my religion, he’s been instrumental in every aspect.”
While Father Pfleger and the church have had a deep influence on his personal, working and spiritual life—even though Kayo is muslim—the music of the church has had a profound impact on his sound as well.
Gospel is woven neatly into the fabric of It Was Fun While It Lasted. Grand, swirling horn sections lay the instrumental groundwork for the album’s intro, “It Ends In Disaster,” while a soulful vocal loop and a tearful, euphonious piano outro make “Grandma’s Boy” sound like a deep cut straight off of Common’s 2005 classic album Be.
“Gospel, I’m not classically trained [in] so I don’t know the technical terms of it, but it’s very rich in sound,” Kayo said. “It’s drums, it’s organ, it’s guitar, it’s bass…. It’s like an orchestra, but without the orchestra.”
Over the course of twelve tracks, Kayo pairs soulful vocal loops and extensive live instrumentation with urgent flows, self-aware lyricism, and a nonstop embrace of the good, the bad, and the ugly. “It Ends In Disaster” lays the conceptual framework for the tracks that follow, highlighting the duality of good experiences versus bad experiences, and accepting that all things eventually come to an end.
“You ain’t seen the type of days where you can only pray it through, and you believe in God so you feel like you should escape it too/Instead you get the brunt of all the trauma that he saved for you,” he spits nearly halfway through the song.
It Was Fun While It Lasted deals with a number of positive and negative experiences throughout but “HURT” is about personal trauma and its various causes, while in “Still” Kayo sees life’s beauty despite its flaws. It is a highly cohesive listen due to its consistent introspection.
Kayo said the album title is directly tied to the ups and downs he has experienced during the last few years.
“That title, to me, the album was talking about these great stories that you hear on ‘Wait On Me,’ and then these terrible stories that you hear on ‘HURT,’” Kayo said. “[Then] these great stories that you hear are on “Still” and these terrible stories that you hear on ’It Ends In Disaster.’ It was that back and forth of [a] great moment, then a bad moment, then a bad one, and a great one.”
While Kayo balances these good and bad experiences masterfully over the first eleven tracks, perhaps no song does a better job of tying together all of the album’s calling cards better than the outro, “WHEN I GROW UP.”
The instrumental lets the light piano passages breathe before being accompanied by a tambourine and some handclap percussion. Over this loop, Kayo pens one final letter to self, a final reminder to embrace everything that life throws his way.
“Ain’t nobody famous for dying too young, nobody cares about the odds you face/You better start searchin’ and get you a purpose, ain’t nobody willin’ to find you one/you’re better off looking inside you huh,” he raps on the album’s closing verse.
On an album that features a number of heavy-hitting guest features—femdot., Ausar, Morgan Gold—Kayo saves his best for last on the outro track, tapping the St. Sabina Youth Choir to provide a soaring, electrifying set of background vocals to close out the album.
Kayo said he used his “one favor” he gets from Father Pfleger every year in order to get the church choir on the project.
“He gave me that thing that I really needed to get [the project] done,” Kayo said.
As if one project wasn’t enough for Kayo in 2023, he capped off his big year by dropping Until His Burial on December 6. Unlike its heady, more conceptual predecessor, Until His Burial sports tracks with shorter run times and a less lyrical focus overall. In other words, he just wanted to rap.
Kayo said it was one of his main producers, THRD, who convinced him to put out the second project after listening to some unreleased songs in Kayo’s Dropbox folder.
“He is listening to the Dropbox one day and he texts me like, ‘Yo, we’re dropping a mixtape,’” Kayo said. “His next text was something to the effect of, ‘Don’t worry about that, though. I’ll figure that out when it’s time; just keep finishing the Dropbox.’”
While Until His Burial is more direct and to the point, it features a similar sound to its predecessor, and brings just as much in lyrical chops. Highlights include “Dreamer Interlude,” The Burial,” and “The Thing is,” all which feature Kayo getting busy over chipmunk soul instrumentals reminiscent of polo shirt-era Kanye.
Despite the looser vibe of the mixtape, Kayo still feels he has something to prove.
“Last album should’ve took some weight off, but there’s just more pressure I’m under/The breadwinner must always have the next to make it last,” he raps in the song’s opening verse.
After Kayo’s prolific 2023, one might assume he’s ready to take some time off. However, whoever makes that assumption simply doesn’t know Kayo; he insists he will be coming with at least one project per year going forward.
“There is no year in the foreseeable future that is going to come without Kayo dropping a project,” he said. “I have the greatest project I have ever done on the way…it sounds incredible.”
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.
