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Lil Zay Osama’s Journey Through Chicago’s Underside

Meet one of the Windy City’s burgeoning rap stars.

This article previously appeared on Audiomack World.

“Why the fuck my camera look like this, dog?”

As everyone in the virtual meeting laughs at this sudden outburst, Lil Zay Osama and his manager engage in a discussion on how to fix his Zoom camera that seems to have been changed without his knowledge. He’s surrounded by a cartoon background of a wooden shed and what looks like dynamite on the floor. Osama’s manager attempts to start walking him through how to change it, but before he can even get it out, Osama has figured out what to do by acting alone. The 20-year-old rapper devised a solution by trying things out until something worked.

Looking at Osama’s career so far, you’ll see that forging his own path has made him into one of Chicago’s most well-known burgeoning rap stars. For nearly the last three years, Osama’s pensive street music has become the soundtrack to the city’s newest trap movement. It started with his viral 2018 breakout single, “Changed Up,” which, to date, has garnered over seven million plays on Audiomack. Now, Osama is adding more color to his story and preparing to pull listeners even further into his uniquely performed world with his forthcoming project, Trench Baby, set for release February 19.

At eight years old, most kids sprint around neighborhoods with water guns in the summer, scraping their knees on concrete. Osama was too busy realizing music was his calling. He was inspired by his older cousin, along with rap mainstays 50 Cent and Lil Wayne, to start recording. “I love the melodic sound, and Wayne was one of the first ones to really master that shit,” Osama says. “And then 50, he was the gangster. He came from the streets and portrayed that.”


As a teenager, Osama started putting out music, beginning in 2012, as Lil Zay. Songs like “My Lil Niggas” and “Die Opps” revealed his proficiency in the drill style of rap that made Chicago one of the most influential hip-hop hubs of the 2010s. While his fanbase was growing, it wouldn’t be long until his experiences in the streets became problematic. Lil Zay Osama was sentenced to juvenile detention and would spend years behind bars, finally re-emerging in 2017.

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Once he got out, Lil Zay Osama knew he was destined to do something special. “Even when I was a child, I always knew I was going to be a star; I was going to be a millionaire and shit,” he says. “I was buzzing before I went to jail, but when I got out, I saw they were still fucking with me. The first couple of songs I had dropped got to buzzing, so I was like, ‘I still got it.’” Osama went to the studio every day, working to make sure his buzz would never evaporate.

This process is how “Changed Up” came into existence. In the two days following its release, he watched the plays “skyrocket,” leaving him nearly speechless. “I ain't never rapped like that a day in my life,” Osama says about his breakout song. “I make rap songs, but I ain't never used that flow. That was just some new shit I came up with that day. I was feeling some type of way about situations that occurred in my past, and I just made a song about it.”

“Changed Up” appeared on Osama’s 2019 debut project, Hood Bible, which featured Lil TJay, Marlo, and Lil Durk. The body of work further defined the variety of styles Osama recorded—from delicate melodies to trunk-crumpling raps. “I gave a lot of different sides of me on [Hood Bible],” Osama says. “I had shit for the white people, shit for the hood motherfuckers, a variety of different shit.”

Osama’s next release, Trench Baby, will be more focused than his debut. Instead of making music for everyone, Osama’s focusing on a particular audience this go-around. “Trench Baby is really more of what my real fans want,” he says. “They want that struggling type shit, that pain shit, that street shit, that drill shit, so it’s all going to be mixed in with each other.”

For Osama, having an audience is everything. He owes it to timing because, if his original jail sentence was kept, his success might not have happened. “I was supposed to have been doing juvenile life, which means I don’t get out of jail until I’m 21,” he says. “I was an H number, that means a habitual offender, and I was also a VJO, which means a violent juvenile offender. I got locked up when I was 15, and I got out when I was 19.

“Nobody has ever, in a juvenile system, got out when they were 19 when they were sentenced to juvenile life. So just for that blessing to come through like that and let me out at 19 instead of at 21, that means I wouldn't be right here, right now. I definitely feel like it’s all because of God.”

As Lil Zay Osama prepares for Trench Baby’s release next month, he’s reminded of what it means to be able to do what he’s doing, for his city, at this level. “It feels great to have all of those people watching and being inspired,” he says. “I’m able to speak some real shit to these people.”



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