Sometimes, you just have to make things happen. For 19-year-old Chicago rapper Calboy, all it took was a stolen computer and a mic that his uncle bought him to get his feet wet with music when he was 14. Inspired by icons like Lil Wayne and Michael Jackson, Calboy used cracked music programs and YouTube tutorials to create his first few songs in his makeshift home studio.

In 2017, Calboy dropped his Anxiety album, shedding light on various mental health struggles. He followed up with his CalBoy The Wildboy mixtape last summer before dropping his breakout single, the bouncy "Envy Me," where he raps and sings about the highs and lows of his burgeoning popularity. After five weeks on the Billboard Hot 100, the song—which has sparked a viral dance challenge—sits at its peak position at No. 41 on the chart, and only seems to be going up from here.

Read all about Calboy's journey from his bedroom to Billboard in XXL's The Break.

Age: 19

Hometown: Chicago

I grew up listening to: "Tupac [Shakur], of course. Michael Jackson, All-American Rejects. As I got older, 50 Cent, G Herbo, Chief Keef. I listen to all type of music. I was listening to The Documentary [by The Game], [Lil Wayne's] Tha Carter. That made me want to rap. Tupac made me want to rap. I listened to a lot of alternative soft rock that made me want to do the harmonizing and singing thing."

My style’s been compared to: "[Lil] Durk. I think it's the voices, because we have totally different rap patterns. The subject matter is close, but we from the crib—Chicago—so I don't look at it no way. I know I'm original. Somebody told me A Boogie [Wit Da Hoodie]. That one don't make sense. Shouts out to Durk. That's my homie. It's all love."

My standout records to date: "Of course 'Envy Me.' 'Tell The Truth' is doing well right now—like 3 million views on WorldStar. 'Envy Me' [has] 20 million. I'm trying to surpass that."

My most slept-on song: "I got a list. 'Bam Bam,' was my first-ever hit. 'Warriors'—that song meant a lot to me. I was feeling like someone when I was singing it. I got a song called 'Kung Fu.' They just real vibes, my real emotion, how I feel. My songs that got that type of feel, I feel [are] slept-on. Even though the music is quality, we didn't package them right. We was learning."

My standout moments to date: "The Big Jam [by] WGCI. The show is in the United Center, where the Bulls play. It's just huge. The biggest show I ever did. It was life-changing. Actually, my cousin Neil Gang called me up because he had some type of tab with the people that was running the show. They wanted to book him, because he got a little buzz, too.  He called me and was like, 'Instead of booking me, I'm telling them to book you. You just bring me up.' He kind of like stepped down just to let me go up."

Most people don’t know: "I was painting and drawing before I was rapping. I was drawing everything from anime to Chibi characters. I just started to get into the paints. I do a lot of those in my spare time. Whenever I got free time, I try to get some canvases done.  I do music but I write. I'm starting a book; I'm like half way through it. I want to get into movies [after] I build my stardom up a little bit."

I’m going to blow up because: "Everybody likes originality. Everybody likes creativity, and thinking outside the box. I think that's what I got over a lot of people.  I'm intelligent. Then, I'm creative. I know what I want. I got vision, and everybody don't know how to bring they visions to life. I think I know how to bring mine to life. Everybody like seeing a person make their dreams a reality. I know I got the capability to do so."

I’m going to be the next: "Michael Jackson."

Follow Calboy on Instagram and SoundCloud.


Calboy The Wildboy

"Envy Me"

"Ku Ku"

"Tell The Truth"

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