CALBOY Talks : Working With Lil Wayne, Mental Health & More

“I identify my problems because I know where I come from, I know what I've seen and I know why I think about certain things. Take a step back, relax and find your happy place.


21-year old Calboy out of Chicago commanded everyone's attention with the powerful debut single, “Envy Me” - the quadruple platinum hit showcased the energy and hunger of a young upstart, and lyrical confidence of a seasoned vet.

Since then he has been one of the most talked-about artists in Hip-Hop. Calboy recently spoke with Disney from Hip-Hop Basement about upcoming projects, his journey in music, mental health, and memories of working with the late Pop Smoke and King Von.

Calboy started rapping around the age of 8 or 9 when he watched his cousins and his father making music. He wanted to emulate that, and it became a passion that he has perfected over the years.

He recalls growing up in ChicagoI kinda loved how we lived- even though it wasn't the best living. It was a lot of us in one crib -- all of us in one house. We did everything together, my brother is like my twin. I protect my sisters with my life. Chicago is just Chicago - but you learn how to maneuver and stay out the way.”

Calboy says growing up in Chicago influenced his music, because it made him tougher and mature faster. “Anybody that knows me says oh you gotta old soul - i had to become a man really fast and provide for my family really fast --- It just makes you stronger.”

“I'm inspired by sound - I'm inspired by the art of boise. I can make a beat out of anything-- I'm just inspired by life.”

The 21-year old listed a wide variety of musical influences, that he didn't limit to just rap. Calboy told us he grew up listening to hometown heroes like G Herbo, Chance The Rapper, and Kanye West. As well as rock group Paramore and pop superstars like Adele and Ed Sheeran (who he wants to do a song with).

One of Calboy’s recent stand-out it's was a collaboration with Pop Smoke and Christian Combs called ‘Diana' ' for Smoke’s posthumous debut album “Shoot for the Stars Aim for the Moon”.

Calboy recalls a chance meeting at the studio with Pop Smoke, resulting in two songs.

“That collaboration came about when I had my old management - I pulled up to one of the sessions and he pulled up. So it was our first time meeting each other, we bumped into each other but our energy was really cool -- We started cooking up right away, and then we made 100k On The Coup (which eventually got put on Rockstars GTA 5)

“His energy was real bright,upbeat, dancy -- You can still tell he’s a street guy, but he didn't bring too much of that to the studio. In the studio it was more fun, party, positive energy - motivating everyone around him.”

Calboy lit up when speaking about the late King Von “Von Crazy, he a character too -- that's another individual with a lot of energy”

“I remember shooting a video with Von, they started betting us money that they could beat us in basketball. So we in the back hoopin, i brought my best friend with me and he kinda hooped for me --He accidentally bust Kind Von in the mouth with his elbow, and he was bleeding all in his mouth. (Von) got up, cheesed real hard and said “Yeah … I like you” that's how i knew this dude cut from a different cloth.

He revealed that through family he and King Von are cousins.

Calboy has been in the studio with Dej Loaf, he reached out to her early on in his career and have been locked in ever since. “We got a record thats fire, super fire -- it's coming though for sure”

The “Envy Me” rapper has collaborated with his contemporaries like Polo G and Fivio Foreign, who are also making a name for themselves in music. He recalls what the recording process is like with those artists. “Polo G is a very mellow boring person - that's one of my dawgs tho, Polo don’t talk much.” He continues “Fivio comes with the party vibes, he dances walking through the door.” “The most fun was with Fvio, the best product comes with me and Polo”

When asked about his growth as an artist since the very early days that followed the success of “Envy Me” Calboy thinks that he’s the best he's ever been. “Everything is more polished, everything is next level -- its second hand nature to me as far as performing and doing anything.”

Calboy recalled how his latest collaboration ‘Miseducation’ (Inspired by Lauryn Hill's iconic 1998 album) with the legendary Lil Wayne came about.