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Calboy is an artist who has experienced some of the best and worst things life has to offer. Sure, he’s made it in one of the most competitive industries on the planet, his debut single went 4x platinum and he’s collaborated with his heroes. But he’s also experienced tremendous loss for a 22-year-old. In a little over two decades, he’s lost friends and family to drug overdoses, heart attacks and coronavirus. He even said goodbye to his cousin, fellow rapper King Von, to gun violence last November. But instead of letting these losses get the best of him, he uses his stories to inspire others through his music.

Back in May, Calboy came by Inked NYC for a quick tattoo session in between events promoting “Redemption,” his debut studio album. While under the needle, he let us in on his entry into the rap game, making his breakthrough single and linking up with Lil Wayne.

Tell us about your upbringing in Chicago.

For me, Chicago was regular, but from the outside looking in, it might have seemed tough to some people. I grew up in a house with a lot of siblings—there were 16 of us—and we did everything together. We didn’t have much, but it was cool because it taught you to grow up fast and be on point.

How did you get into rapping?

I started rapping from watching my pops and my big cousin. I listened to a lot of different music growing up and I wasn’t even 10 when I was like, ‘Man, I can do this.’ So I started to practice, record myself, make my own beats and now I’m a master of it at 22.

We really weren’t close growing up because we lived in different areas. But as he sparked up and started doing his thing, we linked back up and decided to do music together. We started to grow that relationship as we both became somebody, so losing him was definitely tough. I was just getting to know him and to understand him behind the stories or the BS that comes from social media. Beyond all of that, he was a good guy.

Photos by Dylan Schattman

Photos by Dylan Schattman

During your come up, you released a number of mixtapes. What was your process back in the day?

Oh man, I just worked hard. I’ve always made a lot of songs and picked what I thought were the best of the bunch to be on that tape. I started doing that when I was in the eighth grade and I dropped my first music video, “The Chosen One.” It had DJ Victoriouz, DJ Mil-Ticket and DJ Amaris on it, who were all popping DJs in Chicago. They all supported me and I gained a fanbase pretty quickly because I had the support of my city.

Take us through your debut single, “Envy Me.” What went into making that song?

It was just part of my everyday routine that day. Smoke a little weed, get into the creative mindset, run through a bunch of beats and just speak about everything that’s on my mind at the time. I don’t write music down, I just go into the groove and I become one with the melodies, trying to figure out how I flow on the song. Then I dig deep into what I’m going through at that time.

How about your follow-up EP, “Long Live the Kings,” which was dropped during the pandemic?

I knew a lot of people could relate to “Long Live the Kings” at the time because I was dealing with a lot of loss. My homelife in Chicago was crazy. Then I lost a cousin to coronavirus and another cousin due to a heart attack—it was a tough time. All I could think about at that time was all of my fallen soldiers.

Take us through your upcoming debut album and what the process of making it has been like.

Making this album has been crazy because I go into the studio and make, like, six songs a night. So you go to the pot and there’s, like, a hundred and something songs. So the toughest part has been narrowing the songs down, but I put my heart and soul into everything. When I’m making an album, I’m in album mode and I lock in.

Photos by Dylan Schattman

Photos by Dylan Schattman

The album is called “Redemption.” What do you feel that you need redemption for?

My life path. I’m a nerd and a good kid at heart, a product of my environment. I’ve obtained some stability and I moved my mom and brothers out of the hood. Now I’m slowly elevating my loved ones in the hood so they can move out and help their mothers. I’m bettering my situation and, in a fashion, being baptized. I’m revamping my whole situation and I’m on the road to redemption. All of my tattoos have recently represented redemption. Even though my tattoos are so random, they’re all personal and they’re all about what I’m going through in this stage of life. By the time I’m 40 or 50, all of my tattoos will be telling a story.

On the album, one of your big singles is called “Miseducation” and it features Lil Wayne. What was it like working with him?

It was amazing. He reached out to me being like, “Yo, you dope. I see you working.” That was mind-blowing and I would have been satisfied with just that. But he sent me his phone number and we started talking, building a relationship, and I’m learning about who he is. I discovered that Wayne was everything I thought he was.

What’s the story behind the song?

I made “Miseducation” during the “Long Live the Kings” days. It’s a story about losing a loved one to some nonsense in the streets. It’s another redemption story because I was once one of those kids. I kind of felt like I was stuck because I was miseducated and nobody has an OG teaching them the right things nowadays. As I traveled and grew, I met a few OGs who were out here and this song is a story of another miseducated kid losing his life.

Who are some artists you hope to work with in the future?

Future, Ed Sheeran, Billie Eilish… I’ve always said I wanted a hook from Adele. I know that’s going to be very hard, but I shoot for the stars.

Photos by Dylan Schattman

Photos by Dylan Schattman