Lollapalooza 2019: A conversation with Chicago-based hip-hop artist Calboy


Greg Noire/Lollapalooza 2019

Calboy walks between fans during his set. He surprised the crowd by bringing out Chance the Rapper, who he has collaborated with.

Andrea Bian, Summer Managing Editor

Rapper and hip-hop artist Calboy grew up on the South Side of Chicago. He skyrocketed on the charts with his hit single “Envy Me,” which currently boasts over 158 million Spotify streams. Calboy performed at Lollapalooza for the first time Friday to an enthusiastic crowd. He also surprised the crowd by bringing out Chance the Rapper, who features him on “Get A Bag,” a track on his new album “The Big Day.” The Daily caught up with Calboy following his performance to talk about his Lolla experience, his musical influences and his Chicago roots.

This interview has been edited for length and clarity.

The Daily: How was the experience of performing at Lollapalooza, being from Chicago?

Calboy: Definitely a lit experience because it’s my first time doing it, so I had that rush of adrenaline in my system already. So when I jumped out and I saw the crowd’s reaction, it was different than a lot of my other festivals because they knew every word to every song. I feel blessed, and just excited.

The Daily: You brought Chance the Rapper out onstage — how was the experience of being able to bring him out?

Calboy: That felt legendary, too, because I grew up listening to Chance, since “10 Day.” It’s a different type of feeling when you’re on stage with him, after watching him onstage.

The Daily: Given that you’ve grown up listening to Chance, is he one of your musical influences? What other artists influence you?

Calboy: (He’s) one of them. I also listen to a lot of alternative. I like Ed Sheeran. I like the new Billie Eilish, she’s dope.

The Daily: In the past, you’ve talked a lot about mental health and its importance in your life. What encourages you to talk about mental health and how does it influence your music?

Calboy: I feel pretty confident speaking about it because I overcame it. I was in a position where I would never get better to feeling the best I can feel. Other people just need those words of encouragement. I’ll definitely speak on it, to let everybody know it’s okay, that it gets better.

The Daily: One of your most popular songs is “Envy Me.” What’s the inspiration behind that song and what message were you trying to get across with it?

Calboy: I really don’t know the inspiration behind it because I freestyled it. I was in a certain mood at a certain time. As for the message behind the song, it was just sharing my truth, letting everybody know what I’ve been through.

The Daily: So when you were recording it, did you think it was going to have as much success as it did, or that it would be a career-defining song for you?

Calboy: You know, you always keep your hopes high, keep faith, but I wasn’t sure that was gonna be the one. I was just making good music, and hopefully one of them would become the one, and that was the one.

The Daily: Is there anyone you want to collaborate with in the future?

Calboy: Billie Eilish, Ed Sheeran, Travis Scott. I wanna get on another song with Future, and (Young) Thug. I’m just saying — coming soon.

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Twitter: @andreabian_