It’s not every day a respected legend reaches out to a young Hip Hop star to connect. Chicago native Calboy had that opportunity when Lil Wayne hit him on Instagram a few months ago. But the connection almost didn’t happen, thanks to Calboy forgetting to check his Instagram messages.

During his conversation with HipHopDX, Calboy spoke about his unexpected relationship with Lil Wayne and how he almost missed the chance to work with the New Orleans Hip Hop legend.

“What’s crazy about the Wayne situation is he reached out to me on Instagram,” Calboy told HipHopDX. “That’s when I felt like, ‘Man, I’m lit. Wayne reached out to me.’ He was like, ‘Yo, you fire, shorty. What’s the situation like?’ But I didn’t see his DM for like four, five months, bro. It’s just sitting in my DMs, and I didn’t see it and it’s a DM from Wayne [laughs].”


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Calboy’s manager had been looking through the rapper’s inbox one day when he landed on the forgotten message from Weezy and told him he had to respond. When Calboy answered back, Wayne wasted no time sending his number, and they locked in right away.

“We was just talking about all type of stuff,” Calboy added. “He was going through the legal situations before he got pardoned by Trump, so I’m like, ‘Man, I’m sending my prayers to you, bro. Blessings. Keep your head up.’ He’s like, ‘Oh, I definitely need them, bro.’ He just wanted to see what type of person I was, and we just locked in from there.”

Eventually, Calboy and Lil Wayne would start making music together, and that’s how their collaborative track “Miseducation” was born. The OZ and Austin Powerz-produced record finds Calboy and Lil Wayne reflecting on the pitfalls of street life and its relation to the rapper lifestyle.

Initially, the two planned to exchange songs with one another, and Calboy knew he wanted Lil Wayne on “Miseducation.” The “A Milli” rapper said he’d do the record if Calboy lent him a feature on a song but changed his mind after being blown away by what he heard on “Miseducation.” Within an hour, the Chicago rapper had Wayne’s verse, and “Miseducation” would be the start of the rollout for Calboy’s forthcoming album.


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For Calboy, linking up and building a relationship with a legend like Lil Wayne is monumental. The 22-year-old was just a child at the height of Lil Wayne’s iconic mixtape run, and Calboy was one of the many who studied and idolized the Hip Hop legend. Today, Calboy is friends with Lil Wayne and has even more access to soak up game.

“Every time I heard a Wayne project, I’m like fixing to go to the studio,” Calboy said regarding Lil Wayne’s influence on him. “Like that man turns you up like, ‘No, I got to go rap, bro. This man going crazy.’ That was my whole entire life just watching him snapping.”

When asked what’s the best advice Lil Wayne has given him now that he has a solid friendship with him, Calboy said it’s the infamous work ethic Tunechi brings into the studio.

“Mack Maine was telling me Wayne works so much that he needs two different assistants,” Calboy revealed. “When one assistant falls asleep, the other assistant wakes up because nobody’s up enough to stay up with him. The man be in the studio for 32 to 36 hours.”

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Calboy added, “What I got from that was to outwork everybody. I talked to Wayne about it at the video shoot, and that’s what he told me. He’s like, ‘Bro, just outwork everybody. Everybody doing what they do, but nobody works harder than me. That’s how I stayed relevant for so long because nobody works harder than me. We’re in the studio for days. We don’t go home, no shower, no nothing. We in there rapping. And there’s so much on a man brain you could rap all day.'”

Check out the video for Calboy’s “Miseducation” featuring Lil Wayne below, and stay tuned for more of our conversation with Calboy coming soon.