Calboy deserves all his flowers, and he might just be one of the most slept-on artists in the music industry. Born and raised in the South Side of Chicago, Calboy, real name Calvin Woods, creates music from the soul, wearing his heart on his sleeve with each release.
Inspired directly by his surroundings growing up in the hood, from gun violence to overdoses to poverty, it was music that ultimately saved Calboy from being a product of his environment.
Exploding onto the scene with his viral single “Envy Me,” which garnered over 226 million views on Youtube and counting, Calboy would soon declare his place in the rap game, arriving as a breath of fresh air and creating his own lane in melodic hip hop. The song is currently 3x Platinum, peaking at #31 on the Billboard Hot 100.
Fast forward to 2022, Calboy has been vocal about the struggles with his record label, RCA Records. He even surprised released his Black Heart project on his birthday, with features from Joey Badass, Fredro Bang, and Jackboy — only for the label to take it down from all streaming platforms.
Regardless, Calboy keeps his head up and keeps it pushing, creating music for the love of it above all else.
AllHipHop: Who’s your favorite artist to collaborate with? You got some fire ass features.
Calboy: Man, I don’t know off bat. I can say Go Grizzly on the producer side, that’s my favorite producer. Go Grizz did a lot for me. A lot of unreleased. He did a lot on Long Live The Kings. Artists: Polo G or Lil Tjay. They always got good energy. They do their thing.
AllHipHop: Did you listen to them coming up too?
Calboy: Yeah, we all support each other. They still support me, I was in the studio with Lil Tjay a week ago. They still support me, I still support them.
AllHipHop: Bring us back when you were Kidd Cal.
Calboy: Kidd Cal was different. Kidd Cal was experiencing a lot of new experiences, guided by his father. He was the beginning of the Calboy. I’m him still, but it was a lot of vulnerability in that music. I connected with my family members off that music. I couldn’t express how I was feeling, they heard them songs and understood. That was the beginning of Calboy.
AllHipHop: I know you love movies. I was watching the “Black Heart” music video, you were lowkey acting!
Calboy: [laughs] That was my idea, because I got this really bad anxiety thing. When it comes to cameras, I’m like “I don’t know how I look” or “I’m super ugly.” I really get like that sometimes. I’m trying to break that ice because I want to get into the acting. I gotta break that. I’m forever in the mirror, I’m taking little classes.
AllHipHop: I have so much respect for people who take acting classes!
Calboy: Yeah, I’m not trying to be out here not knowing what I’m doing. Coach me. I got the drive for it, you can’t tell me I can’t do nothing. I can do whatever I put my mind to. As long as I keep that passion and that drive in my heart, I can do whatever. But I know what it takes. It’ll take a few classes. It takes some coaching sometimes.
AllHipHop: What makes you strive for greatness?
Calboy: Pain, I’m fueled off pain. A lot of artists are fueled off pain, I was inspired by those artists. I’m definitely fueled off pain. My auntie will tell you what she went through, pulling up to those institutions and all those psychiatric wards. I really went through it. Getting arrested, they gotta come pick me up. I went through all of that. Luckily, I didn’t go through it on a severe type of level, where I had to give years of my life to the system. But it could have been, because I was going through a lot. I used that as fuel to make great music, put my soul into everything I do. That’s why I like to sing, because you gotta come from the gut when you sing. Even though I’m not the most talented singer, it feels better because it’s an outlet. I’m actually letting out my soul when I sing.
AllHipHop: I had B-Real on Shirley’s Temple, he went to a vocal coach who was training opera singers.
Calboy: I was thinking about doing that. On Wesley’s grave, I was thinking of going to a vocal coach, because I really want to blow. Sometimes, I be wanting to blow and get there. But nah, my voice don’t allow me to do that. So I do it to the best of my ability. I’m still a talented individual so I can make a lot of stuff sound good, but I be wanting to get there sometimes.
AllHipHop: He said it has a lot to do with your breathing.
Calboy: Yeah, I’ll YouTube some s### fast. Real life: go on YouTube, type in “singing tips, playing the piano.” I’m teaching myself the guitar. I do a lot of stuff. [snaps] I’m a crazy creative, so it’s nothing I can’t learn. I might drop my sophomore album, or drop a project in the later years… blowing! Everybody’s like “Cal really doing that. He said he was going to do it.” I’m on that type of time.
AllHipHop: You’re drinking tea already!
Calboy: [laughs] I fell in love with tea when I was young, because I was going through panic attacks. I used to wake up in the middle of the night, shirt soaking wet. [pants] Panicking, don’t even know why I’m panicking. I got to the root of the source over the years, but I started going through a lot. Drinking a little chamomile, drinking a little tea, getting into that tranquil space really helped me. I really come from a dark space, drinking tea helped me! That sounds crazy. I started dialing into other cultures, it really helped me.
AllHipHop: Talk about making “Pressure” with Kodie Shane.
Calboy: Kodie sent me a record and I loved it, so I did my thing. I got into the mode. She had a show out in the A, I pulled up and we performed it for the first time. We turned up. I got love for Kodie Shane. Before I was who I was, I was a supporter of Kodie Shane’s. I’m a supporter of the music of the culture. I understand that it’s enough money for all of us. I understand that at the end of the day, where we come from, it’s us versus them.
In any type of situation, you can apply that too. I support everybody that’s working hard, got a flow and got sold to what they’re doing. You know the ones that just started, woke up and decided to be a rapper. Then you know the ones that’s really putting their heart and soul into it, regardless of if they’re good or not. I appreciate the heart, I appreciate the soul. Kodie Shane’s hard though, always been hard.
AllHipHop: It’s so crazy because I had Trippie Redd on my show. He said she low key put him on, took him on his first tour.
Calboy: Yeah? I got a record with Trippie Redd. Well, I was on the record. You know how it goes with me and records. I don’t know if everybody thinks, “I don’t rock with Cal like that,” you feel me? But it’s a thing where I get on the record: “Yo, I want you on this song!” I get on the song and I do my thing, then they put the song out and take me off. Trippie Redd got the record, “MOON WALKER.” “Big bro pulled up, gave me blue cheese.” [sings lyrics]
I don’t remember how the song goes. He stopped by the session and said, “Yo, you fire bro.”
He got a feel of the records I was cooking up. He’s like “I got this record, put your verse on that. That’s hard.” Then he came back in the studio like “that’s hard. I’ve been shooting a video, but if you stay a couple of days, we can shoot your verse into the video.” I stayed a couple of days, he sent me off!
I said “aw they playing with me.” I stayed a couple of days in LA, the man never answered the phone. I thought “okay, they think Cal the victim. They think it’s that type of time,” so now I don’t f### with n*ggas. I really don’t care to be around rappers. N*gga spoiled that for everybody.
AllHipHop: What if he was hella high and forgot?
Calboy: Even if that’s the case, I don’t be wanting to hear… I always felt like that, but nah let me give it a chance. Maybe it’s the Chicago mentality, don’t rock with people. Let me step out of that. Then I stepped out of that, it was the same thing. Nah, we were molded this way for a reason. I don’t rock with nobody. If I rock with you, I genuinely love you. I want to see you win. I want to see you do your thing in real life. I don’t wish no harm, no weapon formed against you. Other than that, I don’t care about what they feel.
AllHipHop: You were also left off Pop Smoke’s album, even though you guys were in the studio together cooking it from scratch.
Calboy: My manager at the time was on some “yo that’s a sensitive subject, maybe we should…” What’s sensitive about that? Me and Pop had a real vibe going on, our energy connected. We shot “100K on the Coupe” video, the song that’s on GTA. You do the heist on GTA V, you gon’ hear Calboy and Pop Smoke on that joint.
We did the video, we was racing their cars. It was a McLaren and something else, we’re racing each other in the video. It was dope, we caught a vibe then. We pulled out the foreigns on the block. We were shooting a video and this was not planned. The kids peep, jump off the school bus and crowd in the parking lot. That’s the viral video of me and Pop Smoke that be going around Instagram. The picture when I was in the blue denim jacket, we had the matching Gucci shoes. That wasn’t planned either. We was clicking in so many different ways, it’s crazy. I rock with dude.
When I rock with people like that, I send them prayers. I send them positive messages. I wish nothing but the best for them, because I’ve lost a lot of people in this. It was sad when we lost Pop, but it was a very emotional moment when I wasn’t on the album. It wasn’t even about me being on the album, to where it’d be a thing “oh, he was chasing the clout. He wanted to be on the album.” If I wasn’t going to be on that album, that song shouldn’t have been on there.
They put the song there, then put my ad libs.
AllHipHop: They didn’t credit you?
Calboy: No, didn’t credit me or none of that. We didn’t talk about that. I made a tweet fussing about it, you know how I play on the Internet. I don’t take nothing serious, but I know other people do so I play like that. Y’all think it’s that? Alright, let me tell these folks what’s going on. I’ll make it viral. I don’t be on that all the time, but I had to because I felt some type of way. I rock with bro. They fixed it for me, but I don’t even feel that.
Calboy: I don’t really feel that. Because we made changes for the deluxe, so here’s the deluxe. I was OG on that b####, don’t play me like that. That’s a personal feeling. I took a couple shots, I’m a tell you my personal feelings. I don’t always tell. [laughs]
AllHipHop: We gotta talk about “Diana,” that’s such a fire record for the females.
Calboy: He said “Yo, I’m trying to do something for the females and try to still keep it my flavor.” His flavor is that bouncy flow, that flow you can do that dance to. You can Woo to. He came up with that, I said “yeah, you’re going in that direction. That’s it right there.”
We had did “100K on the Coupe” the same day. He said “yo, let’s glide on this.” Bro had a different type of energy. He was almost like Von, they guys had the energy to shake the whole room. A lot of artists don’t have the energy. Well, not to me at least them dudes. They come in the room and you know they’re there. They don’t even gotta be talking, just something on your shoulder says turn around and they over there. It’s a few artists I know that’s still living that has that type of energy.
AllHipHop: Who would you say?
Calboy: Lil Tjay. Polo G of course, Lil Zay Osama got that energy. B Bandz, he’s from the East side of Chicago. One of my brothers, he got that energy. You might not know who he is, but you look at him like what’s going on over there? He got that star power, that star energy. He gon’ come to the club, he gon’ make his own show. He’ll say “I am the superstar.”
AllHipHop: You feel like you got that?
Calboy: Of course. That’s why I gravitate to people that got that.
AllHipHop: “Envy Me” blew up because people were dancing to it, right?
Calboy: Yeah, Maneski and G Herbo was the beginning of that. That’s why I forever got love for them guys, because they supported my camp when nobody knew who I was. Herbo and Maneksi, they were supportive. Doowop.
AllHipHop: I love Doowop! He was my FIRST ever Shirley’s Temple episode.
Calboy: That’s why I got love for Doowop. Because a lot of people show love privately, them guys show love publicly and helped me grow my own two legs. A lot of people wouldn’t do that. A lot of people like “you fire shorty, keep doing it!” But you ain’t shouting me out on Instagram though, you ain’t said that on Twitter. Them boys said that. “Little CalTheWild in here with us!” They nicknamed me that, CalTheWild comes from Herbo and Doowop. I ran with it. I got merch with it and everything. Them boys deserve a percentage. [laughs] Chance The Rapper is another one.
AllHipHop: Right! You were on Chance The Rapper’s album.
Calboy: Man, Chance the Rapper is a real genuine soul. I wish nothing but the best for Chance The rapper, I pray for that man. I pray for everybody I love, everybody I care about. I’m stating that for real. Chance showed a lot of love. He said “pull up to the studio, do whatever!” I didn’t get booked for a Lollapalooza. He pulled me up like “Yo, let’s do it.” Gang, let’s “Get A Bag.”
They showed love in different ways when they didn’t have to, and they still do to this day. Chance still talks to me. For me, it’s mind-blowing. Real life, because I grew up listening to these guys.
AllHipHop: A big part of the show is mental health. How are you doing? How’s your mental state?
Calboy: I’m great. It’s always going to be a challenge. It’s always going to be a hurdle, that’s what fuels the great music that I drop. That’s what fuels everything I put into this business. I’m not tripping about a hurdle, because the hurdle made me a million dollars. I love the hurdles. I love the pain, I love the challenge. I love the thrill. I learned to embrace everything, take life for what it is. You’re going to deal with it if you ain’t dead.
AllHipHop: What is your outlook on death?
Calboy: I’ve lost friends from all across the world. I started traveling the world when I was young, when I was 16/17. I’m saying that like I’m old. [laughs] I just turned 23. I’ve been traveling between that time, networking, building relationships, and watching certain people fall out. Certain people leave this Earth. It’s been hard. It’s been tough, especially when you build bonds or especially when you grew up from the sandbox with these people. These people talk to you growing up in the streets, then you lose them. It’s tough, but I learned not to be so down. To use every emotion and every feeling as fuel to the fire, to this madness I create. To this music.
AllHipHop: Anxiety is a feeling of fear, dread and uneasiness. It might cause you to sweat, feel restless, intense and have a rapid heartbeat. It can be a normal reaction to stress. Did you get diagnosed? How was that experience?
Calboy: Yeah. Before that, I was dealing with a lot of it by myself. I wasn’t telling nobody and my family was close, so my family probably was looking at me like “this boy crazy. This boy trippin’ out.” Because I wasn’t telling them, and I usually tell them what I go through. They were seeing the explosions, they weren’t seeing the pains. “This boy trippin’, he on edge,” They were seeing those moments, it probably could create a certain type of image in your brain. But I was really dealing with anxiety on my own. When I started to speak and talk about it, it got better.