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Tour Tales | DJ Caleeb and Taylor Bennett bonded over Amsterdam smoke sessions and live shows

Keith Nelson Jr

 // Feb 28, 2019

Taylor Bennett // Brandon Crudup

Musicians are barely getting a slice of music industry revenue, largely eating off of live performances instead. For 'Tour Tales,' we dig into the rider requests, delayed shows, diligent preparation, and future of touring by talking with the multitude of people that move behind the scenes. Record executives, photographers, tour managers, artists, and more all break down what goes into touring and why it's still so vital to the livelihood of your favorite artists. What happens on tour stays on 'Tour Tales.'


The stars always align for some people. That was the case for 25-year old Haitian-American Caleb "DJ Caleeb" Philogene. Before he was touring around Europe with Chance the Rapper's brother Taylor Bennett, Caleeb -- a fellow Chicago native -- was tangentially connected to the future stars through the burgeoning creative scene of the city. But, it wasn't until Taylor and Caleeb were 4100 miles away from their hometown that they connected deeper than just through music.

"Us going to a whole other country where they don't speak English, we didn't have no choice but to be closer after that trip. We're American. [Me, Taylor and his manager] are three black American boys over in Europe," Caleeb told REVOLT TV.

For this installment of "Tour Tales," DJ Caleeb explains the brotherly bond Chance and Taylor showed backstage, why it's good for his pockets to be a touring DJ, and performing in front of fans that he and Taylor don't understand.



How did you and Taylor link up?

I had known Taylor for years. We had hung out a couple of times before. My manager and his manager were cool, and Taylor needed a DJ for a Europe tour. They reached out to us and we did the Europe tour. It was really funny because I knew him and Chance for years, but they didn’t know me for what I did. I would just be around. But, I wasn’t in their faces.

How long before the tour started did you know you were going to be on it?

A week (laughs). It might’ve been less than a week.

How many shows did it take before you and Taylor developed a good live show chemistry?

Probably two shows. To be honest, we rehearsed a lot. That’s what I like about him. That’s what he made me really focus on. The artist I was working with before, we wouldn’t rehearse. For Taylor, he made me rehearse and he made me go full out (laughs). Mind you, when I’m first doing this, I know him, but I don’t know him like that. So, I feel goofy as hell doing this shit. I’m in a room with people I don’t know, screaming and shit (laughs).



What are the crowds like at his shows overseas?

It’s crazy, bro. They don’t even be speaking English, but they be knowing the words to the song (laughs). But, when we be trying to meet them afterwards, we don’t know a lick of what they’re saying.

Since you and Taylor have a history of knowing each other back in Chicago, was there anything y'all did on the road that helped bond y'all closer?

When we did the Europe tour, it was just me and his manager. So, us going to a whole other country where they don’t speak English, we didn’t have no choice but to be closer after that trip. We’re American. We’re three black American boys over in Europe. When we were in Amsterdam, they had the weed shops. We were hanging out, got to smoke a lot together, and having real conversations. I got to find out more about him and his family.



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Are there any candid moments between Taylor and Chance that can really speak to their bond as brothers?

This one time, they walked in the room and it was Taylor, Chance, and their dad. They all hugged. Chance was giving Taylor noogies and shit. Just some bro shit (laughs).

What was on Taylor’s rider?

What did we have? (laughs). We definitely had some Henny. We had some fruit. Different shows, we had different stuff. It depends on the venue. Some shows would let us pick something from their menu or we’ll just order pizza. One show had a full course menu. I’m talking about real meals. Burgers, fries, salmon, and shit like that.

Were there any people [who] came backstage and showed love to Taylor while on tour?

Yeah. Cousin Stizz, Mikey Rocks from The Cool Kids. As a matter of fact, Mikey was in Europe with us. He came to the show.



Those Chicago moments are legendary. Is touring financially good for DJs?

Yeah. It’s great, actually. Think about it. If you DJ for a living and aren’t in New York or L.A., you’re not deejaying every day. The top DJ in Chicago might deejay four to five times a week. But, let’s say you tour for a month, and y’all have 25 shows, that made you more if you were just trying to get your gigs on the weekend. It’s a large sum at one time, which is dope.

What do you have planned for 2019?

I got a lot planned. I’m going to be doing a lot of shows and parties. I’ll be dropping music as a DJ. I’ll be producing for Taylor. I’ll be producing for a lot of different people. But, I can’t say anything right now.


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