Meet Tobi Lou, the Chicago Artist Bringing the Joy of Cartoons to Hip-Hop

"We have to find creative ways to make shit happen."
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Tobi Lou, Troop, 2018

Tobi Lou, looking at his bright future.

If you took joy, cooked it down to its essential elements, and added buns, you would get Chicago upstart Tobi Lou.

Lou, who got his hip-hop education from classic Biggie tracks, MTV, Fresh Prince, and lunchroom freestyles, has been steadily carving out a new lane in Chicago for the past two years. With a grip of singles and the dazzling Tobi Lou and the Moon EP under his belt, Lou’s music is driven by confidence and a defined—sometimes cartoonish—aesthetic. Yet, assuredness was not always his strong suit.

“My first meeting, you know, just having this A&R tell me, ‘Okay, yeah, we like what you’re doing, we think you’re great. I think you could be huge. What we wanna do is turn you into the next Flo Rida,'” he recalls. “That’s literally the first thing that someone of any importance in the music industry told me after being ignored for so long. I took those words and I didn’t really know what to do.”

That particular piece of advice, if we can call it that, sent Lou into a tailspin of heavy drinking, smoking, writing to David Guetta type beats, and a deep depression. Eventually, Lou declined the deal and maintained his pride. If he was going to fail in this industry, he would fail as Tobi Lou, not as a bootleg Flo Rida.

Keeping with that energy, Lou decided to leave Chicago for LA, in hopes of avoiding more comparisons to contemporaries like Chance The Rapper. According to Lou, his time away from home has enabled him to grow as an artist and continue to refine what he calls the “Tobi Lou feeling,” which he hopes to impart on his listeners.

With a newfound self-confidence and impossibly infectious tunes, Tobi Lou is far from failure. His latest endeavor, the breezy “Troop,” has him working with fellow Midwest artist Smino and director-designer Glassface, who has worked with everyone from Lil Yachty and Khalid to Ms. Lauryn Hill. “Troop” takes Lou’s love for cartoons and feel-good flicks and brings them to life in a That 70’s Show-inspired music video.

DJBooth’s full interview with Tobi Lou, which has been lightly edited for content and clarity, follows below.

DJBooth: What’s your first musical memory?

Tobi Lou: Oh! That would probably be….It’s like blurred. It’s either like a Michael Jackson song, or a Biggie song. I just remember being exposed to MTV and stuff like that. Either seeing *NSYNC, Michael Jackson or like some shit, like Fresh Prince, too. That was really early. I don’t have a definitive musical moment where I was like, ‘Oh, music!’ I just remember little blurs of things.

How did all those blurs manifest into the desire to make music?

I used to rap in class for my classmates and just freestyle and make up funny lines. My thing would just be to try and put my name into every song, my full name. I would just make up silly shit and just always put my name in it. It was really stupid. I didn’t take it seriously until I heard Kanye West. That one kinda changed everything.

What was it about Kanye’s music that made you begin to take your own music seriously?

He was silly and serious, talkin’ about serious shit. Most of all, being weird and true and Chicago. It was just like, ‘Wow, there’s someone from where I’m from, that’s who I feel like.’ I really felt like I was just seeing myself or everything I wanted to be. I was like, ‘Oh wow, okay, there’s a space for the weird people in this industry.’ You don’t have to just be just cutthroat.

Do you stress about trying to fit in?

I came out to LA a couple years ago, and I was sitting at a [record] label, sitting in front of the A&R, my first meeting, you know, just having this A&R tell me, ‘Okay, yeah, we like what you’re doing, we think you’re great. I think you could be huge. What we wanna do is turn you into the next Flo Rida.’ That’s literally the first thing that someone of any importance in the music industry told me after being ignored for so long. I took those words and I didn’t really know what to do.

I sat in sessions, I wrote over David Guetta type beats. I was going crazy. I was depressed. I was smoking a lot. I was drinking a lot. I got kicked out of my mom’s house. All because I was feeling this pressure of being the next Flo Rida, trying to get a placement, trying to do all this dumb shit. I literally just stopped. I ended it. I declined the deal. You know, if I’m gonna do this, I gotta fail it my way. I can’t do it this way.

Which explains your current artistic aesthetic, both in how you dress and your cartoon self. How did you define and then refine your style and approach?

I’ve always loved cartoons. I still watch cartoons to this day. I played semi-pro baseball. It was like professional baseball, where we got paid shit. I was making like $600 a month and living at my parent's house. During the offseason, I would just train and make music.

I love shows and movies in general, but cartoons always had a special place. I just always felt like it’s one of the few things you can make that can connect on so many levels. You can like it when you’re a kid and you can like it as an adult. I just feel like the medium of animation, it just transcends. Everyone can really enjoy it and that’s what draws me to it. I just feel the magic and shit.

The Glassface-directed video for “Troop,” featuring Smino, will be released later today. Starting with Smi, how did you two connect?

I made the song and I just kept hearing the ‘Woowoowoo’ part. And I kept thinking like, ‘Damn, Smino would be dope on it.’ I didn’t really know Smino, I was just a fan. But I feel like every once in a while an artist comes along where I be like, ‘Yo! That guy is dope!’ Before that, it was Chance. I’m a fan of almost everybody from Chicago. Whether it’s Chief Keef or someone like Noname. The whole spectrum from drill to everything.

Smino was in Chicago a lot working at the studio where Chance recorded Acid Rap. I used to go there and work with Cam O’bi. And I knew Chris Classick. He was a fan of me. He said to come through anytime, and he was managing Smino. So I went and sent him a song and I was like, ‘Hey! I’d love for Smino to get on this.’ And I know Smino doesn’t get on many records, so I was cautious. Next day [Classick] says, ‘Yo, Smino loved it.’ He sent back his verse real quick and it was really dope. I hadn’t met him at the time. I didn’t even know him when he made it.

What about Glassface?

We met on a Kanye forum.

Did you meet him on KanyeToThe?

It was called KanyeTalk, I think. And then it was called KanyeLive. And then they changed the name to KanyeToThe. So we met back then. We always stayed connected, but we hadn’t really done work together. And then all of a sudden, we just linked up. Basically, whenever I have an idea for a video, I come to him first because he lets me know if it’s possible. Anything’s possible, but we don’t have money like that. So we have to find creative ways to make shit happen. Whether it’s our creative friends, really talented people, callin’ in favors, just figuring out a way. He’s what propels it or pushes [my vision] to the edge. Even for this idea for this “Troop” video… I fell asleep watching That 70’s Show. I woke up and it was the smoke circle. And I was like: ‘Oh shit, this would be really dope for a video if it was just me and no real people, just animated characters.’

The video is very detailed and uses mixed media, so walk me through the process of putting everything together.

It’s funny because I only know how to make shit at that level, but in the way of just like, scouring the internet. Glassface has a lot of connections with people. It’s really just finding talented people that can make it happen around us and bring them together. Because we had Amber Park, she’s the one that did the Kanye bear. A guy named Ronald did the little animation and he’s from Paris. I didn’t know him before.

No one coming up in Chicago sounds like you. How would you describe this lane you’re defining?

I appreciate you saying that. It’s funny to hear that now because one reason I kinda had to leave, I felt like, was because I didn’t have a voice. I would make a song and they would be like, ‘Oh, this is cool, this sounds like Chance.’ I knew I wasn’t going to make it… You can’t make a true impact if your calling card is ‘Oh, that’s Tobi Lou, he sounds just like…’ You have to be a name for yourself and it took me awhile to kinda get it. If he sounds just like Chance, you’re just gonna wanna listen to Chance. So when you hear me now, you’re getting just me, you can just come to me for that feeling.

How do you define the Tobi Lou feeling?

I still feel like it’s still getting figured out. I’m very inspired by André 3000’s “Hey Ya!” because a lot of people don’t know that that song is like the saddest song in the world. If you listen to what he’s saying, he’s talking about divorce. He’s talking about how love doesn’t last. He even says in the song, “Y’all don’t wanna hear me, y’all just wanna dance.” I thought that was incredible. To hide such pain in such laughter and joy. So it’s something I always aim to do when I have the right track to do it. 'Cause a lot of times, I lose myself in being sad, kinda happy yet kinda sad. Just like damn, what am I? I’m both. That’s why I try to find mediums of a happy-sounding beat so I can get the sad shit out and even vice versa.

What’s your game plan for the rest of 2018?

I’m dropping three more tracks for the next series of Tobi Lou and the "blank." I don’t know what it’s gonna be called yet, but I’m literally making the tracks next week and then dropping them at like the end of March, early April. Then dropping “Numbers.” Then dropping the album.

It sounds like you’re really excited. Are you excited?

I’m excited because I had never put out anything that was considered a collection of songs. I’m excited about the album, but I’m excited ‘cause this year is a very visual year for me. Every song I put out is gonna have a visual. That’s the best part of it for me. For the new artists, I’m trying to be that next generation of, ‘Damn, okay. There’s a new Tobi Lou video out, so what did he do? How did he die?’ I’m trying to die at the end of all my videos somehow.

Transcription by Sara Brown.

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