“Who’s Sean Leon?” is a question that’s become increasingly harder to answer these days. I mean, who isn’t Sean Leon? The Toronto creative is many things at once: a rapper, a songwriter, a director, an iconoclast, the visionary behind PUPIL INC., and the star of our lookbook for adidas’ new Stan Smith. You can now also add another descriptor to that list: a Grammy Award winner.

In March, Leon snagged his very own gold-plated gramophone for his writing credits on Kanye West’s Jesus Is King, which won the award for Best Contemporary Christian Album. Besides being a nice addition to his CV, the artist says collaborating with Ye in the studio lit him up in the best way possible. “Working with Kanye West, I heard things in the studio that were so outrageously fire that my perspective changed and I started reaching even higher,” he shares. “I thought I had always been innovative sonically, but, you know, he is who he is for a reason. And it touched me and affected me deeply. So I’ve just been in pursuit of creating undeniable sounds.”

So, if you’ve been waiting impatiently for Leon to drop new music, you’re in luck: he says he’s got three albums “just sitting on my hard drive, marinating.” The first one he’s rolling out, God’s Algorithm, is an audiovisual experience he began working on when the pandemic first hit. Already known for his chameleonic take on rap and R&B, the artist says it sounds world’s apart from anything he’s ever released.

But what Leon’s been cooking up during lockdown extends beyond music—it’s a full-on movement. After navigating Toronto’s arts scene sans a label since his 2013 debut Ninelevenne, The Tragedy, he’s gathered enough intel to truly follow through on the goal he set for himself from the start: to build a hub that will allow creatives in Toronto to collaborate and thrive as a whole, in lieu of a local arts infrastructure that’s barely there. PUPIL INC., his independent cultural organization, is precisely that—and it’s got a swath of ambitious projects on the way, from films to a fashion line to innovative concert experiences.

We sat down with Leon to chat about his new project, the state of Toronto’s creative scene, and why he wants to plant the seeds that will allow the next generation to feast.

Sean, what’s something you’ve been thinking about lately?
I mean, what not? I guess I’ve been thinking mostly about these projects I’ve been working on. I’m thinking about how I’ve really been staying low the last two years, restructuring on a business side, and bringing in the experts to really help us create and build on the success we’ve already had. But then also artistically, I’ve been stepping out of my comfort zone and continuing to increase what I think my ceiling is through various projects in different mediums. I’m returning to a state of childlike wonder when I approach my art, specifically detaching from personal prestige and awards and money and remembering that the cathartic moment that comes from having a new idea and executing it is what I loved the most. Falling back in love with life, man, is pretty much where I’m at.

You were telling me that working with Kanye West on Jesus Is King really shifted your perspective. Surely, that must’ve been a surreal experience. Talk about the impact it had on you.
College Dropout is the first album I ever bought. I’m from Toronto, so I don’t really brush shoulders with legends like that. I met The Weeknd but only because I was in Calabasas with Ye in the studio and I probably never would have otherwise, because I don’t know… Toronto’s interesting; it’s pretty difficult here to forge relationships artistically with people who are much more established than you. But I was talking to a classroom over Zoom the other day about the music industry, and I was telling them that early on, a lot of people are going to tell you what you’re trying to accomplish isn’t sensible and it’s an impossible feat. And as true as that might be from their perspective, if you can channel that, not internalize it, but use it as fuel to do something that somebody said was impossible for you, you will gain the confidence to do it again. And slowly over time, as you have those conversations in the mirror, you visualize, you manifest, and put in the work, the universe will reward you. I’m a firm believer in that.

So, working with Ye, that’s really what that gave me: just the confidence that I can do anything, you know? Literally anything. That’s why he would run for president. He genuinely felt like he could have been the president. And who knows, maybe he will be. Maybe I’ll be prime minister one day. My dawg will be on my cabinet. We’ll fix things, because I bet you we could do a better job than what’s happening right now. [Laughs.] Time will tell.

“Working with Ye, that’s really what that gave me: just the confidence that I can do anything. Literally anything. That’s why he would run for president. He genuinely felt like he could have been the president. And who knows, maybe he will be. Maybe I’ll be prime minister one day.”

Well, Kanye’s obviously accomplished things in the fashion world with Yeezy that people told him he’d never be able to do. I know you’ve also got a fashion line you’re developing through PUPIL. How would you describe your style philosophy?
I would say it’s a mixture of the Seattle sound, ’90s grunge, with utilitarian, very functional apparel. There’s elements of vintage hip-hop sprinkled in there. I’m very inspired by the Kurt Cobains and the Sub Pop movement. But I’m more focused now on developing our product and investing the money into that, rather than going to a designer and putting up thousands of dollars for a piece that everybody else has. We’re finally developing products from the ground up, from selecting the fabric to the cut to the sewing. So I’m really excited to wear things that are tailor-made for me. Even the clothes that I’ve been working on so far, I really have had no intention of putting them up for sale. This is just for me to wear because it feels great. Of course, I’d love to get to a position, too, where I could partner with adidas and scale up what we’re doing already, because we have ideas and visions and a lot of great minds and people that are dedicated to that. 

I clocked that God’s Algorithm hoodie you were wearing on social media. It looked tough!
Yeah, that’s one of my pieces. I designed that with Ryan Davis. The image on the hoodie is actually coded in binary and there’s a secret message that I haven’t released yet. It ties thematically to God’s Algorithm, which is the mode I’m in now. When I put it out, it was just to show people some of my work, and a lot of people started throwing their money at me. But I’m not really interested in a bunch of people wearing this hoodie yet, to be honest. I like being the only one with it. Actually, I have a few in my closet. You ever see cartoon characters, when they open their closet and it’s the same shirt? It’s like the same thing. It’s my Bart Simpson. 

“There is definitely a disconnect between how talented people are here and how they should be praised and given their flowers.”

Tell me about God’s Algorithm. What does that mean to you exactly?
Well, it’s a project I started at the top of quarantine. So right before COVID hit, we were in the House of Leon shooting a film and working on another album called Full Technicolor, which is completed now. That was such a collaborative process. All my homies would sleep there in the house. We’d wake up and cook and eat together, then cook up again. It was awesome. But I went from that to immediately getting put back into my apartment and having to work again so singularly, by myself. And I started becoming curious with that relationship to my loneliness and how it related to technology. Was technology helping my loneliness or was it feeding it? Basically, it poses the question in 2021 and beyond: When something happens, was it God that made it happen or was it the algorithm?  

So, the project is basically a love story between artificial intelligence and the user. I’m not going to say from whose perspective, because that’s part of the conversation. But it’s something people will need to hear and see and be given an all-encompassing reality around. We’re just building the world in which that music takes place now. I have people who specialize in user experience, augmented reality, and virtual reality collaborating with us making this possible. And sonically, it just sounds like none of my other records. That part is going to drive some people insane, but other people are going to love it. I think it’s going to open me up to new audiences.

When you work on projects with PUPIL, is sustainability and the future of the planet something you guys think about?
Of course. I don’t like to leave any space worse off than when I found it. So, any initiative we’re doing, anything we’re taking part of, we’re always very concerned with its environmental imprint. We try to leave as little of a mark as possible. We’re really following the experts who have already done such a great job and led the way in that. We’re remaining in a state of learning, because the information is changing every day and we don’t ever want to lock in a way of thinking—we want to be open to changes. We shipped our first hoodie in a biodegradable material because we didn’t want to add to the landfills. It’s harder to do at our level, but there are still things that can be done and we’re mindful of it. As we grow, it’s something we’re not only going to take into consideration, but act on.

That idea of leaving a space better off than when you found it—it sort of ties into your approach to the Toronto arts scene too, doesn’t it?  You’ve long talked about how there’s not enough support for talent here, at least in the hip-hop and R&B space, and how your goal is to fix that. 
A thousand percent. I mean, PUPIL is designed to sort of house everybody. I love the idea of putting together all of these GOATs, all of these titans, all of these underappreciated acts under one roof and just having a conversation. I’m a fan of and have collaborated with so many of them, and I know the little thing they’re missing. They just aren’t being offered the opportunities and the platforms to grow organically. And it’s very competitive and things are changing every day. There’s new content every second; since we started this interview, probably like a thousand things came out.

You know the analogy of five fingers versus a fist? There’s a lot of that in Toronto—a lot of little fingers that are trying to make an impact. And it would be much more impactful under one roof—and I mean, like, extreme impact on a global scale. When I’m in Paris, they’re very curious about what’s going on here. But they only have OVO or XO to look to, and beneath that is world-class talent that just hasn’t organized yet. There is definitely a disconnect between how talented people are here and how they should be praised and given their flowers. And that’s beyond music. If you look at the amount of successful exports we’ve had—from models to athletes to producers to designers to fashion houses—there’s a disconnect because there is so much talent here, but we haven’t really been able to empower them or create success stories. 

And why do you think that is? 
I mean, part of it is gatekeeping. The old guard is still very much in control. I’d love to see younger minds and fresher blood in these corporate positions, because I think they’re more in tune and more willing to take the gambles that are necessary for change…. I think, too, Toronto’s fairly young. The renaissance really started in 2009, post-So Far Gone. And so artistically there was a boom, but infrastructure-wise not much has changed. It is very much the same people in the same positions. And I think their biggest concern is selfishly maintaining their comfort in the status quo. I’ve always said the status quo is ground zero. We shouldn’t be comfortable or satisfied with it because it isn’t working. So that should be where we’re starting to build from. That’s what we’re trying to do.


Photographer: Katherine Holland
Creative Director: Alex Narvaez
Producer: Mollie Rolfe
Stylist: Shirin Nadjafi
Makeup & Hair: Sherlyn Torres