How two 23-year-olds put together Canada’s biggest underground rap fest

It was three days before First Class Fest in Toronto was scheduled to kick off when co-founders Jake Pretorious and Leo Strang got the call: Nettspend was dropping out. He wasn’t the first artist to cancel their set – Che and Black Kray had canceled earlier in the week – but Nettspend was scheduled to play a major set the second night of the two-day festival, leaving the organizers in a serious bind.

“You can do everything in your power from a legal and contractual standpoint, from an effort standpoint, but sometimes people just don't want to do things, for whatever reason,” Strang tells The FADER six days later. “We literally got that Netspend call 20 minutes before he made his announcement [...] We were immediately just at the drawing board thinking of replacement artists.”

Ultimately, Pretorious and Strang decided to ask Day 1 headliner OsamaSon if he would perform a second set. “Him and Nett are really the faces of this new underground scene,” says Strang. “So there wasn't really a replacement out there that we felt was fitting besides doing Osama again.” The star of The FADER’s recent documentary Psychotic performed a unique setlist mainly featuring leaks from his previous eras ahead of Lucki’s closing performance.

In the four years since Strang and Pretorious put on the inaugural First Class Fest, the Canadian showcase’s reputation and scale has only grown. The FADER caught up with the 23-year-old festival cofounders to chat about the beginnings of First Class Fest, Canadian rappers to watch, and their favorite memories from the festival.

How did you guys meet?
Leo: Me and Jake met like literally almost four years ago, because our first festival was 2022, not long after we met. But we met when Playboi Carti was supposed to perform in Toronto, and he couldn't make it across the border. And one of our mutual homies threw a— pretty much, like, if you had a ticket to Playboi Carti, come pull up to this party, and we're just going to turn up. We met briefly there, and Jake, at the time, was managing a studio on Queen Street in downtown Toronto. I literally think I pulled up on him the day after and just chopped it up 'cause he was managing a bunch of artists. I was doing YouTube ads for artists, so I was trying to get clients through him. And we ended up going on tour that same week, just a local college tour here in Ontario that was literally an RV bus. There was 10 of us on an RV performing in frat basements in Guelph. That's where we really, really locked in.

When you think about that first festival you guys worked on together in '22 versus where you guys are now, what do you think has stayed the same?
Jake: One thing that I was going to say gave similar vibes to the Parkdale Hall fest was the hecticness of it backstage. That was similar to the first one, but I feel like that first one really trained us for this. Like, we were ready to have that stressful moment backstage and still make it happen,

In the Canadian market, I feel like you guys don’t have a lot of options for underground rap shows.
Jake: No, it's true. There's not much. That's another reason why we want to do this and why we're building this at the moment, because we want to growthe underground scene in Canada. 'Cause there's so much talent in Canada, all over Canada, but there's not a lot of spotlight on it, which I think will change in the coming years.

Who are your favorite up-and-coming artists from Canada that our readers should know?
Jake: Not talking about the artists on the lineup, 'cause obviously the artists or the openers on the lineup from Canada, those are all artists that we've been working with, and we've always liked them. But there's a few artists off the lineup that we didn't add... Personally, I like Amo, Pnkrok, Bronclair... Um, yeah, there's a few. Yurms is another fire artist. There's a bunch of Canadian artists right now doing their thing.
Leo: Offgrid is fire, who performed in '23. Amo's definitely one we champion. And then yeah, all the artists on the lineup we particularly fuck with, like Jahsh, 10kmoss & Wavy Jackson, Sorisa, Sayso...
Jake: Katozai! Those are all Canadian artists that we rep really hard.

When did planning for this year’s festival start? What did that process look like?
Leo: Just the opportunity to get this venue was a little bit of a fluke. The biggest show we've done to date was 1,500 people. So, for us to take this on was like, "Okay, I think we're ready, because we've been working in this genre for three years. I think we have the relationships to book a lineup that's of the caliber that can sell a room like this."
But it was also daunting at the time. But we started like June of 2025, so 14 months out from when the festival actually took place. And it was a crazy, crazy experience. It was really our first time doing negotiations at this level – like, the Lucki negotiation was crazy. Took maybe six weeks to lock that in, from when we first hit them up to when it closed. We had booked Lucki at the time, Nettspend.
That day was fully booked, and then the company that we partnered with for this was like, "Hey, Friday is open as well if you guys want to make this a two-day festival." And we were like, "Okay, if we can get Osamason to headline it, let's do it. And if we can't, let's just make it a one-day festival." And we were able to secure him as a headliner, which was exciting. So then we were like, "Fuck it, let's book the rest of that lineup as well." So that was another crazy thing. But it probably took us three and a half months to finalize the lineup.

What was your favorite interaction that you guys had backstage this weekend?

Jake: Mine was OsamaSon showing love. From Day 1, even before coming to the festival. He called Leo the day that the replacement had to happen. And then when he showed up, he just shows amazing like—he shows so much love. Every time I've ever done a show with OsamaSon, he takes the time to talk with us, and show how appreciative he is of us. So my favorite moment was definitely just talking to Osama. Leo, you're probably going to say the Lucki one.

Leo: Well, I have two, I have two. My first favorite one was on Day 2, during Apollo Red's set, probably a thousand kids rushed the pit, like jumped the fence and rushed the pit, and the police wanted to shut the show off. After quite a few conversations backstage, we were able to have them hold off for a little bit. And we had Osamason's DJ go out and kind of say, "If you want Osama to come out, if you don't have a yellow wristband, you got to get out." And some people started going out.

It eventually got to the point where I went up there myself and just was telling people to get out of the pit. And it was the biggest adrenaline rush I've probably ever had in my life. But when I got off the stage, I was having probably what's called a panic attack. Like, I was just having trouble breathing, and I felt really hot. I was very stressed out. So I walked out the back of the venue and just took off my shirt, 'cause I was like, "I need to get some air." But I saw Osama and his whole team – I was like, "Okay, I'm the organizer of this event, I need to be professional." So I kind of walked to the side to get some air. And then I just heard like, "Leo! Leo!" And I turned around and it was Tezzus. And he just came up to me, he's like, "You did that shit, boy! You got it back!" And the fact that he saw it and recognized in that moment that I probably needed a little bit of a hype-up was cool.

And then, yeah, my second favorite moment was like, I needed a photo with Lucki. The only thing I wanted to get the whole festival was a flick with Lucki going like this [makes “shhh” hand gesture]. It was very hectic when he showed up 'cause it was right after that whole thing, so there was a lot of police, and he also had to catch his flight not long after his set. So as he was walking off stage, I just yelled at him, "Yo, I run this festival, I want to get a flick!" And his manager was like, "No photos! No photos! We're going to the car." But he stopped and me and Jake got a photo with him, which was lit. And that was probably my second favorite moment.