Windsor is a city that lives in the perpetual shadow of Detroit. You can see the Renaissance Center from the riverfront, a constant reminder of the massive hip hop engine chugging away just across the border. But Windsor has its own pulse. It’s a gritty, blue-collar town where the underground scene doesn’t just survive; it thrives on a diet of industrial dust and sheer stubbornness.
Shawn Mailloux, better known to the local circuit as Mailboxx, is currently one of the hardest-working figures in this ecosystem. I’m sitting across from him, and he doesn’t look like the stereotypical rapper that suburban parents fear. He looks like a guy who’s seen some things but decided not to let them break him. We’re talking about the 2020 outlook, his dual life in a metal band and the friction between street life and art.
The conversation starts where most rap stories do: the upbringing. In a genre that often fetishizes the "struggle" for street cred, Mailloux is refreshingly honest about the psychological toll of a difficult childhood. He isn't selling a lifestyle; he's describing a survival mechanism.
"My childhood was rough, it created a rougher exterior emotionally and a shell which you kind of develop in those situations and I carried that with me," Mailloux says. "There were times that I was involved or on the way to being involved in things that I probably shouldn’t have been in my youth, but I chose to take a different route. I basically tried it all and I thought, you know what, I’m not going to do this, this isn’t me because I don’t feel right doing it. I was a troublemaker growing up and I hung around those kinds of people but my mom was adamant about not hanging around those people but I was just trying to fit in. I was the odd guy out and people would try to get me to do things that were funny. I was really bullied a lot when I was younger so people tended to try and influence me because I was easily influenced. So I was in situations where I could have gone to jail or situations could have happened. I kind of barricaded myself from the age of 15 to 19 and separated myself from the rest of the world."
That self-imposed isolation is a common thread among creators. It’s that four-year gap where the world stops and the internal dialogue starts. For Mailloux, that dialogue was set to a specific soundtrack. While he was barricaded away, the airwaves were dominated by the heavy hitters of the early 2000s.
"Yeah, I was into it from my early teens listening to Eminem obviously, Nelly, Country Grammar, 50 Cent, that was the stuff the people I was around were listening to," he says. "My first influence was actually Tupac and that was my uncle showed me that a long time ago. I was probably 13 or 14 and I was like wow, what’s this? I started listening to DMX from there and I’m this skinny white kid listening to Gangsta Rap and I’m just, this is cool. I was never influenced to do the things that were happening inside of it. For me it was just the poetry. I like the way the stories were put together and I liked the poetry behind it."
It’s an interesting distinction. He wasn't looking for a manual on how to be a criminal. He was looking for the structure of the story. But the writing didn't start immediately. There was a detour to Western Canada first. Calgary has a way of chewing up young guys from Ontario who head out there looking for a fast paycheque in the trades or the oil patch.
"No, I only started that in 2009. In 2009 I wrote my first hip hop song. I was around 20 years old and went out to Calgary to look for work and got in some trouble out there, didn’t like it and came back to Windsor and started writing music," he explains.
The name Mailboxx itself feels like a relic of that era—a play on his surname, Mailloux. It’s a bit on the nose, but in a world of increasingly abstract stage names, there’s something to be said for branding that sticks to the ribs.
"It’s something that stuck to me," Mailloux says. "Someone gave me the nickname because of my last name Mailloux. If you stick the l and o close together it kinda looks like Mailbux. I’ve kind of flipped that and said they call me Mailboxx because I deliver messages with my music."
My childhood was rough, it created a rougher exterior emotionally and a shell which you kind of develop in those situations and I carried that with me. There were times that I was involved or on the way to being involved in things that I probably shouldn’t have been in my youth, but I chose to take a different route. I basically tried it all and I thought, I’m not going to do this, this isn’t me because I don’t feel right doing it.
When I ask him about who he’s watching or who he’d want to share a stage with, he doesn't hesitate. He points to NF. It makes sense. NF has built a career on being the "outsider" who focuses on mental health and raw emotion rather than the typical trap tropes of jewellery and bravado.
"NF, 100%, NF’s real and he’s an artist and I like that," Mailloux says.
And while the global stage is the goal, the local stage is where the work happens. Windsor’s scene is often overlooked by the Toronto-centric media, but there is a genuine circuit here. You’ve got venues that have become the backbone of the underground, places where the beer is cheap and the sound systems are loud enough to rattle your teeth.
"Yeah, there is. There’s a lot of talent out here," Mailloux says of the Windsor scene. "There are a lot of us here that are trying to do something so I think the scene’s pretty good. If you come to an underground show there’s a lot of sport and camaraderie, a lot of friendly people coming together to make music and it’s pretty cool. Rockstar Music Hall does a lot of shows, The Backstage, Blanche has had a couple shows and The Sportsman’s Club has shows."
But here is the twist in the Mailboxx narrative. He’s not just a rapper. He’s a metalhead. And not just a casual listener—he’s the frontman for Devilz By Definition. This duality is where things get interesting. Most artists pick a lane and stay in it for fear of confusing their audience. Mailloux seems to relish the friction between the two genres. His recent track, "Really Nice Guy," is a direct challenge to the "tough guy" posturing that dominates both hip hop and metal.
"Yeah, well music is energy delivered to people through vibrations and sounds, so there’s enough of it out there that’s rebellious and people that are going against the system and doing things that they’re not supposed to, giving a mentality of a certain character and I’m the opposite," he says. "Around the same time I started writing hip hop in 2009 I joined a metal band called Devilz By Definition. I took an 8 year break from hip hop to focus on that band and that’s where the Mailboxx persona was born. I was more typical of what you would expect from a rapper, cocky, arrogant, what I thought a rapper should be when I was younger. Over the course of that time I grew as a person and Devilz By Definition helped to shape me into Mailboxx. Mailboxx the persona is owned by Devilz By Definition as well as Mailboxx Music but the purpose is the same, to deliver messages by music. I’m doing exactly what they say you’re not supposed to do. If you’re a rapper you’re not supposed to be out there that way, you’re supposed to be tough and have an image but like you know what, I’m going to be myself and I’m just a really nice guy and it’s true. And when I say that I mean that and everyone who knows me personally knows that. I figured if I put it out there like that you can either love it or you can hate it, there’s no in between."
The "nice guy" angle is a risky move. In rap, vulnerability is often mistaken for weakness. But Mailloux is betting on authenticity. The origin story of his metal career is pure Windsor: a roofing crew.
"In 2009 I had joined a roofing crew and that’s where I met Bruce (Munro) who’s the lead guitar player of Devilz By Definition and he said they needed a drummer," he says. "I said I’ve got experience, I’ll go try out and I became their drummer and about three and half years later I transitioned to vocalist."
It’s a hell of a jump—from the drum throne to the centre stage mic. It requires a different kind of ego, or perhaps, a lack of one. He’s still very much in the thick of it with the band, balancing the aggressive, guttural demands of metal with the rhythmic precision of hip hop.
"Yes, we’re actually in pre-production for our second full length album and we’re going to tour this July so I’m doing both right now," Mailloux says.
His role in the band is specific. He’s the lyricist, the guy who takes the sonic chaos of the guitars and gives it a narrative arc. It’s a collaborative process that stands in stark contrast to his solo work.
"I mostly just write the lyrics," he says. "They put the songs together and then I take the feeling that they’re expressing in music and give it a title. Once I have a title I have a topic and I write the lyrics around that."
We talk about the current state of the industry, specifically the blurring of lines. Lil Nas X and Billy Ray Cyrus might seem like a gimmick to some, but to Mailloux, it’s a sign of where things are heading. He’s planning on pushing that envelope himself, mixing the aggression of metal with the bounce of trap and the soul of 90s hip hop.
"I think it’s great! I think all music is meant to be blended together," he says. "It just has to be done properly and delivered in the right format in order for it to be received properly. I’m planning on blending metal with trap and 90’s hip hop for my second album. I’ve been writing and I’ve got my pre-production with the studio I’ve been working with and I’m about to go record it actually. It’s going to be out in the next couple months, maybe sooner than that."
The workload is staggering. Two albums, two different genres and a DIY ethos that would make most indie artists sweat. Mailloux isn't just writing; he’s producing. He’s the guy behind the board, the guy at the piano and the guy editing the video. It’s a necessity in the modern era if you want to keep the lights on.
"I’m putting myself out there in the music industry in as many avenues as I possibly can," he says. "I produce, I play piano, I make beats, I play drums, I do scream vocals, I do hip hop, I write poetry, I edit videos, I do everything because I want to make sure I’m equipped with all the tools I need to succeed in the business. The last three years I’ve been working on producing. The album “Going Postal” I produced myself start to finish, I just had someone else mix it. So through producing I’ve learned piano and trap drums and I’ve learned how to mix and engineer. So I’ve released my own music on Sound Cloud that I’ve mixed myself and then I release albums every year for Mailboxx. I like this because I’m in control. When I’m with Devilz there are 4 other people and things don’t move the same way because there are other people to consider. I just released a new song on Sound Cloud every Monday for 17 weeks straight."
That 17-week run is a testament to the "grind" culture, but it also shows a musician who is terrified of standing still. In Windsor, if you stop moving, the rust sets in. Mailboxx is making sure that doesn't happen. Whether he’s screaming over a double-kick drum or laying down a verse about being a nice guy, he’s delivering. And in this city, that’s the only thing that matters.
