Killy’s Ascent to the Top of Rap Is a Matter of Perfect Timing

It is early September when I enter the lobby of a downtown condominium near Lakeshore in Toronto after scarcely escaping an onslaught of down-pouring rain. It is here where I arranged to meet Killy, the East End rapper whose music—by strange coincidence— is sonically complementary to the dark grey setting of the afternoon. To put it in his own self-righteous words, right now “is fucking ‘Killy Season.’” Chuckling, he plops himself down onto the couch beside me, proceeding to fumble with a video game controller and follow the prompts that lead him to play. “It’s just my time,” he answers assuredly, when I ask him what “Killy Season” even means. “It’s the season… the season is upon us. He laughs again playfully, but he isn’t joking. ‘Tiiiiis the season.”

In truth, if it’s anyone’s time right now it’s the 20-year-old artist who has a wealth of reasons to believe his confident proclamation. Earlier in the summer, he opened up for the western leg of Lil Pump’s tour and was brought out on stage during Jazz Cartier’s show in Vancouver. “[Jazz Cartier] performed at Rifflandia Festival two years before and I got detained sneaking in. Then two years later he brought me out. It’s kind of cool.” When we chat, it is a day before he leaves to Los Angeles, to perform at Day N’ Night Fest while his newest track, “No Romance,” premiered on OVO Sound Radio. Wildly, he reveals he conjured up all of his musical success in nearly less than eight months.

“My life has changed… my life changes everyday. It’s just going so fast,” he says. “I recorded like three songs in one studio session in 2015 and I released those three songs throughout 2016. And then, I didn’t release another song till the year after. So I had these three songs that I recorded the year before representing me when I was meeting all these new people, and like people were fucking with it. But meanwhile, that was my old music.”

Toronto’s Killy soared to ascension after uploading a music video for his first song, “Killamonjaro.” The video, which now boasts over seven million views on Youtube and 2.2 million plays on Soundcloud, was birthed from spontaneity. Shot at a real-life house party with his friends, the video opens up as Killy emerges from behind a garage door, backlit by white light. He looks like a character from The Matrix—mysterious, dark, and brooding—enticing his listeners to join him on his quest. “I can introduce you to this life we live forever,” he raps slowly, atop a beat that is propelled forward by what sounds like enchanting, ethereal chimes. “[The video] was just to capture my lifestyle and that was my lifestyle at that point,” He says. “It wasn’t like, ‘Oh “Killamonjaro” music video. Everyone pull up.’ We just did it and got it on film. I just wore cool clothes that day and shot the video.”

Londoncyr, who’s been in the room for the duration of our chat and is producer, audio engineer and DJ to Killy, chimes in to interject his own personal anecdote about the song. “I’ve known Killy for a long time, and I had just moved [to Toronto],” Londoncyr says. “And Killy said to me, ‘Yo I just quit my job, I have like 300 dollars. I’m going to just pay this video guy and see what happens and hopefully something comes out of it. So I went to the party, and then this music video happened and it just turned into what it was. You gotta take risks.” “You have to get uncomfortable to get comfortable,” Killy adds.

Right now, the rapper oscillates between the two—uncomfortability and comfort—as he grapples with his increasing popularity and the qualms that come with the territory. Outside, the rain beats down dramatically onto the large window panes in the living room, and, poetically, he points to acknowledge, “I feel like that right now. I feel like I know I’m heading on the right path, but it sometimes feels wrong. If that makes sense,” He continues. “Which it probably doesn’t, but it does to me. I know this is the path that I should be going on, and I’m doing everything I’m supposed to be doing. Everything is good and right but sometimes the cons outweigh the pros, even though it looks beautiful, type thing.” Killy eventually decides his game is too distracting. Turning it off, he proceeds to explain where his writing process stems from and the dark nature of the content he raps about. In truth, representation is chiefly important to the young artist, who being of Bajan and Filipino descent, struggled throughout his childhood with under-representation.

“I was raised in a Caribbean household. My whole family is dark-skinned. Growing up, you get to a certain age where you start realizing things. Like, that’s my family—my dad, my brother, my sister and I would have kids coming up to me being like, ‘why don’t you look like them?’” he reflects. “I never really thought about why I am in this Francophone school where every class is in French, announcements are in French, but I’m the only kid in this whole school that isn’t French. Or like, why am I this kid in Victoria, where it’s a super, predominantly Caucasian, suburban culture that I really just don’t identify with. But I was just forced you know, to be around that. I definitely grew from it and became well rounded and versatile.”

In his second track, “Stolen Identity,” the Vancouver transplant—who moved back to Toronto with his family towards the end of high school—reconciles through song with not looking the same as his family members and peers, while simultaneously asserting that he is steadfast and assured of who he is now. “Music is literally therapeutic for me,” he says, though he didn’t always know growing up it was the avenue he was going to take. “I knew I wanted to be influential, and I was good at music. Then my family moved back to Scarborough and I just went fucking crazy with it. I touched down in Toronto and I was like, finally the shackles are off. Let’s get it.”

Killy’s entry into the music scene thus became an extension of his social life, as he ventured into the burgeoning downtown arts and culture scene. “I started going to parties with like-minded people and started meeting a lot of the creative people in [the city]. I kind of built a little following before I dropped a couple songs on Soundcloud and began doing little shows and stuff. But even before I got booked for those shows people knew me and would be like, so just making those connections before my music was even a thing, was probably my first step into the scene. I realized that there’s no point of making really good music if no one is going to listen to it. So I had to meet the people that could push it. It all happened organically.”

Timing, for Killy, is everything. A tedious perfectionist, the fans who feel that they are hard-pressed to find more than four songs by him online, is an ode to his unwavering love for writing and for presenting songs with a strong, concise concept, which he admits takes him longer than most. “For me it’s just choosing the right words to say what I want to talk about is the hardest thing. Or, I’ll have something I want to talk about, but if I can’t say it with a certain amount of syllables or say it the way I want to deliver it, then I have to find a new concept. It’s almost tactical. I build songs, more than I just go and rap them.” It may seem strange to some, that prior to “No Romance,” Killy has been staying eerily low in terms of putting out music. He could have, very easily swiveled off the axis that was “Killamonjaro,” “Stolen Identity” and “Distance’s” immediate success to propel himself further into the hip-hop stratosphere. Alternatively, he prefers instead to strategically build up momentum with his cult-like online fan base for “the perfect moment,” as he likes to put it. However, “No Romance” was worth the wait, and a perusal through the comments underneath his video on YouTube reveal that fans feel the same, though the demand for him to release more songs is imminent.

In a strange turn of events, the sky clears up dramatically and the sun peeks through the faint remnants of clouds, almost in tandem with the light-hearted turn our conversation takes. “I’ve been discouraged, but I’ve never been uncertain. I was always like, “Oh fuck how am I gonna do this? [I know] I’m gonna do this, but how am I gonna do this? I was never discouraged to the point where I was like, ‘What if?’ It was always just like ‘when?’ ‘where?’” Killy says. Londoncyr then reminds him, “You were always certain. I found this Facebook post actually where you said something about it.” Killy begins to laugh, recalling, “I posted on his Facebook wall… I think he uploaded a beat onto YouTube or something. I was like “Yo, this shit is crazy man, give us, like two years. Get with it or get left. Some shit like that. I would always be talking like that. I still deadass talk like that.”

Our conversation about music seamlessly bleeds into a much more spiritual one, and the three of us—three strangers—sit there, each offering our own opinions about our perspective on life and the future. “If I feel discouraged, I still don’t show it or put that energy into the universe,” Londoncyr advises. Killy nods his head in agreement. It’s philosophical advice, of the 21st-century-Millennial-instagram variety, but it’s not exactly bullshit either.

Andrea is on Twitter.