Toronto isn’t the greatest city on earth if you’re looking for participation. The citizens of North America’s fourth largest metropolis are perfectly happy to just stand by and watch, a fact most astutely observed by artists who often perform to a venue where a majority of the patrons line the perimeter of the space, happily nodding their heads along to the music. It’s a city of observers who appreciate things from a distance, unready to jump in until they’re sure that they won’t be embarrassed by a show of positive feedback. And it’s why Redway is about to board a plane to New York for a pilgrimage he’s made dozens of times in the past four years.
This will be one of the few trips where the 25 year old rapper, born Shane Redway, will be flying. He’s more accustomed to taking the 12 hour trip on the Megabus in order to stay at his aunt’s house for a few months, a ritual he’s been partaking in since 2010 when he decided that he had more to learn from the Big Apple than Hogtown. “People in Toronto always had this perception of me as a cocky, arrogant rapper, and people in New York just thought I was nice with it, so obviously, I stayed in New York more.”
Despite his young age, the Jamaican Mississauga-native has been rapping for over eight years. He cut his teeth battling teens from around Mississauga at events organized through Facebook and held at public spaces like the town’s city hall where the crowd in attendance often numbered in the hundreds. Redway’s biggest hit came when he recorded a single inspired by a Toronto nightlife networking site, tdotwire.com. Titled “TDotWire Freak,” the song garnered local radio play and made Redway into a sort of micro celebrity upon its 2006 release. Leveraging the success of the song, Redway got to working on a debut mixtape, a project that would be hosted by Big Page and titled Rapper Guy. Upon it’s release and lukewarm reception, Redway got a taste of the Toronto politics that would go on to sour his mood for years to come when Big Page had begun to tell people that Redway paid him to host the tape. The rumour hurt Redway’s credibility, but he understood why people weren’t on his side. “People started to say, like, ‘Redway’s trash, he’s not that good.’ But I won’t lie to you, I never had substance then.”
In 2010, Redway started the ritual of shuttling to New York for a few months at a time. Living in New York helped him get away from the politics, but it also helped him learn some lessons from the school of hard knocks. “I thought it was a struggle here, but down there, it’s hard to survive. You need to find money to find time to make music. You got a job, and you got to make enough so you know the rap shit is going to work. It’s real. I’ve been to the cribs of grown ass men, 27, 28 year old men, and those places are like hole in a wall. I went over there and I seen niggas with mattresses flat on the floor, clothes stacked to the side. I wasn’t musically inspired when I was in New York, as much as I was inspired by the determination, of their grind. It really helped me grow.”
Upon his return home, and fueled by the hunger he picked up Stateside, Redway aimed to release a second mixtape. The project was aptly titled Border Living, and though it was better received than Rapper Guy, it still didn’t seem to connect with a local audience that was now paying attention to a former Degrassi actor. Redway moved home to Mississauga, choosing to buckle down and placing his focus on making music. He recorded Live Free and released it in April of 2013, but again, the album failed to connect with the Toronto audience. The city just didn’t seem to be interested in a rapper whose only talent was rapping.
But one track off Live Free, the prophetically titled “Progression,” was produced by a long time family friend who saw potential in Redway that had yet to be tapped. Ebony Oshunrinde, better known to the world now as Wondagurl, had known Redway since she was six years old through her older brother, but once they started to work together in an official capacity, their musical chemistry became instantly noticeable. Soon, Ebony insisted that whatever plans Redway had for the project after Live Free, she wanted to be a part of them.
Now, preparing to release his fourth mixtape in eight years, Redway’s Years Ahead will be produced entirely by Wondagurl. It’s unknown if this project will be the one to finally bless Redway with the respect of his hometown, but during our conversation, he received two phone calls from management companies—one based in Atlanta, and the other in Los Angeles. If the city wants to stand around and watch politely, Redway has no qualms with taking his talents south of the border. We spoke to the rapper before he boarded his flight to find out why he works so well with Wondagurl, the difference between Toronto and Chicago, and his plans for the future.
Noisey: What’s your heritage?
Redway: I was born in Toronto – Humber River Hospital at Jane and Church. My parents came over from Jamaica in ‘78 or ‘79, but for some reason they think they’re still from Jamaica, and they operate as if they were home.
When did you start getting into music?
I remember my brother playing like Bounty Killa CDs when I was a kid, and I listened to Vybz Kartel, old Vybz, like when he was actually black. One of the first rap songs that I heard was “Today Was A Good Day” by Ice Cube. And then the next song after that was “Hate Me Now,” and I used to get scared when I heard that song. When I was younger, I used to play drums. That’s how I got into music, I was really good at drums and they asked me to play at church when I was 11.
When did you start working on making your own rap music?
When I turned 12, I started recording. A group of friends made up a little group called Sheridan ENT. There were like 8 of us, and we would just record in bedrooms and make tracks. One of the homies’ moms would leave for work at 8, and we’d be at his house at like 8:30 for the whole summer, like 4 days a week. That just led me to continue rapping and making tracks. At the time I was just making just song, but I wasn’t putting them anywhere. I was mostly just rapping over industry beats, but I remember that the first original beat I rapped on was a Rich Kidd beat back when I was in the eighth grade. He was one of the first local dudes really into sampling.
Were you influenced heavily by any specific artists?
The three craziest rappers ever, to me, are Ma$e, Juelz Santana, and Jay Z. I love New York in terms of the culture, that late 90s cultures, that whole fly arrogant shit, that “I rap the best and I gotta fucking sick team” type of shit. I love it.
What did you do after Sheridan ENT?
I started to get a rep from battling. After the Sheridan ENT shit, I was a battle rapper. I was just battling niggas in high school. We would go to different high schools, and just battle. It’s a chick’s birthday at St. Francis Xavier, and there’s a house party in Sauga, so 20 niggas are gonna ride through. We’d go to these parties, all different cars, and we use to just roll up and take their bitches and shit. We thought we were the fucking realest niggas, we were reckless in high school. There would be rappers from the rival schools that rapped. So they’d be like “yo lets fucking battle right now,” go to the back and there’s like 40-50 people out there, just battling. I was amazing at freestyling, because I used to watch Smack DVD and think these guys are freestlying, and I got inspired. I found out those guys were actually writing their shit down later, but I wasn’t writing anything.
Tell me about the Mic For Your Life freestyle competitions that were organized through Facebook and would take place throughout Mississauga.
When I went to Mic For Your Life, which was an intense freestyling competition, everyone in the city was in it. Organik [founder of the successful King of the Dot franchise] was in it, battling. Bishop (Brigante) told me, ‘everytime you battle, pre-write your bars, memorize them, and then go in there so it’s like you’re acting out what you’re saying.’ When you’re freestyling, you’re thinking too much. When I was battling Stack Doe, there was like 300 people outside of City Hall in Square One! Johnny Rocks, JD Era were there. Everybody came, it was like “fuck, Red’s battling Stack, this white guy vs. this black guy.” I never wrote anything down at that point. When I battled Stack it was mad iffy, but I held my weight.
How many battles would you say you won during your run?
Honestly, I’ve participated in a good nine semi-pro rap battles, and I’ve won like seven of them. When I battled Arcane, he beat me at the Mic For Your Life competition, he washed me on that.
How did “TDotWire Freak” come about?
DJs at the clubs in Mississauga were playing my dubs to like, “This Is Why I’m Hot” clubs and at parties where Future the Prince was spinning. Future came up in that element, those dancehall, all-ages parties, I remember he had this blue stripe on his mic thing with his logo–an ‘F’ with a crown on the tip. He’s one of the OGs of the party scene when I was young, him and DJ Kicks. That’s how I got poppin too, I would do dubs for DJs, they’d be like “you’re dope, I’ll play the dub.” So I was 17, in the club hearing all the shoutouts, and the owner of TDotWire, Starchild, he hit me up and wanted me to make a track. He knew me off the battle scene, saw me in the club, and knew me from the DJs at Club 108 in Sauga.
What did growing up around a bunch of people who pursued music as a full-time job?
I used to see people that did it, and then they just stopped. That’s my fear, to this day, that I would end up doing something other than music because rapping didn’t work, or something deprived me from chasing or fully achieving what I am supposed to as a rapper. Because end of the day, I’ll see someone that stuck with it and I’m like “oh fuck, they did it.” When I saw Drake first get on, and when I saw Tory Lanez, I was like, I know these niggas. These niggas are actually making it. They’re in the game making it. We used to call each other and send each other tracks and shit.
Why did you start going to New York?
When I was getting plays off “TDotWire Freak,” people started hating on me. i was this 17 year old kid who was at the clubs, and they were just looking at me like “what the fuck are you doing here?” I’m not going to lie, I didn’t help, because I was a really cocky dude. I thought I was the best, I still do. But my attitude made people hate me.
What’s the main difference you noticed between Toronto and New York?
Toronto’s the screwface capital. When you walk down the street in Toronto, you have that arrogance to stare at someone like “what the fuck you looking at?” If that happened in New York, you get shot or killed, or at the very least you’ll get hit with the “why the fuck are you staring at me, I don’t know you.” We do it here because its arrogance: I’m bigger I’m badder. But down there, it’s like, if I don’t know you, move it.
Did you notice anything change in Toronto after you came back?
Niggas in Toronto do certain thing just to make it sound cool, just for the element. Like “yo lets just stay in the studio till 6 am,” just so they can say they did that. When I come back to Toronto that’s why I can look at a lot of niggas and be like yo, you guys really don’t understand the essence of the grind. A lot of these niggas have investors and shit, they don’t have to do that much work, their job is to be a rapper. But then a lot of niggas can’t fly too. They can’t leave, they all got charges.
When did you come back to Toronto?
2012 was when I really started to stay in Toronto more. I wasn’t travelling that much because I was near broke. I fucked up my money with a situation. Just a situation happened, a whole fucked up situation with money and niggas that fucked up. It was either put up all my money and break even, or take a friend, get back, build up, pay back … and I was like fuck it. So I got a job. I figured if I could grind it out in Toronto for three months, then I’m gonna make my money and then go back to New York. But money was low, nothing was coming in. I couldn’t afford studio time, I had no money for mixing and mastering. Even after i got a job, shit was still slow.
What was happening for you, musically?
That was when I started working on LiveFree, which is how I melt Irvin Witlow. I met him online. He was on Twitter, working as an assistant at Rock City at the time and he would give me advice. He was like consulting me, but he was genuinely helping me out. He ended up building up MGK’s brand. I watched MGK’s whole come up through Irv. I was always up to date, and at the same time he’d tell me what i had to do. Irv would always tell me that it’s about the music. Everything else is pointless if you don’t have the music.
How did you meet Wondagurl?
I’ve known Wondagurl since she was six, but we only started working together when I made Live Free. But Ebony’s brother is an event planner, and he’s a real nigga, so we’ve known each other from time. When I knew Ebony, she was mad quiet. She was always upstairs doing her own thing. I remember she was 10, and I heard some Dipset Heatmakerz type beats. I was like “Yo … who made this? This is crazy.” It was too crazy, it legitimately sounded like heavy Heatmakerz. I told her I was going to help her out, but I didn’t. And then her bro called me to the house three years ago, like yo, come to the crib, Ebony’s on some shit. She found that bass and that knock. And I’m just like “what the fuck have they been feeding you, how did you come up with that shit?” That’s when we made “Progression,” and then she wanted to produce my next project. We started working on it after ending Live Free, so we’ve been working on it for a year.
How did “On Fire” come about?
I was stuck listening to Use Somebody by Kings of Leon, and I went to the “Sex On Fire” song. And I just thought that would sound crazy as a sample, so one day I went to Ebony’s house, and the rest is history. One of my homies was playing Kings of Leon in the car like “these niggas are ill.” I’m open to different genres, I’m not strictly into that rap shit. I’m just a genuine guy. I don’t have to be out here saying bang bang raps, but some of the crowds I’ve been around and seen, put your mind in a different perspective.
You’ve been rapping for almost 10 years at this point, but would you still call yourself a rookie?
I guess you can call me the rookie. If you look at me, I’m in the minor leagues. I’m not as successful as anyone in the majors, but I don’t compare myself to them. The only thing I listen to is myself and R&B. I don’t listen to other niggas because I don’t like to grab ideas accidentally. I don’t want to make something that sounds like someone else. I’d rather to listen to something a little more throwback, and grab and inspiration from that instead of the new shit. I’d rather re-create then fall into the cycle.
Boulevard is basically a creative collective, like an extended networks. One day I definitely want my own Rocafella, Jay Z is like my hero. Certain things I may not agree with, character-wise, but you have to respect what he did and soak it up. In that perspective, I don’t agree or respect what he does, but the way he plays the game, I respect the business, that’s how you do it. Can’t work for niggas making money for them.
What are you going to do if this album isn’t successful?
I’ve just got to hit them harder if this album doesn’t reach. Wondagurl will be involved in my career. Sound wise, that’s the new wave, Redway and Wondagurl. Her beats make me want to rap. They’re very hard hitting, the snare is always clean and her high hats are just neat yo. Once I have that and a nice bass line, I’m good. It’s just a chemistry. She knows my personality as a rapper, so she knows how to bring it to life. And we make magic because of that.
Slava Pastuk is a writer living in Toronto - @SlavaP