Happy anytime the homie Redway gets some coverage.

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.”

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