WATCH: Toronto Hip Hop Legend Maestro Is Coaching These Rappers

“Stick To Your Vision’ and ‘416/905’ were legendary moments in my life, not to mention this man’s career. Those two songs let me know that it was possible to make a city so far removed feel like it was a part of it all. Now every song and move I make I think about my people back home and how proud I am of them and they are of me. I owe a part of my confidence as a rapper to Maestro.” – Drake

The rap scene in Canada is a permanent fixture in Hip Hop thanks to artists like Drake, The Weeknd, Tory Lanez, and Belly. Before them, artists like Kardinal Offishall, K’Naan, Choclair, and K-OS held the torch for the Toronto Underground. Even before anyone outside of the 416 area code knew about the 6, Maestro Fresh Wes was the first to spark the Hip Hop flame as a platinum-selling rap artist.

His latest album is a concept-driven effort called Coach Fresh. It is a reflection of who Maestro has always been in his city, the guy young people, especially rappers, go to when they need pointers on their game. His role as a leader (and noted inspiration of Drake and others) takes center stage on this project- but he did not come alone. Maestro and Ras Kass drop some bars like dads schooling their sons on Mr. Evans and the banger Skyscrapers features Kool Keith. Appearances by SkyZoo and Saukrates among others round out the album’s features. Influences like Big Daddy Kane, Rakim, and Doug E. Fresh helped Maestro find his style and there is a refined boom bap feel to his delivery. In fact, New York, namely the Bronx, was foundational in the development of Toronto’s hip-hop scene.

Maestro, born Wes Williams, made the jump from rapping to acting several years ago and has starred in the movies Paid in Full and John Singleton’s Four Brothers. He currently stars as Paul Dwyer on Mr. D, which is available on Netflix Canada and Hulu.

In addition to acting, the rapper has authored the book, Stick to Your Vision: How to Get Past the Hurdles and Haters to Get Where You Want to Be. Wes elaborates on his career change in a forthcoming TEDX Vancouver Talk (his second TED Talk to date and highlighted the fact that being a rapper taught him repetition and preparation, two skills that have transferred to his acting career.

One of the most refreshing things Maestro had to share with the Codeblack Report was that although he’s inspired generations of Canadian rappers, he is also inspired by their success. In an age when it feels like the divide between generations is only getting wider, his full circle perspective is a bridge that brings the culture closer together.

Stream Coach Fresh here and find more info about Canada’s Hip Hop OG on his website or follow @MaestroFreshWes on Twitter.


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