Dear Maestro — Lately I’ve been in my head about which direction to go creatively. I came onto the scene as a hip-hop artist, but I truly have always felt I wanted to explore more. Now, everyone sees me as a “rapper” and I want to show more of myself outside of that. The fear of putting myself out there in a new light is lingering below the surface. Do you have any advice on breaking past the barrier of feeling confined in one genre? — Charmaine

One of my favourite musicians is Quincy Jones. In the 1950s and 60s, he was a jazz trumpet player. So if he stuck to the parameters of jazz, he wouldn’t have been producing disco records for Michael Jackson in the 1980s. That’s what I use as a point of reference, Quincy Jones. Don’t let hip-hop stunt your growth. And a lot of it too is instincts – if your instincts are telling you to try different genres, try different things, then it’s a great time for you to try that genre of music.

Dear Maestro — In addition to my music career, I’ve been a line cook for what feels like forever. I started a plant based cooking channel called Knives and Vibes and I’ve been interested in branching out to new avenues. I love your Maestro Chef Wes series! Do you have any advice about adding new ventures to your legacy? Do you feel like it took time away from your craft? Do you think there is a right time in your career to branch out into new passions? — Lex Leosis 

Because I believe in longevity, I continue going forth and forward and I’m not afraid to experiment. We have so many reference points in terms of US hip-hop artists, like Snoop doing a cooking show with Martha Stewart, to even Action Bronson doing some cooking as well, to artists like Xzibit with Pimp My Ride. So don’t be afraid to venture out. The transferrable skills we learn from being hip-hop artists are the ability to hustle and make something out of nothing. So don’t be afraid to tap into your creativity and go forth and forward. 

Dear Maestro — I’ve reached a point in my career where I have to be extra deliberate in my intentions as an artist. Can you give me some advice about how important legacy work is to you and your career, and how it affects the decisions you make as an artist at this stage of your career? — Keysha Freshh

I came up with a slogan, which is “don’t make records, make history.” The reason I did it is because it’s a great slogan, but at the same time it’s an affirmation which will help me do different things as well. Because you will reach certain points where you feel like you may have a glass ceiling. But once you go back and see what your name stands for, that really helps you go forth and forward and push to continue to inspire. Another thing too is I’ve learned that by helping other people, by helping the youth and younger artists, that’s when the real rewards start coming. 

Dear Maestro — As a young artist from Canada who sheds light on the remarkable journey and unyielding resilience of our people, I’m curious how you navigated the music scene in Canada during a time when hip-hop faced limited acceptance and lacked a substantial audience. Coming from the prairies, I’m struggling to find my audience here. Thank you for your invaluable contributions to hip-hop. — Sinzere

Public Enemy. KRS-One and Boogie Down Productions. Big Daddy Kane. These were international artists that I looked at, just to name a few. Also artists like LL Cool J and Run-DMC. I also had measuring sticks, which were Michie Mee and L.A. Luv, and the Dream Warriors. You could be in the prairies right now, but it’s easier to put out music now, globally, than it was back then when we started. So those were my reference points – I just gave examples of international artists from the ’80s, as well as national artists, local Toronto artists. Those were the artists who inspired me. Now you have artists like Drake, The Weeknd, Tory Lanez. So many different artists that you can see their success. They could be utilized as a measuring stick or a current inspiration to you.  

Dear Maestro — I’m an emcee, rapper, hip-hop artist from Edmonton, AB, which is not predominantly hip-hop in culture. I’ve been rapping for nearly two decades now, but I started at an early age. This led to me often being the first to accomplish certain accolades that didn’t seem tangible and breaking down unexpected doors. It’s one of the many reasons I relate to you. You’ve always been the first rapper from Canada to break down certain doors and accomplish so much. How do you deal with the pressure of always having that hanging over you? — Mouraine

I handle that with great responsibility! That’s why when I performed at the Junos for the Hall of Fame, it wasn’t just for me; it was for hip-hop in Canada. It was for the journey, because I’ve been doing this for 42 years. Thinking about artists that I’m inspiring is what helps me continue to go forth and forward. I just thought of all the artists who grew up watching me, and they are my inspiration. I just had a phone call today with my man Kardinal Offishall, and I called him for advice – I said “How do you make your live show that dope?” We had a great conversation, and I told him afterwards, “You’re my mentor.” And he said “Me?!” I started laughing, and I said yeah, because I know you grew up watching me do what I’m doing, but by me watching you as well as other artists, that’s what inspires me to stay young and continue being relevant. 

Dear Maestro – What’s your advice on feeling like even though you’ve done a lot, you feel like you’re not doing enough? You’ve accomplished a lot, how do you maintain that confidence as an artist? — DijahSB

I just saw Ice Cube perform in Saint John two weeks before the Junos, before my Hall of Fame performance. The way he performed was the same way he did back in the day. That inspired me. I introduced LL Cool J when he performed in Vancouver this past summer, and again, to see the way he still performs, that’s what motivated me to keep doing what I’m doing. So I’ve been fortunate enough to have artists who came out in the 80s still performing on a level that they did when they were in their teens.  

Dear Maestro — I’m from Toronto but have been living and making music in Western Canada more than half my life now. There is world class hip-hop and R&B being made here, but what is it going to take for the rest of the country to shine a light on this region beyond the folk, rock and pop circles?  — K-Riz

There’s nothing wrong with folk, there’s nothing wrong with rock. My inspiration came from rock. One of my biggest songs was “Stick To Your Vision.” That was a rock record. The Guess Who is from Winnipeg, man. They’re a rock group that inspired me. Take your inspiration from wherever you can get it, and be proud of where you’re living at. I’ve never let where I am geographically stunt my growth. Back in the 80s, I was sending my demo tape to whoever wanted to listen to it, and divine timing made things happen when they did. Hip-hop’s in a better place now internationally, and you have better opportunities than you did before. 

Dear Maestro — NADUH is a west coast hip-hop group that is keen to make positive change and heal an overworked, underpaid, and somewhat exploitative industry, but we also recognize there’s a level of “playing the game” required to push through the gatekeeping and barriers in order to be heard. How you decipher what actions to take, while following your moral compass. — Tee Krispil (NADUH) 

That word, “gatekeeper,” is very interesting to me. A lot of people don’t want to accept the fact that they’re their own gatekeeper. A lot of people like to use that word, but at the same time, they’re the same people closing the gate on themselves with their attitudes, their lack of vision, or their lack of ingenuity. I would say to remove certain words from your vocabulary. When I came out, we didn’t have these grants. I paid for my own video myself. My former manager’s mother added in a couple more dollars on top of that, and I was proud of myself to have a video on light rotation on MuchMusic. So all of these things are what helped me. Have you heard of a show called Electric Circus? I saw other acts perform on Electric Circus, I dropped off my demo tape at the reception of MuchMusic, they gave me a call and next thing I know I’m performing on Electric Circus. It did well, they asked me to come back on again, and I didn’t want to because I thought it was a lateral move. But my manager at the time said “If they’re calling you to come back, you must have done something great. Let’s do something even greater.” I performed a song for the first time called “Let Your Backbone Slide,” and the rest is history. So If I believed that there were gatekeepers, that would have been me shooting myself in the foot. Not believing in my potential. 

Dear Maestro — I’ve been putting years into developing my sound and my network and I’m really excited about where things are at. Between starting a new label, running a conference that champions music of Black origin, and making some of the best music of my career; I can’t believe how fast things are developing! I am finding it hard to find balance though, do you have any advice on how I can navigate all these different parts of my career and stay this productive? — Teon Gibbs

You gotta sleep when you can. I just took a nap and I feel revitalized. But if you can create a brand kit of what your company stands for, the direction, when you bring people on they know exactly what you stand for. For me, Maestro Fresh Wes stands for longevity, perseverance, and Canadian heritage. If I’m aligning to do a concert and I’m looking for a sponsor, if I want to step to a Molson Canadian, for example, that’s a company that I can do brand with because they symbolize longevity, perseverance and Canadian heritage. If I want to do a car sponsor, Lincoln is celebrating their 100th year. That’s longevity right there. So I would put together a brand kit, and this is something I didn’t do before. People that work with you, it’ll be helpful for them to see exactly the direction you’re going in. You’ll have less problems, and it’ll be easier for you to have people help you with these conferences, performances, and whatever you’re trying to do. 

Dear Maestro — Being an artist can be a 24/7 type of role. I personally find it draining trying to juggle making the music, booking performances, creating content, and connecting with family and friends. Do you have any advice for how to stay grounded and focused? How can I keep my mental health in check while making art and promoting it? — LEXXICON

We can’t do everything ourselves. If you’re going to have a team, let them know your direction, and you take it from there because you need to rest. We all have mental issues because we’re using our mind as artists. If you can prioritize what needs the most, that’s what I would suggest. For example, right now I’m prepping for a TLC concert that I’m doing. That’s why I called my brother Kardinal. Even though I’m older than him and I was doing shows before he was, he’s someone I can look up to for suggestions. I’m hosting a Winnipeg comedy festival this weekend, coming up. I’m balancing out and structuring my week, I’m structuring my month, and I’m planning for summer tours. Structure will help you breathe, and you’ll know when you need to sleep.  

Dear Maestro — I’m fascinated by how superstars, across all sports, remain at the top of their respective “games” even deep into their careers. We hear of many superstar level athletes creating fictitious enemies or scenarios in order to motivate themselves to climb proverbial “mountain tops” and win again, even after achieving everything there is to achieve. As an all-time great yourself, in one of the toughest businesses on planet earth, how do you remain at the top of your game? — MAUVEY

I like to watch old Muhammad Ali interviews. Because he was like 21 and 22 when he was on top of the world, and I know that wasn’t a time of civil rights. He still was strong enough to be like “This is what I stand for, this is the direction I’m going in. And it’s not only for me, but it’s for my people.” For me, in terms of hip-hop, my direction isn’t just for me, it’s for Canadian hip-hop as well. So I keep that in mind every time I do something. If I’m the godfather of Canadian hip-hop, then this thing of ours, I have to represent it forever. I have to do it in a way that an MC like Pressa, who I just met at the Junos, when he sees me, he sees himself a few years later down the line. I watch old Muhammad Ali videos, but I get a lot of my inspiration from younger artists as well. 

Milestone: Maestro Fresh Wes is on now at Studio Bell, home of the National Music Centre, until February of 2025.

Learn more at studiobell.ca/feature-exhibitions.