Q&A: Maestro Fresh Wes Inducted Into The Canadian Music Hall of Fame | Canadian Songwriters Hall of Fame

By Karen Bliss

Maestro Fresh Wes, The Godfather of Canadian Hip Hop, is getting a lot of love lately. The entrepreneurial rapper whose song “Let Your Backbone Slide” was the first ever hip hop song inducted into the Canadian Songwriters Hall of Fame and long ago branched out into other arts sectors, such as acting, authoring and public speaking, just received the Canadian music industry’s highest honour: he was inducted into the Canadian Music Hall of Fame, at the 53^rd JUNO Awards, March 24, in Halifax, Nova Scotia.

Maestro, whose real name is Wes Williams, was born and raised in Toronto, but has been living in Saint John, New Brunswick since late 2020, with his wife and teenage son.

Throughout his career, which began in the 80s,  he has stacked up many firsts:

• The first Canadian Black artist to achieve a gold, then platinum-selling album, 1988’s Symphony in
  Effect, signifying, at the time, sales of 50,000 then 100,000 units, respectively
• The first Canadian rap single to go gold, with his debut single, “Let Your Backbone Slide”
• The first Canadian rapper to have a Billboard Top 40 hit (1990)
• The inaugural winner of the JUNO Award for best rap recording (1991)

In 1998, his song, “Stick To Your Vision,” from his fifth album, Built To Last, became a top 40 hit, and the title became his message. It features a sample from Guess Who’s “These Eyes,” which this year can be heard in the TV campaign ad for Scarborough Health Network (he has a star on the Scarborough Walk of Fame). He grew up in Scarborough.

When Williams got into acting, he excelled at that too, most notably seen in 41 episodes of Instant Star (2004-2008); 15 episodes of The Line (2009), for which he was nominated for a Gemini Award; and starring in eight seasons of Mr. D (2012-2018).  In 2010, he also co-wrote his self-help memoir, Stick to Your Vision: How to Get Past the Hurdles & Haters to Get Where You Want to Be, with his wife, Tamara Hendricks-Williams; the foreword is by Chuck D of Public Enemy.

More recently, he put out a kids book, 2021’s Stick to Your Vision: Young Maestro Goes to School, expanded even more, hosting a CBC radio show, Maestro in the Maritimes, season 2 of CBC television’s Race Against the Tide, a sand sculpture competition, which led to his desire to produce a TV show, a cooking show called Maestro Chef Wes, now on its second season.  He also released two more Young Maestro albums, Julia The Great (feat. Keysha Freshh) and Stick To Your Vision for Young Athletes — all nominated in the JUNO’s children’s album category (2022, 2023, 2024). On March 1, he also dropped a new compilation album, Rap Prime Minister, named after his 2013 track, “Black Trudeau (Rap Prime Minister).”

In June, he will be the first hip hop artist to receive the Governor General’s Performing Arts Award for Lifetime Artistic Achievement.

In addition to the major awards he’s getting in 2024, Williams is also proud of The Maestro Fresh Wes Scholarship, open to Black and African Nova Scotian students pursuing a career in skilled trades at NSCC Akerley Campus.

He talked with Karen Bliss about the honours, his impact, why he diversified and which calling he thinks he missed.

You’re such an early riser. Anytime I’m offered an interview with you, it’s 10 a.m. or earlier. You’ve probably already been to the gym and made your breakfast. You’re a metaphor for a life of productivity.
I was at the gym. This is lunchtime for me. But don’t forget, I got an hour ahead of you [Atlantic time].

True. Anyway, congratulations on the Canadian Music Hall of Fame induction. You’ve got a lot of big honours with more to come, like the Governor General’s Performing Arts Award. The Canadian Songwriters Hall of Fame inducted “Let Your Backbone Slide” in 2019.  It all started with that song.
Yeah, that song was the foundation, the backbone of the industry, not just the genre of music itself, when you think about it, in terms of Black music altogether. Because after that, labels started. And I say that respectfully because it wasn’t just me; it was, obviously, Michie Mee and L.A. Love. They rock with “Elements of Style” back in 1987. And you already had the Get Loose crew out of [Toronto’s] Flemingdon Park. They dropped their EP, like, 1987, ‘88. So we always had reference points. But when “Let Your Backbone Slide” came out, that was a hit record from the gate, and the visuals helped. Obviously, the album [Symphony In Effect] did what it did. And I had the Dream Warriors as another measuring stick, as well.

My introduction to hip hop was Sugarhill Gang’s “Rapper’s Delight”, back then, but I was a rocker.  I didn’t know about “Ladies’ Delight” by [Toronto-based American] Mr. Q.  Canada was still about five years behind, even with you being the first to have a hit record.
Respectfully, with “Ladies’ Delight,” I’ll be honest. I ain’t never heard of that until recently. None of us did. So, we’re ashamed that we didn’t because I’ll tell you one thing, if we did, oh, my goodness, that would have given us more battery for us to go make sure that that could happen. I think it reinforces the importance of documenting what you do. Always, always document what you have because there’s so much.

You know that movie Star Wars? I always remember them saying this is just one story. There’s a whole bunch of other Star Wars battles going on across the multiverse, that you don’t know about, that happened at the same time.” So, it’s important you document your history, and you keep it moving from there.

You’re young, still [55].  Sometimes people turn down these types of honours because they feel it puts a cap on their career when they have many years left. Obviously, you accepted it, so what is your view of these lifetime honours?
Well, this one specifically, the Canadian Music Hall of Fame, for hip hop. This ain’t just for me. This is for hip hop [laughs]. You know, if I was just to think about it for me, I’m like, “Okay, wow, that’s dope. That’s another thing I could add on, being the first person doing that.” But, if I think about this genre of music, I mean, look at the artists I just mentioned, the Get Loose crew out of Flemingdon Park, ‘87. You mentioned “Ladies Delight” way before that, in the late 70s. When you look at artists, even now and everything in between, we started from the bottom, but now we’re here doing great things. So, this ain’t just about me. If I was just to think about it for me alone, it’d be a different perspective, but I’m thinking about it for the genre of music, especially coming out of Canada right now in 2024. So that’s where my head is at.

For the longest time, really a staggering amount of time, you were the first and only Canadian hip hop artist to have a platinum album [1990]. Then, over two decades later, Swollen Members [2002’s Bad Dreams]. Then, Drake [2010’s Thank Me Later]. Not sure if I’m missing anyone, but all the same, it’s been so sporadic, and yet U.S. hip hop artists dominated the charts here.
It took the right artists at the right time and the right teams with them. A part of my team, realistically, was MuchMusic. You know what I mean? Like the video, it was all across the country. That wasn’t done before. And then radio, that was a part of the team when you think about it.  We didn’t have street teams. We didn’t have A&Rs dealing specifically for this genre of music, right? Everything was new. And, Let Your Backbone Slide was the catalyst to all of that, respectfully.

You are one of the most diverse artists, not just music, but actor, author, speaker. Not everyone does that or can do that. When did you start thinking, for life, I have to diversify, and I have a message to pass on to others?
There’s been different phases of my life and different phases of my career when it showed me and it reinforced the importance of diversifying. I guess back, when I seen Tupac in [1992 movie] Juice. That was right after I seen Ice Cube in Boys in the Hood and Ice-T in New Jack City. Those three movies reinforced that acting is a different realm altogether, where you could use what you learn from music and transition it to the realm of film and television.

Clearly, you enjoy acting. Some people diversify out of necessity.
No, no, no, no, no, no. That was out of necessity, hon. I look like Drake to you? Nah, man. I had to grind. That was out of necessity [laughs].

Yo, fam, I got to try to do different things, man, and continue. Even when I was writing books and moving on, you got to diversify. I got a joke: I said, “I wrote a book called Stick to Your Vision, but I’m no Margaret Atwood. Thank God I can rap good.”  Yes, you diversify, but also don’t forget what fueled everything else you’re doing. What fueled everything else I was doing was hip hop. You feel me?

So, that energy to diversify is a necessity, especially for a Canadian hip hop artist who came out in the 80s. So it wasn’t like I was bored one day, sitting in my fortress or my beach chair, and I’m like, “Let me try thespian artistry.” Nah, it’s like, “Yo fam, you got to eat. Your son’s feet are getting big.” You know what I’m saying? You got to diversify.

Then, COVID hit. Then it’s like, boom, you’re not doing shows. Son’s feet are still growing, man. What are you going to do? You got to find different ways to do things, man. Different ways.  I had a radio show out here in 2020, Maestro In The Maritimes. I put out a kid’s book because. I think I’m being rewarded right now because instead of just twiddling my thumbs, feeling sorry about me, which is selfish, I was helping people, especially the youth. You see what I’m saying? So all these things happening for me now, I’m being rewarded.

And on top of that, you asked me, how does it feel to get this award? If it was just me, it would be great. But because it’s for other people, it’s excellent. Because this represents hip hop. So it’s not just about me. It’s about other artists coming up before and after me.

On top of that, I don’t know if you heard about my scholarship. How cool is that? The committee from the Nova Scotia Community College, they sifted out all those applicants. So I just found out who the brother was. They gave me his number and I just said, “I’m thrilled. I wish you all the best.” He was grateful. Those are the things that mean the most to me, where I’m using my platform here to not only represent my people, but to give back.

You do a lot of speaking engagements for kids. You have to have confidence to feel that what you have to say is of importance and that kids will pay attention. Where did that come from ?
I think a part of me missed my calling. I thought that I would have been a great teacher. You know, I remember we came back to visit Toronto and my son’s favourite elementary school teacher was retiring. So, we got there just before she retired for us to say goodbye. She got to see my son who she had when he was in grade three. And I said, “I think I missed my calling, man. I kind of wish I was a teacher. You’re my son’s favorite teacher. You were strict. But when I asked him who was his favorite teacher, he said you.” And I said, “I think I missed my calling.” And then she started tearing up. She goes, “Wes, you are a teacher. I remember you with all these kids when they were in junior kindergarten, senior kindergarten. You were one of the only parents running with them, playing with them and being there for them, not only with your child, but other children as well.” So she goes, “You didn’t miss your calling. You are a teacher.” And she reinforced the fact, we’re all here to make the younger generation better, be the greatest versions of themselves, regardless of what our titles are. If our titles are MC, that’s great, too.

You’ve tackled so many projects. What else is in the cards? What else have you not done that you’d like to do?
Probably producing more projects, not necessarily always being on camera, but moving back a bit and just transitioning into more production, maybe some directing. But there’s so many things untapped that I’d like to do as long as I have my health and strength.