KARDINAL OFFISHALL: From the Stage to the Executive Suite, This Is Kardi's Business

Michael Raine
July 12, 2022

This article originally appeared in the September/October 2021 issue of Canadian Musician

By Michael Raine

Why Would I do that? You guys are the enemy, Kardinal Offishall thought to himself as he hung out at a friend’s cottage in the summer of 2013. It was a relaxed weekend in Ontario’s posh cottage country for a boat rally to raise money for kids with cancer and, out of the blue, and he’d just been made a surprising offer.

Joining Offishall in Muskoka was Randy Lennox, the then-CEO of Universal Music Canada. “Kardi and I had worked as an artist and label for many, many years and had several successes together from an artist’s perspective,” Lennox recalls now, eight years later, and just a few months removed from stepping down from his latest high-profile gig as the president of Bell Media. “We struck up a Saturday afternoon conversation in which I said, basically, ‘you’re a fantastic artist and a super smart guy — have you ever thought about coming over to the dark side?’ but with a sort of ‘LOL.’ We’ve had much laughter about that since because we’re very friendly, but he looked at me and I said, ‘You know, you are this country’s Jay-Z.’”

In retrospect, that may have been an exaggerated comparison, given that Jay-Z is a mogul whose mega wealth and influence crosses music, entertainment, sports, and even politics. After chatting with Offishall, I get the impression that while tough and smart, no doubt, those traits aren’t matched with the ruthlessness needed to be a Jay-Z. Nonetheless, Lennox correctly saw something unique in him.

“It happened very quickly. Once we came up with it, it was very spontaneous. But I’ll say this, the initial idea was inspired by my respect for Kardinal,” Lennox says.

By that fall, Kardinal Offishall was the new creative executive director of A&R at Universal Music Canada (UMC).

KKARDI AT THE 2021 JUNOS (Photo: CARAS/iPhoto)

“I just came back from vacation, so it was a much-needed recharge or regeneration. I was on a small island in the Caribbean. Our family has a little spot that we go to. It was super awesome. I always say when I go there, it feels like it’s a place that Satan can’t penetrate!” Offishall exclaims as we kick off our conversation over Zoom in the last days of July. His bleached high-top hair is in full form, as he lets out a characteristically sharp and infectious laugh. At this point, we’re just a few months removed from his most recent promotion to senior vice president of A&R at UMC. “For a cool week, I had nobody asking me for anything — I had no emergencies, no fires to put out, no whining artists, and no overzealous managers. Everything was good for a week; it was just me, the wife, and the kids.”

As he explains it, using an analogy that probably few Gen-Z kids will get, his life these days is like level four of Tetris. “Just trying to figure out the pieces and putting them together to make it work. I tell people all the time, for me, it’s an enchanted life that I live. Honestly, and not to get super cliché or whatever, but it’s really just trying to figure out how to take blessings that don’t necessarily fit together, and make them all work within a specific timeframe.”

First and foremost, his priority is being a good husband, father to his three kids – four-year-old daughter, and seven- and nine-year-old sons – and friend. “But then, music is the nucleus for pretty much everything. Music is at the core of everything that I do, whether it’s corporate, whether it’s

creative, sometimes even in my personal life; music is at the core. It’s a balancing act of trying to retain the passion, the memories, all the stuff that made you fall in love with music and has you still in love with music, but then also trying to figure out what it looks like as you continue to forge new paths and move forward,” he says. “You can’t really take the same philosophy and move it forward, because music has changed. The way we’ve consumed it, the way the new generation has consumed it, the way they view it — the things that are heralded, held important, revered — it’s all evolving at a much faster pace.”

By dint of age, now being 45 and having been in the rap game since he was a teenager, Offishall has directly experienced a revolutionary period for the industry, both as an artist and executive. Technological disruptions – from SoundScan’s introduction in 1991, which proved rap’s commercial market was larger than most thought, to streaming analytics now shaping how A&R is done in 2021 – have shaped and reshaped the music industry for the entirety of his professional life.

As well, as a kid he witnessed the birth of Canadian hip-hop in the 1980s and early ‘90s, idolizing his “holy trinity” of Maestro Fresh Wes, Dream Warriors, and Michie Mee. “Also, Rumble and Strong, B-Kool, Self-Defense, so many artists that were around in the ‘80s and were really forging the path. People like DJ Ron Nelson, and Mastermind was a young kid back in those days doing stuff. In Toronto, the Concert Hall era, that’s always gonna be Canada’s entry point,” he says.

Looking back over Canadian hip-hop’s arc, from Maestro to Drake, Offishall sees himself as a bridge. In the historical context, he views the era (late-’90s and early-2000s) in which he began making a name for himself as the bridge between the forefathers of Canadian rap and today’s global stars.

“Before me, it’s like, ‘There’s this thing called hip-hop and let’s just get involved,’ and the era that came after me was like, ‘Okay, it’s established and now it’s time to reap the benefits.’ My era was kind of in between. So, myself, Saukrates, Choclair, Marvel, Solitair, Tara Chase, Jully Black, et cetera, our whole crew at the time – The Circle – we literally had legitimate businesses to where we were selling thousands and thousands of pieces of vinyl in Japan and the U.K. and America and so forth. And that’s really what gave us all our global start outside of the country,” he remembers. “It was fun because we didn’t come from a time where people are like, ‘Yeah, put me on’ or there wasn’t a whole lot of MCs that were signing other MCs. And I’m not taking a knock at it, because obviously part of my story is that I signed with Akon later on in my career, but it just gave us a whole different way of viewing the industry. It also put the power back in our own laps at that time. Our success rate basically depended on how hard we worked.”

Listening to Offishall tell his story, what’s maybe most impressive (or surprising) to me is the sheer confidence he and his crew had, at least in his telling of it. Though it’s changed in the 2000s as Canadian artists have found worldwide success across most genres, really establishing a fresh confidence that there is nothing less-than about Canadian music, we all know that wasn’t always the case. Canadians’ cultural inferiority complex, the assumption that the Canadian version must be inferior to the American version, was previously accepted as an established fact in our entertainment industries.

“At the time that I went down [to the U.S.], we might have been delusional. I say that because I didn’t do it on my own. Think about it like this; we were smack dab in the middle of high school and Saukrates gets signed to Warner Brothers in America,” he says, explaining the years leading up to his own major label deal with MCA Records. That said, Saukrates got signed to Warner in 1996 and was dropped in 1998 before releasing his influential debut, The Underground Tapes, on his own Canada-based label, Capitol Hill. That indie label also released Offishall’s debut, Eye & I, in 1997. But he continues: “Choclair gets a deal up here with Virgin but then, basically, he was also on Priority Records in the U.S. So, as an up-and-coming MC and somebody who was, you know, second or third tier within the crew, I got to witness that happen before I got my deal.”

Also interesting in retrospect is how overt Offishall was in fronting for Toronto. His breakout hit single, “BaKardi Slang” off of his acclaimed major label debut, Quest for Fire: Firestarter, Vol. 1., is all about Toronto slang and popularized calling the city “the T-dot.” Fifteen years before Drake sang of “runnin’ through The Six” (and changed Toronto’s nickname once more), Offishall had the first ever Canadian rap song in the Billboard 100, and it was explicitly about Toronto. As he sees it though, there wasn’t anything unique about it. He was repping his hometown, same as NWA did for Compton, Too Short did for the Bay Area, KRS-One did for the South Bronx, and so on.

“I just think at that time, where my mind was, I didn’t care what anybody else had to think. I was like, “Yo, you’re gonna love my city, and you’re gonna respect us, and you’re gonna scream this stuff out the same way that you scream out other cities and other countries and whatever else.’ That was my dream. I was like, “What I want is for Toronto to be looked at in a certain type of way and on the same level,’ and it was at that time,” he says. “That was the first time that we saw it, and it was dope to be around at that time to see the videos be played on BET and MTV, at a time when those were still a thing. It was an incredible time.”

Canadian hip-hop fans under 30 may not know or appreciate the importance of Quest for Fire: Firestarter, Vol. 1, but its international success really marked the beginning of a new era in this country’s music industry. The album, which included the singles “Money Jane” and “Ol’ Time Killin’” in addition to “BaKardi Slang,” was also co-produced by Offishall himself and introduced a uniquely multinational sound to rap, with Offishall’s Jamaican roots clearly incorporated.

But it’s not just the commercial success of Firestarter, Vol. 1 that remains important, but it was the respect it garnered. Offishall remembers being introduced to Lil’ Wayne in 2006. At that time, the diminutive rapper was at the height of his powers, having just released the first two volumes of the now-classic Tha Carter tribology. “He was such a dope guy and I remember he rapped my verse to me when I met him. I was like, What the…? That was bananas,” Offishall recalls. A couple years later, Lil’ Wayne and Pusha T featured on Offishall’s song “Swag.”

Unfortunately, the next couple years showed the convoluted and frustrating nature of the record label business. His high-anticipated follow-up album, Firestarter, Vol. 2: The F-Word Theory, got derailed when MCA was absorbed by Geffen Records. The album was preceded by the Neptunes-produced single, “Belly Dancer,” featuring Pharrell Williams, but then got shelved. As a result, 2005’s Fire and Glory was only released in Canada via EMI/Virgin Records.

It wasn’t until 2008’s Not 4 Sale that Offishall returned to the American market thanks to a deal with R&B singer Akon’s own label, Kon Live, and Geffen Records. The album entered the Billboard charts at number 40, and most importantly featured Offishall’s most famous song, “Dangerous.” A dozen years later, that song sprung back into pop culture in a way that couldn’t be predicted in 2008 — via TikTok virality.

“These kids that are saying to their parents, ‘Oh my god, this is my new favourite song!’ and their parents are laughing at them, like, ‘Okay, it’s kinda not a new
song,’” he chuckles. It’s similar in his mind to when his hero-turned-friend Dave Chappelle used the unreleased track “Reaching Through the Darkness” during the end credits to his 2017 Netflix special, Equanimity.

“The thing is, it’s hundreds of millions of impressions through TikTok, through streaming, and all this other stuff that’s happened with me doing nothing except raising my eyebrows,” Offishall notes. “I say my life is enchanted because I don’t take any of these blessings for granted. There’s not a day where I wake up and I’m just like, ‘yeah, I should be doing what I’m doing and doing it with the people that I’m doing it with.’ Nah, it’s not a small thing when one of the greatest comedians on the planet in Chappelle is not just a friend, but says he wants to use your song at the end of one of his Netflix specials that will live forever. That’s massive, because the thing is, we look back at Eddie Murphy comedy specials, or Richard Pryor or [George] Carlin, Andrew Dice Clay, or people from that era, people are forever going to look back at these Chappelle series and be like, ‘Man, he is incredible.’ But then when those end credits play and it’s my song, nobody can take that away from you.”

What’s interesting is that those hundreds of millions of impressions via TikTok and Netflix, when viewed from the office rather than the studio, can mean something else entirely. For the artist, viral TikTok videos and high-profile Netflix placements mean influence, cultural cache, coolness, etc. For the A&R executive, that is all data for marketing and career planning. That double-sided view of the numbers – the analytics – is not lost on Offishall. He gets animated talking about it, largely because he has concerns about the over-reliance on analytics by A&R departments.

“We live in a time with music where a lot of the industry is heavy on analytics — less on gut, a lot more on analytics. I think it’s interesting to me, because relying on analytics means you’re relying on the past, because analytics are something that happened already. Analytics are not something that can tell you the future,” he says. “When you look at it at its core, that’s what it is. You’re seeing a trend, or part of a trend, that has passed already. So, now it’s up to you to guess; is that something that’s going to be sustainable, or is it going to fizzle next week or next month?”

Knowing Offishall is a sports fan, I draw that obvious comparison. These days, every team in every major sport uses advanced analytics. And yes, teams rely on past data to identify past trends, but, I point out, they do this to better predict the future. But Offishall is saying the same process can’t apply to music? That what was popular before, and the path songs/artists took to popularity, doesn’t help predict future popularity?

“Nah, because if you think about basketball or whatever, when you’re talking about analytics and percentages, they’re all shooting at one basket,” he responds. “So, when you think about the breakdown of it, it’s like, ‘Okay, if a thousand guys go to that one basket, this is usually what happens.’ You go through the analytics and break it down to get field goal percentages, three-point percentages, whatever, and here’s what’s most likely to happen. But you have hundreds of guys shooting at the same goal. In music, the equivalent would be 100 different nets, with a million different people shooting at the same time, from a million different places, in a million different courts, and trying to gather analytics from that and then make that apply to a singular artist!”

As well, he emphasizes, if he and other A&R executives ignored their guts and only signed artists who fit known moulds, then where would that leave music – or at least the labels? Pretty stale.

“When you think about Public Enemy and their Afrocentric, radically-political views, we didn’t really have somebody that embodied that, at that time. You think about Drake, and the fact that he was able to tap into emotions. Typically, within hip-hop it was super masculine, testosterone-driven, and we all know the positives and the negatives. But when he came along, he brought something brand new that the game did not offer, at least in a real big way, before him. Same with Kanye and everybody else that kind of cuts through, they’re doing stuff that analytics never would have been able to predict,” he continues. “So, I’m saying, if we depended on analytics, maybe we wouldn’t have seen J. Cole, we wouldn’t have seen a Drake, we wouldn’t have seen a Kendrick [Lamar], we wouldn’t have seen a lot of our favourite artists in hip-hop today.”

That brings up another of his concerns. That 10 years ago, the most acclaimed rappers were Drake, J. Cole, and Kendrick Lamar. Today, the conversation remains focused on Drake, J. Cole, and Kendrick Lamar.

“Of course, there’s your Chance the Rapper and Migos and Travis Scott, definitely a good handful of people that came out and are doing dope music, but unfortunately there’s a lot of artists where you’re like, ‘Yo, that artist is ill, love them!’ and then, more times than less, you’re like, ‘What happened to that person?’ because they were fire hot for just a year and a half.”

So, if career sustainability is the problem, how do we fix it? Figuring that out is partly why he accepted Randy Lennox’s offer.


“I’m also somebody that never saw myself as an executive,” he says. “I almost threw up my first day working at the label. Between the anxiety and just some of the things that we were doing behind the scenes, I was like, ‘This is way worse than I thought!’ But the dope thing about being me, and being an executive, is it’s a similar journey as I took being an artist. I say that because I had a conversation with one of my A&Rs yesterday and we were talking about an artist, and we were like, ‘He doesn’t fit in any box. He’s incredible, but where does he fit?’ But then I had to take a step back and I was like, ‘Well, that’s what they used to say about me, too.’ They said, ‘Is he hip-hop or is he dancehall? Oh, he’s Canadian but it leans culturally more American than Canadian.’ So, what I’m saying is I didn’t necessarily fit in a box before, but I made that work for me and was able to have some massive success around the globe. Most of my career was people saying, ‘That’s never going to work; that’s not going to happen.’ And I would say a cool eight times out of 10, I proved everybody wrong. So, on the executive level, there’s definitely things that people are like, ‘Well, why would you do that? That’s never going to happen?’”

“Think about this,” adds Lennox, “how underwhelming Canada’s performance had been in Black music and those genres a decade ago. We both got very, very motivated by the notion of really doubling down in that area. [Hiring] Kardi was one of the major components and, matter of fact, we started to rebuild our A&R team in its entirety at that stage.” But beyond his ability to identify and foster talent, Lennox says he knew instinctively that Kardi would be more than the usual musician-turned-talent-scout.

“I just knew in my in my soul that day that he was going to be this ubiquitous spokesman for the community, in addition to his role in finding talent. Kardi would advise me in governmental

issues, and because he’s so smart, he’d give me his opinion on some of the challenges we were having with Canadian content and radio play and things of that nature. So, he not only had A&R chops and artists chops, he is studied in the condition of our country and the music industry.”

(As a side note, let me add this charming anecdote from Lennox here: “I remember Kardi saying to me, ‘By the way, Randy, do I get to design my own office?’ I said, ‘Have your way with your space.’ So, he came in and he had one of the most unique offices I have ever, ever seen. It was all red and sort of looked like a bowling alley. It was so, so cool, and it was literally 20 feet from my office. You walk in Kardi’s office and your stress level will go down 50 percent. He’s created that environment.” Anyway, back to the story…)

At this stage, Offishall’s fingerprints are all over UMC’s rap and R&B roster. In the last year or so, he’s responsible for joint-venture deal with British mega-producer Harmony Samuels (Ariana Grande, Jennifer Lopez, Mary J. Blige) and signing Juno-winning R&B singer Savannah Ré and Quebec-based bilingual rapper Zach Zoya.

There’s a particular artist, though, who best exemplifies Offishall’s approach to A&R, and his skepticism about analytics. This artist is London, ON’s Emanuel, who has quickly risen from obscurity to be the first Canadian signed to Motown Records in the U.S.

“Here’s an artist that has zero streams, zero views on YouTube, was an orderly at a hospital, overweight, no buzz — all those things, but he had an incredible gift,” Offishall says about Emanuel. “I signed him and Jeffrey [Remedios, UMC CEO,] was like, ‘You know, I hear it and I see it, and Kardi, I will always bet on your passion’… Within a year — within one year — he was able to do 30 million streams. Now, in the grand scheme of things, is that a massive number of streams? If you put it in context, it is. For this random guy that nobody knew about last year to have 30 million streams? But not only that, but to be on some of the biggest playlists around the world at the end of last year, and a lot of these platforms were like, “Oh, the guy to watch for next year.’ That’s just one example of me taking a bet on somebody.”

In essence, he says, with his newfound influence, Offishall is trying to be the label guy he would have respected and wanted to work with 20 years ago.

“I’m saying, that person who is empathetic — not sympathetic, but empathetic. The person that, based on his past, really understands the anxiety that artists go through and that torment that we go through at times, and the consideration that we need. That’s how I use my past experiences is dealing with people, just trying to be a great person.”

Offishall is fully aware that the timing of his promotion – April 2021 – could be viewed as merely a response by UMC to Blackout Tuesday and the heightened focus on the lack of Black executives in music. He sees that meaningful change is often competing with performative corporate gestures.

“I know that I’ve earned it, so in terms of me becoming the SVP, I don’t have any qualms around timing or any of that stuff. I busted my ass for the last few years doing a lot of things,” he says. “But it wouldn’t have been meaningful to me if I got this promotion to be the country’s first black SVP at a label, but then it was just something for the news to bite onto and it was just a cute title or some clickbait and there was nothing that actually happened.”

Likewise, in his capacities as the chair of UMC’s B.L.A.C.K. (Businesses Levelling Access to Change and Knowledge) Label Coalition (BLC) and Canada’s representative on Universal Music Group’s Task Force for Meaningful Change, he remains singularly focused on making decisions that have a substantial impact. For example, the BLC and the Pinball Clemons Foundation earmarking $250,000 for a scholarship program for Black student leaders.

“What does meaningful change look like? We could have just written a couple of cute cheques to people that already get cheques that don’t even need it, and that happens a lot within the charitable community,” he says. “But for us, we’re going above and beyond to make sure that some of these charities that have never received money or that should receive more, that it’s actually going to make a dent, and it’s going to also send the right messages to these other corporations and other people.”

How Offishall thinks about progressive change, and how he wields influence, is rooted in his community, and especially in his mother’s teachings. She is a former teacher who still works in the Toronto school system, and who was involved in creating Canada’s first Afrocentric school.

“My mom has been somebody that has really driven home just a real appreciation for being a servant. My mom, honestly, she should just be chilling, and I swear to you, the only thing she doesn’t have that would make her a Black Panther is a beret. My mom is still constantly trying to figure out how we make the education systems better for Toronto,” he says. “So, for me, I need to be able to continue to do not just surface work. But to actually dig deep and make sure that every opportunity that is given to myself or given to people that I work with, that we really make it count and we make it count big time. At the end of the day, we’re not doing it for the sake of ‘look at me,’ but we want to make sure that our legacy is one that is very, very grounded in love for our community and based in a progressive attitude. Like, how do we build? How do we break the cycle? I think that’s what we’re trying to do right now. Ultimately, all that talking, I could sum it up by saying that meaningful change is change that will break negative cyclical patterns. That’s pretty much what it ultimately means.”

And with that clear and bold statement, our time is up and Kardinal has to run to his next appointment, but not before he expresses a very sincere thanks for wanting to talk to him. For me, there’s no question, he’s one of the most interesting and inspiring folks in the Canadian music industry. Precisely because he’s not Canada’s Jay-Z or our anyone else. He’s pure, honest, compassionate, and smart in a way that is uniquely him. Thankfully we have our own Kardinal Offishall.


Michael Raine is the Editor-in-Chief of Canadian Musician.


• Born Jason Drew Harrow on May 11, 1976 in Scarborough, ON, to Jamaican immigrant parents. The family spent his childhood years living in Toronto’s Flemingdon Park neighbourhood. His mother was a teacher and still works in the Toronto education system.

• He started rapping at 8-years-old. At 14, he performed in front of Nelson Mandela during his first visit to Canada.

• In 1991, a young Kardi, then using the name MC J-Ski, records his first demo and enters a rhyme he wrote with an anti-drug message into a Scadding Court community centre contest and wins. For this he gets to meet his idol, Maestro Fresh Wes. He is also interviewed by Barbara Frum about his anti-drug message on the CBC program The Journal.

• He later changes his moniker to Gumby D, and performs at malls with two friends who call their group the Young Black Panthers. He also uses the stage name KoolAid before settling on Kardinal Offishall.

• In 1993 he co-founded the Toronto hip-hop collective The Circle with Choclair, Jully Black, Solitair, Tara Chase, and Saukrates. The following year, he is featured on Saukrates’ single “Still Caught Up”

• In 1996 at age 20, he signs a publishing deal with Warner/Chappell Music Canada and releases his first single, “Naughty Dread”, which gets nominated for Best Rap Recording at the Junos.

• In 1997 he releases the debut LP, Eye & I. The single, “On wit da Show,” gets on regular rotation on MuchMusic

• Kardi’s first major label album, Quest for Fire: Firestarter, Vol. 1, is released in 2001. The single “BaKardi Slang” is the first Canadian rap song to enter the Billboard Top-100 (peaking at 37).

• Fire and Glory is released in 2005 on Virgin Records in Canada and gets nominated for Rap Recording of the Year at the 2006 Juno Awards.

• Not 4 Sale, his fourth album, is released in 2008. For it, he returns to an American major label, Kon Live/Geffen Records. It spawns the hit single “Dangerous” and for this he wins Rap Recording of the Year at the 2009 Juno Awards.

• In 2008, Kardi is featured on Lady Gaga’s “Just Dance (RedOne Remix)”

• In 2013, he becomes creative executive director of A&R at Universal Music Canada.

• In 2015, Kardi’s releases his fifth studio album, Kardi Gras, Vol. 1: The Clash, which includes the hit single “That Chick Right There.”

• In 2019, his song “Run” is used by the Toronto Raptors as the theme to their championship season.

• In 2020, Kardi is founder and co-chair of UMC’s B.L.A.C.K. Label Coalition, which spearheads improvements to education, mentorship, and progressive equitable infrastructure to increase Black representation within the company. Kardi is also the Canadian representative on Universal Music Group’s Task Force for Meaningful Change.

• April 2021, Kardi is promoted to Sr. VP of A&R at UMC.

Michael Raine

Michael Raine is the Editor-In-Chief at NWC, publisher of Canadian Musician, Professional Sound, Professional Lighting & Production, and Canadian Music Trade magazines. He is also a co-host of the popular Canadian Musician Podcast. Michael has extensively covered nearly all aspects of the Canadian music business, as well as the pro audio, musical products, and the lighting and production industries.