Billboard Canada Hall of Fame: Riley O’Connor on His Lifelong Mission to Put Live Music on the Map in Canada

From hiding Billy Joel tickets under Edmonton bus shelters to helping shape Canada’s modern touring ecosystem, Riley O’Connor looks back on decades in live music.

There are very few people left in Canada’s live music business who can talk about the industry from the perspective of almost every modern era it has passed through. Riley O’Connor can. He remembers when promoters were barely considered part of the power structure, when rock shows fought for legitimacy inside theatres built for symphonies, when radio stations could make or break tours market by market, and when convincing people to attend a concert sometimes meant hiding tickets under bus shelters in the middle of a freezing Edmonton winter.

Long before global touring became the centre of the modern music business, O’Connor was building shows across Canada city by city, helping turn live music into something bigger than just a stop on an artist’s schedule. Over the decades, the longtime promoter and current chairman of Live Nation Canada became one of the defining figures behind the country’s touring infrastructure, championing artists, smaller markets and venues that many larger companies once ignored. Along the way, he worked with everyone from Rush, Bryan Adams and The Tragically Hip to Elton John, Bruce Springsteen and Iron Maiden, while also helping shape Canada’s growing influence within the global live industry.

"Our biggest strength is our creativity and resilience," he says. "I think we Canadians are in a unique position to look at the world differently. We have this built-in sense of collaboration."

Ahead of being inducted into the Billboard Canada Hall of Fame alongside veteran agent Vinny Cinquemani, O’Connor sat down to reflect on the evolution of touring, the changing role of promoters, Canada’s impact on the global business, the future of smaller venues and artists, and why he still believes the live music industry is ultimately built around community.

Vinny Cinquemani and Riley O'Connor will receive the prestigious honour at Billboard Canada Power Players on June 10, 2026, at NXNE. Tickets are available here.

Find the full 2026 Billboard Canada Power Players list here.

You are a believer in mentorship and empowering younger generations within your organization. What was it like for you at that age?

It was more fly by the seat of your pants. There was no guidebook back then, it was just very entrepreneurial. It was survival based. If you didn’t go and do it, no one was gonna help you and no one was gonna make it work for you. You just had to do it yourself, and you learn by trial and error and a lot of failure.

You're one of the first two inductees into the Billboard Canada Hall of Fame. What does that recognition mean to you?

It’s extremely important if it sets up a profile for people to strive towards as a goal, to be at the top of their game in this industry I believe in. This is an extreme honour and I'm really proud that I have something that I can offer to people and give them as encouragement.

This gives people something to strive for, to be not only the biggest in Canada, but to have a global platform and show that Canadians really do punch above their weight, especially in the live music industry.

There have been so many changes in the business throughout your career. Looking back at the beginning of your career, what do you think are the biggest changes?

In the first 25 to 30 years, the biggest change was that the promoter became important as an integral part of the business. That was a radical change in terms of my career path. I always thought that we were gonna be just one cog in the wheel and that was it. Then it changed.

The internet blew up, the record company business and then the profile of shows changed, and then the way artists were really dependent upon the ecosystem to keep them as a career — to be able to earn a living — changed radically. Now they had to go out and perform live because they couldn't depend on royalties and record company contracts. They needed to go out and create a career path for themselves on the live side of the business.

When you started, promoters were kind of at the bottom of the totem pole in the industry. In our interview for Power Players last year, you called it “gunslinger world.” What was different about those days?

I think what it taught you really was to be really good at creating a reason to be collaborative. You had to convince record companies and agents and radio stations to work with you. It became an art to be able to sell what's your story? Why are you gonna be different? Why are you gonna be good for my artist? You had to constantly be innovative and give people a reason to work with you. It wasn't just the money, you had to have a story.

What were some of the ways you were able to convince people back then?

You built a relationship with the radio stations. It was very regionally based in Canada. Radio stations were king and queen in their communities. They were dominant in terms of what demographics listen to.

Rock radio to me was like our bread and butter. Who would be willing to take chances on stuff that was new, and not sort of predetermined by what was popular somewhere in the States? It became a great process. In every market I worked in, I found radio station managers or program directors who were very keen on doing something different in their community. Then it was about creating a promotion around the artists you believed in.

One of the fun promotions I can remember doing, I had Billy Joel in Edmonton. He was very big in very cosmopolitan cities, but here we are playing in Edmonton, a bit of an oil town, roughneck city. How do I make this an exciting event for people going, “I've gotta be there.” Billy Joel already had an established career and his songs were being played, so that was never about, how do I make it work? It's about how do I make this larger than life? How do I make this an event where you've gotta be there?

We went on sale in mid-January or February, it was 25 below zero in Edmonton all the time in winter. I wanted to create the biggest buzz in the city early in the morning, when people go on their early morning drive. I said we'll get a pile of tickets and we'll hide them under bus shelters all over town. We set up the radio at the TV stations at a few key points where we knew we were doing this, and people were literally running out in their pajamas [because they heard it on the radio]. They caught it on film and so that became the news story of the day. People said “Look at all those crazy people running out, I gotta get a ticket too!”

How do you make this fun for the band, for the artists, the managers, the agents, the radio station, the community itself? And we were always doing that. It was always oriented around how you make it fun and larger than life.

When I started off as a promoter in Vancouver, I would talk with my partner Norman Perry about how to get people to come to these punk rock things people were afraid of. We did these stencils on sidewalks. All points to the Commodore Ballroom which is where we would introduce a lot of shows. We get caught, then the city wants us to remove the stencils because we painted it on, and it becomes a news story. Then guess what? Everybody's talking about this band.

It feels like Canadians have had such an outsized role in building what is now a huge global live music industry.

Without a doubt, because if you look at the leaders at Live Nation, for example, you've got Arthur Fogel who came out of Concert Promoters International [CPI] with [Canadian promoter] Michael Cohl. Michael Rapino came out of Labatt Canada and had an association with CPI back in those days. He struck out on his own and was one of the founders and creators of Live Nation.

There's lots of people who have got their early years of training in Canada. Because the country's so vast and it's so geographically different in different areas of the country, with a small population, you really had to come up with a lot of different reasons to make things work. You just thought differently of how to be more creative, and it's a creative business.

What made you want to stay in Canada throughout your career?

I always wanted to stay here. I believed in the country, I believed in the artists that we were producing. I have this whole philosophy about pride of place.

I just love the idea of working into smaller markets in the country. It was always about how you build a bigger feeling for the community.

When I first started as a promoter, American agents thought Canada was just Montreal, Toronto, Vancouver, with a little bit of Calgary, a little bit of Edmonton, and that was it. My thing was, how do I even go deeper into the marketplace?

How have music venues evolved over the years?

The early arenas were just horrid places to play. The old Memorial Arena in Victoria was just a glorified airplane hangar. It was a big cement dome. Who thought this was a good idea?

A lot of performing arts centres had a real thing about rock and roll. “It's not gonna be in our building, Riley.” I kept saying that I'm a taxpayer and the people who are going to our shows are taxpayers and we contribute to the public coffers that build these buildings, so we have as much right in there as anybody else.

Now we’re seeing another venue boom, especially with projects like RBC Amphitheatre, which is set to become a year-round venue.

Doug Ford came in and saw this huge opportunity to revitalize Ontario Place and make it significant for everybody from Torontonians to Ontarians, but it's gotta be animated year-round. And he was correct.

The site would become dead in the winter, and so now it was important. You can't have such a huge swath of our frontage on the water, on real estate, be quiet for six to eight months of the year. It just seems ludicrous.

So he put out the clarion call, and we always knew that for us to continue on down there, we needed to be part of that story. That's the evolution of how we became a new building and a new model that will have an indoor component and be active all year round.

Looking back across your career, who are some of the artists that have been the most significant for you?

As a promoter, I always love working with acts that love to work, that love to go out there and play — bands like Triumph, Rush, Bryan Adams.

Starting around the ‘90s, I just loved working with The Tragically Hip. This is an act that just has such an incredible bond with Canadians. That was probably the first time I would feel that we had our own mythology in music.

Elton John had a mandate of going and playing in as many communities as he could in Canada. The joy that would happen when he played in all these towns and communities was phenomenal.

Doing a national tour with Bruce Springsteen recently was a highlight for me after a long career.

And Iron Maiden — they still go out there and play. It’s still a highlight every time I have an opportunity to work with them.

Looking towards the future, what do you think are the biggest challenges to the live industry?

Post-COVID, this is a different industry. It’s a much more interactive, participatory industry in terms of the fans with the artists. Now our challenge is to make this sustainable.

I have a long working relationship with Blue Rodeo, they’re true troubadours going out there and playing Canada. How do we establish a whole ecosystem for the Blue Rodeos of this world to have a career in this country?

I think of a guy like Tom Wilson, for example, who just loves to go out there and play and be a creative artist. Or Kevin Drew of Broken Social Scene, Amanda Marshall, Jann Arden, these hardworking people. How do we make sure those artists have the constant ability to go out there and earn a living throughout their career?

How do you help establish that?

The way to build an artist's career is to start working with young artists and build the story. I’m fortunate enough to be in a company like Live Nation that has the wherewithal to start developing and providing an ecosystem in communities by building small venues. A third of our shows are club shows, so how do we make sure that those opportunities constantly exist? How do I make sure that we, as an organization, believe that that vibrancy needs to be created in places like Halifax or Vancouver, Calgary, Edmonton, Winnipeg and the medium-sized cities. It's really, really important.

There’s often criticism around Live Nation’s size and influence in the market. How do you respond to that?

I think the perception is out there that we're buying out people. We're not buying out anybody. We create businesses where we build a collaborative partnership with the venues to make sure that we can be part of their success story.

As long as I am around, I will always speak to what I call the little guy. I just believe that we need to be proactive for our artist community. Otherwise, if you just look at the big story of big success or go after what I call the easy money, you lose the infrastructure of that ecosystem, and then sustainability doesn't exist anymore.

I don't know what AI is gonna do to the world, people say it's gonna be the best thing ever and others are totally fearful of it. To me it's a mix of both. What's really important is that artists don’t lose their faith to be creative. Then we're gonna lose a really important aspect of our identity as human beings and culturally in this country.