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Country
Inside Owen Riegling's Two Biggest Shows at Massey Hall and the Grand Ole Opry
In the course of just six days in mid-April, Riegling released his sophomore album In The Feeling, played his dream show at Toronto’s hallowed Massey Hall, then made his debut on the show that made country music famous: the Grand Ole Opry in Nashville, Tennessee.
Billboard Canada was backstage with Riegling before each show, witnessing as the awestruck 27-year-old navigated the feelings of his major week.
At both locations, the meaning was clear. It wasn’t just a big week for him, but for his whole community: his family, his friends, his wife, and a good chunk of the population of Mildmay.
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“I mean, we started planning this like almost a full year ago,” he said of the Massey Hall show on April 18, a day after the album release. “So to see it come full circle after all the prep that's gone into it, with the launch of this album, to get to be here with all my favourite people in such a legendary place — it’s insane.”
Three days later at the Grand Ole Opry House, the home of the oldest radio show in the world, his sentiment was the same.
“It’s something that every kid dreams about doing, especially when they get into this genre. It’s the peak, it’s the pinnacle, it’s the thing that everybody works so hard towards,” he said. “I'm just looking forward to finally stepping in the circle and getting to share that moment with all the people I love.”
In The Feeling is Riegling’s second album and his first since diving into the heart of the country music industry. It’s been a whirlwind for him since winning the Emerging Artist showcase at Ontario’s Boots and Hearts festival in 2022. That started a relationship with Universal Music Canada, which released his debut album Bruce County (From The Beginning). In 2024, he earned his breakthrough when his song “Old Dirt Roads” reached No. 2 on Billboard’s Canada Country Airplay chart.
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New single "Taillight This Town" is already a country hit, reaching the top 10 on the Canada Country chart and charting on the Billboard Canadian Hot 100, but the whole album reflects the crazy few years he’s had. Through the songs, which are infused with storytelling and his small town charm, he shows his growth and transformation as he’s embraced the unknown of big city life and the music industry.
The album is structured like a road trip, with visuals recorded during a journey from Santa Monica to New Orleans. They played out behind him at Massey Hall, which was outfitted with a giant high-def LED screen behind Riegling and his band — something that’s only become possible since the recent renovation of the venue. It felt like an arena show, even if it was at a historic 132-year-old concert hall.
Ironically, the idea for the Massey Hall show came from Nashville. Last May, Riegling was in the studio working on his album with his producer Oscar Charles and session banjo player Matt Menefee, who was raving about a show he had just played at the iconic Toronto venue.
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“I texted my agent and said ‘hey, can we do a show at Massey Hall around the album?’” Riegling recalls. He was pitching it as a far-off aspiration, something to work towards. But a few weeks later, he received a text back. “We got the offer for Massey Hall if you want to do it. So I was like, ok, let’s make this a big thing. It’s a bigger show, bigger production than I’ve ever done. It’s almost kind of hard to believe.”
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The band went out on stage before he did, and he had a moment to himself standing behind the curtain listening to them play and hearing the crowd’s excitement. He was caught between nervous anticipation and emotion. “My jacket was shaking from how loud they were,” he said.
He only spoke to the crowd three songs into his set, and when he did it was a major reaction. He said a couple of words, and the audience erupted. Then he said a few more, and they erupted again. Later, when he finished the crescendo of “Home Less” — a bittersweet song about achieving success but having to leave your familiar experiences and people behind — he got a standing ovation that felt like it lasted for minutes. He had to stop himself from crying before finishing the song.
“I was like, okay, this is my crowd. There is a 0% chance I can mess this up tonight,” he revealed.
Riegling asked the audience if any of them were from his hometown, and pockets of the crowd erupted in cheers — from the balcony down to the seats, but mostly on the floor. It was more than a handful of people. It was a busful. Maybe more than one bus. Riegling joked it might be a record for the most people from Bruce County ever in one place in Toronto.
“If there’s a show that’s driving distance from my hometown, there’s a bus coming,” Riegling reflected later. “Guaranteed.”
He wasn’t joking around. That was evident by the time we met at the Grand Ole Opry House in Nashville a few days later.
As with Massey Hall, his first time attending the city’s most legendary country showcase was when he set foot on the stage to play.
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“A lot of firsts this week,’ he said breathlessly backstage before the show, in a dressing room named after longtime Johnny Cash collaborator and solo artist Marty Stuart.
Owen Riegling backstage at the Grand Ole Opry in Nashville on April 22, 2026.Big Loud Records
Stepping onstage for a debut at the Grand Ole Opry is a major rite of passage for any young country artist, and it wasn’t lost on Riegling.
“This is truly the highest highest honour and this is the biggest moment in my entire career,” he said onstage, stepping into the legendary wood circle transported from the Opry’s original home at the Ryman Auditorium in downtown Nashville. Though he hadn’t been there yet, he definitely understood its significance.
Riegling has been living in Nashville full-time since January of this year. He signed with country juggernaut Big Loud Records (home of huge artists like Morgan Wallen) in the U.S. in 2025, a label partnership with UMC in Canada, and has settled there after travelling back and forth to record and do business.
In The Feeling is his first co-release on both labels, and it’s an attempt to show his widening audience who he really is: the humble kid from Mildmay who appreciates blue collar honesty while remaining reflective, appreciative and emotional.
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Ironically, despite his new hometown, he recorded it outside of the usual Nashville recording infrastructure. Though he did have access to some well-seasoned musicians (they’re easy to find in that city), 90% of the album was recorded between Riegling and his producer Oscar Charles — one on guitar, one on drums. They locked in and recorded it all in two weeks in Charles’ basement home studio in Franklin, Tennessee, 20 miles south of Nashville.
“It was very organic, very stripped, very real,” Riegling said. “You can feel the songs pushing and pulling, and there's a lot of mistakes and wrong notes.”
Riegling was put on the veteran producer’s radar by Big Loud SVP of A&R Sara Knabe, who sent him the title track of In The Feeling — one of the two songs he played at the Opry, alongside his hit “Old Dirt Roads.” They were put together to write a song that didn’t end up coming out. Instead, they made a whole album together.
“It was just a natural feeling,” he said. “We didn't hire a bunch of musicians. It was me and him and a couple of other buddies just playing. There were some overdubs, but other than that it was all live. I've become pretty good friends with a lot of A-list session musicians over the past decade. There’s so much talent here. But there's something a little bit different just making music with friends. The chemistry is different.”
For Riegling, the approach fits what he wants to get across in his music: his true self.
“I think through and through, this record has me on it,” he said.
Even if the album is about Riegling forming his identity away from his hometown, they will always be there to support him for his biggest moments.
Riegling said he had about 30 people in his party with him for the Opry show, many packed into his place in Nashville. Then there were another “50 or 100” who made the trip themselves, some driving nearly 12 hours overnight to be there. (I can attest — multiple Uber drivers asked why there were so many rowdy Canadians in town.)
There were eight artists on the bill for his night at the Opry — including heavyweights like The Oak Ridge Boys and The Band Perry — but he had one of the biggest reactions of the night. When asked if there were any Canadians in the house, people all over the venue stood up from their church pew-like seats and cheered. Some started a standing ovation — a rarity for an artist making their debut. They even got an “Owen” chant going.
“That’s the kind of support I have from my hometown,” he said. “I’ve had that from day 1, which is unbelievable. I started out playing in the corner of bars, getting my friends to come. All of a sudden we were putting bars at capacity, and those people that were in those early bars, listening to me singing Eric Church covers, are the ones that are here at the Opry, and the ones that were at Massey Hall. They make it feel like I’m at Harley’s in my hometown, and I’m at the Opry.”
They had come in straight from Broadway, he bet, a stretch of downtown Nashville where honky tonk bars serve bucketfuls of beer while singers belt covers in close proximity from venues named after stars like Jason Aldean, Kid Rock, Jelly Roll and Lainey Wilson. It’s maybe the highest concentration of live music on any street in the world.
That’s where Riegling spent his first trips to Nashville, soaking it in as many tourists do. But now, he’s part of the industry, spending his time in studios, publishing companies and record labels on the legendary Music Row. It’s where Elvis, Dolly Parton and Willie Nelson recorded, and where Big Loud sits now.
“I remember coming here for the first time, which was probably like seven years ago,” he said. “Just going down Music Row and walking in front of Big Loud and just knowing that they're like the home of some of the biggest acts in country music, like ‘holy crap, this is where it goes down.’ Right now, there’s a huge sign in their front yard that says ‘Owen Riegling, In The Feeling, out now. It’s like a full circle.”
Stay tuned to @billboardca on Instagram for exclusive backstage interviews and clips from Owen Riegling's Grand Ole Opry and Massey Hall performances on May 7.
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