Blue Rodeo spent 2025 celebrating a big anniversary, one that most bands never see. The group has toured the country for its 40th birthday, filling venues coast-to-coast, and will wrap it all up with two nights back home in Toronto at the iconic Massey Hall on January 23 and 24. Plus, they recently took part in a career-covering documentary, Blue Rodeo: Lost Together, streaming on CBC Gem. Not a bad way to turn 40.
But it was a moment 41 years ago that changed everything for singer-songwriters Greg Keelor and Jim Cuddy, when the duo was at its lowest point.
Cuddy and Keelor had met in high school, and when Keelor started playing guitar at age 21, they began writing songs together. They’d tried to make it happen in Toronto first, releasing a single as the new wave-flavoured band the Hi-Fi’s in 1980. It was a Keelor/Cuddy composition called “Look What You’ve Done,” and it did nothing.

“We moved to New York in 1981,” says Keelor. “Everything in Toronto had shut down. There was nowhere to play if you played original music.”
Regrouping in the Big Apple under the name Fly to France, they continued as an alternative band, but with no more success. The songs were coming along, albeit with a New York new-wave edge, and early versions of songs such as “Rose-Coloured Glasses” were edgy and rough, at a much quicker tempo. After three years with little to show, Keelor had had enough. Thankfully, it was a lonely listen to a classic Canadian album that set them on a new course.
“I was listening to Gord’s Gold in a bar in New York with my headphones on,” remembers Keelor. “It just sang so deeply to me. I remember deciding that I wanted to move back to Canada.”
Cuddy agrees: “We decided we were done with all attachments to the current music, we’re not going to do anything like that anymore. We were going to take Gordon Lightfoot’s greatest hits, Gord’s Gold, as our template, and just strum the songs together.”

They came back to Toronto with a lot of material. It just needed to be reworked into this new concept.
“We had songs like ‘Outskirts,’ ‘Rose-Coloured Glasses,’ ‘Floating in a Pool,’” says Cuddy. “’Try’ was written just at the end of our stay in New York, and it was really written as a kind of R&B song. It was much faster when I first wrote it, and it really kind of sucked, and I knew that. We put it into its simplest format, just slowed it down, and it was actually really nice.”
The pair connected with Toronto musicians Cleave Anderson, Bob Wiseman, and Bazil Donovan, using a name they’d already come up with in New York: Blue Rodeo. They developed a new sound that still had some edge to it, a bit of wildness (thanks to Wiseman’s left-field keyboards), and the country-folk they admired in Lightfoot. Although it wasn’t called that at the time, Blue Rodeo was at the forefront of the alt-country scene, about to break in 1986 through the debut albums of Steve Earle, Lyle Lovett, and Dwight Yoakam.
It was happening in Toronto, too. Blue Rodeo discovered the club scene had changed.
“When we left in ’81 it was dead,” says Keelor. “But when we returned, Queen St. West was happening, and it was cool to be Canadian.”

Blue Rodeo quickly became one of the big names on Queen West, with audiences especially loving “Try.”
“We didn’t think it was different, but we quickly realized that nobody sang like that, and certainly nobody sang falsetto,” says Cuddy. “We didn’t think it was that big a deal, but the song got such a strong reaction. We played in the Horseshoe, and we had to play it twice. People would come up and make us do it again in the third set. We realized we had something, we didn’t know what it was, but we knew we had a song that really got people’s attention.”
And that attracted the record labels. They signed a deal with indie label Risque Disque, which negotiated a distribution deal through Warner Music Canada. Rush producer Terry Brown came on to produce the group’s debut album, Outskirts, the title track was released as a first single in March of 1987, and then… crickets.
“It was a bomb,” says Keelor. “We were taken out by our marketing manager and told this record wasn’t going to happen.”
Not one radio station had picked up the single “Outskirts.” Months went by. Then the label tried a second single. Again, radio ignored it, until the song found a champion on TV.
“John Martin [program director] on MuchMusic played ‘Try,’” says Keelor. “He loved the song, but he hated the video. Still, he kept playing it and playing it. ‘Try’ was a hit, so that opened the door for us. That’s a very exciting time when a record goes Top 10. That’s a pretty Beatle-esque moment in your career.”
Thanks to MuchMusic’s lead, radio stations across the country were playing ‘Try,’ on both rock and country stations.
“I thought that’s great, that’s fantastic, and we were selling singles, selling records,” says Cuddy. “But I didn’t realize it was actually creating the platform for us to have a career. I didn’t realize the power of radio.
“We’d go to places, and all of a sudden they would be full. We’d go to Halifax, and it would be full. How did this happen? We never even thought about it. We just thought we were a live bar band. If things were happening, it was just a little blip. We never had any clue. Which was good for us, because we never made any plans, like ‘we gotta have a hit single.'”
Back in 1987, Warner Music’s Dave Tollington, the band’s label champion, told RPM Magazine that breaking “Try” in Canada “took a long time and … at the same time though, it’s going to be selling for a long time.” He sure was right about that.
Blue Rodeo would go on to have lots of other hits. Cuddy and Keelor were made Officers of the Order of Canada and, in 2024, were inducted into the Canadian Songwriters Hall of Fame. Later hits such as “Lost Together,” “5 Days in May,” and “Hasn’t Hit Me Yet” are huge fan favourites, but “Try” remains the group’s most popular song. Cuddy, who turned 70 on December 2, says he’s still not tired of it after 40 years of touring.
“I’m happy to do it,” he says. “I’m happy to do it because I think people are looking at me, thinking that I’m too old to hit the high notes.” He hits them every time.
