Massey Hall, filled with guests for a Live at Massey Hall set, in 2014. For seating, Massey is the largest performance hall in Toronto. (Mitch Fillion)

Enrico Caruso crooned there. Jack Dempsey put up his dukes there. And George Gershwin rhapsodized in blue there.

But next month it will be the successful but hardly illustrious indie-rockers Hidden Cameras playing history-laden Massey Hall, at a cut-rate price to boot.

The Massey stage used to be the brass ring and holy grail for musicians, especially the singer-songwriter types. It was the house of Lightfoot, Joni and Neil – a Carnegie Hall-like aspiration and destination where a headlining gig was a dreamed-of milestone for Canadian artists.

These days? Not so much. The Grand Old Lady on Shuter Street used to be discriminating, but in her dotage, she’s happy to have any visitors at all. “The music business has changed,” says veteran Toronto promoter Gary Topp. “And Massey is under the gun to put asses in seats.”

Is that what it’s come to for the hallowed Hall? People used to go there just to say they did.

Now, there are more music venues, more outdoor festivals, fewer headline acts that can fill the hall on their own, and fewer still that can afford to. But the Massey is finding ways to compete, albeit sometimes with non-marquee names and bargain ticket prices.

Interior view of Massey Hall, complete with stained glass windows, from public archives. (Library and Archives Canada)

“It’s about introducing people to the hall for the first time,” says Jesse Kumagai, who took up his post as the new director of programming, marketing and business development earlier this month, “both from the artist’s side and the audience’s side.”

When Mr. Topp and Gary Cormier, together known as The Garys, were booking acts into Massey in the 1990s, there wasn’t much competition. The concert landscape has crammed up considerably since, with major music festivals happening almost weekly in the summer. (Who would ever have dreamed of something called CBCMusic.ca Festival 30 years ago?)

The festival boom has probably crested, but concert rooms competing with the heritage property – owned by the non-profit Corporation of Massey Hall and Roy Thomson Hall – crowd up the scene all year long. And more is to come: An ambitiously overhauled Sound Academy will be booking bands soon.

Another problem with Massey is that it’s the biggest hall (capacity 2,600 or so) and one of the costliest too. Why would Rufus Wainwright, who previously performed his Rufus Does Judy concerts at Carnegie Hall and the London Palladium, bring the show to Massey when he could present it at the decommissioned Hearn Generating Station, for this year’s Luminato, instead?

“It’s an awfully expensive place,” Mr. Topp says of Massey, which is staffed by union crews. “Unless you can fill it, promoters won’t promote there. And there’s not that many artists that can play that size venue.”

And for many of the acts that can fill the hall at Victoria and Shuter streets, it makes more financial sense to play one night at bigger venues such as Molson Amphitheatre and Air Canada Centre rather than multiple shows at Massey.

Great Lake Swimmers performing at Massey Hall July 8, 2014. (Mitch Fillion)

In reaction to all the competition, one of the things Massey programmers have done is to establish the Live at Massey Hall series. Now in its third season, the popular program pairs Canadian indie acts on double bills at bargain ticket prices that bottom out at $18.94, a nod to the year the Victorian pile was first opened. The concerts are elegantly filmed and viewable online.

Massey continues to operate even as it undergoes renovations that will intensify in 2019, when the building will shut down for an extended period.

Mr. Kumagai, the corporation’s head of programming from 2003 to 2014, returned to the organization in an expanded role after a stint with the concert-biz colossus Live Nation Canada. He sees the Live at Massey series as a way to break down the barriers to getting in the venerable building. “Putting on a concert here is more expensive for everyone involved,” he says. “With this series, we’re getting young people in here to be able to see a band in a proper listening room.”

The ticket prices are partially subsidized, with grants coming from Ontario Media Development Corp. and Toronto-Dominion Bank, the lead sponsor for the series. And while the program is part of Massey’s ongoing investment in artist growth and audience incubation, the concerts can be seen as a short-cut for emerging performers to get into the plush-seat venue.

“There are certain artists or groups that, when they play Massey Hall, you know they’ve arrived,” says veteran Canadian music journalist Larry LeBlanc, who cites the gale-force folk-rocker Matt Andersen as one such example. “When he played there and filled it, I knew he’d come a long way.”

Mr. Andersen, while benefiting from Massey’s laudable system of nurturing ascending artists, did not make it into the hall through the Live at Massey series, and neither did Ron Sexsmith. The gifted songwriter dreamed of playing the hall ever since he moved to Toronto as a teenager, and resolved not to play Massey until he could do it as a headliner, not as a supporting act.

Main exterior entrance of Massey Hall. (Richard Beland)

“I feel I’ve been working my whole life towards it,” says Mr. Sexsmith, who made it to Massey under his own steam in 2006 and has headlined the hall multiple times since. “I feel whenever I step out on the stage, I have a right to be there. It’s something to be worked for, and not something to be handed.”

Bernie Finkelstein is a Canadian music executive and talent manager who, with business partner Bernie Fiedler, used to book artists into Massey when a different Trudeau was Prime Minister. He remembers getting singer-songwriter Murray McLauchlan through the building’s giant red doors for the first time in 1975. “I didn’t want to see Murray in Massey without every seat sold. We waited until the right moment, because it was too important not to. For my artists and myself, Massey was a special place. It was the pinnacle.”

As for Mr. Fiedler, who still books Gordon Lightfoot into Massey regularly, he traces the building’s loss of gravitas back to 1982. “The minute the Toronto Symphony Orchestra left, I saw Massey Hall’s integrity slipping,” says the former owner of the Riverboat folk club in Yorkville. “They started booking rock ’n’ roll acts, which they would have never done before.”

On Aug. 4, the next edition of the Live at Massey series pairs the art-rock provocateur Peaches and Joel Gibb’s tuneful folk-rock jamboree Hidden Cameras. Asked if Massey’s prestige has been lessened by discount seats, Mr. Kumagai shoots down the notion. “I don’t think it takes away from the artist’s credibility or the importance of their music,” he says. “The attendance for the shows is the sign that they have a right to be there.”

One of Toronto’s top talent agents agrees. “I don’t think the program has cheapened anything,” says Jack Ross, who mentions an unnamed female singer-songwriter who headlined the hall a few years ago but, because of the high cost of using the venue, came away with less money than the stage hands. “Massey wasn’t built for the elite. It’s a theatre for the masses.”

In April, Newfoundland’s Amelia Curran took part in the Live at Massey series, splitting the bill with the semi-active Rheostatics. While she understands the venue’s status, she doesn’t believe in over-romanticizing it. “Playing there is something you want to happen when you’re established on your own,” she says. “It’s a reward you get for working really hard for several decades.”

Rheostatics perform with special guest Amelia Curran at Massey Hall. (Jag Gundu)

“But then again,” Ms. Curran continues, “are we holding this place too precious, and keeping it in this insular club? How else are artists and audiences going to meet in this great venue if we’re keeping it on reserve?”

Also weighing in is singer-songwriter Justin Rutledge, who has yet to headline the venue, but did share the stage there with Blue Rodeo – “one of the great nights in my life” – in 2006. He supports the Live at Massey program. “For $20, you’re going to see your band,” says the soft-voiced troubadour, who was born across the street at St. Michael’s Hospital in 1979. “And as an artist, you’re going to fill the room.”

Packing the room, that’s what it comes down to. When the businessman Hart Massey gifted the hall to the city in 1894, he stipulated many things, including an institutional mandate that the building be for “the largest number of people” to attend events “at a minimum cost of admission.”

One hundred and 20 years later, his will is served, one turnstile click at a time.