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On Wednesday at Toronto’s recently reopened Massey Hall, Sugar, Sugar singer Andy Kim hosted his 17th annual star-studded Christmas show.Tom Pandi/Massey Hall

We laughed. We cried. We took the Stairway to Heaven with Rush guitarist Alex Lifeson.

On Wednesday at Toronto’s recently reopened Massey Hall, Sugar, Sugar singer Andy Kim hosted his 17th annual star-studded Christmas show. Midway through the three-hour extravaganza, the city’s Mayor, John Tory, surprised Kim by presenting him with the key to the city, causing the 75-year-old pop star to break down in tears.

Between equipment changeovers that disrupted the flow between the short sets by veteran and newcomer Canadian artists alike – including Tyler Shaw, the Pursuit of Happiness, Ron Sexsmith, Georgia Harmer and William Prince – the occasionally flustered Kim filled the breaks with small talk. Mentioning that the day had been proclaimed Andy Kim Day by the city, he suggested he might now have the civic superpower to eliminate people’s parking tickets.

Apropos of nothing, the Montreal-born singer also mentioned the Montreal Canadiens hadn’t won a Stanley Cup since 1993. Long-suffering fans of the Toronto Maple Leafs, who have haven’t experienced a Cup-winning parade since 1967, were in no mood to commiserate. Neither was the Mayor, who joked that not only would he not allow Kim to take care of any parking infractions, but he would also have the singer’s car towed.

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Gary Slaight.Jag Photography/Massey Hall

Tory then presented Kim with the city’s highest honour – resulting in what Kim called an “emotional moment.” Later, to close the show, he was joined by the night’s musical guests for crowd-clapping renditions of his signature hits Rock Me Gently and Sugar, Sugar.

It was one of several highlights in an evening that saw the idiosyncratic appearance of an eccentric chanteuse, a sudden punk-pop eruption, the commemoration of a late philanthropist, a dynamo turn from Canada’s Queen of R&B Soul and an unexpected rush of Led Zeppelin.

Sister Mary come to me: Clad festively in green, the cult-favourite singer Mary Margaret O’Hara performed a short number a cappella in the dark before leading (though perhaps that’s the wrong word) the house band on a charmingly chaotic version of Blue Christmas that Elvis Presley would have admired. The whimsical O’Hara has an odd vocal tick in which her singing speeds up momentarily, like a cassette tape on fast-forward. She is a nationally treasured oddity, seasonal or otherwise.

Not-so-silent night: Though there is a cozy and casual mood to the Andy Kim Christmas shows each year, nobody told singer Jully Black, who has only one furnace setting: full blast. After a potent version of Silent Night, she rocked hard on Glass Ceiling, a message song with revival-tent energy. There was much applause, and the building’s newly restored stained glass withstood the moment.

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Midway through the three-hour extravaganza, Toronto's Mayor, John Tory, surprised Kim by presenting him with the key to the city.Massey Hall

Talent on display: Seven-time Juno winners Billy Talent roared with tightly wound punk-pop verve on one song that was new (End of Me) and another that was old (Fallen Leaves). Singer Benjamin Kowalewicz has a showman’s panache – he is as comfortable on stage as the rest of us are in our living rooms.

A stage by any other name: In a tribute to Allan Slaight, host Kim mentioned that if you didn’t know the late media mogul and philanthropist’s name, it was only because Slaight had preferred it that way. It was an interesting remark, given that Kim was standing on the Allan Slaight Stage in the Allan Slaight Auditorium of Massey Hall. Son Gary Slaight and wife Donna Slaight spoke briefly. The latter created the Centre for Addiction and Mental Health’s Gifts of Lights program, the charitable cause of the evening. The former runs the Slaight Family Foundation, which donated $15-million to the recent renovation of the 127-year-old building,

A segue to heaven: Along with members of Billy Talent and Saskatoon’s Southern-styled rockers the Sheepdogs, progressive rock duo Crown Lands performed a towering Led Zeppelin medley. Sporting a glittering jumpsuit, Crown Lands singer Cody Bowles shared vocals on the J.R. Tolkien-inspired Battle of Evermore with Billy Talent’s Kowalewicz and East Coast-bred singer-songwriter and CBC Music host Damhnait Doyle. The mandolin-dappled epic led into the guitar solo from Stairway To Heaven, capably handled by legendary Rush axeman Alex Lifeson. Since Rush drummer Neil Peart died in 2020, the famed Canadian trio has been inactive, though Lifeson is featured with Metallica’s Kirk Hammett on a new song released last week by Rage Against the Machine guitarist Tom Morello – hopefully the beginnings of a Lifeson re-emergence.

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