Michael Bolton Charms Windsor with Timeless Hits and Holiday Classics
519MAGAZINE.COM

Michael Bolton Charms Windsor with Timeless Hits and Holiday Classics

Michael Bolton brought the Christmas edition of The Symphony Sessions to Windsor on Thursday night to the delight of a sold-out Caesars Windsor Colosseum. The show packed in about a dozen Bolton classics and a few seasonal favourites.

The 65-year-old crooner put on what felt like a televised Christmas special like the ones Elvis and Johnny Cash used to do every year. The show was packed with great music, even great musicians and a grand sense of humour. He playfully batted away proposals of marriage with cute responses like "Have we met?" to an adoring audience dominated by middle-aged women.

The show picked up speed as it progressed and the hits just kept flowing, ever slightly mixed with a couple Christmas songs (all of them from 1993’s This Is the Time: The Christmas Album). It was a good selection of hits from his 20-plus studio albums and the atmosphere was very laid back. He appeared to enjoy just being there with 5,000 of his closest Windsor friends and a small string section composed of local musicians.

The show was packed with great music, ever great musicians and a grand sense of humour.
Dan Savoie519 MagazineDecember 17, 2018

Standouts of the night included a series of duets with New York singer Sam Fly. If she looked familiar, that’s because she starred in an E! Network TV docu-series, *The Platinum Life*. Fly’s voice was keyed in perfectly with Bolton’s and the duets sounded phenomenal. Another key moment was a musical interlude where we heard a sax and piano solo.

Windsor fans were treated to an extra Christmas song that he hasn’t performed elsewhere on the tour so far – Santa Claus Is Coming To Town. He also revealed his plans to release a documentary on the music of Detroit, which he's expecting to release in the future.

While his long golden locks might be a bit shorter now, his voice was still as majestic as we remember.

Share 𝕏 f in

About Dan Savoie

From coast-to-coast newsrooms to the gritty pages of Rolling Stone and Metal Hammer, Dan doesn’t just cover the scene—he’s embedded in it. He’s traded stories with a "who’s who" of rock royalty, locking horns with legends from KISS to Metallica. Whether he’s dissecting a riff or landing a world-class exclusive, Dan delivers the raw, high-decibel truth of the industry. Living the dream? Maybe. Documenting the legends? Every damn day.

Keep scrolling for more stories