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 Murray McLauchlan moved downtown and never looked back. Armed with a guitar and a backpack, he ran away from home at the age of 17 and headed straight to Yorkville. He wound up crashing at the Village Corner coffeehouse, sleeping on a mattress in the basement and soaking up the sounds of guitarists like Amos Garrett and Jim McCarthy and folksingers including Al Cromwell and Elyse Weinberg. The Village Corner had been the place where artists like Ian & Sylvia, Gordon Lightfoot, David Wiffen and Bonnie Dobson all got their start.   The son of a trade unionist, McLauchlan developed an artistic flair while attending Central Technical School, where he took classes from renowned Can...

Gordon Lightfoot got his start on Yonge Street, not in Yorkville. Although the bard of Canadian song is often associated with Yorkville’s Riverboat coffeehouse, where he first became a star while performing weeklong stints in the mid-1960s, his first real home as a solo artist was Steele’s Tavern, at 349 Yonge. A two-storey operation run by Greek restaurateur Steele Basil, Steele’s was sandwiched between Yonge Street’s famously competitive record stores: Sam’s and A&A’s. There, in the upstairs Venetian Lounge, Lightfoot performed his songs for anyone who would listen, often competing with the clink of beer glasses and televised hockey games for people’s attention. Lightfoot had traveled ...

Neil Young returned to the city of his birth in 1965, determined to break into Toronto’s flourishing music scene. He’d arrived with his Winnipeg group, the Squires, but their new folk-rock sound fell on deaf ears. Even changing their name to Four to Go failed to make a difference. So Young parted ways with his bandmates and launched himself as a solo folksinger. Before leaving Winnipeg, Young had become enamored of Bob Dylan’s music and taught himself to play “Four Strong Winds,” Ian Tyson’s Canada-referencing response to “Blowin’ in the Wind.” He’d also encountered Joni Mitchell, who was performing at the Fourth Dimension coffeehouse with her husband. After the show, Young went up to Joni, ...

The sensitive rapper toughens up on his latest. “I’ve got enemies,” he admits on “Energy.” Drake then takes shots at his adversaries on dark tracks like “No Tellin’” and “Used To.” But his vulnerability shines through on “You and the 6,” where he confesses that his mother and his hometown of Toronto “raised me right.”

The Toronto rapper and singer has never been shy about his feelings his hometown or the women in his life. Both subjects dominate Drake’s eclectic fourth studio album, originally to be called Views from the Six in reference to his beloved Toronto. The cover shows him sitting atop the CN Tower. Then there’s “Weston Road Flows” and “9,” where he claims to have flipped Toronto on its head. While he’s unequivocal about his hometown, his relationships with women are less certain. On the island-flavored “Too Good,” his “he-said-she-said” collaboration with Rihanna, he complains, “You take my love for granted, I just don’t understand it.” On “Pop Style,” he worries that he simply “can’t trust nobod...