A Chance Encounter at a Toronto Restaurant
In July 2022, Drake walked onto the stage at Toronto’s Budweiser Stage, joining the Backstreet Boys for a rendition of their hit, “I Want It That Way.” The performance was born from a casual meeting while the band was in town for their “DNA Tour.”
The group was dining at a local restaurant when they were approached by staff. “The maître d’ is like, ‘Excuse me, Drake is here and he would love, when you’re finished, to be able to come over and say hi,’” member Kevin Richardson told Billboard in June 2024. During that dinner, Drake revealed that one of the group’s songs soundtracked his first kiss at age 13.
An Unexpected Stage Debut
The connection proved strong enough that Drake accepted an invitation to join the band on stage. Standing before the Toronto crowd, the rapper offered a rare glimpse into his adolescence, recounting his bar mitzvah and the moment he felt his social standing shift.
“At 13 years old, I had a bar mitzvah, and at my bar mitzvah, for the first time in my life, this girl I was in love with came up to me while one of the greatest songs in the world was playing, and she asked me if I would dance with her,” Drake told the audience. “It was the first time I ever felt acknowledged, and it was the first time I ever felt like, you know, I had a shot at being cool.”
Cementing a Pop Culture Legacy
The appearance was well documented, with Drake jokingly referring to himself as the “sixth member” of the group. This collaboration stood out for its deeply personal, nostalgic origins.
For the Backstreet Boys, the night became a definitive memory. Richardson noted that the interaction was particularly meaningful for his own children, serving as a highlight of their time on the road.