Can You Guess Which Rapper Had His First Kiss While Listening to the Backstreet Boys? I Bet You Can
· Vice
Truth be told, it might be a pretty easy guess. In a June 2026 sit-down with Billboard, the Backstreet Boys dropped the name while sharing the humorous anecdote. There’s nothing like learning a mainstream rapper apparently had you on his teenage make-out mix CD.
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The story came up while the Backstreet Boys were discussing their families. To hear them tell it, there was a time when their respective children didn’t even realize just how iconic their dads are. For Kevin Richardson’s kids, the realization came around the time of their DNA Tour, which kicked off in 2019 and went until 2023.
Richardson called it “the coolest thing that ever happened”, in his kids’ opinions. But what really had the light bulb going off? Apparently, that had everything to do with a dinner in Toronto. When the tour rolled through the city around 2022, Richardson said he and his two sons went out to dinner at what just so happened to be Drake’s favorite restaurant.
“The maître d’ is like, ‘Excuse me, Drake is here, and he would love—when you’re finished—he would love to be able to come over and say hi,” Richardson continued. In the video interview, he mimicked the shocked expressions on his sons’ faces. “My kids were like, ‘Dad!’”
Imagine Having a Backstreet Boy for a Dad and Not Even Realizing How Famous He Is
So, it seemingly took Drake’s endorsement for Kevin Richardson’s kids to finally contextualize their dad’s star power. He then recalled some of his conversation with Drake at the restaurant.
“He told a story about, like, his first kiss was to one of our songs,” said Richardson. But the real kicker came when Drake asked to join the Backstreet Boys on stage in Toronto. “He was like, ‘Could I come through?’” Richardson added.
So, of course, the Backstreet Boys had Drake come through. During that July 2022 stop in Toronto, Drake surprised fans when he appeared on stage with the group to assist with “I Want It That Way”, which he repeatedly called “the greatest song in music history”. But before that, he shared the same story with the crowd about his first kiss.
“I was 13 years old, and I was an awkward kid,” he began. “And I was in love with this girl at the time, and she would pay me no mind … At my bar mitzvah, for the first time in my life, this girl who 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.”
He continued, “It was the first time I ever felt I had a shot at being cool. And the song that she wanted to dance with me to was the greatest song of all time, one of the greatest songs ever made.” Drake then added, to cheers and applause, “And if she could see me now, you know what I’m saying?”
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