The Backstreet Boys are presenting this as a wholesome generational moment — Drake, one of the biggest artists in the world, crediting their music for his formative romantic memory. It's legacy validation wrapped in fan service.
Here's what nobody's asking: What song? The Backstreet Boys have decades of material, and Drake conveniently left that detail vague. That's either strategic mystery or proof even he can't remember which 90s banger soundtracked his first kiss.
The encounter happened during the DNA Tour stop in Toronto — Drake's hometown. Kevin Richardson recounted the story to Billboard on June 24, 2026, saying Drake asked, 'Could I come through?' before joining them on stage for 'I Want It That Way.' The interview was conducted by Jerah Milligan.
Drake keeping his actual song choice secret is either masterful PR or proof that even Champagne Papi can't distinguish 'Quit Playing Games With My Heart' from 'All I Want Is You.' Either way, the Backstreet Boys just got their flowers.
The Backstreet Boys have been serving nostalgia for over three decades, but even they seemed unprepared when one of hip-hop's biggest names came crawling back to his musical roots. In a Billboard interview published Wednesday (June 24), Kevin Richardson revealed exactly what went down when the boy band rolled through Toronto on their DNA Tour — and let's just say, Champagne Papi showed up in a major way. According to Richardson, the group had just finished dining at a restaurant that happens to be Drake's go-to spot in his hometown.
The maître d' interrupted their meal with news that would make any pop star's kids lose their minds: "Drake is here, and he would love — when you're finished — he would love to be able to come over and say hi." Richardson described the look of shock on his sons Mason and Maxwell's faces as priceless. "My kids were like, 'Dad!'". But the real bombshell dropped during their conversation.
Drake told the group a story about his first kiss — and apparently, one of the Backstreet Boys' songs was playing in the background. Richardson recounted: "He told a story about, like, his first kiss was to one of our songs." The Toronto native then asked if he could join them on stage that night, leading to an impromptu performance of "I Want It That Way" with Drizzy himself. The Billboard sit-down wasn't just about Drake worship, though.
The interview also featured some "This or That" questions, including the divisive query that's torn boy band fans apart for decades: *NSYNC or O-Town? Nick Carter, ever the contrarian, chose O-Town — despite acknowledging they're friends with everyone involved. "I'ma say O-Town," Carter declared.
AJ McLean and Howie D both came down firmly on the *NSYNC side of the fence, with Howie D explaining his college connection to Chris Kirkpatrick sealed the deal for him. Beyond the throwback trivia, the Backstreet Boys are gearing up for their return to The Sphere in Las Vegas, where they'll resume their Into the Millennium residency celebrating 25 years since "Millennium" dominated the Billboard 200 charts for 10 consecutive weeks. McClean promised fans an immersive experience: "We're taking people on a journey... taking you back to 1999." They've also dropped "Bottle Up" for Paw Patrol: The Dino Movie, proving they're still finding new avenues to stay relevant in an industry that ate boy bands alive once before.
