Very few of the early aughts boy-banders successfully transitioned to solo acts. Surprisingly, Jesse McCartney ranks among them. At 12, he joined Dream Street, a quintet aimed at young adolescents. Despite popularity among middle schoolers, Dream Street was relatively obscure and after three years, in 2002, it went the way of all boy-bands—disbandment. When McCartney reemerged two year later, former fans—now teenagers themselves—recognized their first crush in the older, swooshier-haired blondie. McCartney has continued to age with his audience, trading in his surfer-bro bangs for a gelled-up crew cut. And while he’s not as big as, say, Justin Timberlake, his staying power is rare. It’s that bubblegum past, a lingering nostalgia that only ups the fun of his ultra-pop singles. —C.J.F.