When House of Balloons emerged from its vaporous cloud of internet mystery in early 2011, it wasn’t clear that The Weeknd was about to help shift the course of mainstream pop. If anything, the album’s pervasive moodiness seemed to work contrary to the pleasure and liberation pop usually promised. It was’t a party album—it was an after-party album. And like any after-party, whatever fun it had to offer was tempered by the queasy sense that the fun had already been had—and that burning the candle in hopes of more would only reveal how desperate and sad it all was. As for Abel Tesfaye, the man in the middle? Yes, his voice was beautiful: High, sweet, and fragile, with a way of fluttering around its upper reaches (a method he said he learned from listening to Ethiopian pop as a kid). But when your idea of romance is “Bring your love, baby, I could bring my shame/Bring the drugs, baby, I could bring my pain” (“Wicked Games”), it doesn’t exactly make you sound like a fun date. Interesting, sure. But, like, who would want to hang out with this guy? And yet the music managed to capture a seductive loop of melancholy and debauchery—the perilous lows of chasing highs—rarely heard in pop or otherwise. Drake brought him in early, of course, drafting Tesfaye to co-write five songs on 2011’s definitive playboy’s lament, Take Care. (Just ask Drake: It’s lonely at the top.) And alongside Tesfaye’s other two 2011 albums, Thursday and Echoes of Silence—all collected later on Trilogy—House of Balloons was an early swell in a wave of albums by artists like Frank Ocean, Miguel, and Beyoncé that recast R&B as one of the more experimental and creatively fertile sounds in modern music. “And when I’m over only pray/That I flow from the bottom/Closer to the top/The higher that I climb/The harder I’ma drop,” he sang on “The Morning.” Maybe. But it hasn’t happened yet.