Sex, Drugs and R&B: Inside the Weeknd’s Dark Twisted Fantasy

When he first started recording as the Weeknd, Tesfaye was an unlikely star. “I was everything an R&B singer wasn’t,” he says. “I wasn’t in shape. I wasn’t a pretty boy. I was awkward as fuck. I didn’t like the way I looked in pictures — when I saw myself on a digital camera, I was like, ‘Eesh.‘” Instead of his face, his album art and videos featured black-and-white photos of artful nudes — a topless girl in a bathtub, a woman’s ass in a party dress. The aesthetic was American Apparel-style hipster catnip, right down to the Helvetica font.

Early Weeknd songs were atmospheric and chilly, their thick narcotic haze sliced by his broken-glass falsetto. The lyrics were an addiction counselor’s worst nightmare: pills, pain, shame, serotonin, danger. He and his crew posted three songs on YouTube and started spamming their friends on Facebook, then watched the play counts slowly climb. “I don’t know how many it actually was, but it felt like a million,” Tesfaye says. “Five hundred plays? Holy shit!” Toronto being a small town in some ways, the songs were heard by Drake’s manager, Oliver El-Khatib, who posted them to the OVO blog, where they promptly blew up. “Apparently, Drake wasn’t even fucking with it at first,” Tesfaye says today. “Oliver was the one vouching for me.”

The then-anonymous Tesfaye declined all interviews. In part, it was because he worried he wasn’t well-spoken enough: A high school dropout, he used to do crossword puzzles to improve his vocabulary, and to this day, he often wishes he were more articulate. “Me not finishing school — in my head, I still have this insecurity when I’m talking to someone educated,” he says. “I don’t want them looking at me like this fucking retard — no disrespect.” For months, no one even knew if the Weeknd was a person or a group. That’s when Tesfaye realized he “could run with the whole enigmatic thing,” he says now. “If it backfired, I probably would have been doing interviews. But people were kind of liking me being a fucking weirdo.”

The three free mixtapes that followed — House of Balloons, Thursday and Echoes of Silence (all later repackaged and sold as Trilogy) — made him a darling of indie circles, and Tesfaye isn’t shy about praising them. “I probably could have toured off Trilogy for the rest of my life,” he says. “It definitely changed the culture. No one can do a trilogy again without thanking the Weeknd. A lot of artists started doing things faster and quicker after that: Justin Timberlake dropped two albums in a year, Beyoncé dropped a surprise album.” He’s equally proud of the music itself: “I’m not gonna say any names, but just listen to the radio. Every song is House of Balloons 2.0.”