Nobody makes feeling bad sound as good as The Weeknd. Even the singer’s sunniest tracks (“Can’t Feel My Face,” “Starboy”) feel anchored by darkness—the sense that pleasure is pain and beauty decays and you can’t have the night without the morning after. The brainchild of Toronto singer Abel Tesfaye, the project took off in 2011 with a string of mixtapes (later collected as 2012’s Trilogy) that forged cavernous, falsetto-driven R&B with narratives drenched in drugs, sex, and other regrettable decisions—a sound both sensuous and detached, featherlight and dead heavy. One of the earliest musicians to find his footing on the internet, Tesfaye originally offered his music through YouTube and free downloads, a move that felt radical then but is common now. Ethiopian by heritage (his parents immigrated to Canada in the late ’80s, just before he was born), Tesfaye—out from behind the mask of making art online—has since come to represent the changing face of Toronto, rooting himself not just in an international musical community but in a specific diasporic experience. Tesfaye’s music has become a symbol of hedonism pushed to bleak excess, with a series of albums—including 2015’s Grammy-winning Beauty Behind the Madness, 2016’s multiplatinum Starboy, and 2020’s dense and atmospheric After Hours—whose narrators can’t seem to say no even if they hate themselves for it later. And though his music has gotten a little brighter over time, the prevailing mood remains heavy, even unsettling—the ride you want more of even when you’ve had too much. Speaking to Apple Music about the persona behind his songs, Tesfaye said, “I’m a chill person. That guy is who I am, but it is who I am to myself and in my writing. Sometimes you take him and then you create more, and then it becomes this beast. You add more to him, and then it’s uncontrollable—its own character. It’s like Scarface, the villain: It’s horrible, but you can’t stop looking at it.” Though he didn’t release a new album in 2021, he was a constant part of the cultural conversation, releasing a slew of singles, performing at the Super Bowl and on Saturday Night Live (think: “Ladies and gentlemen, The Weeknd”), and winning the Apple Music Award for Artist of the Year.