Even as a teenager, Conan Gray seemed to have already lived many lives, a reality he’d lay bare on both a popular vlog and later in his pensive, poignant pop tales. Growing up outside Austin, Gray began posting videos of acoustic covers before creating his own synth-tinged originals, drawing from the incisive, introspective confessions of artists like Taylor Swift and Lorde on tracks like 2018’s suburban-teen anthem “Generation Why.” Still, the singer/songwriter speaks not only to Gen Z but to anyone who feels crushed by love—or simply the whole world—states he reflects upon with timeless wisdom on his 2020 debut album, Kid Krow.