Confessional rap from one of the genre's elite

It's 2011, and I'm watching Late Night With Jimmy Fallon. The musical guest for the night is Odd Future, a little-known Los Angeles collective. In low-pitched, sinister tones, the masked rap insurgents growl out lines about ashing blunts, music blog beefs and serial killer Jeffrey Dahmer.

- BHANUJ KAPPAL

At one point, Tyler runs towards Fallon's desk, and it feels like all hell is about to break loose. But he just tries to get Fallon and the guests to sing along. Even then, all of 19 years old, Tyler was the group's talisman. More than any other Odd Future member, he combined the militant menace of Wu-Tang Clan with the blog-era's ironic cool and the chaotic-neutral energy of the early 2010s Internet.

Goblin (2011), his first studio album, is rap music filtered through the punk nihilism of Sid Vicious. Unlike Eminem, though, Tyler wouldn't stick to the shock-jock routine. Starting with 2015's Cherry Bomb, he pivoted away from horror-core, each record pushing into more expansive—but still experimental—territory. On each of his last three albums—Flower Boy, Igor and Call Me If You Get Lost—he adopted personae as a way to deconstruct different aspects of his personality, his early "burn-it-all-down" antagonism replaced in favor of introspection, lyrical maturity, and an ear for the tuneful croon.