Label: Roc-A-Fella/Def Jam
Producers: Jeff Bhasker, Mr. Hudson, No I.D., Plain Pat, Kanye West
Features: Kid Cudi, Young Jeezy, Mr. Hudson, Lil Wayne

You’d be hard pressed to find someone who will make the case that 808s & Heartbreak is Kanye’s best album. His most influential? Perhaps. The one that changed the trajectory of his career? Definitely. But the best? That’s a tough argument to make. It might be correct, though.

Lost in the discussion of whether Drake bit the 808s sound and sensibility to start a new age in hip-hop, and the question of what Kanye was even doing here, singing stream-of-conscious, despair-filled pop songs over spare electronic beats, is that this is a focused thesis statement of an album. For three albums, Kanye had won us over. He was hip-hop’s everyman, an artist that put seemingly every thought in his head on record, and we loved him for it. More than that, it brought him increasing levels of success at every turn. By Graduation he was, against all odds, our biggest star. 808s was supposed to be his missive from the top. The message it brought: None of this was worth it.

We all know the story of this album; Kanye’s mourning album that’s really a breakup album, following the sudden losses of the two most important women in his life. And it is a raw outpouring of loss and bitterness, but it’s also something more than that. 808s is a reflection on a Faustian bargain gone wrong, a message from a man who achieved everything he wanted—fame, fortune, critical adoration, and a place in canon—but realized too late that it was at too high a cost and, to his horror, there was no going back. 808s is the sound of living with decisions you regret.

Much ink has been spilled on the sound of this album; it either pioneered or helped define a new epoch in hip-hop, spawned the genre’s next ascendant star and eventual usurper of Kanye’s throne, and it still serves as the linchpin needed to understand Ye’s career. The weirdness of this album—and the fact that it seeped into the mainstream—is the best case for following Kanye wherever his mind takes us, even when (like right now) he’s giving you exactly what you don’t want. It’s telling that, after calling MBDTF his “best” album, he returned with Yeezus, an album that follows the template he set out with 808s to the letter.

It’s even more telling that, in 2015, Kanye took the stage at the Hollywood Bowl to perform the album for two nights in its entirety. It’s the only album he’s ever done that for, and it’s hard to imagine it happening for another. —Brendan Klinkenberg