5. 808s & Heartbreak (2008)

The bravest album Kanye ever released, 808s & Heartbreak upended hip-hop's status quo even more radically than The College Dropout four years before it. He had toyed with AutoTune as a way to communicate paralyzing sadness in his verse on Young Jeezy's "Put On," a bleary-eyed, robotic mewling spree that showed him in the midst of a gruesome downward spiral. For 808s, the culmination of that spiral, he went all-in, flipping a technology that had been associated with audacious T-Pain party tracks into an instrument of despair. Crushed by his mother's death and his breakup with fiancee Alexis Phifer, Kanye channeled his depression into bleak electronic song-caskets and pained singing straight out of a '90s emo band's basement. (If you thought Kanye's rapping was clumsy ….) The album certainly has its drawbacks: It finishes with a whimper, not a bang. It introduced Kid Cudi to the world at large. Listening to Kanye play the victim is almost unbearable. But 808s shines in the way all Kanye albums shine: It challenges our expectations (letting the spare digital wasteland of opener "Say You Will" drift uninterrupted for three minutes was a bold choice) and it rewards our appetites. The first eight tracks are all masterful pop songs with serious replay value. When's the last time you listened to "Street Lights"? It's dope.