Everyone knows the Kanye West story by now, and it reads like a crash course in bold artist decisions. Sped up soul samples. Popped pink Polo collars. The list goes on, but perhaps the boldest was 808s & Heartbreak, the project that provoked a collective "WTF?" reaction from the hip-hop community when songs began leaking in late 2008. The world's biggest rapper was singing about emotional turmoil, in Auto-Tune, and it came completely out of nowhere (as opposed to The Love Below when Andre 3000 had already been on his weirdo steez for years). Like anything groundbreaking, the LP has its fair share of haters, but it was still wildly successful, and about as bold of a move as you can make.

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