Wisely or not, rappers have never been shy about flexing their pipes. And while there are those who know what they’re doing — think Bone Thugs n’ Harmony, or André 3000 — many more, well, do not. With the release of Kanye West’s 808s & Heartbreaks, an album entirely and inauspiciously devoted to the emcee’s singing voice, rapidly approaching, we’ve taken a look back at ten memorably off-key performances that demonstrate just how we arrived at this moment. Cover your ears!