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10 Cringe-Worthy Moments of Rappers Singing Badly

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!

2003: There are, perhaps, worse pieces of overplayed, half-sung drivel by 50 Cent (“Candy Shop,” anyone?), but his mumbled delivery here might well be his very laziest.
2008: Snoop had long since settled into a safe groove by the time Ego Trippin dropped, so hearing him go a little nuts on this seventies throwback was sort of a treat. Except for the vocals – completely buried in a super-cheesy Vocoder effect, not Auto-Tune, for those scoring at home – which rendered the song more parody than homage.
2008: When Jay-Z was announced as the headliner for this year’s Glastonbury Festival in England, Oasis’ Noel Gallagher took offense, saying hip-hop was wrong for the treasured annual event. Hov calmly let it slide until his set, when he tromped out with a guitar slung around his neck and cheekily croaked through a massive sing-along to Oasis classic “Wonderwall.”
10 Cringe-Worthy Moments of Rappers Singing Badly