The Top Ten Best Worst Singing Rappers

The Top Ten Best Worst Singing Rappers

These days, there's nothing attention grabbing about rappers who sing, whether it's Andre 3000's amped squawk, an Auto-Tune-enabled Kanye West, or Lil Wayne's upcoming Riker's Island shower room spirituals. This week the canon sees new album additions from one-time Goodie Mob member Cee-Lo Green, whose stint in Gnarls Barkley saw him clocking up mainstream riches as part of Gnarls Barkley, and Kid Cudi, who is effectively a new era rapper styled as a singer. Dig back a little deeper though, and you'll find a vault of under-appreciated songs from rappers who pledged allegiance to singing quite horribly but to utterly entertaining effect. Here are ten of the most enjoyable worst.

Flavor Flav, "Let It Show"

He may be hip-hop's best ever hype man, and supposedly able to play over ten different instruments, but Public Enemy's firebrand should stick to nonsensical ad libs—not attempts to hit the high notes. The opening track to Flav's little known and rightly over-looked solo album, Hollywood, showcases a level of unhinged warbling that even Ol' Dirty Bastard would consider off-key. Then for kicks, the album's closing cut, "Hotter Than Ice," has him going country and western, lamenting how "my whole world turned to yellow snow" over a beat that sounds like something the late schizophrenic oddball musician Wesley Willis would conjure up.

The Notorious BIG, "Playa Hater"

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In what may be the worst ever example of the human lifeform singing, Big croons his way through a robbery scenario in a style more asthmatic than soulful. You'd suspect that whole thing was a sly dig at Puffy's attempts to get him to roll out commercially-friendly songs, if only the king Bad Boy himself didn't join in half-way though the proceedings.

Beastie Boys feat. Biz Markie, "Bennie And The Jets"

"Just A Friend" may be hip-hop's most crowd-participation-friendly sing-a-long moment, but it's Biz's collaboration with the Beastie Boys that takes the off-key spoils. The team's attempt to tackle the Elton John number "Bennie And The Jets" originally appeared as a free flexi-disc with Grand Royal magazine back in the mid-'90s. Brilliantly, at times it sounds like Biz has no idea what the original lyrics are, so instead he falls back on slurring syllables together as he blunders through the track.

Cru, "Lisa Lipps"

Though they never quite made it on Def Jam, Cru nevertheless hold a fond place in the hearts of hip-hop nerds, if only for mustering the most ever references to Hunts Point hookers on any one album. That project, Da Dirty 30, also brims with horridly-sung moments from group member The Mighty Ha, whose gruff, sandpaper-textured voice stumbles through "Papa Was A Rolling Stone," "Ain't No Sunshine," and "Yesterday" on the song "Lisa Lipps." An ode to a lady with very special oral talents, he helpfully explains, "Lisa Lipps was a rolling stone/Wherever she slapped, slobbed, was her home." (Bonus: The album also has Cru letting serial rap crooner Slick Rick break into song on the cautionary "Just Another Case," which also references Phil Collins.)


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