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”

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.)

NWA, “I’d Rather Fuck You”

It was p-funk karaoke night up in Compton when Eazy E decided to sing over Bootsy’s Rubber Band’s “I’d Rather Be With You.” Giving the proceedings an extremely profane and salacious twist, he relays how he’d “rather fuck with you all god damn night cause your pussy’s good” while explaining that he’s “fuckin’ all your friends cause you ran your mouth like I knew you would” and promising that “we can do it doggy style, or you can get on top.” Squeaky-pitched, jheri-curled rappers have never been so proud.

Mary J Blige feat. Grand Puba, “What’s The 411?”

As part of acclaimed rap crew Brand Nubian, Grand Puba helped usher in the ’90s with raps buoyed by Nation Of Islam rhetoric. Then he went on to kick-start the flow of hip-hop dollars going fashion designer Tommy Hilfiger’s way and drop a debut album, Reel To Reel, that was a master class in effortless braggadocio. The project also featured the peculiar “Baby, What’s Your Name?” wherein he sings abysmally but totally straight-faced over a Donny Hathaway sample. But it’s his cameo on Mary J Blige’s “What’s The 411?” that shows Puba’s true misguided confidence as he goes line for line and note for note with the Yonkers chanteuse. In fairness, Mary J rhymes as badly as Puba sings, but Puba slurring “And today your dream comes true” is less smooth lothario than just plain deluded.

Rhymefest feat. Ol’ Dirty Bastard, “Build Me Up”

While Kanye West’s most theologically-inclined pal holds down sole rapping duties on this tale about a girl who turns down his amorous advances, it’s the chorus from the Wu-Tang Clan’s most certifiable that really tugs at the heart strings. Mangling his way through The Foundations’ “Build Me Up Buttercup,” Dirt Dog perfects a a singing style pitched somewhere between drunken bawling and the sound of a skulk of amorous foxes. It sounds strangely festive, too.

Q-Tip, “Barely In Love”

Originally planned for a 2002 release, the one-time A Tribe Called Quest leader’s attempt to re-cast himself as a legit singer would have pre-dated Outkast’s “Hey Ya” and maybe brought him Andre 3000-level crossover success. Instead, the album was held back by his record label until 2009, by which point there was nothing novel about rappers moving beyond being merely rhymers. Ultimately it was a delay to be thankful for, with Tip’s nasally whine proving better suited to spitting, not singing—by the time he hits the chorus point on “Barely In Love,” you suspect Tip wishes he was a member of Yes.

Slick Rick, “Mona Lisa”

Rap’s greatest storyteller and ginormous gold chain collector, Slick Rick’s never been shy about breaking out into song. Here he sets up a standard girl-rap tale, complete with the immortal dis “Sit down, eat your slice of pizza and be quiet” and a guy called Trevor whisking Rick off to a party with “some real mature women.” At which point they see Mona strolling glumly down the street, giving Rick an excuse to sing “Walk On By” falsetto style. Who needs Auto-Tune when you can just sing really badly in a really high pitch?

Master P, “Ooh Shit”

Technically, the No Limit head honcho’s “Ooh Shit” only features one sung line, but in tackling Marvin Gaye’s “Sexual Healing” the southern rap impresario shows real dedication to the cause of off-key crooning. After rapping “Before we did it, popped in the Marvin Gaye tape,” he breaks out into song, suavely declaring “There’s nothing wrong with me fuckin’ you!” Juvenile and horrendous to the ear, it’s ignorant rap par excellence.