Listen to Five Iconic Rappers Sing ... Sort Of

[caption id="attachment_71407" align="alignnone" width="640"]Notorious B.I.G. at MSG, October 1995. Photo: David Corio/Redferns Notorious B.I.G. at MSG, October 1995. Photo: David Corio/Redferns[/caption]

Steel-lined ears are a bonus when it comes to embarking on a listen to Tyler, the Creator's new Wolf album, with the Odd Future lad stepping out of his comfort zone and sparking the project into life by opting for some cringe-inducing crooning on the opening title track. But young Tyler's shenanigans aren't anything new in the world of hip-hop and knowing him, there's a good chance it's not meant to hone in on things like key anyways.  Here's a salute to five legendary but proudly tone deaf rappers.

1. The Notorious B.I.G.

Biggie's lyrics are often acclaimed for their dark strain of humor, but he went well beyond the call on "Playa Hater" when he announced that "for my last hit I'd like to you back to the classics, B.I.G. style of course." What follows is a horrifying peak into a disturbing world where tipsy rappers slur their hearts out at the sort of karaoke spot that serves Georgi not Ciroc.

2. KRS-One

As the leader of Boogie Down Productions, KRS-One fronted up one of hip-hop's greatest ever golden era crews. While doing this, Kris was also apparently secretly rocking a playlist that included the Beatles' "Hey Jude," Billy Joel's "It's Still Rock and Roll to Me" and super-pals Paul and Stevie's "Ebony And Ivory." We know this because KRS couldn't help breaking out into interpolations of all three during his crew's years of dominance.

3. Eazy-E

While recently-departed N.W.A. member Ice Cube was ushering in the '90s by penning some of hip-hop's smartest and most vitriolic political commentary, his former cohort Eazy decided to cue up his copy of Bootsy's Rubber Band's "I'd Rather Be With You" and run through his own off-kilter and extra-vulgar rendition of the song. Eazy's side-career as a lewd wedding singer alas never took off.

4. Biz Markie

Biz is unrivaled when it comes to rappers who sing excruciatingly badly but with much glee and gusto. "Just a Friend" might be the sing-a-along crowd pleaser, but his hook-up with the Beastie Boys for a lark through Elton John's "Benny and the Jets" is a whole other beast altogether.

5. Slick Rick

Because how else do you end a song about a disastrous flirting exchange that goes down in a pizza parlor than by suddenly breaking out into a falsetto version of "Walk on By"?