Producer: Marc Nilez
Album: Legendary Classics Vol. 1
Label: Nature Sounds
Meeting through the Trackmasters' Tone, the artist currently known as R.A. The Rugged Man and Biggie Smalls are responsible for quite possibly the most offensive rap song ever. Known to the industry as an uncontrollable troublemaker, R.A., the original wild-boy white rapper, was inked to Jive in the early '90s.

When R.A.'s label caught wind that the Rugged Man was going in the studio with Biggie Smalls, they asked him to churn out something along the lines of “Juicy,” so they could market to radio, piggybacking off the success of Ready To Die. But the Rugged Man did just the opposite. With other plans in mind, the devious MC would go on to craft one of hip-hop's most vulgar and unrefined hip-hop records of all time, “Cunt Renaissance.”

The title itself was cringe-inducing, featuring that most taboo of curse words: the dreaded C-word. R.A. allegedly recorded his verses first, and not to be outdone by Crustified, Big went in and laced arguably the nastiest verse of his career—anal, oral and fisting were all name checked here. The result was dope if also disgusting. And while Crustified never matched the solo success of Big, he was able to bring out of the King of New York's nasty side.