Producer: Steven "Stevie J" Jordan, Sean "Puffy" Combs
Album: Life After Death
Label: Bad Boy
Likely inspired by West Coast potty mouth Too $hort; Biggie Smalls hosted a collection of “Freaky Tales” of his own on “Nasty Boy.” Recounting various sexcapades, Big kissed and told in the nastiest way possible.

Whether it be the half-Indian lover he called Tonto, or freaks down for the one night stand, Big was getting it in on the female tip—and was arrogantly unapologetic about it. While it's always debatable whether or not you liked the song, there's no denying you got a hearty chuckle when you first heard the feces-related opening skit. That's that shit.