Station: Power 99
DJ: Lady B
Best Punchline: “If you're a sucker rapper, I'll name you Snoopy/Turn your girl into a Cool J groupie/Beat you in the face until the shit looks goofy/Then fuck your girl 'til she has to dookie.”

It's hard to believe that the man responsible for this dizzying freestyle was only 17 years old. That would put LL closer to Bow Wow's debuting age than Jay-Z's. The young prodigy was rapping better and more passionately than almost all of his elders, and kicked a new style, more technical than that of, say, the Sugar Hill Gang.

While on a promo run in Philly for his 1985 debut, Radio, Cool James blazed the airwaves and crushed all preconceived notions of what a rapper (a kiddie rapper at that) was supposed to sound like. He also took T La Rock's hit and made it his own, leading Def Jam to ask “T La who?”