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The 50 Best Radio Freestyles

24. Eminem "Wake Up Show" (2000)

Station: KMEL/Power 106
DJ: Sway & Tech
Best Punchline: “I smoked crack today, yesterday, and the day before/Saboteur, walk the block with a Labrador/Strapped with more coral for war than El Salvador/Foul style galore/Verbal cow manure/Coming together like the eyebrow on Al B. Sure.”


When Eminem first burst on the scene in 1999 with “My Name Is,” those not in the know probably assumed he was just an edgier version of a boy band member. Little did they know, Em was one the underground's greatest battle and freestyle rappers. It was this appearance on The Wake Up Show that helped Eminem catch the attention of Dr. Dre and Jimmy Iovine.

After signing on the dotted line, the Detroit emcee proceeded to pull off an almost impossible feat, becoming the only rapper to successfully dominate the pop charts as well as the underground battle rap circuit. Somehow Em was able to walk that fine line, appealing to casual rap fans as well as snobs with his hilariously layered lines.

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