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The 50 Best Radio Freestyles

23. Cassidy "11 Minute Freestyle" (2004)

Station: Hot 97
DJ: DJ Enuff
Best Punchline: "I aint' no pretender, ya remember the Free stuff/And that'll happen to any nigga think he tough."


In 2003, Cassidy was little more than a mixtape rapper with a cosign from Swizz Beatz. Sure, we'd heard a few loose tracks, and caught wind of rumors that he'd dismantled Freeway in a freestyle battle. But by 2004, Cass had a single with Kells, and was starting to ring bells. Still, it wasn't until he kicked this 11-minute freestyle on Hot 97 that we recognized just how serious he was.

Cassidy beasted over some classic instrumentals while Swizz did what he does best—ad-libbing and hyping up the crowd. The combination was sheer musical mayhem.

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