10. Notorious B.I.G. & Lil Cease "Last Freestyle" (1997)
Station: KMEL/Power 106 DJ: Sway & Tech Best Punchline: "I make your mouthpiece obese like Della Reese."
Just six days before he was tragically murdered in Los Angeles, Biggie Smalls visited San Francisco's KMEL for his last recorded radio interview. Sway & Tech were able to get B.I.G. to dish on Tupac's death, Puffy, and the East vs. West Coast beef. Luckily they also convinced Frank White to kick a freestyle alongside his protege Lil Cease—actually he didn't need much convincing. As usual, Biggie was ready to go.
Sure his bars were borrowed from Life After Death, but the world had yet to hear the record. This definitive freestyle would become an important piece of hip-hop history, nonetheless.