Station: Hot 97
DJ: Funkmaster Flex
Best Punchline: "Everybody look at you strange, say you changed/Ugh—like you worked that hard to stay the same."
On Devil's Night 2006, unstoppable Hov dropped by Hot 97 to appear on Funkmaster Flex's show and promote Kingdom Come—Jay's first album since his short-lived retirement.
At the time, Jay was still parked behind a desk as President of Def Jam Records, so it was no surprise that a handful of artists on the label were less than pleased that their boss's LP was immediately made a priority. In the interview with Flex, Jay addressed disgruntled Def Jam acts LL Cool J and Method Man, as well as longtime adversaries Jim Jones and Cam'ron.
Afterwards, inspired by Basquiat with his chariot on fire and his mind on Pluto, Hov not only kicked one of the best freestyles of his illustrious career, but some of his most vigorous rhymes ever. Over Kanye's “Grammy Family” instrumental, Jay started by poking fun at the Dipset's label home, “I'm so independent I might buy Koch.” He went on to reflect on Martin and Malcolm, Big and Pac, Jesus and Judas, and the perils of success—lines that would later wind up in his song "Most Kings.”
Jay was back in a major way, and the almost-five-minute freestyle counted dozens of quote-worthy lines. While many of Jay's enemies saw the God MC as vulnerable and soft due to his shiny new job title, this freestyle proved he hadn't missed a step. The only part we can't figure out is why he didn't spit bars like these on Kingdom Come.
4. Jay-Z "Grammy Family Freestyle" (2006)
Station: Hot 97