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5 of the Greatest Hip-Hop Radio Freestyles of All Time

While freestyling has become something of a lost art, Noisey selects 5 iconic radio freestyles in hip-hop history.

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Freestyling is a lost art in hip-hop today. It’s one of the foundational practices that built hip-hop as a culture. Rappers would huddle on street corners and alleys to freestyle in large ciphers for minutes at a time.

Eventually, hip-hop would ingrain itself into the larger music business. As a result, freestyling became a fixture in radio to market rappers as the best in their class. Hot 97 with Funk Flex, Rap City with Big Tigger, Sway in The Morning, all of these platforms would do numbers in marketing and showed their raw skill and talent on full display.

But there are hundreds of freestyles across hip-hop’s illustrious history? What are some of the best? Noisey has selected five of the greatest radio freestyles of all time from some of the best rappers to ever grace a microphone.

Five of The Best Radio Freestyles in Hip-hop History

Jay-Z’s ‘Grammy Family’ Freestyle on Hot 97 (2006)

In 2006, Jay-Z was embarking on his grand comeback. He was three years removed from his grandiose ‘retirement’ after The Black Album. Hov wanted to be more of a mogul first, perhaps tout the next great rapper in his footsteps.

But he........

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