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 could never quite kick that rapping bug. His freestyle over DJ Khaled, Consequence, and Kanye West’s “Grammy Family” proved that he was still the cream of the crop. “Hov got flow, though he’s no Big n Pac, but he’s close, how I’m supposed to win, they got me fighting ghosts,” he raps, looking up at the ceiling.
Black Thought’s Funk Flex Freestyle on Hot 97 (2017)
Ten minutes of some of the best rapping you’ll ever hear. “I’m sorry for your loss, it’s a body dead in the car, and it’s probably one of yours,” he raps at the start. What followed was an onslaught of bars over Mobb Deep’s “The Learning (Burn)”.
“How much more CB4 can we afford? It’s like a Shari law on ‘My Cherie Amour,’” he spits elsewhere. Sure, there may be examples of rappers going the distance with their rapping. But few parallel the internal rhyming and imagery Black Thought puts on display for Funk Flex.
Big L and Jay-Z on ‘The Stretch and Bobbito Show’ (1995)
Big L remains one of the biggest ‘what ifs’ in hip-hop history. His only album, Lifestylez ov da Poor & Dangerous (1995), was heralded as a classic upon release. However, he was tragically killed in 1999 at a far too young 24 years old.
His freestyle alongside a pre-Reasonable Doubt Jay-Z is even more reason to believe he was the next big rap superstar. “I started smokin’ dust and been insane since/This rap s**t was a great gift/The other night some snake riffed and got a hot lead facelift,” the Harlem rapper snarled. Extremely vivid rapping on display from an artist gone far too soon.
The Diplomats’ Freestyle on ‘Rap City’ (2003)
While Jim Jones and Juelz Santana spit their share of hard verses over Scarface’s “My Block“, Cam’ron made his bars look effortless. He saunters up to the mic with a wad of cash and litters off lyrics while he counts through it.
“Who more realer? Weed in the four wheeler/Eff Mike, ’til you see me, you never saw ‘Thriller‘,” he scoffs. Meanwhile, it doesn’t look like he lost count of his money one time.
Lil Wayne’s Freestyle on ‘Rap City’ (2007)
Freestyling is Lil Wayne’s bread and butter. He’s famously said that he never writes down what he raps, every lyric flowing from a pure stream of consciousness. Consequently, he approached shows like Rap City the same way he would a normal mixtape cut.
No wonder he would turn his 2007 outing on Rap City into “Live From 504” from Da Drought 3. Here, he disses Philly rapper turned podcast Gillie Da Kid and invents new ways to tell us he’s the best rapper alive. “I gets hotter by the tock before I sizzle to death/I just tell the clock, ‘gimme a sec,’” Wayne boasts.
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