The Best Radio Freestyles of All Time

by

Freestyling is an art form that dates back to hip hop’s origins. Radio stations have been the main hub for rappers to showcase their skills as freestyles happen during a press run, usually in the promotion of a new release. These freestyles are usually spat over preexisting beats but can also go over original production in some instances. There are many conflicting interpretations of what a freestyle can be. Some view it as a verse that is “free of style,” meaning that it can be pre-written or improvised. On the other hand, purists view a freestyle as a verse that is crafted on the spot. Some of the best radio freestyles in rap history have become heavily discussed moments in hip hop culture. This list takes a look at the greatest radio freestyles of all time.

Not all freestyles are improvised or recorded live. Therefore, this list consists of freestyles that were performed on radio shows. Any radio freestyles were eligible, and the criteria were based on the quality of bars, flow, and performance. Some freestyles contain lyrics from existing songs, which are generally ranked lower because of that. Look at the list, starting from number 10 and working up to number 1.

10. King Los – “5 Fingers Of Death” On Sway (2014)

The greatness of King Los‘s “5 Fingers of Death” freestyle is that the bars are improvised but are still top quality. The performance starts off relaxed and gradually escalates into an energetic freestyle that only gets better with each beat. It is a masterful demonstration of rapping great lyrics off the cuff. Los even gets Sway involved as he asks Sway mid-rap to suggest random words to mix into the freestyle.

9. Loyle Carner On Fire in the Booth (2017)

Loyle Carner delivered his landmark Fire in the Booth freestyle on the heels of his now-classic debut album, Yesterday’s Gone, back in 2017. The album was a sincere portrait of his personal life, contrasting with his freestyle as he showcases his ability to spit quality bars in a completely different setting. He starts over “Dust 2 Dust” by Chillinit, Huskii, and Flowz, a beat that is entirely different from the more subdued style of production that he typically raps on. He occupies a different lane within the UK rap scene, but this freestyle shows he belongs among the greats.

8. Avelino on Fire in the Booth (2017)

Avelino’s first two appearances on Fire in the Booth were in 2015, the second being his legendary freestyle alongside Wretch 32. By the time he came back for Part 3, he had built a name for himself in the UK scene, yet he still appeared as an underdog. The most impressive thing about Avelino’s third Fire in the Booth is that he raps over a Coldplay instrumental and to a significantly faster beat than usual.

Despite that, he did not miss a beat and made every line very clear. The wordplay in this freestyle is immaculate. He manages to weave in so many different references to the point where if you divert your attention for a second, you just might miss them. It’s the kind of freestyle where one will catch new lines with every revisit.

7. JAY-Z – “Grammy Family Freestyle” On Funk Flex (2006)

In 2006, JAY-Z returned to rapping after his short-lived retirement three years prior. Many doubted Hov’s skills at the time, especially around the release of his criminally underrated Kingdom Come album. The surrounding context makes his “Grammy Family” freestyle much more impactful. It was a monumental moment in hip hop as JAY-Z casually delivered one of the greatest freestyles ever. The freestyle is not even that long and still makes a grand statement of why Hov is the greatest. His flow, rhyme schemes, double entendres, combined with his confident approach, makes the freestyle legendary and completely eclipse the original “Grammy Family.”

6. Kano on Fire in the Booth (2016)

Much like the “Grammy Family” Freestyle, Kano’s 2016 Fire in the Booth was a reclaiming of the throne he once held. It was a grand return to the scene in promotion of Made in the Manor, released after a six-year break from music and is now an all-time classic. The beat of choice, J Dilla’s “Let the Dolla Circulate,” goes perfectly with Kano’s commanding rap voice. It is a masterclass in delivery as the beat is so spacious that it feels like Kano is delivering a powerful speech. He goes in for eight minutes and doesn’t miss a beat, even when Charlie Sloth cuts the beat for the last few bars.

5. Wretch 32 on Fire in the Booth (2017)

Wretch 32’s fourth appearance on Fire in the Booth is considered the best for a reason, but his fifth appearance two years later also deserves a high rank. Wretch’s ability to extend metaphors for an entire verse makes him one of the best. He rhymes over a stripped back version of Kanye West’s Blood on the Leaves, allowing him to meditate on recent events in the world. Wretch amazes even before the drums come in after rapping for three minutes. He then finishes by saying, “And if they don’t say I’m nice then they didn’t play it thrice,” as it takes that many listens to catch every detail.

4. Eminem, Royce Da 5’9″ & Mr. Porter on Tim Westwood (2010)

This particular freestyle appears more as a casual cypher between three friends. These friends happen to be legends. The Alchemist mans the decks and beats as Eminem, Royce Da 5’9″, and Mr. Porter rap for three rounds. Throughout the freestyle, the three continue to impress each other and encourage one another to step their games up. They each bring a unique style to the table. Porter is relaxed, Royce is aggressive, and Eminem is the quiet assassin. He stands quietly until it’s time to spit with intensity. Tim Westwood stands amazed as the three consistently out rap each other, resulting in one of the best radio freestyles.

3. Wretch 32 & Avelino on Fire In The Booth (2015)

Wretch 32 and Avelino pulled up to Fire in the Booth in 2015 to promote their collaborative mixtape. In my opinion, they ended up delivering two of the greatest verses in hip hop history. These verses were career-defining moments for both of them, making Avelino a force to be reckoned with, and solidifying Wretch as one of the greatest. Avelino raps with more emphasis on wordplay and schemes, whereas Wretch’s verse is heavy on metaphors and entendres.

Avelino sets the bar incredibly high, commanding the mic over Don Trip’s “All on Me.” Wretch does not flinch for a moment and quickly leaps beyond that bar with his verse. Charlie Sloth is so impressed by the verse that he wheels the track and has Wretch do his again. Wretch goes even harder on the second try, leaving Charlie speechless. Both verses are easily the greatest in the show’s history.

2. Big L & JAY-Z on Stretch & Bobbito (1995)

1995 was the year Big L released his first and only album during his lifetime. The record, Lifestyles ov da Poor & Dangerous was legendary as it displayed Big L’s incredible and highly influential rap style. That same year, L appeared on Stretch & Bobbito, one of the most important radio shows of the ’90s. He was joined alongside a pre-Reasonable Doubt JAY-Z, and together, they delivered one of hip hop radio’s most iconic freestyles.

Over Miilkbone’s “Keep It Real,” Big L and JAY-Z trade verses and raise the bar for each other. Big L went the hardest, spitting clever bars like, “I’m so ahead of my time, my parents haven’t met yet.” Jay’s flow is so far removed from the albums he would eventually put out, but the talent was there as he cleanly transitions between flows.

This freestyle is not only impressive because of its verses, but it happened at a time when radio was the only way to hear your favorite rapper debut unreleased verses outside of seeing them live. Radio freestyles were not the well-produced, polished events that they are now. The greatness of the freestyle was discussed in the 2016 documentary, Stretch & Bobbito. This freestyle is undoubtedly the greatest of its era.

1. Black Thought On Funk Flex (2017)

Black Thought’s 2017 freestyle on Funk Flex’s Hot 97 radio show hit the internet like a meteor. He singlehandedly raised the bar for what a radio freestyle should be, and he did it by rapping the way he has always delivered. Over Mobb Deep’s “The Learning,” Black Thought relentlessly raps for 10 minutes. Throughout the freestyle, his energy and lyricism never dip in quality, leaving the viewer holding onto every single lyric. Funk Flex’s reactions throughout the verse display just how filthy the freestyle is. In just a single take, this freestyle allowed Black Thought to showcase his skills as one of the best rappers ever.

The impact of this freestyle was almost immediate as one could witness the reactions in real time. Days after, he received his flowers on The Tonight Show. He even performed the freestyle in its entirety in Boston a few months later. Black Thoguth forever raised the standard for freestyling, positioning himself as an eternal legend.

Overall, these are the best radio freestyles amongst an extensive lineage of performances that have been a longstanding tradition in hip hop. Here are some of the best freestyles that did not quite make the list but still deserve mentioning: