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The Sideline Observer

Sports and Culture Commentary

Top 15 Greatest Radio Freestyles

For hip-hop heads that grew up in the internet age, radio freestyle videos have been an unavoidable part of the culture. With nationally syndicated stations like Sway in the Morning and Funk Flex accruing hundreds of millions of views annually on freestyle videos, performing on air has become a rite of passage for young rappers, and an outlet for legends to flex their muscles.

Fortunately for fans, the added pressure of rapping for millions of people around the world has led to some incredible freestyles. To shed some light on some of the best ones, I sifted through every radio freestyle video I could find from Sway and Flex this decade (2010s) and compiled a list of my favorite 15. Obviously, I probably missed some and this is subjective, so please don’t dox me just because (insert obscure rapper’s freestyle exclusively uploaded to Vimeo) didn’t make the list. Let’s get into it.

15 — Papoose (Sway 2012)

Sounding like a less nervous Jay-Z, Papoose tore through each beat in the five fingers of death. Even when he got some of the strangest techno instrumentals Sway could’ve possibly dug up, Papoose effortlessly shifted pockets and kept going. With great lyrics and an impressive vocabulary to accompany the impeccable flows, this is one of the most impressive Sway in the Morning freestyles I’ve seen.

14 — Joe Budden (Flex 2016)

At the time of his monstrous appearance on Funk Flex, Joe Budden was a relatively unknown rapper among the younger generation — more known for his outspokenness than his music. In retrospect, Budden’s body of work is ludicrously underappreciated with as many lyrical and conceptual gems as almost all of his more popular counterparts. Admittedly late to the game, this freestyle was the sole reason I decided to listen through Budden’s discography. Watching it makes me regret not hopping on his bandwagon before he retired.

13 — Token (Sway 2016)

For most seasoned veterans in hip-hop, some of the bars spit in this verse would have been among the best in their career. The fact that Token was barely 17 years old at the time with a small fan-base and still had one of the most popular freestyles in Sway’s history is mind boggling. Even if you don’t love his music, this freestyle is prodigious and deserves a listen.

12 — Cory Gunz (Flex 2017)

As far as Young Money lyricists go, Cory Gunz is one of the most technically gifted in the collective’s history. The flow and breath control throughout this freestyle are some of the best on this list. Cory’s lyrics are every bit as sharp — satisfyingly recited with conviction in complex rhyme schemes. Gunz is somewhat underrated, but he gained a new follower in me with this performance.

11 — Tory Lanez (Flex 2017)

Lately, Tory Lanez has been busy starting Twitter beef and handing out diss tracks to respected rappers (one who appears later on this list). Lanez even proclaimed himself the best rapper alive, and, while I don’t agree at all, I can’t deny that he’s backed up every claim he’s made with amazing music. Each beef he’s started has stayed within the confines of the booth and pushed the competitive hip-hop culture forward, earning Tory Lanez my respect and attention. Perhaps a precursor to his recent shift towards ripping apart rappers, Lanez’s spot on Flex isn’t short on wince-inducing bars. In hindsight, Lanez may have been more qualified to start challenging top tier rappers than many fans, myself included, initially gave him credit for.  

10 — Royce da 5’9” (Flex 2018)

In anticipation of his upcoming album, Book of Ryan, the legendary Detroit rapper appeared on Flex to rip an almost ten minute verse over Nas’ N.Y. State of Mind. Royce’s marriage to such a legendary instrumental is seamless and his bars have a level of creativity and wittiness only found in Slaughterhouse verses. His performance was expectedly amazing and if you haven’t listened to Book of Ryan yet, go do that. now.   

9 — JID (Flex 2017)

Fresh off the release of his masterpiece debut album, The Never Story, the 27-year-old Atlanta Dreamville signee appeared poised to make a lasting mark on hip-hop. Over two iconic beats, JID put his incomparable flows and eclectic lyrics on full display during his freestyle. Flex looked outright lost in JID’s endless stream of unique references and multiple-entendres for most of the video.

8 — Mickey Factz (Sway 2016)

Far and away the most unknown freestyle on this list, Mickey Factz’s verse on Sway’s Friday Cypher show is downright genius. I’ve been religiously listening to hip-hop for a long time and have never heard pop culture bars as clever or well put together as the ones in this freestyle. If anyone knows of anything in a similar lane that can top this, point me in that direction.

7 — Childish Gambino (Sway 2013)

With a winter fur hat draped over his headphones and a Pax in his hand, Gambino delivered the most thoughtful and conversational verse I’ve seen on Sway in the Morning. His subdued tone and existential lyrics fit Drake’s Poundcake instrumental better than Drake. While I love the musical direction Gambino’s gone, revisiting this freestyle makes me hope he isn’t done rapping.

6 — Mysonne (Flex 2018)

Mysonne’s appearance on Flex is absolutely beautiful. The once-imprisoned grizzly veteran in the game methodically recites ten minutes of powerful lyrics about systemic racism, sexual assault, redemption, and much, much more. It’s extremely rare when an artist can convincingly get their message across and paint a vivid image of their perspective, and Mysonne did it flawlessly. At its core, the flows, references, and wordplay are in a class of their own, but the overarching importance of Mysonne’s message within the context of his life make this one stand out.

5 — Joey Badass (Sway 2016)

Though only 21 years old at the time, Joey had been modern hip-hop royalty since his 2012 debut mixtape, 1999. Already considered one of the best lyricists alive, Joey came into Sway’s Universe and confidently cruised through the five fingers of death, while simultaneously dismantling fellow NY rapper Troy Ave. Prior to Joey’s appearance, Troy Ave released a track called “Badass” that heartlessly took shots at Capital Steez, Joey’s close friend and collaborator who committed suicide at the age of 19. Joey didn’t hold back.

4 — Cyhi the Prynce (Flex 2017)

In a promotional run for his long delayed and heavily anticipated debut album, No Dope on Sundays, Cyhi cavalierly gave Flex raspy gold for five minutes. It’s moments like this one that help explain why so many of Kanye’s bars in the past have been so slick, as Cyhi’s credited as a lyricist on much of his earlier music. It’s good to see such an absurdly talented emcee finally getting an opportunity to shine, even this late in his career.  

3 — King Los (Sway 2014)

If I wasn’t limiting each rapper to one entry on the list, Los would appear twice in the top five. If you somehow missed Los’ two Sway freestyles, he raps completely off the top for almost ten minutes both times. The fact that he was able to conjure up so many intricate bars that flowed cohesively on the spot is difficult to comprehend. Sway even started feeding him words and topics that he incorporated seamlessly. From a talent standpoint, this guy isn’t human.

2 — Black Thought (Flex 2018)  

What can be said about this freestyle that hasn’t already been said? Black Thought barely breathed for ten minutes. Everything he said was poetic, ruthless, and fascinating. There are literary references, elongated metaphors, and multiple entendres that would take hours to fully dissect and decypher. Credit where credit is due, Black Thought’s freestyle is a masterclass on rap.

1 — Loaded Lux (Flex 2017)

It might be a semi-unpopular opinion to place Lux above Black Thought, but this is the single greatest radio freestyle I’ve ever seen. Loaded Lux is a legendary battle rapper and it comes across clearly in his performance and delivery. Every bar is atomically meticulous and his gritty vocal tone makes the freestyle sound violent. Lux set the bar ridiculously high with this one.

 ~~Honorable Mention~~

Shia LaBoeuf (Sway 2016)

This ain’t the academy, dog.

-Andrew Gonzales

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