If someone asked me what I wanted to eat for my last meal, I would say forget the food. Play these 5 classic freestyles and I’ll rest peacefully.
Jokes aside, the 5 freestyles listed here merely reflect the rich, long history of freestyling as a unique subsect of hip hop. Tracing it back to the 1980s, freestyling was originally understood as a written rhyme that was “free of style,” or conceptually disorganized, yet lyrically abundant. However, after its redefinition in the late 1980s and 90s, freestyling became known as a form of unwritten, improvisational rap where the artist rhymes “off the top of the head.” Freestyling can be characterized as its own category of hip hop, and as such, it requires the artist to use a different skill set than they would if they were creating a studio-produced track. Listed below are what I believe to be the four most important elements of a classic rap freestyle.
| Length | Lyricism | Flow | Was it pre-written? |
| Typically, longer freestyles are more impressive because it is less likely that they are pre-written. Consistency is also key here. | Arguably the most important elements of a freestyle, wordplay and vocabulary are a means of flaunting lyrical expertise and mastery of language. | A measure of range, the artist’s ability to adapt to different beats by changing their rhyme scheme and flow is an important criteria. | Although it sounds counter-intuitive to the definition of freestyling given above, many freestyles nowadays are pre-written. Personally, I think that a pre-written freestyle doesn’t necessarily disqualify it; however, it is all the more impressive when they are improvised. |
With these elements in mind, here are my 5 personal favorite rap freestyles in no particular order!
- Black Thought Funk Flex Freestyle (2017)
If you didn’t think Black Thought was one of the greatest MCs of all time, his freestyle at Hot 97 with Funk Flex solidifies it. Rapping for over 10 minutes, Black Thought maintains flawless breath control, cadence, and articulation. His lyricism and wordplay are insane, and some of his many references include F. Scott Fitzgerald, Hamlet, and the institution of Sharia law.
2. J. Cole L.A. Leakers Freestyle (2021)
Almost 12 years in the making, J. Cole’s L.A. Leakers freestyle was released during the promotion of his highly-anticipated album The Off Season (2021). Cole raps over two iconic beats, Souls Of Mischief‘s “93 ‘Til Infinity” and Mike Jones‘ “Still Tippin,” creating such a quick, effortless flow while maintaining incredible rhyme schemes.
3. Griselda Fire in the Booth Freestyle (2020)
Equipped with the beat of their in-house producer Daringer, Griselda’s appearance on Fire in the Booth communicates the group’s hunger and drive for prominence in the rap game. Benny the Butcher starts the freestyle off coolly with a verse that showcases his raw story-telling abilities and Conway the Machine takes over in the second verse with such effortless word-play that he has listeners shaking their heads during his entire verse.
4. Eminem Westwood Freestyle (2009)
Viewed over 77 million views on YouTube, Eminem’s 2009 freestyle on TimWestwoodTV is one of the most legendary rap moments on the internet. His use of multi-syllabic rhymes is extremely hard to achieve, especially considering the number of times he switches his flow to the beats of the acclaimed producer, The Alchemist. If there’s anything to take from an Eminem freestyle, it’s that his lyrical prowess is untouchable.
5. J.I.D. Funk Flex Freestyle (2017)
Rapping over Screwball’s “F.A.Y.B.A.N.” and Biggie’s “Who Shot Ya,” J.I.D.’s Hot 97 freestyle proves once more that his delivery is one of a kind. Despite Funk Flex’s impassive presence, he raps smoothly and confidently over both tracks, switching his flow constantly in true J.I.D. fashion.
Honorable Mentions: Big L’s ‘98 freestyle, Mos Def’s freestyle in the documentary, Freestyle: The Art of Rhyme, Meek Mill’s freestyle in Dru Major’s 2005 DVD The Lost Tapes, Logic’s 5 Fingers of Death freestyle on Sway in the Morning, Childish Gambino’s Hot 97 freestyle, Young M.A.’s Funk Flex freestyle, Kendrick Lamar Funk Flex freestyle.
Words and Stick Figure by Yara Choeb