These Legendary Freestyles by Iconic MCs Will Go Down in Hip-Hop History
Whether in the streets or under the spotlight, freestyling is an art form that deserves respect. Read for some of the best freestyles in history!
By D.M.Dec. 8 2023, Published 9:04 p.m. ET
Few expressions capture the raw essence of hip-hop more authentically than freestyling.
The art of freestyling, where rappers unleash unscripted lyrics off the top of their heads, has produced some of the most iconic moments in the genre’s history.
From cyphers and diss tracks to the verses dropped during radio show appearances, the best freestyles are a testament to an artist's skill.
Let’s take a look back at some of the standout freestyles in hip-hop history that have undeniably made a lasting impact on the culture.
Megan Thee Stallion’s "LA Leakers' Freestyle" (2022)
In addition to being a GRAMMY-award-winning MC, Megan Thee Stallion has dropped some notable freestyles. She appeared on the LA Leakers show in 2022 and wasted no time showcasing her raw authenticity.
Megan effortlessly navigated the beat with a commanding presence, addressing everything from her rise to stardom to the drama in her personal life.
Many commended Megan for her ability to switch flows while rapping to a futuristic beat and later, Warren G & Nate Dogg's "Regulate.”
Meek Mill's "Back to Back" Freestyle (2018)
Meek Mill performs on stage.
On the heels of their feud, Meek Mill put his disdain towards Drake aside, freestyling to his song “Back to Back” during an appearance on Funkmaster Flex’s radio show.
The song originally served as Drake's response to Meek’s diss track, "Wanna Know," in the summer of 2015. Meek’s freestyle, which was later released on his official SoundCloud account, showcases a lyrical prowess that transcends the past tensions between the two superstars.
Black Thought’s HOT 97 Freestyle (2017)
Black Thought performs at the 2023 Roots Picnic.
Black Thought, the frontman of The Roots, graced the airwaves of Funkmaster Flex’s show in 2017 and delivered a banger.
His freestyle, which lasted for nearly 10 minutes, unfolded as a masterclass in hip-hop storytelling. Black Thought's freestyle on HOT 97 garnered widespread acclaim, as his lyrics were a blend of social commentary and autobiographical narratives.
Eminem's "Westwood" Freestyle (Featuring Royce Da 5'9" and Mr. Porter) (2010)
In 2010, Eminem, Royce Da 5'9", and Mr. Porter appeared on Tim Westwood’s BBC radio show for a cypher that has since gone down in history.
The chemistry between the Detroit natives was undeniable, as they effortlessly navigated through an array of topics and delivered a memorable freestyle session.
The Notorious B.I.G.'s "Wake Up Show" Freestyle (1997)
Biggie Smalls’ 1997 freestyle on The Wake Up Show is arguably one of the greatest rap moments of the 1990s. The appearance would be one of Biggie’s last public sightings, as the rapper was gunned down just days later.
Video from the interview was published on YouTube 15 years after it aired. Since then, the clip has been viewed more than one million times.
Jay-Z's GRAMMY Freestyle on HOT 97 (2000)
Jay-Z's freestyle on Funkmaster Flex’s radio show demonstrated the Brooklyn rapper's versatility and quick-witted lyricism.
The appearance came after the MC retired from making music, stepping away from the industry for three years.
The anticipation made way for a promising return. With confident delivery, Hova solidified his status as one of hip-hop's most formidable forces.
The author’s content and opinions have not been pre-reviewed, approved or endorsed by Discover.
