In his 2003 book, There’s A God On The Mic, Kool Moe Dee wrote: ‘There are two types of freestyle. There’s an old-school freestyle that basically rhymes that you’ve written that may not have anything to do with any subject or that goes all over the place. Then there’s freestyle where you come off the top of the head.’ 

Although freestyles have been commonly and historically associated with hip-hop and rap, the art of simply improvising lyrics prevails in spoken word, poetry and various mediums of expression. In the 1950s, older genres such as jazz attempted to break free of traditional genre-specific constraints and developed the likes of free jazz in defiance of fixed metres or tempos. The common denominator is freedom, in both structure and content. Looking at various genres, from Jamaican dancehall to British grime, we’ll explore the origin, importance and future of ‘the freestyle’.

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The birth of freestyle rap

Freestyles are the epitome of improvisation and creativity, taking away the comfort of preparation and predictability to test rappers’ skills ‘off the dome’. Although historically intertwined, freestyling and battle rap are not the same thing. It’s important to draw a distinction while acknowledging how they have supported each other and sharpened the best rappers and MCs of modern music history. 

The Sugarhill Gang gave us the first recorded hip-hop track with their seminal 1979 hit, Rapper’s Delight. (L-R Wonder Mike, Master G and Big Bank Hank) (Photo by Michael Ochs Archives/Stringer/Getty Images)

The earliest recorded hip-hop song is widely believed to be the Sugarhill Gang’s ‘Rapper’s Delight’, released in 1979. The opening lyrics, ‘I said-a hip, hop, the hippie, the hippie’ and the fact that the song was recorded in one take would set in motion the flippant, organic nature of both ‘old-school hip-hop’ that followed it and the ‘new school’ that would follow suit from 1983 onwards.

However, like most musical legacies in contemporary society, the actual institution and technicalities of freestyle started from a small but mighty Caribbean island named Jamaica. In the island’s iconic sound system culture, where the likes of ska and later reggae and dancehall were played, the stage was a powerhouse from which two people were elemental: the deejay and their master of ceremonies (MC) who would hype the crowd. The deejays (not DJs – who are called selectors) rap or chant over riddims in what is referred to as ‘toasting’, a practice harking back to West African griots. In the late 60s and early 70s, toasting became a more popular form of entertainment as sound systems (traveling deejays and producers with large speakers and a library of beats and riddims) also flourished. In the early 70s, an 18-year-old kid, born in Jamaica and now living in the Bronx, named Clive Campbell hosted a ‘back to school party’ so his sister could buy new clothes for the incoming academic term. Better known as DJ Kool Herc, the ‘founding father’ of hip-hop, he would go on to spin funk and soul at this party, which would be the first of many.

Freestyle rap battles

Learning from DJ Kool Herc, a young Grandmaster Flash, of ‘Grandmaster Flash and The Furious Five’ fame, would go on to pioneer the art of hip-hop djing and also the concept of battle freestyling aka rap battles.

In a genre as competitive and brutal as the burgeoning hip-hop scene, where music often mirrored lifestyle, skill was just as important as image. Only through sheer braggadocio could rappers reign supreme – and freestyle battles put their talk to the test. Freestyle battle raps would showcase a rapper’s ability to improvise, story tell and humiliate all at the same time. In 1981 Harlem, things were revolutionized. Kool Moe Doe of ‘Treacherous Three’ fame – an MC known for his sharp lyrical wit – was at a live set where ‘party’ MC Busy Bee Starskii was hosting and riling the crowd up by calling names out. Unluckily for Busy Bee, Kool Moe Dee jumped on stage and demolished him in a scathing lyrical freestyle.

Freestyles allowed young up-and-coming MCs to showcase their talent – for example, a 17-year-old B.I.G’s freestyle on his home turf of Brooklyn shows his cadence and confidence were already in place, giving us a glimpse of the star he would become.

Jay-Z p freestyle rap
A young Jay-Z came to prominence taking on Big L in a legendary freestyle battle on the Stretch and Bobito radio show in 1995. (Photo by Dave Allocca/DMI/The LIFE Picture Collection via Getty Images)

A top contender for one of the most legendary freestyles is Big L and Jay Z’s freestyles at the Stretch and Bobito radio show in ‘95. At the time, Jay-Z was virtually unknown and Big L was very much still on the rise, a month away from dropping his debut album Lifestylez Ov Da Poor & Dangerous. Both young and hungry, the competitive tension in the air could almost be heard over the audio. Over 10 minutes, the two go back-and-forth – swift, smooth and savage.

Eminem takes freestyle mainstream

No one has sparked greater mainstream focus on battle rap than Marshall Mathers, aka Eminem and his debut film 8 Mile, released in 2002. Loosely based on his life, the film centres on the efforts of a white rapper trying to break into hip-hop, building his confidence and reputation through rap battles. The movie and it’s music resonated so powerfully that the original soundtrack debuted at No.1 on the US Billboard charts and Eminem got his first No.1 US Single with ‘Lose Yourself’.

Eminem brought freestyle bang into the mainstream with the loosely autobiographical movie 8 Mile in 2002. (Photo by Archive Photos/Stringer/ Moviepix/Getty Images)

With his fast, multi-syllabic rhymes and often blistering delivery, Eminem managed to bring freestyle rap to an audience that had grown up in the 90’s ‘golden age’ of hip hop with gangsta rap and R&B possessing the public’s consciousness. 

Grime and the UK freestyle scene

Across the pond in the UK, a different form of freestyle was forming. Forged through generational migration of the iconic Windrush Generation and their children, Notting Hill had its first carnival in 1959, organised by Trinidadian activist and journalist Claudia Jones. After this, the famous Notting Hill Carnival would descend upon West London every summer, celebrating Caribbean culture with food, dance and, most importantly, music. With huge crowds baying for entertainment, countless sound systems of different genres and musicians would pop up on the carnival route – reggae at one, dancehall at another, jungle nearby. There was truly something for everybody. Jamaica’s sound system culture, transported and solidified through generational immigration, birthed the likes of jungle, garage and grime. All of these subgenres started on the same premise of the double act duo of the MC and DJ. 

Grime has often been referred to as hip-hop’s younger British cousin, but it is actually garage music’s moody little brother. But where garage was champagne bottles and light, feel-good tunes, grime was low-pitch basslines, darkness and hoodies. 

Bugzy Malone - grime freestyle rap
The UK Grime scene has given us plenty of beefs played out through freestyle diss tracks, including the infamous back and forth between Bugzy Malone and Chip. (Photo by Andrew Benge/WireImage/Getty Images)

Iconic grime clashes that have been etched into history include the likes of Kano v Wiley and Bugzy Malone v Chip, both generations apart but exciting and dynamic, especially the latter, which would culminate in an intense back-and-forth that would keep listeners up all night eagerly awaiting disses dropped in the early hours.

The same bravado and quick wit required of East Coast battle rappers would be the weapon of choice in East London clashes, as grime golden kid rapper and producer Maxsta testifies: “My earliest memory of listening to freestyles is grime artists doing them around 2005, bars were far more important than polished, proper songs.” 

This focus on lyrical technique meant that artists would rap the same bars over different beats. Indeed, at the grime sets so prevalent in the early ‘00s that made a comeback in the mid-’10s, young and hungry MCs would engage in lyrical warfare over iconic instrumentals such as Ghetto Kyote, freestyling on pirate radio with twenty rappers to one microphone.  

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Freestyle goes viral

Clashes and rap battles are all rooted in the performance and strategy aspect of freestyling that has branched out into hip-hop. The flair and fearlessness of freestyles – trusting yourself to be fast enough to formulate ripostes that will decimate your opponent and impress your audience.

Maxsta’s understanding of freestyles echoes Kool Moe Dee’s, “Personally, a freestyle is two things: it could be rapping off the dome randomly, but as we’re seeing more and more it’s turning up with prepared lyrics to perform over any beat, where there is no chorus or structure. It’s freestyle content.”

Yemi Abiade, a London-based writer, cultural commentator and co-host of hip-hop podcast ‘Rhymes Like Dimes’ agrees with the growing popularity of ‘recycled’ bars for a younger audience with a shorter attention span and different priorities – pointing to the increasing use of social media platforms such as TikTok and Instagram, where users have about 20 seconds to catch audience attention amid an oversaturated feed of content and endless scrolling. “The newer generation of commercial rap stars that came up via the internet don’t have the 

arena to practice, they came up doing specific things that catered to a certain audience.” Niche and specialised subgenres of hip-hop, such as Atlanta Trap or Chicago Drill focus less on lyrics and more on production and image, distinctive through their tempos and style rather than lyrical prowess.

All it takes is one viral clip to be catapulted to fame, and thus, burgeoning musicians are polished and poised before the record button is pressed. Their freestyles are rewritten, reworked and recycled to present the final product. “Being a great MC is still very important in some circles, and the freestyle aids that respect. But you don’t expect Lil Yachty or his ilk to be a great freestyler because that’s not what he does, or what people listen to him for,” Yemi adds. 

The future of freestyle

In addition to showing off lyrical prowess, freestyles can also serve as homage where rappers freestyle over the instrumentals of iconic songs – as chart-topping Potter Payper did with the instrumental of rap favourite ‘Cry’ by Swiss

In Jamaican dancehall, popular riddims are circulated so that people can release their own verses and leave it to party-goers to pick up their favourites. Indeed, some versions of popular riddims include Beenie Man’s 1996 international breakout ‘Who Am I’ on ‘Playground Riddim’, recently used by Mahalia and Burna Boy on ‘Simmer’. In popular rap, tracks titled ‘freestyles’, such as Headie One and Drake’s ‘Only You’ or Stormzy’s 2016 ‘One Take Freestyle’, refer to loose, unstructured songs with no chorus or body – simply straight rap.

Ultimately, the purpose of freestyles has undoubtedly evolved since the inception of hip-hop in the ‘70s, rooted in black diaspora practices from West Africa to New York via Jamaica. Where MCs and rappers were rated on the strength of their technique, lyric giants could both wow and sharpen each other with roundtable discussions-turned-freestyle-cyphers such as this classic with DMX, Big Pun, Mos Def and more. However, as mainstream attention turns from lyrics to aesthetics, major labels and musicians alike are looking to cater to that – with less focus on skill and more on relatability, image and virality. 

Although platforms exist to showcase freestyles, such as the US Breakfast show ‘Sway In The Morning’ – remember “You ain’t got the answers Sway!”? – and Charlie Sloth’s ‘Fire In The Booth’ in the UK, they have become nothing more than pit stops on press tours when artists have a project to promote. On full-length albums, freestyles almost serve the same purpose as an interlude, they punctuate the album with a couple of minutes where the rapper will attempt to show that they still have ‘grit’. With viral freestyles on platforms such as TikTok and Instagram becoming unwitting marketing tools, the word freestyle has evolved so differently from the streets of Harlem in the 70s.

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