5 iconic freestyles from hip hop legends
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5 iconic freestyles from hip hop legends

“If you just freestyle, everybody is gonna go, ‘Freestyle.'” — Cam’ron

No matter what your preference on the intricacies of hip hop, one thing that can never be denied is the potency of a fire freestyle. Some freestyles act as a catalyst for songs, or beefs, or even entire albums. Some, however, go on to define an entire career for a rapper. Below, we’ve picked out five of our favourites.

Simply put, if an audience can pick up what they need from a simple freestyle then it always bodes well for the rapper holding the mic. What it also does is provide the rapper with a chance to go off the dome, exercise their lyrical muscles and provide a searing reminder of the competitive streak within all hip hop.

Some of the greatest artists in hip hop history have been known as a fire-breathing freestyler. While the most obvious candidate is the Rap Olympic runner-up, Eminem, someone who made his name battling other rappers. there are plenty of other instances when freestyling has spiralled out of the spontaneous and straight into the history books.

Whether it is Biggie Smalls, Em, Jay-Z or another hero, freestyling is no longer seen as the freebie it once was. It has now become a necessary part of every rapper’s arsenal. If you can’t destroy a clip with a mic and a beat, then you’ll never make it.

Below, we’re picking out five of our favourite freestyles of all time.

Best freestyles of all time:

Nipsey Hussle (2010)

Back in 2010, Nipsey Hussle was still an upstart rapper struggling to make a name for himself in the crowded world of hip hop. Signed to Epic Records, Hussle released the first three volumes of his Bullets Ain’t Got No Name mixtape before opting to leave the label. Strapped for cash and providing almost no marketing for Hussle’s release, the rapper decided that he would have to bring his music to the people in any way he could.

When he stopped by the radio station Hot 97.5 in Las Vegas in the summer of 2010, Hussle freestyled as a way to emancipate himself from the more dire circumstances surrounding his record deal. It’s natural and clever, as Hussle often was, but lyrical as well. Hussle had a remarkable ability to jump from topic to topic without ever feeling disjointed or disconnected. It was a natural talent, and one that the rest of the rap world sorely misses today.

Eminem (1997)

Hip hop provided Marshall Mathers with a source of solace. When he was rapping, all his troubles momentarily flew away as he slipped into his Slim Shady alter-ego. It provided Eminem with a vehicle to plough all his pent up anger into, unleashing a style and a rapid flow that still beggars belief. His big break came in 1997 when he made an appearance at the Rap Olympics. Although he finished second, in the long run, Eminem proved to be the real winner.

In a fortuitous slice of luck, an intern from Interscope Records was in attendance and immediately knew that Shady was destined for greatness. Following the performance, the intern passed it on to the label’s head honcho Jimmy Iovine, who was in total awe. “I heard something in the kid who gave it to me,” Dre’s partner in crime, Jimmy Iovine, told Rolling Stone. “He was 19, an intern.”

Shady was then asked to perform a freestyle on San Francisco’s KMEL 106 FM following the rap battle as his stock continued to climb. It had helped to break hip hop careers in the city across the ’90s and had garnered a strong reputation. If you could do it on this stage, you weren’t to be underestimated. After hearing the tape, Dre had an incessant urge to hear more from Eminem and tuned into the freestyle to see whether he was the real deal or if he’d flop.

Wu-Tang Clan (1993)

In order to figure out who would get to rap over Wu-Tang Clan certain verses, RZA would have the MCs face off head to head, often forcing them to improvise their lines to see who would get to appear on the track. This gladiator style of rhyming favoured the precise flow of GZA, who usually got slotted towards the end because no one could follow him, the attention-grabbing rhymes of Raekwon, and the scene-stealing buffoonery of ODB, who all appear on most of the LP’s tracks. To see a great illustration of this process, there’s footage from the 36 Chambers era to demonstrate how quick-witted the members had to be if they wanted to appear on a song.

Raekwon leads off, as he was known to do, establishing the meter without a beat behind them to lay into. Method Man, Masta Killa, and Inspectah Deck follow, bringing their signature styles out: Method is choppy but creative, Masta is heavy on playing into the group’s dynamic, and Deck is heavy on alliteration and wordplay. Ghostface Killa and GZA flaunt their lyrical styles, but it’s U God who caps the whole thing off. Slower, more deliberate in his choices, and less flashy than the others, U God actually might have the best structures and performed verse of the entire freestyle.

RZA and ODB are absent from this appearance, but it just goes to show how fluid and adaptable the Wu-Tang Clan were, and still are today. The 36 Chambers era found the Wu staging a nine-man reclaiming of the east coast as the hip hop epicentre, bringing the genre back to the hub that it first originated, setting an example for the next generation of MCs. Wu-Tang is, after all, for the children.

Biggie Smalls (1989)

We’re revisiting a moment when history was made, and Biggie Smalls stepped up to the mic to deliver one of his most impressive freestyles of all time, all at the tender age of 17.

Looking back at the illustrious but short career of the late rapper Christopher Wallace, AKA The Notorious B.I.G, it’s easy to get caught up in the glitz and glam of the ’90s rap scene—but there’s one moment that defines the man he would become. In 1989, in front of a neighbourhood crowd, Wallace delivered a stunning freestyle that would highlight the power of poetry in his words.

With a baying crowd, likely all gathered to see either the rise or fall of a battle rapper and revel in either destination, Biggie gets to grips with the beat insanely quickly and shows a command that belies his age. Highlighting his innate ability to ride and create a flow without fuss or fury, it would be a staple of his career and mark him out as one of the greats.

Jay-Z (2000)

There are countless impressive freestyles from Jay-Z. Undoubtedly one of the most important hip hop legends in modern times, Hova has delivered many moments where he has dazzled his audience and left the world in no doubt that Jay is at the top of the pile.

Arriving at the iconic British radio DJ, Tim Westwood’s studio, Jay had nothing to prove. A consistent discography that had provided him with enough kudos and critical acclaim had confirmed Jay was already a hero. But, with a mic in front of him, he delivers one of his finest verses.