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The Life and Death of the Freestyle Mixtape

The freestyle mixtape wasn’t just a service to the fans, it was a representation of hip-hop’s core. Now it's dead.
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The art of competition has always been one of the cornerstones of rap, if not it’s entire foundation. From its humble beginnings to its golden days, one of rap’s most distinct characteristics is that the artists within its boundaries are always in their own corners, never fully in support of anyone or anything that could compromise their own legacy, and that’s what makes it great. Between album sales, lyrics, stardom and, now, remaining in the good graces of the internet, rap has always been about not just being great, but the best.

Over the last three decades of hip-hop, specifically, the “freestyle” became a small but formidable arena in which that sense of competition was heightened. At its roots, freestyling was the ability to rhyme words, usually in a rap battle, in an improvisational form. The best emcee was always the one who could cloak their noticeable lack of preparation the best with intricate rhyme schemes and hard punchlines right on the spot.

However, the freestyle form that had an even bigger effect on hip-hop culture, and raised the stakes of competition even higher, isn’t even technically freestyling. The term would, at some undefined point, become synonymous with that of the remix and the cover. A “freestyle” was no longer a rapper improvising their way through a song, but rather, a remix to an already noteworthy song in which another rapper would write lyrics to that song’s beat “free of style.”

Compare the traditional freestyle with that of Lupe Fiasco’s “freestyle” over a “Dead Presidents” instrumental. The lyrics are clearly written, refined and calculated to fit perfectly over the beat. Although it isn’t a freestyle in terms of the original definition, this type of remix would become what rap fans obsessed over for years, with every artist attempting to best their fellow artists over their own songs. With that, came the freestyle mixtape.

Mixtapes, in their original form, were also something much different. The form of mixtape we know and love today was more than likely started as a result of DJs, such as New York’s DJ Clue, breaking from the traditional norms of the mixtape industry, and creating compilation tapes of new artists looking to break into the scene. As the mixtape became bigger, DJs became both gatekeepers and authorities for new music, and as the internet’s rise spawned websites like Datpiff, rappers now had a new outlet for their music that didn’t necessarily have to involve a record deal.

The rise of the “freestyle” was running almost parallel to that of the mixtape. With just a few short keystrokes in a YouTube search, you can find myriad classic freestyles from the late '90s from legends such as Big L, Tupac, Biggie, Jay Z and more. In one such video, there’s a roundtable of Mos Def, Canibus, Big Pun and DMX “freestyling” a capella, with clearly pre-written material, as each emcee tries to outmatch the other. Despite the lack of true improvisation, the competitive aspect is there, and the end result is just as magical. Even if the rappers’ bars weren’t completely new to them in the moment, they were to anyone watching.

Eventually, as the demand for freestyles naturally grew, and the ability for DJs, radio hosts and the iconic Big Tigger to get rappers to spit their hottest lyrics over the most classic of instrumentals, the idea of compiling these scattered moments into one mixtape emerged. Instead of the occasional, sporadic freestyle from an artist like Fabolous arising from a DJ Clue-hosted mixtape, why not just have Fabolous release an entire mixtape of his own with the same concept?

The freestyle mixtape was its own tour de force. It didn’t ascribe to any regulatory notions of what rap should be, and instead, artists decided for themselves how best to compete in an industry run by labels looking to gain an upper hand on their fame before they could. It was its own entity; a culmination of both the rise of DJ-hosted street albums and the increasing demand for rappers to out-rap their biggest rivals on their own songs, and it was saving careers.

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Our memories of the golden age of freestyles and the freestyle mixtape shouldn’t lie in its originality, but in its value to the struggling rapper as a lifeline to their fans. When Clipse decided to release their infamous We Got It 4 Cheap mixtape series, it was in the midst of an ongoing battle with their label following the release of their hit album Lord Willin’. The tapes not only offered fans the chance to hear Pusha T rap over songs like Ghostface Killah’s “Daytona 500” or Common’s “The Corner,” they provided fans the chance to hear Pusha T rap... period. If a particular rapper couldn’t push their music through the proper channel, then why not just spend time recording over music that already had?

For others, such as Chamillionaire and his Mixtape Messiah series, freestyles were an outlet to maintain relevancy that had begun to dwindle after a hot start. In Cham’s case, Mixtape Messiah was an opportunity to stay connected, and without it, his career would have likely died out several years earlier than it finally did in 2009. With freestyles over everything from “I Get Money” by 50 Cent to “Kick, Push” by Lupe Fiasco, Chamillionaire’s freestyle mixtapes not only helped him stay relevant by having him try to out-rap the song’s original artists, but by also letting him attach his name to the notoriety of theirs. The freestyle mixtape, for many artists, was communalistic.

In addition to Clipse, Chamillionaire and Crooked I, whose Hip-Hop Weekly freestyle series spanned a whopping 52 weeks in an attempt to gain notoriety after label troubles at Death Row kept him out of the spotlight for years, the freestyle mixtape was also an important part of Lil Wayne's rise to superstardom in the mid '00s. Da DroughtDedication and No Ceilings were all freestyle mixtape series that allowed Weezy to assert his dominance over other rappers. Especially on Da Drought 3, where Wayne utterly eviscerated nearly every popular song at the time—from Beyoncé’s “Upgrade U” to DJ Unk’s “Walk It Out”—making it known that he was, in fact, the greatest rapper in the world, and if anyone disagreed with him he would just rap over their beat and prove it.

The freestyle mixtape would eventually die out, and there are ample reasons for its death. Today, the industry that was once dominated by major labels has transformed into smaller, independent pockets of artists, who maintain more creative control over their music than ever before. It feels as though the industry has split itself into two parts—the artists who strive for quality and the artists who strive for quantity. Each has their own distinct version of creative control, and there are now fewer artists stuck in the middle waiting out some label deal, hoping to record anything even if it’s over another rapper’s beat.

The internet age, for everything that it did to create the sensation of the freestyle mixtape, is also responsible for its demise. The concept of the freestyle mixtape is one that spawned out of necessity, whether that was a newcomer, a struggling artist stuck in the middle, or a great rapper looking to destroy his peers. However, that necessity all but dissipated with the proliferation of professional and label-sanctioned streaming platforms, the rise of social media, an overabundance of information, and therefore an overabundance of music. The anticipation of a freestyle mixtape from your favorite rapper didn’t seem to matter as much when the competitive stakes weren’t as high.

Eventually, with a premium placed on individual songs, surprise albums, and the idea that anyone and everyone can release music to the internet, the freestyle mixtape became nothing more than white noise; a drop in a pond that sits under a perpetual rainstorm of new releases. The competition of rap transformed itself into something else entirely, and that new DNA shows almost no traces of the freestyle in it.

If you look hard enough, you can still find plenty of individual freestyles floating around the internet on a daily basis. The same radio shows will invite rappers on to spit a few bars over the latest beats, and at times, you might even come across something special, lyrically speaking. There’s a component missing, though. One that almost feels indescribable. Each freestyle now feels like a puzzle piece separated from its contextual box, and we, the listeners, have no way to discern how one freestyle is better than the next. Hip-hop’s competitive nature has always been what’s made its dominance over recent pop culture so fascinating, and the small but important iteration that the freestyle mixtape was to that dominance can never be forgotten.

The freestyle mixtape was a saving grace, a show of talent and, more than anything, an outlet to fame. Today, it’s dead and buried.



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