Challenge: Enter a Rap Battle


Have you ever freestyle rapped? Please, right now, take the time to try it. Go to YouTube, find an instrumental, and just try to rhyme in rhythm off the top of your head about whatever you want. Seriously, try it. I’ll wait here.

See also: I Won an Evangelical Christian Rap Battle

How did it go? The reason I ask is because I find freestyle rapping to be challenging and incredibly fun. I also happen to really like money and, during my four years at NYU, freestyle battle rapping was lucrative enough for me to serve as my “college job.” Granted, freestyle battle rap is an even more specified niche than freestyling (or the umbrella of rap battles for that matter), but after taking a few years away from it, I’ve recently stepped back into ring and it’s as fun as ever. I currently hold two titles — UCBEast’s Battlicious and Spike Hill’s Freestyle Mondays. The topic of freestyle rap’s appeal comes up in conversations from time to time. Thus, I’m more than happy to share what it is about freestyle battle rap that I find so appealing.

I believe there’s still some confusion in circles in regard to rap battles (especially post-8 Mile): many just assume every rap battle is a freestyle, as if the realm of competitive rhymes were reserved for the extemporaneously ones created on the spot. This isn’t the case. There’s both pre-written and freestyle rap battle circuits, and if you’ve seen a major rap battle in the past five years, the overwhelming odds are that it’s from one of the pre-written leagues. URL/Smack, King of the Dot, Grind Time and any of the larger leagues which have been steadily growing in popularity since 2008 or so have been pretty transparent about their competitors duking it out with pre-written rhymes, but this element is embraced as part of the sheer entertainment spectacle.

These artists spend weeks and sometimes months crafting absurdly complex lyrics with intricate wordplay and then perform them a cappella with no microphones in active one-on-one competitions that can last from three minutes to an hour in front of hundreds of people in attendance and thousands on internet pay-per-view. For the level of competition that’s expected, it’s exceedingly rare a performer will gamble on a moment of spontaneity and create a rebuttal on the spot. When purists of both pre-written and freestyle camps disparage the other, what both miss is that they’re really too different to compare. The rules are different, what makes for a great performance is different and the skill-sets required to do either well seldom overlap.

But while both are under the umbrella of “rap battles,” a niche in itself within the still somewhat-niche counter-culture that is hip-hop, the expectations for a freestyle battle are entirely different. Mostly, it’s the allure of the unknown. Two adversaries on one stage in that one moment have to muster whatever skill they can to win the crowd, and must do so within the rhyme schemes, the English language and rhythm of the beat. With the pressure on, these 30 second rounds can feel like the absolute longest or shortest of one’s life. You don’t just need to think on your toes and create something on the spot, but you have to entertain an audience in the process.

But, beyond the challenge, it’s also the triumph of when these moments of creation work. While the nature of freestyle rap battling can lead to lesser match-ups that are either laughably bad or unbearably middling, the times when things click are incredible. Seeing an MC uniquely diss their opponent in a moment of spontaneity that they couldn’t possibly prepare for, and then their opponent using that same insult they’ve just heard and flipping it back at their opponent for a barb that’s twice as sharp creates the unique magic moments that freestyle battle rapping is all about. It’s arguably the closest live hip-hop comes to jazz improvisations.

A decade ago, when the post-8 Mile wave of popularity raised freestyle battle rap’s profile, it caused a plague of rappers allegedly pre-writing their verses before battles. While I’m not denying it’s wholly possible someone could have thought to rhyme “keep it real,” “meal” and “Ally McBeal” in the heat of the moment, just about the worst thing one could do in a freestyle rap battle would be to “kick a written.” The two battles I just participated in included certain obstacles to ensure pre-meditating any lines would be impossible. Saturday’s Battlicious — where comedians who rap and rappers who think they’re funny square off — utilized suggestions from the audience for the rappers to base their rhyming attacks around. Yesterday’s Freestyle Mondays utilized both a spinning wheel and a plinko board (dubbed “Plink, Yo!”) to determine either the category of a subject matter to battle under or an additional challenge such as having to battle yourself in a mirror or wearing a blindfold while your opponent selects a random item from the audience and puts it in your hand, meaning you have to not only figure out what an item is based solely on touching it, but then rap about it as well.

It can be stressful, it’s often challenging, and there are moments when it’s even terrifying. Whether competing or participating, the battles where everything clicks feels like a triumph for the human race as a whole. Admittedly, that may be a touch hyperbolic, but these freestyle battles carry with them the overall vibe and atmosphere not of a testosterone-heavy “who can make the best celebrity genitalia comparison” environment, but feel like big parties that happen to have rap battles in the middle of them. Even as someone who makes rap music and enjoys and appreciates all that goes into songwriting and rehearsed performances, I still like battling because, frankly, it’s fun.

Now that you’ve gotten that first freestyle out of the way, go try it again. I’ll see you in the ring.

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