The tried-and-tested Greatest Rapper of All Time discussions are always dragged down by including factors such as ‘commercial success,’ which unfairly skews results towards late ‘90s/early 2000s MCs. It’s also tough to gauge how Biggie, Big L and Big Pun might have developed had they been around long enough to have careers that lasted over a decade. Rap magazines and hip-hop websites have a long, storied history of attempting various types of polls, super-scientifical breakdowns and veiled opinion pieces in order to troll their readers and generate ‘healthy discussion.’ Kool Moe Dee famously graded himself and his competition on the back of his How Ya Like Me Now album (and was generous enough to provide an updated version of the Rapper Report Card for ego trip’s Book of Rap Lists in 1999 where Lauryn Hill took top honours).
The Source crowned Biggie Smalls as the illest MC of all time in their breakdown featured in issue #150, but by #253 the big fella had slipped down to third place after top dog Rakim and Nas. Hip Hop Connection, the world’s longest running rap magazine, until it’s demise in 2009, polled 100 rappers on their favourite masters of ceremonies and crowned Rakim Allah, while the result of the Unkut comment section vote in the same year saw KRS-One come up trumps. At least half of Rap Twitter seems to carry a torch for Jay Z as the undisputed king, but I suspect that they’re just Tidal shareholders in disguise.
The fact is there is no way to accurately compare the different disciples from the various eras of rapping. How can Grandmaster Caz, Melle Mel or Spoonie Gee be judged against modern MCs who exist in an entirely different landscape? Attempts to create arbitrary categories such as ‘Storytelling,’ ‘Concepts’ and ‘Sticking To Themes’ and such are demanding that to be the best MC you have to be the most versatile. This is another bias forced upon us by the recorded era of hip-hop, once again placing the house party and park jam era at a distinct disadvantage. It also presents the idea that to be a specialist is a bad thing. When you listen to Big L, you don’t sit there thinking, “This is cool but I wish he would have made more songs focusing on social issues instead of all these witty punchlines!”
Likewise, the majority of modern rappers suck on stage. Having not cut their teeth in the Latin Quarter era where the crowd was likely to start throwing bottles at you if your live show was lacking, ‘90s rapper dudes don’t stand a chance against Big Daddy Kane and LL Cool J. By the same token, the period where DMX, Ja Rule and Eminem could sell 10 million CDs without breaking a sweat was another universe altogether. Audiences demanded different things by that point–radio hits and video rotation were a major part of the game, and demanded a different skill set. Fans wanted big personalities, slick production, and musical escapism. How can Kool G Rap and Rakim compete in that sort of landscape? Fast-forward to now, where even the big names are struggling to sell a million albums. Are sales suddenly not part of the argument? Are we rating the greatest rapper by the number of blog posts made about them? In that case, Kanye West has got this shit on lock.
It’s time to face the facts–there can be no accurate discussion as to who’s the greatest until hip-hop music is dead and buried, or has become another marginal genre that only music buffs care about. Otherwise it’s simply a series of hollow justifications about why your particular favourite is better than the other guys. For my vote, Kool G Rap is number one, based on his flow, wordplay and influence. But a case could be made for any number of great rappers, and you wouldn’t be wrong. Slick Rick is responsible for some of the most memorable and enduring records in hip-hop, but wasn’t interested in rap battles and freestyling because he’s Slick Rick The Ruler and doesn’t need to lower himself to the level of these peasants. If Tupac changed your life when you first heard him, then he’s the best to ever do it. It’s as simple as that. The Greatest Rapper of All Time will always be in the eye of the beholder…unless that particular beholder claims it’s Lil’ Wayne, natch.