This was the part where I started to get a headache. After feeling relatively comfortable with my choices up till now, including Andre 3000 and Jay-Z at #8 and #7, respectively, organizing the top 6 turned out to be a fairly Herculean feat. I should correct that. #1 was pretty damn easy. Organizing the next five was rough, because seriously speaking, any of the next five gentlemen on this list could have placed anywhere from #2 to #6 depending on how I was feeling. So without further ado, let’s move forward!

6) Slick Rick

Representing: The Bronx

Here’s another guy that I feel gets really short shrift when it comes to these types of lists. When he arrived in 1985, as part of Doug E. Fresh’s Get Fresh Crew, he was lightyears ahead of other rappers. While most emcees were still in “throw your hands in the air and wave ’em like you just don’t care!” mode, Slick Rick was a storyteller and a character. Everything about him was novel-his style of dress (which included roughly 6,500 pounds of jewelry in addition to his trademark eye patch), his British accent (much more pronounced when he’s rapping as opposed to when he’s just speaking) and his style of storytelling. He was vulgar, campy and groundbreaking all at once. He’s also the victim of more bad luck than any other rapper in existence. His career has been held up by immigration woes, a lengthy separation from Doug E. Fresh and, most importantly, a period of incarceration that lasted for most of the Nineties. Wipe out his jail sentence, add in a more consistent schedule of releases, and we might be looking at a #2 finish instead of a #6 one.

(random note: can someone PLEASE remaster The Great Adventures of Slick Rick? The sound is horrible!)

5) LL Cool J

Representing: Queens

In terms of pure longevity, James Todd Smith pisses on every solo rapper in existence, with a span of hits that surpasses two decades. Even though there’s been a significant dropoff in quality for the last decade or so (chalk that up to blindly chasing trends), he hasn’t lost his skill for rhyming. He’s just lost his skill for making good records. Think about his versatility-he was certainly the Alpha Dog back when he started in ’84-’85 and he can still hang with the Big Dogs in 2011. He’s done it all; rock-influenced tracks, slow jams, brag raps, socially conscious music. Hell, the guy’s even done a rendition of “Who’s Afraid of the Big Bad Wolf?”-something I’m pretty sure he’d like to forget. Let’s also remember that LL is arguably the greatest live performer in hip-hop history. He’s rocked with Rick Rubin, written for Run-DMC, been produced by everyone from Puff Daddy and The Trackmasters to Erick Sermon and Funkmaster Flex. Adaptable, versatile, able to annihilate Kool Moe Dee, MC Hammer and Ice-T in a single song (no emcee has withstood more verbal jabs than LL), he’s a certified legend in not only hip-hop, but in music period.

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