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A few years ago some friends and I got into a barbershop-esque email discussion, the aim of which was to determine, once and for all, who was the greatest hip-hop MC of all time. No question that discussions like these take place daily on street corners, barbershops and blacktops throughout America. It’s also no question that these discussions never come to consensus. The best you can say is that MC’s like Rakim, KRS-One, Notorious B.I.G, Nas, Jay-Z and LL Cool J are typically on the list, along with the hottest rapper of the day.


As the conversation meandered on, one of my friends brought down the hammer and said,  “We can debate this greater rapper business from now until the end of time. Let’s just say Jay-Z is the greatest hip-hop icon ever, and here’s why: 1) Longevity 2) Rap Skills/Prolificiness 3) Street Credi4) Marketability and 5) Business Holdings. Do I need to break it down anymore?” He didn’t, but since not everyone is a hip-hop head like my friends and me, I will.


Longevity
Jay-Z has hovered around recorded hip-hop since 1989, but since his first album Reasonable Doubt was released in June of 1996, let’s say he’s been out front for nearly 14 years. Though there are a few rappers who have been around longer—most notably Will Smith, LL Cool J, Queen Latifah and KRS One-—14 years is a long time in hip-hop. Add to it that Jay-Z has recorded consistently for those 14 years so it’s safe to say that he definitely gets high marks for longevity.


Rap Skills/Prolificness
In “Ether” Nas’ classic battle tune against Jay-Z, he chastises Jay for being a flunky and a waterboy to Brooklyn rappers Jaz and the legendary Big Daddy Kane. Unfortunately, what Nas viewed as being a waterboy was actually a hip-hop apprenticeship. Like all the greats, Jay-Z paid his dues studying his craft from the ground up. In any field this is the best way to learn. If you were to listen to Jay-Z pre-1996, you’d hear a talented rapper still looking for his own distinct sound. For instance, in 1990 on Jaz’s “The Originator” video, Jay deployed a speed rap style that was effective but clearly not unique.


Four years later in 1994 when he recorded his first solo video “I Can’t Get With That”, Jay had slowed his flow down, but still made use of the wiggity wiggity, diggity diggity style of Das Efx. Still you could hear a much more unique style emerging.


By 1996 Jay had worked out the majority of his stylistic and song writing kinks. So when Reasonable Doubt was released that year, it was not your typical debut album. Instead it was a 15 song musical and lyrical tour de force that demonstrated that not only could Jay go toe-to-toe freestylin’ with Notorious B.I.G on “Brooklyn’s Finest”, but he could also wax intropsective about the guilt and emotional drain of drug dealing on “Can I Live” and “Regrets”.


To put the accomplishment of Reasonable Doubt in perspective, let me flash back to a conversation I had with a young record executive at Flavor Unit back in 1993. At the time we were both attending a breakout session at the “Black Music Expo”. During that session there was an opportunity for unsigned rappers to show their stuff. The best of the bunch was a young rapper from Asbury Park, New Jersey that went by the moniker of “Darkman”. By all accounts, this cat was bananas and had everybody in the crowd noddin’ and boppin to his flow.


After the session, I asked the exec what he thought about “Darkman”. His answer was as cogent as it was succinct, “He was nice as hell, but can he make songs? People don’t buy freestyles, they buy songs. The people that are the nicest with freestyles are usually the worst songwriters.”


This lesson about freestyling and songwriting was something that Jay-Z learned well during his apprenticeships with Jaz and Big Daddy Kane. Jaz was a great freestyler from Jay-Z’s Marcy Projects. The problem was his songs were not well structured, so his label had to take action.


What they did was have him write and performs songs like “Hawaian Sophie” that just weren’t representative of his persona or his skill set. On the other hand, while Jaz struggled, Big Daddy Kane flourished because he was able to write songs and was still able to throw in a freestyle from time to time. Jay-Z applied these lessons learned to Reasonable Doubt and it’s a big reason the album is viewed as a classic and has had such an impact on hip-hop.


Reasonable Doubt was so good that most rappers would have rested on their laurels and maybe come out with a couple of other albums that were solid but not great. Not Jay-Z. He continued to work on his skills and grow as an artist and never coasted. So in these past 14 years Jay-Z has produced 11 albums, and of those 11, only one- In My Lifetime, Vol. 1 has possibly been questionable.


To put Jay’s prolificness in better perspective, let’s look at Jay’s closest rivals: LL Cool J and KRS One. LL Cool J’s first album Radio came out in 1985—11 years earlier than Reasonable Doubt. In 24 years, LL has released 12 studio albums—only one more than Jay. Meanwhile KRS One’s first album Criminal Minded was released in 1987. In 22 years, KRS has released 20 albums. An impressive feat, but though KRS releases album’s at a slightly higher rate than Jay, his albums haven’t had the same consistent quality level that Jay’s have.


Simply put, the combination of Jay-Z’s rap skills and prolificness are second to none.

Tagged as: hip-hop | jay-z
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