Jay-Z: The Journey of an Icon

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.


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.

Street Cred

Street Cred

In some ways, street cred is akin to the Horatio Alger “rags to riches” tales of the 19th century. Unfortunately, where Alger essentially told stories that exemplified hard work, determination, courage and compassion for his fellow man, the hip-hop take on Alger substitutes compassion for your fellow man with violence or exploitation for your fellow man either through drug dealing or just plain thuggery. Many a rapper played into this aspect of street cred, only to be exposed as a “studio gangster”. Jay-Z is no studio gangster. Though he may have taken artistic license with some of his street tales, it’s common knowledge that he was involved in the drug game both in Brooklyn as well as Trenton, New Jersey.

What’s interesting about Jay-Z’s street cred is that his narrative was never about a drug dealer who became a rapper. Jay-Z was a rapper who turned to drug dealing when it looked like he would never get a record deal. This minor detail is important to Jay-Z’s street cred, because though there are many fans in hip-hop that romanticize the street life, there are others that are into the craft and the journey of the rapper. So just as there are tales of Jay-Z dealing drugs on streets of Brooklyn and Trenton, there are also tales of Jay-Z battling MCs lyrically in the parks, projects and on street corners throughout New York and New Jersey

Those battle tales also fit nicely with Jay-Z’s rhyme style: the evolution of his so-called “Divine Flow”. Though not the dominant portion of Jay’s street cred, the divine flow does play an important part. For those of you unfamiliar with this phrase, it is the label given to his ability to go to the studio, listen to the beats and kick out rhymes without using a pen and a pad. This ability, though not essential for lyrical greatness, scores points with hard core hip-hop heads; and because his flow is his credibility, it allows Jay to branch out in his music to gain a wider audience without losing his core constituency.

I can’t think of any other rapper that could rap to a sample of Annie’s “It’s a Hard Knock Life” and still maintain his street cred. To put a finer point on things, Jay’s street cred has at times transcended hip-hop. On his 2004 album, The Black Album, Jay-Z rapped, “I don’t wear jerseys/ I’m 30-plus/ give me a crisp pair of jeans/[expletive] button up.” After that rhyme throwback jersey sales at Mitchell and Ness dropped considerably.


If icon status was only based on longevity, rhyme skills and street cred, then it could be argued that other rappers are every bit the icon that Jay is. Where Jay begins to distance himself from the pack is in his packaging and marketing; his branding, if you will. From a branding perspective it’s instructive to compare Jay to LL Cool J. LL has been a successful rapper for approaching a quarter century and unlike Jay he was one of the art’s first megastars. Jay cannot make that claim.

LL was also one of the early rappers to strike paydirt with his acting. However, once LL got into the acting business it seemed like he merely dabbled in hip-hop and these days he’s obviously more interested in acting and maintaining his physique than recording serious hip-hop. In that way, he’s compromised his brand. We all recognize LL Cool J as a star, but his “brand” is more hip, than hip-hop.

This brand murkiness isn’t present with Jay-Z. Everything he does reinforces his brand as a “hip-hop hustla”. If I were to speculate on how he developed such a rigorous brand discipline, I’d have to say it came from the experience with his second album My Lifetime. Released in 1997, the album was well received both critically and commercially. However there was one aspect of the album that Jay refused to overlook–the (Always Be My) Sunshine song and video.

That song and video made him look like a P Diddy follower. Though he and his most hardcore fans recognized this flaw, most artists would have been happy to have such a successful sophomore album and would have moved on to the next project without addressing that very small blemish.

Not Jay-Z. To shore up his hustla brand, Jay-Z released his Streets Is Watching “movie”. Though far from an artistic statement in the way that Reasonable Doubt was, Streets Is Watching was still a unique product. It was a long form music video that brought many of his songs to life and whose concept and narrative structure in it’s own way paid homage to the proto hip-hop classic The Hustler’s Convention.

Additionally, it showed early Jay-Z videos–those recorded prior to Reasonable Doubt. Such an intense collection of images overwhelmed the Diddy-esque (Always Be My) Sunshine imagery and re-established Jay-Z’s “hustla” brand. It was brand discipline at its best.

Business Holdings

Given that his first album, Reasonable Doubt was released on his own Roc-a-fella label, Jay-Z has been a businessman as long as he’s been a professional rapper. While Reasonable Doubt was the work of a rapper who’d mastered his craft, Jay’s business skills were not initially on the same level. To paraphrase an early Roc-a-fella employee, neither Jay nor his then business partners Damon Dash and Kareem Burke had ever even held a job before, so their professionalism was lacking. The employees example was that they didn’t even know that employees should be given lunch breaks.

Still, what Jay may have lacked in polish, he more than made up for in instincts, hustle and fearlessness. In that regard Streets Is Watching was not just a turning point in Jay-Z’s rapping career but in his business career as well. Not only was it a branding tool, but it was also a totally different product. Knowing that producing a movie was expensive, Jay and his partners decided they needed some help with the funding and approached their distributing label Def-Jam to fund the project.

Def Jam balked. Rather than fold up their tent, Jay and his team pressed on with the movie. This was his first experience in product diversification, and a year later in 1999 Jay founded the Rocawear clothing line then three years later RocFilms was founded.

Clearly, Jay isn’t the only rapper to have his own clothing line; P-Diddy’s Sean Jean is still doing quite well. Nor is he the only rapper to have his own film company; Master P’s No Limit Films was probably more commercially successful than Rocfilms. Yet both his clothing and films have turned profits and if those were Jay’s only business ventures they would be impressive. They’re not. Jay is also a minority owner of the New Jersey Nets and is a principal owner of the 40/40 sportsbar.

In short, over the past 13+ years, Jay has evolved into a respected businessman. Is he hip-hop’s most successful businessman? No. That distinction probably goes to Russell Simmons. Still the fact that Jay-Z the businessman doesn’t pale in comparison to Simmons is noteworthy.

The Icon

Where hip-hop is concerned, what is an icon? For some it may be that person or persons who extended the reach of hip-hop, and took it to a higher level. For me that sounds too much like commercialization to be a complete definition. For others it’s that person whom, when you see them or hear their name, you immediately think of hip-hop in all of its dimensions. Though that would be my definition, objectively speaking it opens the door for an argument that eschews the commercial aspects of hip-hop in favor of “keeping it real”.

In the interest of fairness lets conflate the two. A hip-hop icon is somebody that extends the reach of hip-hop while simultaneously conjuring up the current as well as the historic dimensions of hip-hop. With that in mind, it can be argued that Russell Simmons has probably done more to extend the reach of hip-hop than any living human being, and more importantly, that Jay-Z has benefited from his efforts.

Though this argument has more than a little credence, it ultimately breaks down for two reasons: 1) influence is part of being an icon, but not all of it and 2) Simmons still needed a cadre of rap talent to build hip-hop up. When you hear the name Russell Simmons, you do think of hip-hop (and business), however when you hear the phrase hip-hop, you’d never immediately think of Russell Simmons.

Jay-Z will never be considered as historically influential as Simmons. By historical standards Simmons is a hip-hop pioneer, he was there nearly from the beginning. Yet therein lies the true point. For all of his pioneering efforts in hip-hop, there is a piece missing on Simmons’s CV. You can’t picture him standing in front of a DJ with two turntables in NYC in the mid- to late-’70s moving the crowd. There is no problem picturing Jay-Z doing that very thing. Similarly though we can picture Simmons standing in corporate boardrooms making deals on behalf of hip-hop, we can also do the same with Jay-Z.

More than any other figure in hip-hop, Jay-Z has been able to mine and leverage more dimensions of hip-hop culture than anybody in its history, all the while maintaining the essence of his persona. For this reason he is undeniably hip-hop’s biggest icon. Given his relative youth — he’ll be 40 in December — and ambition, I wouldn’t be surprised if he’s the one to add one more dimension to the hip-hop iconography–political/social impact.



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