Just How Real Are These Hip-Hop Icons?

Written by J.Monkey. Posted in Lists

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Published on May 04, 2011 with 15 Comments

Keep it real‘ isn’t just a cliché sentence rappers drop in their ad-libs, it used to be an integral part of hip-hop. With the rise the stardom of Ricky Rozay and his fabricated rap persona the credo seems to have been retired, but was it really ever that real in the first place? TRU takes a look at ten icons of rap (in no particular order) and how real they’ve actually kept it.

10. Rick Ross

Image: Don mega status, ultimate hustler, pushing white like a snowplow.
In reality: Rick Ross was a Correctional Officer. In this function he presumably came across many tales of gangsta livin’ that he decided to use as inspiration in forging a rap career. It worked. His gruff voice and authoritive delivery came along just as trap rap rose to the top and a star was born. Rozay stays rapping and shooting videos like the shiny suit era never ended and his co-signing by rap superstar Jay-Z and impeccable choice of bombastic beats don’t hurt either.
How real?: To quote the late, great ODB: “lo-o-ow down, as you can go, below zero, without a doubt”


Image: Comic book supervillain.
In reality: Upcoming golden age mc and KMD member Zev Luv X lost his crew member and brother Subroc in a tragic car accident. Shortly after that their upcoming second album got canned due to the label folk losing their nuts about the controversial cover art. He later resurfaced as MF DOOM, a supervillain wearing a mask who had impressive associative rhymes that stunned many with their creativity.
How real?: Not real at all, at least not in the traditional sense. The DOOM persona fully complements the music and vice versa, so the character Daniel Dumile has created is an integral part of his art as a whole and in that way a lot ‘realer’ than many rappers perpetuating a facade with their own face.

8. Slick Rick

Image: Ladies man, king of storytellers, connoisseur of golden jewelry.
In reality: Take a look at that fellow. The jewelry pretty much speaks for itself and you only have to listen to a couple of his classic songs to catch his storytelling prowess. I always assumed some of his tales of conquering women were slightly overblown since, let’s be honest here, we’ve all added a dash of exaggeration to our tales of conquest every now and then when hanging with the homies. It’s what men do, we’re wired that way.
How real?: Still pretty damn real. The Ruler proved he knew the bad end of a crime story with his jail sentence and for the ladies man part, come on, who can rock an eyepatch with more swagger? Ladies?

7. Eminem

Image: Split personality, deranged psycho/caring father, occasional social commentator.
In reality: When Em debuted with ‘The Slim Shady LP‘ he launched his alter ego that gave the album it’s title into the public consciousness as well. On his subsequent albums came increased room for the more straightforward part of his personality and tracks about his place in society. But he never fully turned his back on the shock-rap that catapulted him into stardom.
How real?: I feel confident in saying that he never actually tied a rope to his penis and jumped from a tree. Ranging from psychotic to cartoonish, the Slim Shady character was extrapolated from Em himself, his anger, frustration and homicidal fantasies poured into an insane alter ego. The character is made up, the emotions are real.

6. Ol’ Dirty Bastard

Image: No father to his style.
In reality: Within the powerhouse that is the Wu-Tang, filled with kung fu mythology, 5% ideology, gambino tales and intricate rhyme schemes, Ol’ Dirty Bastard was the perfect loose cannon that could add some levity, unpredictability and raw funk when needed. Meth introduced him on the infamous radio skit from ‘Enter The Wu-Tang (36 chambers)‘ as the one with ‘no father to his style’ and his first solo album contained a piece of Shaw Brotehrs movie dialogue talking about the next chamber (“There is no 36th. -I know, I want to create a new chamber”).
How real?: ODB seemed to have no filter whatsoever and produced pure strain of thought rap even if his grip on reality wasn’t always that steady. In his honour, I’d like to send a “shoutout to the eskimos!”

5. Jay-Z

Image: Ultimate hustler, from the street corner to the corner office.
In reality: Ultimate hustler, from the street corner to the corner office. Okay, several stories contain exaggeration about his status on the streets but they’re all at least partially autobiographical. While his biggest hits are mostly concerned with flash (even at a time when the fledging Roc-a-Fella Records barely had the funds to furnish their office), the most critically acclaimed gems in his catalogue deal with both the excitement and anxiety from the life of a hustler and his place in society as he rose on the ladder to success.
How real?: Pretty real. During the early years the Roc spent a lot of cash portraying a lifestyle that was a huge strain on their budget, but the investment paid off. You only have to open up a Forbes magazine to be assured that budgets have not been a big concern to Shawn Carter for quite some time. An abundance of personal songs and a (Damon) dash of flash was the recipe to Jay-Z the icon.

4. Nas

Image: From street poet to mafia don to street poet again.
In reality: When his classic debut album Illmatic dropped it set the stage for a deservedly confident writer, astute observer and unique voice: Nasty Nas y’all. Everybody besides Nas seemed to recognize this (aside from a couple mountain climbers who play an electric guitar, maybe) as he kept reaching for the mafia don swagger many of his peers obtained and became platinum stars with. It didn’t feel like a natural fit for Nas, who despite dropping several worthwhile songs, kept struggling with his public image for years. It took a beef with Gloria Carter’s boy for Nas to get back to his roots and smarten up.
How real?: Nas is no gangster. Several of the Esco era songs still work on the strength of his talent as a writer but it’s clearly not Nasir Jones his story we’re listening too. When Nas finally realized people wanted to hear him speak he started turning in some of the strongest material since his debut.

3. Biggie

Image: The black Frank White
In reality: One of the best rappers to ever grace the mic. Frank White was the name of the lead character in early ’90s mob flick ‘King of New York‘ and among rap afficionado’s Biggie certainly held that title. Growing up around Fulton Street in Brooklyn, where his mother tried her hardest to keep her boy on the straight and narrow, he eventually drifted onto the corner selling rocks to buy diapers for his kid. “Because the streets is a short stop. Either you’re slingin’ crack rock or you got a wicked jump shot“.
How real?: Only slightly real (*ducks for cover*). Of course BIG knew the life he rapped about given the evironment he came from and several of his songs have very personal content. But he never was a don high up in the crack game, because he had the good sense, talent and opportunity to turn rap into his major hustle at the right time in his life. Unfortunately, his end did mirror the classic mob movie ending, a sad case of life imitating art.

2. 2Pac

Image: Intellectual thug, social commentator, rebel to society.
In reality: It’s hard to overrate Pac’s contribution to hip-hop culture. Sure, he might not have been the most technical rapper and his musical choices (though often solid) weren’t paragons of experimentation, but if Pac had one thing it was heart. His public felt fully involved with every word he uttered even far beyond the grave and he was a voice for those without a voice. Rebelling against injustice as he saw it, holding a non-conforming stance towards his peers in rap as well as various politicians and African-American leaders, and always speaking from the heart, wether in hardcore thug rap, loverman mode or as commentator on the ills of society.
How real?: Really real. It doesn’t matter he sometimes seemed contradictory on tracks. Every word Pac put on record was spit by a man with full belief in what he said and he subsequently inspired generations with his conviction.

1. Kanye West

Image: Creative genius/egomaniac
In reality: Opinion is divided on Yeezy and will probably always remain so. Some can’t get past his arrogance, others don’t care as long as the tunes back up the big mouth. The self-styled ‘voice of his generation‘ bumrushes award shows, doesn’t give a f*ck about a teleprompter and makes declarations about himself laced with so many superlatives you’d think you’re watching the home shopping channel. That being said, he’s had an amazingly consistent run of awesome records that he has written and produced too.
How real?: As real as it gets. Kanye wears his heart on his sleeve so much it leaves bloodstains. Hate on him all you want, the man already has an insane track record of both critical and commercial hits. It’s hard to stay humble when you’re stuntin’ on a jumbotron.



1982 was when Jaap van der Doelen aka J.Monkey shot his way out his mom dukes. A mere two years later he was already battling Big Brother and The Illuminati. Whenever he has time to spare from those efforts he writes (about music, mostly), hosts a radio show and designs graphics for a living. He lives in The Netherlands where he continues to be winning.

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There are currently 15 Comments on Just How Real Are These Hip-Hop Icons?. Perhaps you would like to add one of your own?


    • Run away, your sheet is showing.

      • good read. only thing is, kanye, by the admission of the back of his own records, as well as by the claims alleged by many others, doesn’t write any lyric he records for himself, or if he does, has a small role in their creation, and there have been many rumors of ‘ye paying for the creative rights to other artists beats (putting his name on the work of others), dr. dre style.

    • Run away, your sheet is showing.

  2. Good post, I think you nailed a lot of them.
    Hip Hop Is Life, showcasing the best in underground Rap and R&B
    —— http://www.hiphopislife.blogspot.com ——

  3. Were is Big Pun?

    Do some look into big pun (the legacy documentary is a great start)

    Dude really lived his shit and had a great sense of humor.

    • Haven’t seen the Legacy documentary but I own both the albums he did in his life and a copy of the Still Not A Player documentary on DVD, I’ll look into Legacy. Pun was defintely an awesome emcee but the object of the post wasn’t to list the realest emcee or anything like that. I wanted to take various emcees and juxtapose their public image with their real life, and get as many different answers as possible.

      • Legacy is a great doc you’ll really enjoy it.

        I forget people don’t recognize Big Pun as much as those other artists you posted, and your job is to get hits.

  4. Beautiful read, one of the best I’ve ever seen on The Rap Up. Word up on that Nas analysis and the Pac shit too.

  5. not that good of a post, man. Your definition as to what is “real” is vague at best, and fluctuates with every definition you provide. Sit down, man.

    • My idea of how ‘real’ a rapper is is simply answered by asking in how far do the tales described in the artist’s lyrics reflect the actual life of that specific emcee (is there even another one?). Where do you believe that definition fluctuates?

      • Need some aloe, Goethe?



  7. Hey nice post,You have described it in a good way by mentioning it as reality and and how real it is. I liked it.

  8. In my opinion you did not accurate portray Eminem. You got his alter ego pretty well but I believe slim shady was just a persona used for his music and his drug abuse fueled most of that content. When it’s strictly Eminem rapping about his life and experiences and thoughts on the world they are pretty accurate to what he lives and how he grew up before becoming a rap phenom.

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