Convicts Talk About Why Jay Z's 'Reasonable Doubt' Is Still Every Hustler's Favorite Album

To pay homage to the record's 20th anniversary, we talked about its legacy with the men who took Jay Z's words to heart—the gangsters and drug dealers who lived the life that Hova rapped about.
June 25, 2016, 1:00pm

Jay Z's Reasonable Doubt turns 20 today and, in retrospect, its release in 1996 was exactly what East Coast hip-hop needed. Filled with vivid storytelling of street hustling, drug trafficking, and Brooklyn bravado in both its lyrics and skits, Hova's debut studio album brought kingpin tall tales to popular culture without sacrificing any authenticity in its portrait of the criminal underworld.

The theme of the record plays on movie scenes from Scarface and The Godfather, but also explores Jay Z's own forays in crime, which he officially left behind while recording the record. "I had been trying to hold on to two branches and I said, 'I'm going to put my all into the music, to make a legitimate life for myself,'" the icon told The Guardian in 2010. "I never turned back."


But even though he stopped selling drugs and living the street life after his debut, Jay never stopped hustling. Instead of signing to a major label, he started Roc-a-Fella Records with Dame Dash to release Reasonable Doubt, the type of entrepreneurial masterstroke that he'd repeat again and again over the next two decades. His business may have become legitimate, but Jay's do it yourself or no one will do it for youattitude paralleled the same stuff his was rapped about.

On Reasonable Doubt's 20th anniversary, we talked to the men who took Jay Z's words to heart, the gangsters and drug dealers who were living the life that Jay Z rhymed about. To them, this music was more than entertainment, it was their reality accurately depicted and shared on a global scale, set over DJ Premiere beats. To pay homage to the hip-hop classic, we spoke to a variety of prisoners who were incarcerated for some of the same crimes Hova detailed on his debut. We asked them to reminisce on the album's importance, and give us their take on why Jay Z is still your drug dealer's favorite rapper.

Walter "King Tut" Johnson
52-Years-Old from Cypress Hill Projects, Brooklyn
Serving a Life Sentence at FCI Otisville in New York for a Federal Three Strikes Law Conviction

Jay Z did his homework when he put Reasonable Doubt together. Jigga reached deep down into the core of his soul and pulled out the recordings of his life. He ingeniously described the people, places, and things that transformed him into the "Holy Grail" of the hood. He is the Sun Tzu of Brooklyn. He set out to confirm the value of his existence through music. The album was a dedication to those who questioned their own potential or allowed themselves to be trapped by the designs of life.

The record captivated the minds of its audience in the same manner that The Godfather and Scarface did. Once it touched your life, it left an indelible scar. Jay Z understood that there was a vicious dynamic being set in motion, and for him to truly enjoy the spoils of war, he would have to become invincible to the repercussions of the game. Jay Z understood that the world was large enough for those who play fair to play the game for real. He left those with small minds to the streets because they refused to use their creativity to expand and venture upon legitimate sources. He borrowed Machiavelli's mindset in The Prince: "A prince must be a lion to chase away wolves, but also be a fox to escape traps."


Jay Z wanted men to own their manhood and be able to envision themselves being owners and caretakers of their own lives, businesses, and properties. He wanted us to be prudent businessmen, instead of allowing other businessmen to profit off of our misery. To street dudes, Jay Z is the comrade that made it out of the game, and sacrificed everything just to dedicate a detailed description of how we can get out. In his music, he is giving us a map, keys, tools, and a path. Those who were true to the game recognize the gift that he has dedicated and pursue it with appreciation. Jay Z is the gatekeeper and through his lyrics, passion, love, and leadership we can rise above every disaster in our lives and find our true calling.

Andre Cooper
36-Years-Old from Chester, Pennsylvania
Serving Three Life Sentences at USP Hazelton in West Virginia for Racketeering, Drug Dealing, and Homicide Convictions

I'm making short-term goals when the weather folds/ just put away the leathers and put ice on the gold . Jigga's words were near and dear to me, as well as to all the young hustlers around the city. I was 16-years-old when Reasonable Doubt hit the scene and it just so happened to be the same time that I saw my first ten bands from pushing powder on the streets of Chester, Pennsylvania. 1996 was a crazy-but-memorable year. I say a memorable because we followed Jigga's lyrics to a T. I was trying to live what he was rapping about. But unfortunately, this would also be the same year that would mark the beginning of my 44-count federal racketeering indictment where the government said I agreed to form a cocaine enterprise with a few other 16-year-olds.

Before I got arrested, I was living it—from the drug dealing, the pistol action, partying, knocking down all the sexy young girls, to all the other aspects of a young rich nigga life. But I wanted to do it better since Jigga was showing us how to do it on an epic level. He kept us young hustlers and gangsters on our toes. When Jigga rapped about something, you knew it was official. So you either had to do it, or you made it your goal to acquire the money in order to cop it.


By me starting so young in the underworld, at the age of 14, and trying to live up to the likes of Jay Z, I got caught up in the streets. Which, eventually led me to where I sit today in a federal maximum-security prison with three life sentences. As the 20th anniversary of Reasonable Doubt comes up, I'll remember the great inspiration that Jigga gave me, but it's also a reminder of my downfall. I guess the album was sort of like a gift to Jigga, and a curse to the young gangsters from the slums who didn't do it right like he did.

"He brought the crack game to the rap game, and all the hustlers, street dudes, and gangsters was feeling what he said…"

Arthur "Plex" Pless
43-Years-Old from Miami, Florida
Serving a Life Sentence at USP Coleman II in Florida for a Drug Trafficking Conviction

I was hustling up in Jacksonville, Florida when I first heard Reasonable Doubt . I had these two hoes with me, we were in a rental van headed up to Georgia to pick up some bread, and one of the chicks put it in and cued it to "Ain't No Nigga." I loved the groove, the lyrics were witty and tight, but I didn't really react to the song until Foxy came on. I was like, "Who is that?" The two chicks were like, "Jay Z."

When we got back to Jacksonville I ended up stealing the bitches' CD. I took it to the trap, and me and a couple of my partners vibed to it. Some of the homies were like, "Man, if you don't take that bullshit out!" They weren't giving it a chance because Jay had that NY flow and the production was East Coast, but I kept pumping it, and pretty soon other nigga's started pumping it. Reason being, we were just figuring out that dude was "real."


Jay Z was the drug dealers' rapper. His lyrics embodied everything that niggas in the game aspired to be, like in the song "Never Change":

Lost 92 bricks had to fall back/knocked a nigga off his feet/had to crawl back…Had A1 credit got more crack/From the 1st to the 15th gave it all back/If I'm not a hustler what you call that?

Shit like that speaks to the heart of street niggas because if you've really been in the streets, you know it ain't all gravy. Nigga's gonna take some losses, but you have to "crawl back." I don't know Jay, but I know the game. I lost my life to it. So I know he's either lived it or has been really close to it, because his numbers and accounts all add up.

John "Shakim Bio" Edwards
46-Years-Old from Jamaica, Queens, New York
Serving a Life Sentence at Mansfield Correctional Institution in Ohio for Aggravated Murder, Drug Trafficking, and Felony Assault Convictions

In the early 90s, I was knee deep in the streets, so my insight into Reasonable Doubt is different than most. At this point, Kool G Rap had the East Coast gangster rap on smash when it came to talking about the real street shit. You had other rappers who spoke on street shit too, but there was no real hustling rapper talking that talk until Jay Z got the East Coast, mainly New York, in a chokehold. The Reasonable Doubt LP changed the game.

Jay Z was coming from a hustler's point of view. He was painting pictures with words and nigga's in the streets had never heard it so raw like that. I heard Jay Z live on the radio doing an interview. When he spat a freestyle, I was convinced he was the shit. Biggie was the King of New York, but Jay Z was knocking on the door with that heat. I got to hear a few more joints like "Ain't No N igga" featuring Foxy Brown and "Can I Live," but when I heard "Can't Knock the Hustle" and got to see the Hype Williams video for it, I was hooked. Jay was spitting the street shit that hustlers knew and lived for.

I knew Jay was either right there in the mix or around those who played that game. In other words, he brought the crack game to the rap game, and all the hustlers, street dudes, and gangsters was feeling what he said and cosigned the lyrical content. It was authentic. I got almost every song he made that's available [to me in prison]—Jay Z's that dude.

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