Twenty-Five Years Later: ‘Reasonable Doubt’ and the Iconic Career of Jay-Z

It’s safe to say that twenty-five years ago, none of us could have possibly foreseen what Jay-Z would go on to become and how important he would be to hip-hop. In twenty-five years, the kid from Marcy Projects whose grandma fed him banana pudding would go on to have fourteen #1 albums, sell fifty million albums worldwide, become owner of the Brooklyn Nets, president of Def Jam, and one of the owners of the iconic Roc-A-Fella Records that gave us legends like Beanie Sigel and Kanye West. He accomplished all this while simultaneously developing into one of the greatest emcees of all time—and, oh yeah, becoming a billionaire!

Whether you feel he’s the greatest emcee or not, one thing that cannot be disputed is that nobody has done what Jay-Z has at this level for this long. Before their fallout, another thing we can say is Jay-Z, Dame Dash, and Kareem “Biggs” Burke showed us what happens when we are defiant—when we do shit our way and don’t play by their rules. Can you imagine what would have happened if Jay gave up after all those labels turned him down? Reasonable Doubt is what started this all. This is not only one of the Holy Grails of hip-hop but one of the greatest albums in the history of music. The Source realized they made a mistake by giving it four mics on the first review, so they backtracked and gave it five mics years later. The original review was done by Charlie Braxton. In the original review, Charlie Braxton wrote: 

“With the release of his Roc-a-Fella debut LP, Reasonable Doubt, Shawn Carter (aka Jay-Z) moves from hip-hop sidekick to Mafia-style front man, blowing up the spot with vivid tales about the economic reality fueling what’s left of contemporary ghetto politics. In terms of subject matter, Jay-Z isn’t saying anything new. It’s the same ol’ criminal melodrama that you hear on so many LPs nowadays.” 

To an extent, Charlie was right; from 1995 to about 1997, Mafioso rap was as common as auto-tune is in 2021. In that span of time, we got some of the greatest albums ever. Only Built 4 Cuban Linx, Doe or Die, It Was Written, and Life After Death also come to mind when I think about the Mafioso era. Selling drugs on wax was—and still is—nothing new. What made Reasonable Doubt different was how Jay painted incredibly descriptive pictures of the lifestyle all while showing you the mental side of hustling. We saw a young man who knew he was in too deep but was in love with the money. “D’evils,” produced by DJ Premier, was one of the standout examples. In between telling us how money turned childhood friends into rivals and how anybody has a price, Jay showed us he was more than just another dude talking about drugs, money, and hoes. He proved he was a legit lyricist whose wordplay was untouchable. Peep these lines from the second verse: 

Thinkin’ back when we first learned to use rubbers

He never learned, so in turn I’m kidnappin’ his baby’s mother

My hand around her collar, feedin’ her cheese

She said the taste of dollars was shitty, so I fed her fifties

About his whereabouts, I wasn’t convinced

I kept feeding her money ’til her shit started to make sense

Who could ever foresee?

We used to stay up all nights at slumber parties 

Now I’m tryna rock his bitch to sleep. 

The wordplay in that verse was crazy. You can tell he was definitely a student of hip-hop. The wordplay here is reminiscent of one of his early mentors and one of my favorites: Big Daddy Kane. That second verse was only the setup for the third verse, which needs to be thrown in the pot for one of the greatest verses ever. 

Was thought to be a pleasant guy all my fuckin’ life

So now I’m down for whatever, ain’t nothin’ nice

Throughout my junior high years, it was all friendly

But now this higher learning got the Remy in me

Liquors invaded my kidneys

Got me ready to lick off, Mama forgive me

To understand that line, you would first have to have seen Higher Learning. In case you haven’t, lemme break it down. In the movie Higher Learning, Remy, played by Michael Rappaport, was a kid who was extremely friendly but wanted to fit in. He later joined the Nazis and ended up killing Deja, played by Tyra Banks, before killing himself. In Jay’s verse, of course, we all know Remy Martin is liquor. When I finally caught that line, my jaw dropped. 

Then, my jaw dropped again when he said:

Come test me, I never cower

For the love of money, son, I’m givin’ lead showers

Stop screamin’, you know the demon said it’s best to die

And even if Jehovah witness, bet he’ll never testify, D’Evils

That line is saying “Jehovah”—another name for God—sees everything, even a murder, and never, ever tells. The brilliance of that verse alone should tell you the level of lyricist he is. 

Notorious B.I.G. & Jay-Z

The Commission album is on my list of things in hip-hop that I wished would have happened. If “Brooklyn’s Finest” was any clue of what was about to happen, it’s safe to say we got robbed, man. From my understanding, Jay did his verses first and B.I.G. came back and did his weeks later. Despite that, they sound like they were in the studio together. Can you imagine what fourteen songs of those two together would have sounded like? B.I.G. made Jay better and vice versa. Apparently, at the end of “Brooklyn’s Finest,” Biggie said, “Most hated in California,” and Jay said, “Nope, not today,” and had that line cut out. 

Over the years, many have questioned the authenticity of some of Jay-Z’s lyrics. Last year, comedian Faizon Love said that Jay-Z’s lyrics sound like they’re out of an episode of Miami Vice. Now for me, personally, I have never met Jay-Z, so I can’t tell you some story about him carrying bricks in a duffel bag. But when former rival Cam’ron comes out and says it’s “a lotta truth” in some of Jay-Z’s lyrics, and when his former right-hand man Dehaven tells the story about him being shot in a drug deal gone wrong—which became the first verse of “Dead Presidents II”—you have to acknowledge that every rapper is going to embellish some, but there’s definitely some truth in these verses. Jay doesn’t get enough credit as being an amazing storyteller, but “Dead Presidents II” sums up his skills. Seeing the video of the original version of “Dead Presidents” is what made me say, “I wanna be like this muthafucka right here.” The DJ Premier-produced “Friend or Foe” was probably the smoothest and calmest robbery I’ve ever heard on wax. How the hell are you a drug dealer/Jack boy with charisma!!!! Earlier when I said that everyone in 1996 was telling drug tales but Jay actually explained why, on the beginning of “Can I Live” Jigga said: 

We hustle out of a sense of hopelessness, sort of a desperation 

Through that desperation, we become addicted 

Sorta like the fiends we accustomed to serving

But we feel we have nothing to lose

So we offer you, well, we offer our lives 

What do you bring to the table?

That, right there, summed it all up for every hustler who was hustling. Now, I’ve heard Nas was supposed to be on “Can I Live.” As epic as that record was, a ‘96 Nas and a ‘96 Jay together would have been some monumental shit. And am I the only one who thought Foxy Brown was half black and Filipino after hearing “Ain’t no Nigga” after Jay spat?:

Fresh to death in Moschino, Coach bag. Lookin’ half black and Filipino…

Over the years, Jay has had verbal spars with everyone from Prodigy to Mase. “22 Two’s” was a clear indication that he was 100 percent with that shit, plus the end of the song was hilarious. Listen, I’ll be here forever talking about this masterpiece. When Clark Kent pulled a young Shawn Carter off the streets and put him in the booth, it’s safe to say it all worked out in the end.

Original Album Promo