“I’m out for presidents to represent me.” If ever there were a hip hop lyric that so precisely reflected a rapper’s mindstate (while still foreshadowing his future), it’s the chorus on Jay Z’s early single, 1996’s “Dead Presidents II.” A reference to the deceased Presidents whose pictures were now synonymous with certain denominations of American currency, the particular line—first uttered on wax by Nas two years prior on “The World Is Yours”—became a mantra for many in the hip hop community. For Jay to sample this particular Nas line as the chorus to the first single off his debut album Reasonable Doubt meant that his purpose in rap was clear. There was no doubt money was his ultimate goal. Perhaps that is why he still stands as one of rap’s biggest, if not the biggest, success stories of his time.

Jay Z is and always has been about his paper, as the lyrics of “Dead Presidents II” explain. (“I gross the most at the end of the fiscal year than these n****s can wish to.”) As hip hop began its mainstream infiltration, with money makers like Puff Daddy at the forefront broadcasting his lavish lifestyle, a well-respected credible rhymesayer with Platinum aspirations like Jay Z was met with much admiration. Hip hop has always held its truth tellers in high regards, and Jay Z’s authenticity had been street verified.

True, twenty years after the release of Jay Z’s classic single, there are significant differences in the artist’s music and lifestyle. The irony? Well, present-day Jay Z would cough up a high-pitched laugh at his younger self’s bank account. He’s more than tripled his worth on God’s green Earth, and that’s without mention of the marital property. If hyphenated Jay-Z was spending money from ‘88 in ’96, then non-hyphenated Jay Z has enough bank for the next five generations of Carters. Much has changed for the rapper since the song was recorded. For the better, that is. The self-proclaimed drug dealer-turned-music mogul surpassed expectations, rising to become President of legendary rap label Def Jam and then carefully marrying into pop star status. And this song—though extremely cocky and a bit depressing now—was and still is, at least very honest in its intentions.

Why depressing now, you might ask? Yes, Jay’s rap talent, in all its perfect glory, has been well-documented. With its impeccable wordplay, cleverly calculated alliteration, and multi-syllabic rhyme style, Jay’s skill bordered on poetic back then. He opens, “Who wanna bet us, that we don’t touch lettuce, stack cheddars forever, live treacherous, all the et ceteras…” Brilliant, right? Well, 20 years ago, it seemed more impressive. To an aspirational fan base, it was a hopeful outlook on the future. Today, to that same fan base, it’s a regrettable look back on how much better Jay Z is living. Jay’s big money talk back seemed attainable to his peers, despite his attempt to seem heavier than the next man. But the gap between his 2016 earnings and the rest of the 99% is more subtly addressed in his music these days.

But as much as it pokes at your inner financial insecurities, Jay Z’s “Dead Presidents II” is as authentic as they come. For Jay, it was just an introduction for what was about to come. In a few months, he would drop what he considers his best album, and what critics say is the classic one that set his career in motion. Reasonable Doubt would add layers to the back story to today’s most celebrated hip hop husband and father. But “Dead Presidents II” vividly opened that book. A biopic, which, ’til this day has only been written by him in this form. And to think that the same man who once proclaimed that he “dabbled in crazy weight [and] without rap…was crazy straight,” abandoned those drug dealing ways for the same game he insisted he could have done without. It’s telling.

Metaphorically speaking, “Dead Presidents II” boasts Jay’s pre-Vol. 1, mid-90s rap similes. “Your paper fall slow like confetti” and “fake thugs unplugged like MTV” are just two of the song’s lines that do not survive the trip back to the future. But, while taking a trip down memory lane, they accurately reflect the pulse of where hip hop was in 1996. And at that particular time, Jay Z—the rapper—was ahead of his time. And where business moves were concerned, he was about to pass them twice. The CEO’s mind and marketing plan would push his rap career further than any other rapper’s. And it all started with “Dead Presidents II.”

Indeed, the life and times of S. Carter have been quite good. He went from the Presidential Rolex he name-dropped on “Dead Presidents II” to rolling with President Obama. He’s still got a good life, man.

(Photo: Al Pereira/Michael Ochs Archives/Getty Images)