Jay-Z's Reasonable Doubt Turns 20: Why It's The Best Album In A Masterful Catalog

We look back at Jay-Z's landmark debut LP, Reasonable Doubt, which turns 20 tomorrow. 

“If you in your car--I don’t care if it’s winter--I want you to put all your windows down.”

-- Jay Z, 1999

Reasonable Doubt gets lumped in with Only Built 4 Cuban Linx and It Was Written as part of that post-G Rap mafioso wave, but it wasn’t, at least not really. Jay was too earnest, too happy. Ghost is wildly funny, but he and Rae didn’t do anything as laugh-out-loud hilarious as “22 Twos.”

The It Was Written retrospectives are lying to you. It wasn’t some maligned record that we all found Jesus on 15 years after the fact. It was a hit to lots of people, an affront to the vocal minority who wanted Illmatic 2, a well executed, clumsily conceived move to those in the middle. Nas was trying to make sure he didn’t have to rent clothes for the Source Awards again. He didn’t bother to smooth the landing.

Jay didn’t have to. Reasonable Doubt opened--a week before It Was Written--to more or less zero fanfare. He wasn’t a nobody, like he might try to convince you, but it was a crowded market. He was the “In My Lifetime” guy. He had to build a world, but he didn’t have to deconstruct (or worse, ignore) an old one.

Reasonable Doubt is a genre record. It’s also an outlier. It’s from a time in Jay’s life, and in rap generally, when waiting a year for Mary to do a hook was shoring up your commercial concerns. Get Biggie on a song? I dunno, have the producer rap whatever for the hook, we’re going to lunch.

(“Aint No” is mostly written off today--that Four Tops sample, allegedly a Dame idea, doesn’t play at all--but Foxy does say “Eating shrimp scampi with rocks larger than life,” so.)

It dropped June 25, 1996, but it’s a winter album. “Can’t Knock the Hustle” isn’t for sweltering afternoons, it’s for rolling down the windows when it’s a little painful. “Politics As Usual”: “The price of leather’s got me deeper than ever/ And just think: winter’s here/ I’m trying to feel mink.” On “Can I Live,” he’s jetting to Maui and Vegas to dodge the snow, rental NXS, comped suite.

A social experiment: ask people when Jay Z’s creative peak was. Some people (the first poptimists, the Timb poptimists) might say Vol. 2, but nearly half of everyone will say Reasonable Doubt, and the other near-half will say the first Blueprint. The second group will, for the most part, begrudgingly admit that Jay was rapping better on Reasonable Doubt. They’re right--partially.

Those are Jay’s masterpieces; as great as he’s been, he’s never made an album that approaches either one. But if you go through his catalog step-by-step, there should be no doubt that he hit his peak as a rapper around the turn of the century, with Vol. 3 and The Dynasty. (“So Ghetto,” “Intro,” “Come and Get Me,” “This Can’t Be Life,” etc. etc. etc.) He was skittering in and out of the drum programming, he was conversational, he was technical, he was threatening, he was endearing, he loved you then he hated you then loved you again.

This was before he swiped Young Chris’s whisper flow, when the lukewarm Diddy numbers from Vol. 1 matured into bona fide hits, when the kingpin on I-95 became the kingpin in the Def Jam lobby.

So why does Reasonable Doubt hold up as the classic? Well, first, it holds up both in historical context and in a vacuum--perhaps better in the vacuum.

About the vacuum. Jay didn’t have to finesse his persona because he hadn’t made Illmatic two years prior, but he was also free to operate simply because Reasonable Doubt is a Serious Rap Record. There are the tortured recollections repurposed as threats (“D’Evils”), somber pledges to dying friends (the new “Dead Presidents,” not the one from the white-label), there are pool tables with made men and pool parties with your girlfriend (but only briefly, then it’s back to the money).

And the money isn’t the Bad Boy money, it’s the ‘88 money, the now we fight for blocks with buildings money. If Cuban Linx was “cinematic,” Reasonable Doubt is Shakespearean, all betrayals and double-crossings and turf wars and moral dilemmas. Buying the Lexus is a sober matter, the stick-up at the hotel on “Friend or Foe” ends with a cackle. Jay’s the disaffected opportunist, selling crack because of Reagan and wearing suits because it’s in his blood.

Put it this way: Jay sold the not-of-this-world gangster thing so well that he said he initially only wanted to do one album, and to this day people believe him.

About the vacuum. Reasonable Doubt doesn’t actually fit that neatly into 1996. The shimmering keys on “Can’t Knock the Hustle” don’t really fit any year, and when in history do you place the “Regrets” beat? Sonically it’s almost a counterpoint to New York rap from its year, none of the Hitmen’s sheen or RZA’s off-kilter menace.

At its meanest, the LP leans on DJ Premier, who firms up “D’Evils” and “Bring It On” with keys and strings, respectively. Having Premo at all was a coup. The last time they worked together was in ‘99; there’s always been that rumor that he was around for the “Ether” session, but I find that hard to believe.

Even if Jay isn’t the world-class technician he’d later become, he has those effortless passages on “Politics as Usual,” the wrapped-around bars on “Dead Presidents,” the one-act play on “Friend or Foe.” I remember a Larry King(?) piece on Jay from before The Black Album, where he’s explaining to Larry what “flow” is and why he’s the best at it. Larry--again, I think it was Larry--asks him if he has any shortcomings, and Jay pauses and says something like “I don’t have the greatest voice.” It’s true, but it also gives a youthful sort of hope to the whole thing: maybe the 50 Gs to the crap shooter are aspirational. The middle class is dead, etc.

About the vacuum. Nine months after Reasonable Doubt, Jay popped up on Life After Death, playing Monopoly with real cash and losing money on the Lakers. When Big passed, Jay stepped into that King of New York role. That’s what Nas never got: the king’s a figurehead.

So Diddy was around for the follow-up. Maybe the shift is exaggerated, since various Hitmen had hands in “Imaginary Player,” “Where I’m From,” and “You Must Love Me.” But Vol. 1 also had those clumsy stabs at radio with “Sunshine” and “I Know What Girls Like.” (“Lucky Me” is also a bit much for my tastes, but Wayne has the lyrics tattooed on him so I’m lenient.)

In the summer of ‘98, Jay started becoming the household name he is now. Swizz and Timbo were hanging around, Annie was there. It was the shiny suit era with some grit injected.

Blueprint came out on 9/11. Jay’d held you down for six summers. It was another Serious Record, and that was all he needed: The best rapper alive was The Best Rapper Alive, and it was a wrap. Your dad knows him.

All of Jay’s work since 1997 has been self-referential, in a way: even American Gangster, the album of his that’s most often compared to Reasonable Doubt, has songs like “Ignorant Shit” and “Say Hello,” where he’s musing on his place in pop culture and the way rap is treated by the press at large. He’s bring the Nets to Brooklyn, he’s shouting out Ludacris. The Black Album was about leaving behind the rap industry, because Jay, for a time, was its most astute critic.

Reasonable Doubt exists outside of all of that. In the vacuum. If he made it in 1998, it would have been seen as a one-off, an experiment--if it was seen at all. If you come out of the gate with a “Money, Cash, Hoes,” you’re not a Serious Record artist, and you can kick rocks.

None of this is to suggest that Reasonable Doubt was made cynically. How could it be? The emotional breakdown at the end of “Regrets,” the joy screaming out the sunroof. It was merely calculated, the origin story for the larger-than-life drug dealer who couldn’t help but make a rap record, who had actually been studying the form seriously for more than half a decade.

In or out of the vacuum, Reasonable Doubt is Jay’s best album, the crown jewel in perhaps the greatest career rap’s ever seen. Diddy isn’t allowed these, because he danced onto TV screens in a very un-Serious way. But what Jay and Diddy have in common is a keen awareness of how they’re seen by others. Jay’s debut cast him as being above the fray, too important for the petty squabbles but rich enough to settle lawsuits that came with them. And no matter what came later, that would always be Jay: trying on leathers, stashing away the furs.