Jay-Z never sounded hungry. That’s the striking thing about Reasonable Doubt, Jay’s landmark debut, which celebrates its 20th anniversary on Saturday. There’s some debate on the matter, but legend has it that Jay had already built up a small fortune on the drug trade before recording his debut album. He’d made his debut on Jaz-O’s “Hawaiian Sophie” in 1989, and he’d appeared alongside some big rappers and even toured with Big Daddy Kane. But his focus was elsewhere. And even though we already hear him as a fully formed rap monster on Reasonable Doubt, he also sounds like someone who doesn’t need rap. Jay says it himself on “Dead Presidents II”: “I dabbled in crazy weight / Without rap, I was crazy straight / Potna, I’m still spending money from ’88.” At the time, there were plenty of other New York rappers talking about street life: Wu-Tang, Mobb Deep, Nas, the Boot Camp Clik, Jay’s “Brooklyn’s Finest” guest Biggie Smalls. But all of them, even Biggie, sounded like they might still have a little dirt under their fingernails. Jay arrived sounding like he was used to the finer things, and it’s what set him apart.

If you read interviews with the people who were around rap music at the time, the word “arrogance” comes up a lot. Jay’s aloofness put people off. But that overwhelming confidence had everything to do with his rise, too. A couple of years later, when Jay became the world’s most popular rapper, he’d adjusted his flow a bit, and he’d moved musically beyond the classic mid-’90s New York boom-bap of Reasonable Doubt. But that disdainful swagger was still the single greatest animating force behind his music. Unlike the rappers who came later, Jay never claimed that he wasn’t a rapper, that he was just a hustler who happened to be good at rapping. But Jay might’ve been the first rapper to give off that impression. As dense and layered as his raps were, he still seemed to be indolently playing around with words, to be treating music as a hobby. He made it sound easy.

But that wordplay was dense and layered, more drunk on language than Jay would ever be again. He’d pile meanings up, leaving you with these tangled, impossibly cool jumbles of images and innuendos that you could spend weeks picking apart: “Fuck ‘em, they hate a nigga living this life / In all possible ways, just know the Feds is bugging my life.” Telling stories about bloodshed, he could sound both haughty and ruthless, and even then he’d find ways to dazzle with pure cleverness: “I kept feeding her dollars until her shit started to make sense/cents.” And he did it with an eye for cinematic dazzle, masterfully overseeing the sonic character of the album and making sure that it all fit the image he was projecting. Even then, Jay knew that what mattered wasn’t just what he said. Even more important was how he said it.

Musically, Reasonable Doubt exists within the context of mid-’90s New York rap, and most of the album’s producers, like DJ Premier and Clark Kent, were important parts of that world. But from those producers, Jay figured out how to pull a certain sense of luxuriant slickness. The tempos never rush, and there’s no noise or clatter in this version of the New York sound. Instead, it’s all tinkly sweep. The music is a way of reinforcing what Jay’s already telling us: He’s not a street soldier; he’s a boss, relaxing to orchestral jazz in a penthouse suite somewhere. Something as nasty as the deeply funky bassline on “Ain’t No Nigga” is a relative rarity. Instead, we hear strings and pianos and harps. On “Brooklyn’s Finest,” thanks to the presence of Biggie, Jay gets breathless and intense, eager to show he can hang with the best in the world. Everywhere else, he’s in pure recline mode. The album’s secret weapon might be Ski Beatz, who gets four tracks, more than any other producer. Up until that album, Ski had mostly been known for working with Camp Lo, an eccentric fashionista duo who came off like ’70s-obsessed dandies, a sort of New York version of OutKast. Jay kept that gentlemanly stylishness intact, and he backed it up with heavy street shit. It was a serious combination.

Now: Reasonable Doubt was not a hit, and that mattered. It came out into a crowded marketplace, with noted Jay-disliker Tupac Shakur still enjoying how many eyez were on him. It charted no higher than #23, and it took six years to go platinum. Rock critics didn’t notice it at all, and I can remember confused conversations with coworkers who insisted that no, listen, this Jay-Z guy is going to be important. Jay had a character, but he didn’t have a gimmick or an immediately catchy sound, so he lagged behind more colorful peers like Busta Rhymes. So Jay diagnosed the problem: His music was too insular and complicated to resonate with a mass audience. And he went about fixing things, adapting a post-Puffy aesthetic and gunning for crossover hits on just about every album he released afterward. “I dumbed down for my audience to double my dollars,” Jay himself admitted, in song, seven years later. And it worked! Two decades later, the Jay we know is nothing like the Jay of Reasonable Doubt; he’s even lost the hyphen and the umlaut in his name. But he kept the thing that mattered the most: The regal, aristocratic bearing, which turned out to work just as well even in the context of Annie samples.

Today, Reasonable Doubt may or may not be your favorite Jay-Z album. But one thing is for sure: It is Jay Z’s favorite Jay-Z album. Nobody has fought harder to build up the album’s reputation than Jay himself has. He brings it up in virtually every interview, and he devoted large portions of his great book Decoded to untangling its lyrical intricacies. The album itself is at the heart of Jay’s messy public split with Dame Dash and Kareem “Biggs” Burke, his original Roc-A-Fella business partners; Jay was reportedly so pissed off that they wouldn’t give him the Reasonable Doubt masters that he took the Roc-A-Fella name away from them and wrote them out of his empire. It mattered that much to him.

And 10 years ago, I watched Jay celebrate the album’s 10th anniversary in a show at New York’s Radio City Music Hall, still one of the best live rap productions I’ve ever witnessed. Jay performed the album in the grandest, most generous fashion imaginable. He wore a white tux, came on stage in a 1996 Lexus, and performed every track on the album with the help of a 50-piece orchestra that included ?uestlove, Just Blaze, nine horn players, and a harpist. Jay rapped the whole album back-to-front, starting with “Regrets” and ending with a triumphant “Can’t Knock The Hustle,” with Beyoncé filling in for Mary J. Blige and somehow singing the hook even better than she had. Alicia Keys and Chris Tucker and LeBron James were in the audience. It’s the only show I’ve ever been to where every member of the audience got a gift bag, and I wish I still had the T-shirt that came in mine. The entire show — which came right at the end of Jay’s fake retirement, shortly before he released the limp Kingdom Come and wounded his great legacy — was an absolutely peerless piece of self-mythologization. And maybe the best thing I can say about Reasonable Doubt is that it justified everything Jay did to build it up. Jay would have greater triumphs in the years that followed, but Reasonable Doubt is a special album, the only one of its kind.