Which isn't to say he wasn't cutthroat about certain things. Jay was originally signed to Payday Records, but when the label didn't support him like he wanted, he teamed with friends Dame Dash and Kareem "Biggs" Burke to form his own company, Roc-a-Fella Records. This wasn’t your typical music-biz operation -- Mary J. Blige and other contributors were reportedly paid with bags full of cash -- but it suited Jay’s purposes. As he told Yahoo! Music in 1999, Payday "didn’t know how to work a record." He added: “The things that they were setting up for me I could have done myself. They had me traveling places to do in-stores, and my product wasn’t even available in the store."
If there's one thing Jay knew about, it was supplying product. In hustling, he’d found a way out of poverty, but throughout Reasonable Doubt, he hints at the remorse he feels flooding his community with crack. He also catalogs the spoils and thrills like someone who’s maybe not ready to give it up, though by his own admission, he was.
"I didn't want to sell drugs," he told Yahoo! “I wanted a better life. I wanted to perform and I didn't know where performing would take me exactly, but I knew it would take me far away from where I'd come from."
It did -- eventually. Reasonable Doubt produced two top 10 Rap Songs hits and reached No. 23 on the Billboard 200. It wasn't bad for a relative unknown, but he wasn't doing Biggie or Tupac numbers. It would take his third album, 1998's Vol. 2... Hard Knock Life, to really set him on a path toward world domination. That album reached No. 1, as did the nine that followed. And yet many look back on Reasonable Doubt as Jay's finest hour. Here's a track-by-track take on the first chapter in a great American success story.
(Note: The bulk of Jay Z's catalog is exclusive to Tidal, so only three Reasonable Doubt songs are embedded below.)
“Can’t Knock the Hustle,” feat. Mary J. Blige: After some interpolated Scarface dialogue about getting deeper into the drug game, Jay gets on the mic to justify his exit. He’s got “short-term goals,” as he says in the opening line, but he’s clearly packing long-game skills. In between choruses form Mary J. Blige -- part lover, part mother, pure inspiration -- Jay jokes, boasts and sneaks in Pete Sampras references like only he can. “Let’s get together and make this whole world believe us,” he raps toward the end, ever-so-briefly accelerating his flow as producer Knobody’s lax beat thuds behind him. He can't help but get ahead of himself.
“Politics as Usual”: Gliding smoother than producer Ski’s Stylistics sample, Jay cruises through your town “on some do-or-die sh--.” He’s moving product, making money and coming to terms with the sacrifices inherent to the lifestyle. “It’s a lot of big money in my sentence,” he raps to cap a line about the Magnavox TV in his car. It’s a lot of pain buried between the lines.
“Brooklyn’s Finest,” feat. Notorious B.I.G.: The greatest MCs in BK history couldn’t sound more different on the mic. On this vicious and thrilling duet, Biggie rhymes milkshake-thick about his none-too-sweet business tactics (“shoot your daughter in the calf muscle”). Hova has the higher, nervier voice, and if he’s not quite as cold-blooded with his rhymes, he still has “pistols blazin’, hot like Cajun,” and he still manages to keep pace with his more established collaborator. Call this one a draw.
“Dead Presidents II”: Over a mournful sample of Lonnie Liston’s Smith's “A Garden of Peace,” Jay delivers some of the LP’s rawest street reporting. The first verse centers on a fellow dealer getting shot up, while the second finds Hov moving on, “swinging for the fences” despite the danger at every turn. He opens the third verse with some pure wordplay about how he’s “mic-macheted your flow,” and while he sprinkles in a few more criminal references, the kick he gets from rhyming seems to replace the thrill of the hustle.
“Feelin’ It”: The light and bright Ahmad Jamal jazz sample provides an apt backing for this weed-fueled bit of self-reflection. With a glass of champagne in one hand and a joint in the other, Jay thinks about his mother’s nightmares about him getting shot -- then gets back to counting his money and making it with chicks who might not dig him if he were broke. “I know, I contradicted myself,” he raps, one step ahead of the criticisms he’s sharp enough to see coming.
“D’Evils”: Born in a dream of Jay’s and executed brilliantly by DJ Premiere, who pits Snoop Dogg against an Allen Toussaint gospel record, “D’Evils” is Hova realizing he’s in a horror movie and refusing to hide in the closet. The best verse—in the song, and on the entire album—is the second, wherein he details kidnapping the a former friend’s baby momma. Despite all the demons infesting his soul (money, power, etc.), this song isn't an exorcism. It’s a descent into hell he’s accepted.
“22 Two’s”: Based on a freestyle Jay used to kick at Mad Wednesdays, the weekly event referenced in the intro skit, this chest-out brag-fest really does contain 22 uses of “two, “too” and “to.” Even without the gimmick, Jay is on fire, boasting about how he’ll blast you and then show up acting all sarcastic at your funeral. Interestingly, the outro skit involves Mad Wednesdays hostess Maria Davis lecturing about the importance of black-owned businesses. Even when he’s supposedly in frivolous hip-hop battle mode, Jay’s thinking big picture.
“Can I Live”: “We all fiends/ Even the righteous minds gotta do it,” raps a stressed-out Hov over a deceptively easygoing Isaac Hayes sample. Doubt about drug life is creeping in hard-core, though the song’s most famous line is pure baller ambition: “Rather die enormous than live dormant.”
"Ain't No Nigga," feat. Foxy Brown: This battle of the sexes really shouldn't have been a contest. Jay gets two verses, and Foxy Brown, who was just 16 years old at the time, only gets one. And yet the newcomer wields her sexuality like an AK in a verse she reportedly wrote in just 20 minutes. When she plays hip-hop Lady Macbeth and starts taking credit for Jay's rise ("but now you style, and I raised you"), Jaz-O's jiggly-butt bassline assumes a new level of funkiness. Foxy doesn't even care if he cheats -- she'll be home chowing on scampi, waiting to give him some loving he won't find elsewhere.
"Friend or Foe": If Shawn Carter was ready to give up hustling, Jay Z was still game to play kingpin every once in a while. On this bit of one-sided dialogue (a format Eminem would use to chilling effect in “97' Bonnie & Clyde”) Jay dresses down a couple of punk dealers encroaching on his territory. "Chance is slimmer than that chick in Calvin Klein pants is," he says, assessing the possibility of anyone making money on his turf. There are no bridges or hooks -- just a pimp-strolling DJ Premier beat and crates full of Jigga bravado. It's one of the more lighthearted tracks on the album, even though it nearly ends in a shootout.
"Coming of Age," feat. Memphis Bleek: The importance of mentorship cannot be overstated. In a reversal of the previous track, Jay spends the final verse of "Coming of Age" giving pointers to the rookie pusher who idolizes him. The kid is played by Memphis Bleek, an eager pupil who enters into the partnership like it's a marriage ("from now until death do us part"). Jay's main piece of advice is to "keep your cool," and the contrast between his relaxed flow and Bleek's hyperactive spitting adds some extra dramatic flair.
"Cashmere Thoughts": A pimp walks differently than a drug dealer, and that's why this satin-covered, champagne-soaked player's anthem sounds the way it does. DJ Clark Kent kills it with his sample of Hamilton Bohannon's "Save Their Soul," and Jay swaps drug references for lines about corrupting his neighborhood in different ways, namely "spitting venom up in the minds of young women.”
“Bring It On,” feat. Sauce Money and Jaz-O: Jay yields the spotlight to associate Sauce Money and mentor Jaz-O, who take the first and third verses, respectively. Both get better lines -- Sauce with a rock-hard Wu-worthy flow, Jaz with breathless speed -- and yet Jay’s mafioso mouth-running is more memorable. “Money make the world go 'round, so I made some to spend,” he says, certain no one can argue with logic like that.
“Regrets”: With sunny keyboards compliments of producer Peter Panic and some of Jay’s most somber, reflective lyrics, “Regrets” is like a summer jam for Camp Crystal Lake, the fictional setting of Friday the 13th referenced in the second verse, where Jay’s trying to square his actions with the effect they have on his mother. “I'm caught up all in it,” he raps, “they make it so you can't prevent it.” In the final verse, things get damn near Shakespearean as Jigga chats with the ghost of a dead friend, pondering whether to blast another old friend he’s been beefing with. He decides it’s one regret he’s not ready to live with.
Much of Reasonable Doubt is now exclusive to Tidal. To listen to the entire album, visit Tidal.com.