This series will work as a walkthrough of Jay-Z deep catalogue, as well as a dive into my relationship with one of my favorite bodies of work in music. No skimming, no mincing words. If you want more background on the inspiration for this random endeavor, please check out the preamble. Let’s dive in.
Reasonable Doubt is unrefined, but genius.
If there was a way I would describe Jay-Z’s legendary debut, it would be that. He was about 26 years old by release date, old for 90s rappers debuting and that age felt on the LP. The album feels wise off rip, smooth and luxurious boom bap production bouncing as Jay raps about drug trades, Cristal by the bottle, and how racism keeps him tied to “sports and entertainment”. Considering he was rhyming since childhood and drug dealing just as long, that world-weary wisdom bleeds through far more than your average MC’s introductory project.
At the same time, however, that guise of maturity is a mask. Jay’s glorification of excess and violence makes the album comparable to a classic mafia flick. For every moment Hov waxes poetic on being smart, he also leans back on street rep and the pure thrill of spewing bars. “Brooklyn’s Finest” sees him and Notorious B.I.G brazenly embrace rhymes and crimes as equal paths to success. The track embodies the theme this album presents. It’s grounded by the balance between underworld life, the art it inspires, and the relationship both play in getting to that penthouse view of “success”.
Now, this duality is Hov’s bread and butter, and to have it so soundly established on a debut is incredible to think about in hindsight. You feel it when Jay asks for a break from his anxieties on “Feelin It” or when he tries to cover that paranoia with splurges on “Can I Live.” Both are prime examples of the “luxury” and “coke” lanes of rap folks like Griselda and Rick Ross are blatantly influenced by, but here the execution is raw and, in many ways, unrefined.
That unrefined element arguably makes this LP the most unique in Jay’s discography. This is a Jay before he found his blueprint, so to speak. A track like “Dead Presidents II” feels like something only an unfiltered Jay-Z would make. Chilling keys, slick drums and an iconic Nas sample somehow play backseat to one of Jay’s best string of verses, a track is both pure hip-hop love but also a peek into Hov’s mindset on money, danger, and the risk-to-reward ratio crime brings.
“Murder is a tough thing to digest, it’s a slow process/And I ain’t got nothing but time”
Jay-Z on “Dead Presidents II” is at his scariest, a reminder that this was before Hov became a pop culture icon.
That lack of refinement has some drawbacks, though. The tracks where Hov goes more materialistic feel like demos for the better bling-era stuff he would deliver later on. “Ain’t No” feels like a weak attempt at the “established MC brings on a rookie” concept, where Foxy Brown dominates an obnoxious 90s pop rap beat (which is ironic, given “Coming of Age” is on the same LP and is a touchstone for that kind of track). “Cashmere Thoughts” is a do-nothing track that, on re-listen, just serves as a snack break between two outstanding highlights. Even the flexing here feels small stakes for Jay, who for all intents and purposes, tries to make BIG music. They feel small, listles, and in a way dated in a bad way, a critical flaw in some of Jay’s subsequent records.
And yet ultimately, for an intro to Jay-Z, it’s fantastic. I’d say that some of this album’s best tracks are some of Jay’s best all time; when you consider that he himself ranked this as his best album, it makes sense. It’s Jay before he settled into his artistic method, still fresh from his past street life and prepping for his future tycoon/rap life. It’s home to some of his most unique tracks. Above all, it’s the foundation from which he would build his fantastic catalogue.
Bonus Thoughts:
- Couldn’t work the song “D’Evils” in but holy crap that is one of the BEST rap songs I’ve ever heard. The way Jay raps over the collections of samples in a clear story about friendship shattering over underworld ties, the wordplay on lines like “feeding her dollars ‘til s*** started to make sense (cents)”, the evil atmosphere…top tier Hov.
- The record absolutely peaks in its first half for me, but I think in a way that makes the highlights on the backend that much more special. “Coming of Age” launched Memphis Bleek’s career and the closer just confirmed that. “Regrets” is an underrated track too.
- If I could go back in time, I would have done whatever it took to put Raekwon in “Bring It On,” given he was an expert in the mafioso rap brought in by Only Built 4 Cuban Linx.
- You’ll see later on but some of Jay’s later LP’s haven’t aged all that well…but the boom bap and jazz rap influence on this one (for most tracks) has really held this one up almost 30 years later.
