On June 25th, 1996, the most prolific rapper of all-time made his debut as a 26-year-old former-crack-dealer-turned-emcee. Calling himself Jaÿ-Z, he set about crafting one of hip-hop’s most revered albums – although it wasn’t as highly-praised at the time.

As XXL writes, the album sold “just 420,000 copies its first year out, peaking at No. 23 on Billboard’s album chart, and wasn’t certified platinum ’til 2002.”

“He had spent eight years in the doldrums,” said Nick Raphael, the man who signed Jay to a world record deal with Northwestside Records.

“He had released that first album, Reasonable Doubt, on his own record label, with his business partner, Damon Dash. No one wanted to release him.”

“None of them were f—king with us,” Jay writes in Decoded.

“Not Columbia, not Def Jam, not Uptown. Sometimes there was talk of a single deal, but whenever it got to the point where it was supposed to be real, the label would renege.”

“If I showed you the reviews written at the time about the album – ‘This guy’s the death knell of hip-hop; It’s the beginning of the end; It’s so obvious’ – some of those people, ten years later, wrote the review to say Reasonable Doubt is the greatest hip-hop album ever made,” Raphael adds.

“We named the album Reasonable Doubt because like with anything you do in life, people are going to judge you,” Jay told VIVA’s Word Cup in 1997.

“So the album is basically on trial – whether you like it or you don’t, it’s reasonable doubt.”

In the tradition of our ode to Black Star, allow us to take a walk down memory lane and revisit the album, track-by-track.

1. “Can’t Knock The Hustle” feat. Mary J. Blige

“Last seen out of state where I drop my sling/ I’m deep in the South, kicking up top game/ Bouncing on the highway, switching four lanes/ Screaming through the sunroof, Money ain’t a thang!”

How many opening songs remain one of the best in an artist’s catalogue, years later?

Jay opens his solo career with a certified hit, not to mention a Mary J. Blige feature. The skit intro doesn’t do much for the song, but the rest is classic Jay Z: rapping about all of hip-hop’s familiar tropes, only better than just about anyone.

“At my arraignment/ Screaming, all us blacks got is sports and entertainment.”

Here’s where Jay is the best at what he does: existing in the middle between mafioso rap and so-called “conscious rap.” He could be rapping about money, drugs, and women for ninety percent of the song, but he’ll toss in a line like the one above to make you think.

“This is one of the things that makes rap at its best so human,” Jay writes in Decoded.

“It doesn’t force you to pretend to be only one thing or another, to be a saint or sinner. It recognizes that you can be true to yourself and still have unexpected dimensions and opposing ideas.”

As the man has rapped before, “I’m like Che Guevara with bling on, I’m complex.”

One more note on this song – an interesting side story about how Knobody ended up producing “Can’t Knock The Hustle”:

“My brother and I were part of a rap group,” Knobody told HitQuarters in 2005.

“I was rapping and also producing tracks with my partner Sean C. At that time, I was about 20 years old and still at college. My brother didn’t want to continue with the rap group, but the last track that I’d produced for us, I thought was really good. Sean and I took the track to Roc-A-Fella’s Damon Dash, who lived across the street.”

“The whole time after we gave Dame the beat and after he picked it, from then on we called like every week like, ‘What’s up? Can you find out what’s up?’” Knobody told XXL.

“They’d be like, ‘He’s writing.’ So I don’t know if he was actually writing. Dame just told me, ‘Quit calling me.’”

2. “Politics As Usual”

Ski Beatz doesn’t get enough credit for this one – I’ll take this beat over a large swath of Jay’s entire catalogue.

What’s interesting about “Politics As Usual” is that Clark Kent nearly produced the record instead of Ski. The two had sampled the same record, unbeknownst to each other, and brought their records to Jay Z.

“It’s crazy, ’cause the same day that Ski brought him that beat, I brought him the same beat like an hour later,” Clark Kent told XXL.

“Jay was like, ‘Dag, I think yours is a little better.’ ’Cause mines was pretty sounding, because I made it big and very clear. But Jay was like, ‘You know how we do it, and real is real. He gave it to me first.’ So he did his version instead of doing my version of the same thing.”

“My portfolio reads/ Leads to Don Corleone, n—a please.”

“I think he was trying to tell the story of a young hustler from the streets,” Ski told SoulCulture.

“He was trying to rise and get the only money the way he knew at the time, selling what he was selling and doing what he was doing”.

3. “Brooklyn’s Finest” feat. Notorious B.I.G.

In a genre famous for its love of skits and interludes, the opening of “Brooklyn’s Finest” — “okay, I’m reloaded!” — remains one of hip-hop’s most memorable.

This song also stands out as the only true collaboration between Jay and Notorious B.I.G. – Biggie died less than a year later.

“It’s very rare in hip-hop where you make close friends,” Jay told VIVA’s Word Cup in 1997.

“I mean, y’all meet at such a late age. Y’all ain’t grow up together. Y’all ain’t played kick the can, or skully together […] It’s very rare that me and [Big] clicked like that.”

The two seized the opportunity to trade over-the-top bars, pushing each other to deliver their best.

“Time to separate the pros from the cons/ The platinum from the bronze/ That butter soft shit from that leather on the Fonz.” – Jay Z

“[Biggie’s rhymes] could be about the most outrageous things – hijacking a subway, pulling off an armed heist, robbing one of the New York Knicks – but he’d ground them in details that made them feel completely real, even when you knew he was just f—king with you,” Jay writes in Decoded.

“Shoot your daughter in the calf muscle/ F—k a tussle/ Nickle-plated/ Sprinkle coke on the floor, make it drug related.” – Notorious B.I.G.

There’s also this noteworthy anecdote in Decoded about how the song got off the ground thanks in part to Bernie Mac:

“When Big came through one of my sessions to see Clark [Kent], Clark played him the beat for ‘Brooklyn’s Finest.’ […] When Big said he wanted to get on the track, I went into the booth and started laying down vocals. Big was in the back of the room smoking and nodding. He didn’t get on that night, though; he said he wanted to go home and think about his verses. In that moment, I gave his coming back to be on the song a fifty-percent chance of actually happening. There was a fifty-percent chance he was just talking s—t like an industry n—a. We went to see Bernie Mack (sic) later that night and really clicked. He sent the song a couple weeks later.”

4. “Dead Presidents II”

In one of the most freestyled-over beats ever, Jay delivers another performance for the ages.

“Who wanna bet us that we don’t touch lettuce/ Stack cheddars forever/ Live treacherous, all the etceteras/ To the death of us, me and my confidants/ We shine, you feel the ambiance/ Y’all n—as just rhyme.”

The interesting story is how the song came to be “Dead Presidents II.” Originally, the song came out as a single (combined with “Ain’t No N—a”) ahead of the album’s release. For the album, Jay switched things up.

“The new verses on Dead Presidents II were to give people more of him,” Ski told SoulCulture.

“Back then, we didn’t really do remixes so for an emcee to give you an extra verse was just a bonus for you […] When I made the ‘Dead Presidents’ beat, I first heard the Nas record [‘The World Is Yours’]. I was inspired by the music […] I just went into the crates and tried to find something which made me feel like that and I found the Lonnie Liston sample and I threw Nas’ sample on top as a tribute because I loved the song so much.”

5. “Feelin’ It” feat. Mecca

“If y’all n—as ain’t talkin’ ’bout large money, what’s the point?”

Five songs in, and we’ve got one of the strongest opening runs in hip-hop history. Put these first five songs on any album, and it’s automatically a hit. Now imagine having them play back-to-back-to-back-to-back-to-back on your debut album. Oh yeah, and one of them features Biggie. Who else but Jay Z has done this?

“If there’s five records on anybody else’s album, you go, ‘This is kinda alright!’” Young Guru told the Combat Jack Show.

“The bar is super high for him.”

On “Feelin’ It,” Jay leaps over that bar, delivering another memorable performance over Ski’s luxuriously jazzy production.

“My job was to capture what he was saying and what he was feeling and turn it into music,” Ski told Classic Albums: Reasonable Doubt.

“Every song was a movie, so I was basically creating the soundtrack, the score.”

“Even if it ain’t sunny, hey, I ain’t complainin’/ I’m in the rain doin’ a buck-forty, hydroplanin’/ What, shorty? (Where you disappear to, son?) Maintainin’/ Puttin’ myself in a position most of these rappers ain’t in.”

Interestingly, the song wasn’t meant for Jay Z.

“‘Feelin’ It’ was my song originally and was for my album,” Ski told SoulCulture.

“I took the record to Dame and Jay was there and I was like ‘check out this song it’s gonna be dope’ and I played it for Jay and he was like ‘I want that. You’re gonna have to give that up, I need that song.’ He kept the hook and even took the same way I rhymed on it and rhymed with the same flow, but he told me he would do so.”

6. “D’Evils”

A good barometer for measuring an artist’s impact is looking at how many times their work has been referenced by other artists. In Jay Z’s case, it’s surprising how many times his rhymes from “D’Evils” have resurfaced in other emcees’ catalogues. Take this small segment:

“Nine to five is how you survive; I ain’t tryin’ to survive/ I’m tryin’ to live it to the limit and love it a lot/ Life ills, poison my body/ I used to say f—k mic skills/ and never prayed to God; I prayed to Gotti.”

It’s hardly more than four bars, but it’s been sampled and paid homage by the likes of J Cole, Lupe Fiasco, Chubb Rock, and Apathy. That’s pretty damn impressive.

“It’s funny because Jay called me and did the whole rap over the phone and told me which scratches he wanted to use,” DJ Premier told 3RRR in Australia.

“So all those scratches were his idea, and I just flew them in accordingly to sound like the way I do my scratches. But he already had the concept down before he had the lyrics down.”

For Jay, that concept was rapping about the seemingly inescapable nature of crime.

“It gets dangerous/ Money and power is changin’ us/ And now we lethal, infected with D’Evils.”

“The first defense of a lot of people who take the criminal route is that they had no choice, which is almost true: Most of us had choices, but the choices were bleak,” Jay writes in Decoded.

“The street life was tough and morally compromised and sometimes ugly, but a dead-end nine-to-five job at permanent entry level wasn’t all that attractive, either. The righteous seed in a hustler’s mentality was this: He wanted something more for himself.”

7. “22 Two’s”

Taking a break from the album’s general mood and feel, Jay flexes his lyrical dexterity on this one, cramming 22 two’s into a verse.

“That was my secret weapon,” Jay told XXL.

“Any show I did, I would pull that out. I had that way before. I just did the second verse when I did the album.

“To all my brothers it ain’t too late to come together/ Cause too much black and too much love equal forever/ I don’t follow any guidelines cause too many n—as ride mine/ So I change styles every two rhymes.”

“In the beginning, you listen to those records […] the structure was crazy,” Jay told Classic Albums: Reasonable Doubt.

“[There] was no sing-along chorus; it was couplets coming at you a million miles an hour. I wasn’t even concerned with people singing along.”

The song places Jay as a performer at one of Maria Davis’ Mad Wednesdays, which he used to frequent.

“She had an event that Jay would go to every Wednesday and perform,” Ski told SoulCulture.

“She was a big part of his career too because a lot of people would go and see him perform there. So we decided to use her at the beginning of the skit. The whole ‘Mad Wednesdays’ event was a big thing in New York City at the time.”

8. “Can I Live”

“We hustle out of a sense of hopelessness, sort of a desperation. Through that desperation, we become addicted, sorta like the fiends we accustomed to serving. But we feel we have nothin’ to lose, so we offer you… well, we offer our lives, right. What do you you bring to the table?”

According to Jay Z lore, this track holds the distinction of containing the last rhymes Hov actually sat down to write.

“What happened was, I was doing that song with someone else, and they heard the first verse and they was like, ’Man, you take that song. Finish it, ’cause it sounds like you got a lot more to say,’” Jay told MTV News in 2007.

“So I just wanted to get it down quick, I didn’t want to keep going over it. It was like [the album’s] mastering time, so I just sat down in the booth and wrote that [verse].”

“I’d rather die enormous than live dormant, that’s how we on it.”

Also from that interview: According to Irv Gotti, at one point, Nas was slated to deliver a guest verse on the song. Can you imagine?

On a side note, it’s interesting that this track is one that stood out to Young Guru and turned him into a fan.

“Illin’ for revenues Rayful Edmond-like/ Channel 7 News, ’round seven jewels, head dead in the mic.”

“When he said the Rayful Edmond line, I was like, ‘How does anybody outside of D.C. know about Rayful Edmond?’” Guru told the Combat Jack Show.

“And then the way he said it […] if you really was from the area, what he’s telling you is, ‘I’m watching the news and the way they did Rayful was bad.’ […] It’s a very stark image in anybody’s mind that used to watch the news in D.C. […] Those lines for me brought me into Jay. Jay’s honesty.”

9. “Ain’t No N—a” feat. Foxy Brown

There are two stories about this song worth telling, as far as I’m concerned:

i) This song led to Jay Z signing a world record deal with Northwestside Records/BMG.

“I found Jay Z because a friend of mine who ran a dance label in New York was distributing his album,” Nick Raphael, the former head of Northwestside Records, told HitQuarters in 2005.

“Will Socolof of Freeze Records sent me a CD and a video and said to me, ‘This guy is incredible, but he needs a bigger label to take over. Are you interested?’ The record he sent to me was ‘Ain’t No N—a’ and I went crazy, thinking that I had to sign him.”

(This interview has some good gems about Raphael’s discovery of Jay Z.)

ii) This excerpt from Decoded about Jay Z’s encounter with Biggie during the filming for the music video in Miami:

“Big loved to smoke, but I could count the number of times I’d smoked trees […] I come from that class of hustlers who looked at smoking as counterproductive. We used to judge n—as who smoked as slackers, or workers […] But when Big asked me to smoke with him, I told myself, ‘Relax, you’re not on the streets anymore.’ […] So I smoked with Big – and he smoked blunts. The last time I smoked, whenever that was, I’m sure I was hitting a joint. A couple hits later and I was high as s—t, sitting there, feeling outside of time, slightly stuck, and laughing uncontrollably. Big leans in so only I can hear him. ‘I got ya.’”

10. “Friend Or Foe”

“Considering the size of his catalogue and the depth of his talent, it is surprising that Jay hasn’t done more non-autobiographical storytelling,” HipHopDX writes.

On this one, Hov narrates the inner monologue of a drug kingpin, sizing up an outsider encroaching on his turf:

“You’re twitching, don’t do that, you making me nervous/ My crew, well, they do pack, them dudes is murderers/ So please would you, put your hand back in sight/ They don’t like to see me nervous you can understand that, right?/ You draw, better be Picasso, you know the best/ Cause if this is not so, ah, God bless.”

As far as songs go, this one stands out for being notably short: less than two minutes, and just one verse. Of course, the story continues on In My Lifetime, Vol. 1, when Jay drops “Friend Or Foe ’98.”

11. “Coming Of Age” feat. Memphis Bleek

The song that introduces a young Memphis Bleek to the world.

In Decoded, Jay shares an interesting story about how Bleek nabbed the spot on Reasonable Doubt:

“I had this verse that needed a younger voice on it, but a young voice that was rough and full of ambition, and I just got a feeling from this kid […] I didn’t just give him the verse, which I’d already composed. After all, I had no idea if he could pull it off. First there was a test. I collared him and said, ‘Look, I’m making an album and you can be on it, but you have to learn this song in twenty-four hours.’ […] He took the paper I handed him and looked it over. I’d written the verse down for him in some chicken scratch, and when he held it up, I could tell he was thinking, Shit, I can’t hardly read this […] He came to my apartment the next day and spit the whole thing like he’d been doing it his whole life.”

“In reality, that really is me, because we’re from the same building,” Memphis Bleek told Classic Albums: Reasonable Doubt.

“He was the guy coming through with the fine women, fly cars, the jewellery. I was always the young guy looking up, but never said nothing.”

12. “Cashmere Thoughts”

If I’m dropping a song off Reasonable Doubt, it’s probably this one.

Thematically, it sticks out from the rest of the album, and if you’re asking me, it doesn’t really stand up to the rest of the track listing. (I don’t give “Ain’t No N—a” much weight either, but that’s another discussion.)

“‘Cashmere Thoughts’ was almost like a joke,” Clark Kent told Complex.

“You hear the way we’re talking back and forth on that record? That’s me and him talking pimp s–t, because we did that all the time. ‘Cashmere Thoughts’ is from the name Cashmere Jones, which was Jay’s pimp name and alias. We were just bugging.”

I can forgive Jay for one lacklustre song on an otherwise classic album.

13. “Bring It On” feat. Sauce Money & Jaz-O

This one features another of the album’s best beats, courtesy of DJ Premier, and all the emcees show up to play.

“We locked out D&D studios and I would be in the lab by noon, going from one room to another working with producers,” Jay writes in Decoded.

“I don’t think I slept for weeks at a time back then. I was living off pure adrenaline.”

“He would book my room, the A Room and the D Room, which was a newly built studio space in the back that they later tore down,” DJ Premier told Observer.

“He would have them all blocked so that he could knock out three or four songs at a time.”

Sauce Money kicks it off with a classic verse, delivering one of the album’s most memorable couplets:

“Said we was garbage, so f—k college/ Street knowledge amazes the scholars/ When we coin phrases for dollars.”

“It was a war in the studio,” Sauce Money told Classic Albums.

“They were so lyrical, it was like, ‘I gotta step up.’”

From there, Jay and Jaz-O deliver memorable verses of their own, Jay rapping of “mannerisms of a young Bobby DeNiro” and Jaz spitting about “tip scales from mail to keep n—as off balance.”

As good as the song is, it stands out for what it could have been. According to Dame Dash, Sauce Money and Jaz-O weren’t the original guest features in mind.

“Nas and AZ was supposed to be on ‘Bring It On,’ they kept not showing up,” Dash told MTV.

“That’s when we wanted to put out the Firm. They didn’t show up. We was meeting and they was saying, ’Yeah,’ but they wasn’t showing up. We would be waiting and we would be getting offended. So we brought Sauce [Money] and [Big] Jaz on the song.”

Forget the Nas rumour on “Can I Live.” THIS is a song that would’ve fit him and AZ perfectly. It doesn’t take stretch of imagination to picture the two flowing over of Premo’s production.

14. “Regrets”

“This is the number one rule for your set/ In order to survive, gotta learn to live with regrets.”

A perfect ending to a near-perfect album.

Blurring the line between autobiography and fiction, Jay closes things off by reminiscing solemnly about selling “it all, from crack to opium,” and mourning the death of a friend.

“As sure as this Earth is turning souls burning/ In search of higher learning turning in every direction seeking direction/ My mom’s cryin’ ’cause her insides are dyin’/ Her son tryin’ her patience, keep her heart racin’/ A million beats a minute, I know I push you to your limit/ But it’s this game love, I’m caught up all in it.”

“The album as a whole was like a conversation I was having with the listener about real feelings and emotions,” Jay writes in Decoded.

“I wanted to end [the album] with regret, that last feeling you have before you go to sleep, or feel when you wake up and look at yourself in the bathroom mirror.”

After an album full of excess – riches, women, and criminal life – Jay ends things at his most human, revealing the trade-off for all of the mafioso life’s grandiosity.

“That’s the beautiful thing of Jay, and I think that’s why he’s been able to be as successful as he is,” says Rapsody.

“He’s still complex, and he still knows how to use complex similes and metaphors, but the average person can still get it. It’s not too far over your head.”