Everyone is familiar with Shawn “Jay-Z” Carter’s illustrious rise from successful drug dealer to billionaire businessman (and a business, man!) and arguably, the greatest rapper of all-time, but before he became a filthy rich rap superstar and bagged the flyest chick in the game who not only rocks his chain, but also his wedding ring, he had to pay his dues (a concept that is completely nonexistent in this current age of microwave hip-hop…but I digress). After getting his start appearing on his mentor, Jaz-O’s 1989 debut album, Word To The Jaz, he would go on to make a handful of cameos on different artists’ albums (i.e., Original Flavor, Big L, Big Daddy Kane and Mic Geronimo). These cameos would help raise Jay’s profile and after linking with Dame Dash and Kareem “Biggs” Burke to form Rock-A-Fella Records, Jay would be the label’s inaugural artist, releasing his debut album, Reasonable Doubt in June of ‘96.

As Jay has mentioned before (and I’m paraphrasing), the album title references those who doubted his rapping ability, which he humbly deemed reasonably, but was out to prove them wrong, and we all know how that played out. Jay would call on a handful of producers to sculpt the sound of Reasonable Doubt (including DJ Premier, Ski-Beatz and DJ Clark Kent) and would invite a few guests to make cameos as well. Even though he felt “it should have went triple”, Reasonable Doubt would earn Jay a platinum plaque, a shit load of critical acclaim, and the album is widely heralded as a classic and one of the greatest hip-hop albums of all-time.

I’ll admit, I was a little late getting into Reasonable Doubt. My summer of 1996 was consumed by three other albums that I’ll be discussing very soon (I’m sure you can figure out at least one of them), and I didn’t start delving into Reasonable Doubt until the following September. But if my memory serves me correct; Reasonable Doubt made for great fall music.

Legend has it (and by legend, I mean from the mouth of the legendary, DJ Clark Kent) that Jay-Z only planned to make Reasonable Doubt and then exit the music game forever. Man plans, God laughs, and Shawn Carter’s been laughing his way to the bank and goat status ever since.

Can’t Knock The Hustle – The album opens with a recreated scene from the classic movie, Scarface before the first song of the night starts, which was also the third single released from Reasonable Doubt. Knobody (what an alias) chefs up a bassy and cool backdrop that sounds like its submerged in water, while Jay-Z proudly boasts about his drug dealer lifestyle (“We do dirt like worms, produce G’s like sperm, till legs spread like germs, I got extensive hoes, with expensive clothes, and I sip fine wines and spit vintage flows.”) and brashly tries to defend it: “At my arraignment, screamin’, “All us Blacks got is sports and entertainment,” until we even, thievin’, as long as I’m breathin’, can’t knock the way a nigga eatin’, fuck you even.” Mary J. Blige (who by 1996 was well on her way to becoming crowned the Queen of Hip-Hop Soul) stops by to add her signature adlibs and sings the hook, which was a pleasant but obvious attempt to make Jay’s underworld rhetoric more digestible to the masses (aka make it sound more commercial). I’ve never been crazy about this record, but it’s still decent.

Politics As Usual – Jay gives us more drug dealer talk with this one. This time around he balances bragging with sharing some of the stresses and mental anguish that illegal business can bring: “Ya’ll feel a nigga’s struggle, ya’ll think a nigga love ta, hustle behind the wheel, tryin’ to escape my trouble? That’s out there greetin’ me, I’m talkin’ sweet to ki’s, cursin’ the very God that brought this grief to be.” Ski gets his first production credit of the night and builds a super soulful groove around a Stylistics record that works as the perfect backing music for Jay-Z’s conversational style. This one still sounds as amazing as it did twenty-five plus years ago.

Brooklyn’s Finest – The Scarface character from the intro returns to let off a few rounds and shares a few words to introduce the next record that pairs Jay with another Brooklyn legend, The Notorious B.I.G. DJ Clark Kent (with a co-production credit going to Dame Dash) loops up a funky Ohio Players joint to back the duo’s verbal sparring, as the two kings exchange witty hustler heavy rhymes. Big may have been the more established and celebrated of the two emcees at the time, but Jay matches him bar for bar on this one. This is a superb record that lives up to its title. Continue to rest easy, Biggie.

Dead Presidents II – Part 1 of this song was the promotional single for Reasonable Doubt and the version used for the video. Both versions use the same instrumental, but have different lyrics, and while I love the “Rico, all good just a week ago” line from the original, Jay sounds way more comfortable and polished on the sequel (who can ever forget the classic line: “I dabbled in crazy weight, without rap I was crazy straight, Patnah, I’m still spendin’ money from eighty-eight”?). Ski keeps the soulful vibes coming, this time building the dope backdrop around a brilliant Lonnie Liston Smith piano loop, and he uses the notorious Nas line for the hook that Jay would later reference during the two titan’s epic feud a few years later (“You made it a hot line, I made it a hot song”). This is an undeniable classic that still sounds fire.

Feelin’ It – This was the fourth and final single released from Reasonable Doubt. Ski uses another jazzy piano loop, accompanied by poppin’ drums to create this elegant instrumental that features Mecca singing on the hook and finds Jay enjoying the fruits of his illegal labor: poppin’ bottles of Moet and Cristal, driving fancy cars and smoking weed with beautiful women on exotic islands. Ya feelin’ it? Yeah, me too. Legend has it that Ski made this instrumental for Camp Lo but decided to give it to Jay at the last minute. All respect due to Sonny Cheeba and Geechi Suede, but I’d say Ski made the right decision.

D’Evils – Premo gets his first production credit of the night, crafting some dark boom-bap with a few classic vocal snippets scratched in to the hook, as Jay embraces “d’evils” that he confesses possess his soul and have him selling death to his own people and feuding with childhood friends over drug territories: “We used to fight for building blocks, now we fight for blocks with buildings to make a killin’, the closest of friends when we first started, but grew apart as the money grew, we grew black-hearted, thinkin’ back when we first learned to use rubbers, he never learned so in turn I’m kidnapping his baby’s mother.” This has to be the darkest record in Jay-Z’s catalog and probably the song that started the “Jay-Z’s in the Illuminati” rumors. A chilling, but great record.

22 Two’s – This one begins with Maria Davis, who actually used to to host an event called Mad Wednesdays in New York City, introducing herself and her event, before spotting Jay-Z in the audience and asking him to come to the stage and “kick a freestyle,” to which he obliges. Ski’s darkish (we’ll call it tinted) backdrop comes in and Mr. Carter takes a brief break away from his drug dealer themes to get into some emcee shit. Jay starts thing off by borrowing ATCQ’s “Can I Kick It?” call and response, and when he doesn’t get the participation from the crowd that he expected, he hi-lariously mumbles, “Ya’ll muthafuckas must didn’t hear that Tribe Called Quest shit, let’s do it again” (Tribe Degrees of Separation: check). As the song title suggests, Jay gets off a verse that includes twenty-two two’s (technically, he gets off a combination of twenty-two two’s, too’s and to’s), before deviating from the concept during his second verse, but he still kills it. If you’re listening to Reasonable Doubt on cassette, this record concludes side one. So, if you don’t have auto reverse, get up and flip that shit over, homie!

Can I Live – Irv Gotti (credited as DJ Irv in the album’s liner notes) gets his sole production credit of the night and he sticks to the soulful theme, looping up some classic Isaac Hayes (I love the boomin’ horn loop) for Jay to discuss more of the stresses that come with hustlin’ and the addiction to the money and lifestyle that keeps him in the game. Yet another great album cut that sounds better than most of the album’s singles.

Ain’t No Nigga – This was the second single released from Reasonable Doubt and it was also included on The Nutty Professor Soundtrack. Jay-Z let’s his mentor, Jaz-O handle the production on this one, as he flips the often used and very familiar Whole Darn Family loop for our host to spew bars filled with misogyny and materialism. Foxy Brown pops in at the tail end of the song to get off a few bars that rebuttal and co-sign Jigga’s male chauvinistic antics. I never cared much for this one. Easily my least favorite record on Reasonable Doubt.

Friend Or Foe – One of the attributes that has always set Jay-Z apart from his contemporaries is his ability to rap as if it’s just the two of you in a room having a conversation. Well, on this one you feel like a fly on a wall, as Jay confronts some out-of-towners (whom you hear talking shit about Jay during the skit before the song begins) trying to come in and set up shop in his territory: “Let me guess, they said it was money ‘round here, and the rest is me stoppin’ you from gettin’ it, correct? Sorry to hear that, my guess is you got work at the hotel, I’ll take care of that, you’ll soon see, now please, give me the room key, you’re twitchin’, don’t do that, you’re makin’ me nervous, my crew, well, they do pack, them dudes is murders.” Premo builds the backdrop around a blaring semi-wacky trumpet loop that matches Jay’s light-hearted approach to what should be seen as a serious situation. Dope song concept and brilliant execution by one of the best to ever do it.

Coming Of Age – This one pairs Jay with his protégé, Memphis Bleek, as the two mimic their raps career roles, with Jay playing the seasoned hood drug kingpin and Bleek plays the young, hungry and eager kid trying to get his feet into the drug game. Clark Kent lays down a smooth backdrop to hold down Jay and Bleek’s Goodfellas theatrics that I actually appreciate more now than I did back in ‘96.

Cashmere Thoughts – Clark Kent gets his final production credit of the evening and he keeps it funky as chitlins but still as smooth as a newborn’s ass. Speaking of smooth, Jay sounds so slick on this track that he talks the instrumental out of its panties with his cool and effortless flow: “I’m smooth but deadly like a pearl handled pistol, honeys hum in melody when I rub it like crystal, the proper etiquette, when I drop the subject, verb then the predicate with this rich nigga rhetoric”. Dope record with an equally dope song title.

Bring It On – Premo serves up a dimly lit emotion stirring backdrop with a well-placed Fat Joe vocal snippet on the hook, as Sauce Money and Jaz-O join Jay on this mafioso cipher session. All three parties bring their A-game, with Jay barely out dueling his mentor, Jaz-O (the “money makes the world go around so I made some to spin (spend)” line was too tough), but Premo’s masterful production work is the true winner on this track.

Regrets – The final song on the proper album finds Mr. Carter revisiting a couple of situations from his street pharmacists past that he wishes would have played out differently. Peter Panic provides the soulfully somber instrumental (who’s drums are almost nonexistent) to help comfort and console Jay through his painful reminiscing. Solid record and a fitting way to end the album.

Can I Live II – On the 1998 remastered version of Reasonable Doubt (which I also have a copy of) or if you stream it on your favorite DSP, this bonus track exists. The sequel has nothing on the original, and other than Jay’s mention of Pac during his first verse (“Don’t even hate one those who hate me, I got Pac on”), there’s not much to remember about this one.

Reasonable Doubt is Jay-Z’s drug dealer manifesto that not only gives you a detailed look into the life of Shawn Carter and the mechanics and workings of the underworld, but it also highlights Jay’s undeniable emcee wit and chiseled wordsmanship. Throughout Reasonable Doubt, Jay makes the listener feel like they’re riding shotgun with the Brooklyn emcee, while he navigates his luxurious whip through the New York City streets, feeding you his conversational style bars, while the phenomenal batch of soulful instrumentals back his “rich nigga rhetoric.” Several “drug dealers turned rapper” have tried to emulate the greatness of Reasonable Doubt, using the album as their blueprint (no pun intended), and a few have come close, but none have matched Jay-Z’s debut masterpiece. Reasonable Doubt has stood Teflon through time, leaving no one a reason to doubt it’s classic status.

-Deedub