Jay Z's Best Songs Before "Reasonable Doubt"

Jay Z’s Reasonable Doubt has been described as one of hip-hop's most mature debut albums ever. If the Brooklyn upstart already sounded like a sage veteran on his '96 opening statement, that’s because, well, he kind of was one. He had already been recording for a full decade.

The man born Shawn Carter was just 16 in 1986, when High Potent, the Brooklyn crew he'd joined under his mentor Jaz-O, released its lone single "H.P. Gets Busy." Jay would go on to play sideman for Jaz on his fellow Marcy Houses native's solo singles “Hawaiian Sophie” (1989) and “The Originators” (1990), before making cameos on records by Big Daddy Kane, Big L and Original Flavor.

While Jay officially only released one single—“In My Lifetime”—prior to Reasonable Doubt, some fascinating demo recordings from this period have emerged via mixtapes and the Internet over the years, offering a peek at his growth from gimmicky rapid-fire rhymer to the sophisticated don of Reasonable Doubt. Though spotty in terms of audio quality and dated, occasionally, by Jay's propensity for double-time flows, this material combined with some of Jigga's more choice cameos represents at least an album's worth of notable, yet mostly little-known, pre-Reasonable Doubt material.

Here's a look at Jay Z's Best Songs Before "Reasonable Doubt"

Written by Jesse Serwer (@JesseSerwer)

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High Potent "HP Gets Busy"

Circa: 1986
Producer: Jack Walker, The Jaz

There’s little about Jay’s appearance on “HP Gets Busy,” the lone single from Brooklyn crew High Potent, that hints at the greatness to come. The track is fairly typical of the drum machine-driven mid ‘80s rap records made just before Marley Marl brought sampling into vogue, right down to the cheesy keyboard sounds. But as an archaeological artifact, the track—which sees a high school-age Jay rhyming alongside the elder Jaz-O and little known, Marcy-reared footnotes Easy LB and Joy—is priceless.

Jay-Z and Sauce Money "Nuthin But Love"

Circa: 1994
Producer: DJ Clark Kent

Unless you were in the streets in Brooklyn in the mid '90s or a hip-hop A&R man in those days, you probably never heard the demo recordings that Jay-Z made with DJ Clark Kent back when they were new and fresh. Fortunately for Hov completists, DJ Rhude liberated a healthy portion of these tracks on his 2001 mixtape, BC: Before the Roc, including this collab with frequent cohort Sauce Money over a soulful, Marvin Gaye sample. Among the statements on the circa '94 track is perhaps the earliest lyrical expression of J-Hova's career-spanning Messianic complex: "If Tyson was slicing through tracks/Your screaming Jesus Christ is back and god knows he can rap."

The Jaz f/ Jay-Z "It's That Simple"

Circa: 1991
Producer: Prince Paul

Remember when Nas accused Jay of jacking his style from Illmatic, claiming he used to rap like Fu-Schnickens? Well, actually Jay was chasing spiritual residuals with his tongue-twisting lyrical miracles before Fu Schnickens, or their Chi-town counterpart, Twista. As a sideman for fellow Marcy Houses native Jaz (aka Big Jaz and Jaz-O), Jay brought a head-spinning, double-time flow to his former mentor’s 1990 single, “The Originators.”

While that track sounds impossibly dated today, see “It’s That Simple” from Jaz’s To Your Soul LP for a Jaz n’ Jay collab that holds up better. With production from Prince Paul, “It’s That Simple” could easily pass for a forgotten Native Tongues project, or perhaps a lost cut from KMD’s Mr. Hood. Notably, Jay, legendary for not writing rhymes and spitting from the dome, begins his verse claiming the opposite: “Freestyle rhymes are easy to come by/A pen and a pad when it comes to this one guy.”

Jay-Z f/ Jaz & Sauce Money "I Can't Get Wid That"

Circa: 1994
Producer: DJ Clark Kent

Like most tongue-twistin' raps from the '90s, Jay's double time flows on "I Can't Get With That" sound seriously dated—especially if you're not old enough to remember when such lyrical theatrics were considered halfway cool. But "I Can't Get Wid That"—the B-side to Jay's debut single "In My Lifetime"—has a buttery, piano loop beat from DJ Clark Kent that make the goofier moments ("Well check out the J, check out the A, check out the Y... Z!") go down a lot smoother. And, when Jay slows things down, he's got some slick one liners that still make us stop and laugh ("I'm nicer than a bitch, ask this nigga Dash/Now he don't count cause I'm making his ass rich").

Jay-Z and Sauce Money "Pass the Rock"

Circa: 1994
Producer: DJ Clark Kent

It's always amusing to revisit sports references on old rap tracks. It's just impossible for them not to sound dated at 20 years old. Point in case: Jay and Sauce Money's circa '94 demo "Pass the Rock," a coke rap over a Clark Kent-produced vibraphone and piano loop delivered entirely in basketball-themed double entendres. (Get it, "rock" = "rock"?)

Try not to crack a smile at lines like: "I gotta get the AC Green/ In other words I run the streets 360 like Dominique," or "I get the payoff in the playoff, never get sweeped/I three-peat, but who could ever lose to the Heat?" Hearing "Pass the Rock" now for the first time is a bit like watching a two-decade-old reel from Sports Center. But if the Internet and hip-hop were a thing back in '93, a leak of this rare gem would have been quite a conversation starter on the blogs.

Big Daddy Kane f/ Scoob, Sauce Money, Shyheim Jay-Z, Ol' Dirty Bastard-"Show and Prove"

Circa: 1994
Producer: DJ Premier

Before his name carried weight in the hip-hop game, Jay found himself playing bit roles on some seriously heavyweight, if not exactly legendary, posse cuts. BK rap legend Big Daddy Kane took Jay under his wing in the early '90s, bringing him on tour as a sort of sideman/opening act (though Jay would actually rhyme in the middle of Kane's sets, during costume changes) and featured him on “Show and Prove,” a '94 track which brought some of Brooklyn's finest MCs together over a hard-hitting DJ Premier beat.

Okay, not all of the talent was fine. “Show and Prove” has the misfortune of beginning with Kane dancer Big Scoob’s Onyx-meets-the-Pharcyde flow, an absurdly affected style that makes Jay's double-time raps sound futuristic by comparison. Jay for his part found himself unfortunately sandwiched between an energized, “Shaft”-singing Kane and an all-the-way-turned-up ODB. Though he doesn’t exactly outshine him on the track, watch the video for "Show and Prove" closely: Jay seems to be on the receiving end of some seriously side-eyed glances from his former mentor BDK.

Big L f/ Grand Daddy I.U., Jay-Z, Lord Finesse, Microphone Nut, and Party Arty "Da Graveyard"

Circa: 1995
Producer: Buckwild

Like “Show and Prove,” "Da Graveyard" from Big L's 1995 debut Lifestylez Ov Da Poor & Dangerous is an overlooked but action-packed posse cut notable for its talent roster. Similarly, Jay’s verse is far from the track’s strongest, or his best work from this period. In fact, his double-time schtick comes across as particularly gimmicky here. But, with a roster including the late Big L, Lord Finesse, and Grand Daddy I.U. trading verses over a dank, grimy beat from DITC’s Buckwild, “Da Graveyard’ as a whole represents one of the most memorable tracks from Jay’s days before the Roc.

Original Flavor f/ Jay-Z "Can I Get Open"

Circa: 1993
Producer: Ski

If you were to make a movie about the Roc-A-Fella era, “Can I Get Open” from Original Flavor’s ‘93 album Beyond Flavor would probably be the soundtrack to your opening credits. The track marked the start of Jay's partnership with Dame Dash, who managed Original Flavor, as well as with other key players from the ROC's early days, like producer Ski (who made all of Original Flavor’s beats as well as being its lead MC), Tone Hooker (the Original Flavor-MC-turned-Roc-A&R is credited with naming the label), and the group's DJ, Chubby Chub, whose mixtapes would play a key role in pushing Jay’s music to the streets in those days.

On “Can I Get Open,” however, Jay was still a rapid-fire specialist rhyming too fast for us to feel him 20 years later. While it’s easy to dismiss Jay’s verse on the song as straight cornballism (He starts his verse asking “Hey Karl, Kan-I?” for one thing), remember that Ready to Die and Illmatic were still a year away at the time, and high-energy, uptempo songs like this were the order of the day for East Coast rap. More than any of his other cameos in the pre-Reasonable Doubt days, Jay’s performance on “Can I Get Open” had heads taking notice, thanks to his crafty timing and quickly switched-up flows.

Mic Geronimo f/ Ja Rule, Jay-Z and DMX "Time To Build"

Circa: 1995
Producer: DJ Irv (Irv Gotti)

It’s hard to believe today, but when Jay-Z, DMX, and Ja Rule appeared on “Time To Build” from Mic Geronimo’s 1995 album The Natural, they were the no names. You could say the track, an Irv Gotti-produced posse cut with a thumping sample of Eric B. and Rakim's "Eric B. is President," was something of a turning point for all four MCs, as Jay, X and Ja would grab seats one by one at rap’s power circle, while Geronimo reverted to irrelevance.

X and Jay sound particularly hungry on the track, which was recorded amidst simmering tensions between the two due sparked by a friendly but unresolved battle in a Bronx pool hall in the early '90s. In fact, Jay actually directs several subliminals at X in his verse. The pair would collaborate often in the ensuing years (on Jay's "Money Cash Hoes," X's "Blackout," etc.) and even tour together (on '99's Hard Knock Life tour)—hell, they were supposed to form a group, Murder inc., with Ja Rule— but the relationship between them would never be smooth.

Jay-Z "Reach the Top"

Circa: 1995
Producer: DJ Clark Kent

"Reach the Top"" is among the tracks on a demo that former Loud A&R execs Matty C and Schott Free remember Jay-Z and Damon Dash handing them at an impromptu meeting at a McDonald's during the 1995 Gavin Convention in San Francisco. Issues clearing the song’s Marvin Gaye sample, and Loud label head Steve Rifkind’s reluctance scuttled a potential deal, but the track turned up a year later on A Jump on Thangz, a 1996 mixtape by former Original Flavor DJ DJ Chubby Chub. While the track itself remains little known, Jay's motivational rap proved to be truly prophetic.

Jay-Z and Sauce Money "Get Off My Dick"

Circa: 1994
Producer: DJ Clark Kent

Jay-Z's never made songs just for laughs, but he's always had a healthy dose of humor in his music. "Get Off My Dick" might be his most purely comedic record ever, highlighting the chemistry between Jay and Sauce Money as the frequent collaborators take turns dismissing old “classmates,” male groupies, and other assorted herbs asking too many questions on the street. (Sample lyric from Jay: “Niggas who jock need to be shot/'Cause even if you're shit went triple platinum I'm like heh...could have been better, ak.")

While Sauce would essentially wind up just a footnote in the Roc-A-Fella saga, fading from view after appearances on Jay’s first three albums as well as Streets is Watching, he and Jay recorded quite a bit together in the days leading up to Reasonable Doubt. Had hip-hop not moved from a group-driven genre to one centered on solo achievement around this time, Jay and Sauce Money might have wound up becoming one of rap's great duos.

Jay-Z & Big L "The 7-Minute Freestyle"

Circa: 1995
Producer: Mufi

Jay-Z's most famed pre-Reasonable Doubt apperance isn't a song, but this February 23, 1995 freestyle session with the late Big L from Stretch Armstrong and Bobbito's Thursday-night radio show on New York's WKCR. The consensus years later is that Hov met his match that night, in a Big L already at the top of his game (L's debut Lifestylez ov Da Poor and Dangerous was already in the bag at this time).

Granted, Jay's verses have some misses that would probably make him cringe today—even harder than he does in those Samsung commercials. (Seriously, what was up with that "Bitta Boo Boo Boo Bam" stuttering baby talk thing he does in his second verse?) But he definitely shows flashes of the brilliance to come ("I'm too cocky, to stop me you gotta kill me/And when I'm gone you can still feel me") on what has come to be known over the years as simply "The 7 Minute Freestyle." The recording (over Milkbone's "Keep it Real" instrumental) is so legendary we named it No. 1 on our list of the 50 Best Radio Freestyles.

Jay-Z "Broken English"

Circa: 1994
Producer: DJ Clark Kent

The best tracks from Jay's circa-94 demos with Clark Kent feel like prequels to Reasonable Doubt, just more raw. Turning a sample of KRS-One's "Talk broken english and drug selling" line from Boogie Down Productions' "My Philosophy" on its head, "Broken English" is a Hustling 101 class in the tradition of B.I.G.'s "Ten Crack Commandments" and Reasonable Doubt's "Friend or Foe," with a similarly playful sense of humor: "I spend every dollar like it's my last, cause it might be/I stay away from hoochies that love Guccis and Louis/Vuitton the Don—before I spend, do me."

Jay-Z "What's in a Name"

Circa: 1994
Producer: DJ Clark Kent

Some of the most ingenious rap songs are based on a simple gimmick. Think of GZA spinning every record label’s name into his yarn on Liquid Swords’ “Labels,” or 50 Cent putting the whole industry on notice with his individualized threats on “How to Rob.” Jay’s "What's In A Name" might have been up there with those tracks had it seen the light of day when it was fresh, or properly mixed.

Like a lot of the demo tracks Jay recorded with Clark Kent, "What's In A Name" later turned up on a mixtape from Original Flavor DJ Chubby Chub. The audio is rough and many of the figures referenced in the song have been forgotten by time, but listen closely and you’ll hear a Jay already proficient in layered lyricism that takes more than several listens to peel away.

A lyrical exercise using other rappers’ names (“So bring a Gang Starr, I throw a bolo, and run up on a Tribe a niggaz... K-Solo”), “What’s In A Name” is full of rhymes designed to go over your head the first time—except when Jay feels generous enough to clue you in: “Cause I kill at will like solid water, dude/You niggas dont get it— kill at will, solid water... Ice Cube" (Kill at Will was the name of a 1990 Ice Cube EP). A line Jay would later reuse on the remix to Ray Cash's "Bumping My Music."

Jay-Z "Understand Me"

Circa: 1994
Producer: Peter Panic for Supermen Productions

Produced by Peter Panic for Clark Kent's Supermen Productions, "Understand Me" is one of the more illuminating pre-Reasonable Doubt tracks to come to light via mixtapes. The Tupac-inspired track borrows its sample and theme from 'Pac's "Pain" ("Maybe if they tried to understand me, what should I do?/I had to feed my fuckin' family, what else could I do?"), with Jay breaking down the existential complexities of hustling in the easily relatable fashion that would become a trademark: "I'm from the projects, wasn't for me/By nineteen, I'd be in jail, smoking or buying the key/Which one would you choose out of the three?/Yeah I know, go for the 40 G's/It's no longer for the family, they no longer need/But for the greed, getting props, and being top seed."

The tone of this one is dark and haunting, a pitch-perfect prequel to Reasonable Doubt's tracks like "D'Evils" and "Dead Presidents" marred only by the rough audio—like many of the Jay demos that have turned up, it's made it to the Internet and CD mixtapes only after multiple dubs on cassette tape.

Jay-Z "In My Lifetime (Big Jaz Remix)"

Circa: 1995
Producer: Big Jaz

A year after pressing up the original, Ski-produced version of "In My Lifetime" and selling it themselves through an early version of Roc-A-Fella, Jay and Dame Dash picked up a deal with Payday Records, the hip-hop imprint run by dance music kingpin Patrick Moxey of Ultra Music. (In fact, some versions of the single actually bear the Ultra imprint). For this second, 1995 edition of the 12”, they added a remix of "In My Lifetime" from Big Jaz that was essentially an entirely new song, with a slower, more melodious, piano-driven beat and a haunting R&B chant jacked from Soul II Soul’s “Get A Life.”

Matching the probing question at the heart of the song—What’s the meaning of life?—with lyrics that justify the pursuit of money at all costs, while offering a 360-degree view of the hustling lifestyle, “In My Lifetime” 2.0 (which would later be included on the soundtrack to 1998’s Streets is Watching) set the tone for Reasonable Doubt both musically and lyrically. The original version of "In My Lifetime" had its merits, but this was the track Jay needed to finally set his career in motion after years and years of false starts.