For more than 25 years, Hip-Hop fans have debated who is better between The Notorious B.I.G. and JAY-Z. Both men’s names are perennially heard in conversations about who is the greatest MC of all-time. For them, however, there was something bigger than Hip-Hop: Brooklyn.

Fans have not been the only ones sizing up Jay vs. Biggie. For years since B.I.G.’s passing, Jay has referenced his fallen friend, sometimes drawing a favorable comparison and other times carrying a decided chip on his shoulder.

The MC born Shawn Carter has heard his critics over the years and addressed Biggie advocates head on, in song’s like Pusha-T’s “Neck and Wrist,” where Jay raps “They like, ‘If Big was alive, Hov wouldn’t be in his position.’ If Big had survived, y’all would have got The Commission,” referencing the super-group that he and Christopher Wallace were considering putting together with Puff Daddy, Charli Baltimore and Lil’ Cease, prior to B.I.G.’s untimely demise. He suggests that rather than being competitors, they would have teamed up.

JAY-Z Raps About Where He’d Stand In Hip-Hop If Biggie Was Alive

In other instances, Jay has been more defiant like on The Black Album’s “What More Can I Say.” Hov, who often references Biggie lyrics in his rhymes, has come under attack for not just paying homage but potentially plagiarising. On that song he raps “I’m not a biter, I’m a writer for myself and others / I say a B.I.G. verse, I’m only biggin’ up my brother / Biggin’ up my borough / I’m big enough to do it. I’m that thorough. Plus, I know my own flow is foolish.”

Later in the song, he doubles down on that last point about his flow, saying “Pound for pound I’m the best to ever come around here. Excluding NOBODY.” It’s not necessarily a shot at Biggie directly, but the implication of the “GOD DID” MC’s declaration is crystal clear.

Going back to Jay’s words about bigging up his borough, throughout both his and Biggie’s catalogs, each makes extensive references to their shared hometown of Brooklyn, New York. While other greats like Big Daddy Kane and Masta Ace stood before them, Biggie and Jay cemented Brooklyn’s legacy as a hotbed for legendary MCs forever more. And, perhaps, their pride was never more prominently displayed than on Reasonable Doubt‘s “Brooklyn’s Finest.”

“Brooklyn’s Finest” Was Never Supposed To Happen

Given the enormity of the song, one would think that it was the work of a shrewdly calculating Jaÿ-Z, as the NYC upstart trying to make a name for himself, to get the then undisputed King Of New York on his record. In reality, it was quite the opposite.

DJ Premier Gives The Inside Story On The Making Of Jay Z’s Reasonable Doubt 20 Years Later

In a 2016 interview with HO7 97’s Ebro In The Morning Show, DJ Clark Kent, who brokered the collaboration, says the song was never supposed to happen. In fact, Clark, who worked closely with Biggie and produced the track that would become “Brooklyn’s Finest,” had gone out of his way to not let Biggie hear the beat.

“I was in a session with Big and he heard the beat by accident,” said Clark in the HOT 97 interview. “It was purely [by] accident. I didn’t want him to hear it ’cause I figured he would like it, and he did, and he wanted it. And, he was like ‘Let me get that.’” After explaining to Big that the track was already committed to Jaÿ-Z, Biggie was insistent, saying “Nah, man. F__k that. I need to be on that record.’”

Even after Clark relented and agreed to talk with Roc-A-Fella’s Dame Dash and Jaÿ-Z about Biggie joining Jay on the record, there were a number of major hurdles that needed to be climbed to make the duet a reality. For starters, there were legal and economic terms that needed to be worked out, IF Jay agreed to let Big on the record.

The D.O.C. Explains Why Biggie Is His #1 MC

Perhaps an even bigger impediment, however, was that Jay had already recorded the whole song. “I get in the studio, I lay the beat, Jay goes in, and he does the whole song,” said Clark of another instance of Jay’s uncanny ability to lay his verses in one take from his head. It wasn’t until after the record, originally meant to be titled “No More Mr. Nice Guy” or “Once We Get Started,” was done that Clark casually suggested “Yo, you should let Big on the song.”

Eventually, both Jay and Dame said Big could get on the record, and here’s where it gets really interesting. What Clark Kent says next makes it indisputably clear that both men wrote their verses specifically with the other in mind for what was effectively shaping up to be a battle.

After securing the Roc-A-Fella team’s permission to introduce them to Biggie, since they had not previously met, Clark went downstairs to get B.I.G., who had actually been waiting in Clark’s car the whole time. When Clark returned so quickly, the room filled with laughter, realizing how Clark had manipulated the situation.

10 Reasons Why JAY-Z & Biggie’s “Brooklyn’s Finest” Almost Didn’t Happen (Video)

Clark says of the historic meeting, “They met each other and it might have been two seconds of conversation. And then Jay stood there for 20 to 25 minutes listening to the beat, and then goes in the booth and does what you hear, and comes back out and goes ‘Are you ready?'” Effectively, Hov re-wrote his entire part of the song on the spot, knowing he was competing with B.I.G. Only Jay knows whether those verses were in fact new or rhymes he had in the tuck for momentous battles like the one that was about to ensue.

Clark continues, expressing Biggie’s disbelief at what had just transpired. “Big was like ‘What the f__k are you talking about??’ And, then he looks at me and goes ‘What the f__k did he just do??'” The legendary DJ and producer explained to Biggie, “Well, I told you he doesn’t write rhymes. He thinks them and he goes in and he does it.” He continues recapping Big’s reaction, saying “He was like ‘Clark, that s__t was crazy!'”

How Biggie Went From Ashy To Classy: By People Who Styled Him

What the man born Rodolfo Franklin says last about Biggie’s response cements that, in that moment, B.I.G. also saw the forthcoming collaboration as a battle in disguise. He says Biggie’s response to Jay’s question about him being ready was “Nah. Nah. I’m not ready. I’m going to come back for this.” Clark says Biggie did not return until two months later to lay the vocals that completed one of the greatest Rap collaborations of all-time.

It’s unclear whether Biggie actually had Jay’s new verses or wrote from memory, though he was tight with Clark and likely would have had access to the vocals. But everything about “Brooklyn’s Finest,” from the way the two men approached it to how their vocals were laid, was set up like a battle.

Instead of each MC having his own whole verse–or Jay having two and B.I.G. having one as was customary in those days–each had six rounds of approximately four to six bars each pitted back to back against each other…like a battle. And, battles are meant to be scored, with the hopes of declaring a victor.

Scoring Jaÿ-Z and Biggie’s Battle On “Brooklyn’s Finest” Round For Round

In the case of “Brooklyn’s Finest,” the stakes were who would hold the title best MC from the borough, with much wider implications extending to NYC, the globe and potentially all-time history. So, let’s get into it. Here is how we score Biggie and Jaÿ-Z’s historic battle:

Round 1

Jaÿ-Z: “Ayo, peep the style and the way the cops sweat us / The number one question is can the Feds get us? / I got vendettas in dice games against a__ bettors / And n____s who pump wheels and drive Jettas / Take that wit’ ya!”

Biggie: “Hit ya! Back-split ya! / F__ fist fights and lame scuffles / Pillow case to your face, make the shell muffle / Shoot your daughter in the calf muscle / F__k a tussle, nickel-plate / Sprinkle coke on the floor, make it drug-related / Most hated”

Round 1 Winner: Biggie. Score = 1-0. Jay’s verse features some braggadocio but does not have any consistent theme or direct much aggression toward his opponent, save for “Take that wit’ ya!” Biggie, however, comes out in full Battle Rap mode, stating that this is a fight to the death, and he is bringing weapons. He tells a full story in just a few bars, where he threatens family members and ends with the perfect alibi.

Round 2

Jaÿ-Z: “Can’t fade it / While y’all pump, willie, I run up and stunt silly / Scared, so you sent your little mans to come kill me / But on the con-trilli, I packs the MAC-milli / Squeezed off on him, left them paramedics breathin’ soft on him / ‘What’s ya name?'”

Biggie: “Who shot ya? / Mob ties like Sinatra / Peruvians tried to do me in, I ain’t paid them yet / Tryna’ push 700’s, they ain’t made them yet / Rolex and bracelets is frostbit, rings too / N____s ’round the way call me Igloo, stick who!? / Motherf____r!”

Winner: Jay-Z…by a hair. Score = 1-1. This was a tough one. Thematically, both verses are similar. Each features tough talk about how they’ve handled precarious situations in the past. Jay gets style points for flipping “con-trilli” and “Mac-milli.” Big gets a bonus for throwing a not so subliminal jab at Tupac by starting with “Who shot ya?,” since that previously-released song is part of what fueled the battle between the two. Ultimately, Jay takes it for telling a story and finishing with the clever reference to mouth to mouth resuscitation.

Interestingly, Jay’s verse may provide a clue as to whether Biggie wrote his verses while listening to Jay’s. Hov’s start of “Can’t fade it” seems to just be a random exclamation that doesn’t tie into the rest of his stanza. However, when we go back to Biggie’s first verse, we hear him end it with “Most hated.” Jay’s start now closes Biggie’s verse before Hov begins his next verse. It’s possible Big ended his verse in order to line it up with Jay’s following line. Or, maybe Jay ad-libbed the line after hearing Big’s verse, in order to make the transition seamless. Clark, if you’re reading this, Heads want to know.

Round 3

Jaÿ-Z: “JAY-Z, Big Smalls, n___a, s__t your drawers / Brooklyn represent y’all, hit, you fold / You crazy, think your little bit of rhymes can play me? / I’m from Marcy, I’m varsity, chump, you’re JV / Jigga Jaÿ-Z”

Biggie: “Biggie, baby / My Bed-Stuy flow’s malicious, delicious / F__k three wishes, made my road to riches / From 62’s, Gemstars, my mom’s dishes / Gram choppin’, police van dockin’ / D’s at my doors knockin’ / Keep rockin’, yeah!”

Winner: Biggie. Score = 2-1 in his favor. This verse furthers the notion that Big had Jay’s vocals while writing his verses. Once again, Biggie starts his rhyme in a way that completes Jay’s previous verse. More importantly, both MCs use this round to big up the the Bed-Stuy section of Brooklyn from which they hail, as they compete for the title of best in the borough. It’s possible Biggie remembers this from when Jay recorded his verse, but that still would have provided him with an advantage.

The comparison ends there, though. Hov’s rhymes are incredibly simplistic in this verse, especially when compared to the complex cadence and wordplay from the Notorious one. He strings together several encrypted references to detail how he made his dream of escaping his circumstances in Brooklyn real.

Round 4

Jaÿ-Z: “No more Mr. Nice Guy, I twist ya s__t / The f__k back with the pistols…blazin’! / Hot like Cajun / Hotter than even holdin’ work at the Days Inn / With New York plates outside / Get up out of there, f__k the ride!”

Biggie: “Keep your hands high, s__t gets steeper / Here comes the Grim Reaper / Frank White/ Need the keys to your innkeeper / (That’s right) / Chill, homie, the b__ch in the Shoney’s told me / You’re holdin’ more drugs than a pharmacy / You ain’t harmin’ me, so pardon me / Pass the safe, before I blaze the place / And here’s six shots just in case”

Winner: Biggie. He’s up 3-1. But, is this a fair fight? Like Jaÿ-Z, Biggie also reportedly had an impeccable memory. At a minimum, Biggie heard Jay lay his verses in the studio that night. But, the detail in which B.I.G. responds to Jay’s verse here would be uncanny if he was not using Jay’s actual verse to write his own.

The “Gimme The Loot” MC takes in Jay’s concern about being at a hotel while carrying weight, and slips into Frank White mode (the King Of New York) to rob the “Can I Live” MC. Big also throws in details about how he found Jay.

Round 5

Jaÿ-Z: “For ‘9-6, the only MC with a flu / Yeah, I rhyme sick / I be what you’re tryin’ to do / Made a fortune off Peru / Extradite, China White, heroin / N___a, please, like short sleeves, I bear arms / Stay out my way from here on (Clear). Gone!”

Biggie: “Me and Gutta had two spots / The two-for-five dollar hits, the blue tops / Gotta go, Coolio mean it’s gettin’ too hot / If Faith have twins, she’d probably have two Pacs / Get it? (uh) 2 Pac’s?”

Winner: Jaÿ-Z Down 3-2. Jaÿ-Z goes directly at Biggie on this verse more than on any other, and he attacks B.I.G. both as a rapper and on a street level. He warns that from 1996 on, he is the illest MC. Jay also questions the significance of Biggie’s former status as a dealer, suggesting that he, himself, was the one actually moving weight and making real money. Lastly, Jay literally tells Big to stay out of his way from here on, to which Big responds “Clear.” That Jay did this with almost no preparation makes it all the more impressive.

In his verse, rather than fire back, Biggie takes aim at himself. Once again, he references his ongoing feud with Tupac Shakur. Rather than take another shot at Pac, Biggie pours gasoline on the rumor that was circulating about Tupac and Faith Evans, B.I.G.’s wife, having an entanglement. He suggests that the then pregnant Faith might be having Tupac’s babies. Biggie’s rhymes are decidedly strong, but this is a curious tact to take in a battle.

Round 6

Jaÿ-Z: “Time to separate the pros from the cons / The platinum from the bronze / That butter-soft s__t from that leather on the Fonz / A S1 diamond from a I class don / A Chandon sipper from a Rosé n___a / Brook-Nam, sippin’ on”

Biggie: “Cristal forever. Play the crib when it’s mink weather / The M.A.F.I.A. keep cannons in they Marc Buchanan’s / Usually cuatro cinco, the shell sink slow / Tossin’ ya, mad slugs through your Nautica / I’m warnin’ ya!”

Winner: Jaÿ-Z. The battle ends in a 3-3 draw…or does it? Both of these verses are among the shortest on “Brooklyn’s Finest,” but Jaÿ-Z uses his more economically. His whole stanza is about separating himself from the competition; presumably Biggie. Each of Jay’s metaphors is meant to establish his superiority, and he does so with a wide-range of witty references–especially that one to “The Fonz.”

Biggie’s verse by contrast is his least cohesive. This more than any of his others on the songs, just features a series of unrelated lines, save for his possible response to being called a “Rosé n___a” by exclaiming “Cristal forever” (though that line ultimately would not age well).

How Do You Compare The Incomparable?

With B.I.G.’s advantage of having heard Jaÿ-Z’s “Brooklyn’s Finest” verses at least once, and having two month to prepare to Jay’s 20 to 25 minutes, this battle should have been a wash. In the early stages, it looked like B.I.G. was going to take it easily, particularly since he won the rounds so convincingly.

So, the question arises: Did Biggie throw the fight? It’s quite possible he did not want to outshine Jay on his own record, especially since he likely knew how that might negatively impact Jay’s rising star. If B.I.G. had torched Jay, would Jay have re-recorded his verses? Would Roc-A-Fella have put the record out? Would a Biggie “victory” have even counted, given the discrepancies discussed above?

Clark Kent Says Hip-Hop Owes Kool Herc & It’s Time To Pay Up

The reality is, a tie likely was the best possible outcome. Biggie could not have wrecked Jaÿ-Z on his own record and, given B.I.G. status as the King of New York, there’s no way he could have let the lil homie outshine him either.

Tragically, the song was one of only two official collaborations from the two members of the would be Commission. Jay later joined Biggie on “I Love The Dough” from B.I.G.’s Life After Death double album. While both songs are stellar, “I Love The Dough” did not have the same competitive spirit between the two. It was if, after their first collabo, they transitioned into the partners of which Jay spoke on “Neck and Wrist.”

D-Dot Compares Biggie’s Work Style To JAY-Z’s (Video)

The bigger question, however, is whether a clear victor on their first collaboration would have even answered the question of “Who is Brooklyn’s Finest?” Comparing the two legendary artists’ catalog is not a fair fight either, given how much more voluminous Jay’s is to the fallen B.I.G.’s.

One thing is for certain though, had Jaÿ-Z and Biggie Smalls had more time together, there’s no question what their competition would have been doing. That’s one question they answered emphatically on the chorus to “Brooklyn’s Finest.”