For our second edition of “After Further Review,” me and Jeff Weiss, author of the new 2Pac vs. Biggie:An Illustrated History of Rap’s Greatest Battle, talk about one of hip-hop’s most storied live freestyles, involving two soon-to-be-giants, before they began taking lyrical (and perhaps literal) shots at one another.

OW: Jeff, start us off with the background behind this. Where/when was it recorded? I’ve always thought of it as the “Mister Cee freestyle” but this was clearly at a show somewhere.

JW: The freestyle was recorded during Big Daddy Kane’s set at the 1993 Budweiser Superfest — the Made in America Festival for the early Clinton era. A beer commercial with rapping and a “phat” foam of New Jack Swing. The Madison Square Garden date also included Levert, Patti Labelle, Bell Biv Devoe, SWV and MC Lyte. Kane was firmly in his Chocolate City Sex book era, so his gold scepter lacked the uh, polish of ’88. But the guy still rapped with the hunger of a man who had been subsisting strictly off hand-fed grapes.

OW: And both Pac and Biggie were in the house?

JW: At the time, Big and Pac were amidst their short-lived blunts and friendship bracelets era. Pac was in town to shoot Above the Rim and running with criminal kingpins like Haitian Jack and Jimmy Henchman. Biggie was still a year away from releasing Ready to Die, so his reputation pretty much existed off the strength of “Party and Bullshit,” the “Real Love” remix, and the ragga cut with Super Cat. Mister Cee was Kane’s DJ, who happened to have discovered Biggie the year before. And since rap shows didn’t regularly pack the Garden, it’s unsurprising that he invited his protege to come on-stage to cypher. It was a huge look. Bringing Pac, just two months after Poetic Justice, ensured the “oh shit” moment.

OW: So Pac was actually the bigger artist at this particular moment?

JW: As someone who didn’t live in New York in ’93, there’s an element of speculation involved. But it’s almost impossible for anyone outside of the most dedicated Stretch and Bobbito tape hoarder to argue that Big was the bigger star in ’93. Pac had already done Juice and Poetic Justice, and was fresh off the success of “I Get Around.” He’d also solidified his East Coast credentials with Strictly 4 N.I.G.G.A.Z. the most New York record of his career with Stretch from Live Squad producing half of it, and a posse cut with Treach and Apache.

OW: In terms of what we remember though, Biggie’s verse outshines everyone else’s.

JW: Biggie wound up getting the most attention. The Mister Cee bootleg famously appeared on Hot 97, mixtapes, and at the Tunnel. Within the five boroughs, DJs frequently cut out before 2Pac’s bars. But if you lived outside the Eastern seaboard and weren’t plugged into tape trading culture, your first exposure to the freestyle might well have been it’s inclusion on the 1999 Funkmaster Flex compilation, The Tunnel.

OW: Taking a step back to look at the freestyle as a whole…no shots at Scoob here but can we just say that in the history of epic hip-hop cyphers, Scoob’s lead-off verses might rank amongst the most cringe-worthy of all time? Think Nas on “Live at the BBQ” or Insepctah Deck on “Protect Ya Neck” and then imagine the exact opposite of that and you get Scoob kicking things off with that weirdly whiny flow. Too harsh?

JW: It’s safe to say that Scoob is the rap equivalent of being the fourth astronaut to land on the moon. He is a Final Jeopardy question. The only contemporary equivalent is Big Sean on “Control.” It’s a shame that the Internet wasn’t around when this happened because the phrase “renegaged” would never have come into vogue as a reference to being destroyed on a track. We would have just called it being “Scoobed.”

OW: And how the hell did Shyheim get onboard here? Scoob at least made sense – he was down with Mister Cee and Kane but Shyheim was still in his pre-pubescent “rugged child” mode and here, he gets to jump on after Biggie and Pac.

JW: There’s a video interview where Shyheim says that he’d been tagging along on the entire Superfest tour because Kane was his godfather. It actually makes sense because the first time most people heard him was on “Show and Prove,” the posse cut with Scoob, ODB, and a then-unknown Jay-Z, released the following year

OW: What always strikes me about this freestyle is that Biggie basically gets the biggest applause line of the night simply by shouting, “where Brooklyn at! Where Brooklyn at!” Compared to the polite but rather lukewarm reception Scoop got as the lead-off, in six words, Biggie elevates the entire affair to a whole new level. Maybe that’s the benefit of hindsight at play; as you note, in ’93, Biggie hadn’t yet ascended to the Notorious B.I.G. phase of his career so he was still mostly local (I’m guessing) but it’s remarkable how the crowd responds to him.

JW: For Biggie, the freestyle seemed like another battle royal victory in the quest for King of New York. It’s easy to forget that October of ’93 was a period of flux. Death Row hadn’t officially crushed the buildings, but that was their biggest year. Wu-Tang was still largely an underground phenomenon. Illmatic was several months away from release and Biggie was in record label limbo, thanks to Puffy getting his Uptown Records contract abruptly terminated by Andre Harrell. He’d recently returned from a stint selling drugs in North Carolina and for all practical purposes was just another very gifted Unsigned Hype winner, albeit one with a major buzz.

OW: I think one other reason this freestyle lingers is that him and Pac seem genuinely on good terms with one another. Was their friendship real back in ’93?

JW: From all accounts, the friendship was definitely genuine. To my knowledge, this video that dream hampton released on the web last year is the only one that captures them together, but it’s pretty evident how close they were. After hearing “Party and Bullshit,” 2Pac became a major fan and apparently had reached out to strike a friendship after an early Biggie show in Virginia. Biggie knew him well enough to tell Vibe in 1996 that 2Pac wasn’t the Tupac that he’d once known, but instead was Bishop from Juice.

OW: It’s hard to reconcile their BFF camaraderie here with Pac dropping “Hit ‘Em Up” just three years later.

JW: The thing about “Hit Em Up” is that no one has ever contradicted any of the claims. I’m not sure if 2Pac’s couch is still out there with a permanent imprint on it from when Biggie slept on it, but I’m almost certain he did offer him a place to crash when he got kicked out of Faith’s house. And as for the stuff about 2Pac and Faith, I got pretty reliable confirmation from a close source that it happened.

OW: At least Biggie could joke about it.

Jeff Weiss’s new book, 2Pac vs. Biggie: An Illustrated History of Rap’s Greatest Battle is out now on Voyaguer Press.

P.S. Notably, the fact that neither of us even brought up Kane’s verse probably is a statement in and of itself.

P.P.S. This also reminds me of how awesome a chop job was done on the “Cussin, Cryin'” drums. Was that a 45 King discovery?