Before Big L brought Jay-Z along with him to The Stretch Armstrong and Bobbito Show on February 23, 1995, for their epic freestyle session, the two up-and-coming rappers had already battled each other in Harlem.

Speaking to HipHopDX, Lord Finesse – the man who discovered Big L, added him to his Diggin’ in the Crates crew and produced a majority of his debut album – recalled the battle.

“People don’t know [Jay-Z and Big L] actually battled each other in Harlem,” he remembered. “And I wish somebody videotaped that, because that woulda been a classic to this day.”

In a separate interview, Roc-A-Fella co-founder Damon Dash spoke about the battle. “The most legendary shit was the battle with Big L and JAY-Z,” he recalled. “They had a straight up battle on 139th Street. We walked over there and it happened. I thought JAY did well because 139th Street didn’t boo him off the block. It was like a tie but he was really on [Big L’s] block.”

Finesse talked about how much respect L had for Hov and vice versa, “I can tell you L was a Jay-Z fan, just like Jay-Z was a L fan. L was also a DMX fan. He loved DMX. And I think after that battle between Jay and Big L, Big L was like, yo, I wanna put Hov on [a song].”

This would lead to Big L putting Hov on the posse cut “Da Graveyard”, which also featured Lord Finesse, Microphone Nut, Jay-Z, Party Arty & Grand Daddy I.U., one of the greatest posse cuts in rap history.

A few years later, with Hov at the top of the rap game, the two rappers began talks about Big L signing to Roc-A-Fella, before his untimely death on February 15, 1999.

Before [Big L’s impending deal with Roc-A-Fella], it was Children Of The Corn. That was Cam’Ron and that was Big L and that was Ma$e but it was also Bloodshed, who died. They used to all come to my house. I was an older dude, older than them, and I had money and shit. I had my own apartment. They smoked weed and I used to drink. When I used to come in at like five in the morning, they might be coming out. I’d see them out smoking blunts. I’d be like, ‘Yo come in the house.’ They were the only dudes I would kick it with like that. They were like the younger guys that I used to hang out with. We were really like brothers. He could have been big. He woulda got to Roc-A-Fella and who knows who he coulda connected with over there. Who knows how he would have carried that and conducted himself.”

Dame Dash Hasn’t Listened to JAY-Z’s “4:44” | HipHopDX