DJ Stretch Armstrong & Bobbito Remember Legendary Big L, Jay-Z Freestyle


The iconic on-air duo reflects on bringing two future rap legends together on the mic


I’ll be honest with you, that night is not truly vivid in my head because at the moment it wasn’t really any different than the myriad of shows Stretch and I did over eight years. We had no idea Big L was going to be as exalted as he is now. We had no idea Jay-Z was going to be a platinum artist. In ’95, these dudes were just up-and-coming cats, no different than Kage or Pharoahe Monch

We already had Nas on the show three times before Illmatic came out, Redman, Poetical Propets, who became Mobb Deep—so many cats who came up there unsigned that wound up changing the face of the rap industry. But there were enough people that came up and rocked it, that didn’t go anywhere. So we knew this has potential, but it wasn’t like, Oh my god, people are going to remember this freestyle for the next 15 years! It was more like, OK, I’m fucking tired, Stretch is fucking tired, it’s 2:30 a.m., we gotta rock ‘til 5 a.m., and we got two nasty motherfuckers

I remember asking them, “Do you guys want to get on together?” Stretch and I would often ask two great artists that we thought could have a rhythm to get on. I’ve learned since that Jay and L had already known each other, and had battled in Harlem, so they already had a rapport, so I can’t really take credit for having them on the show together. I think L and Jay had a competition amongst themselves and amongst their crews, but it was never transparent or citywide-known. And on that night, they both had their own distinct styles and did their thing.

It wasn’t a battle. I don’t think anybody got off the mic, like, yeah, I destroyed homeboy. Nobody was calling up the show afterwards like, yo, L killed Jay on that. I used to answer all the phone calls, so I could tell you. Nah, they both did their thing.

Jay and L had something brewing. They did their verses and L was straight fire, Jay was a cocky bastard back then. I remember Jay came up like maybe three or four times, never really said that much, always sort of had a chip on his shoulder. The way he carried himself was so extra, like the nastiest motherfucker on the planet. In my head I was like, you’re nice, B, but dude, you haven’t sold any records. But I guess he proved his point years later—he always had a vision for his ability to rhyme, even early when he had no album deal and was coming up doing shows.

The amazing thing about L was that he was a very provocative MC with his lyrics, but off the mic, he’s like the coolest kid in the world. Really quiet, humble. He didn’t say much, just sort of played his lane. I was cool with L, played ball with him once in Harlem. Really, really nice kid. I’m so happy that even past his death, people still remember him, his ability to rhyme, his wit.

Jay got all the credit that was coming to him; he’s sold records, toured the world. He got what he worked for. L didn’t necessarily. So the fact that they did that freestyle together and it’s revered like—to me it’s the most classic freestyle out there. Somebody put a video on my Facebook page of a girl karaokeing in New Jersey, and she picked the Big L/Jay-Z freestyle. The DJ played the instrumental and she’s doing L and Jay’s verses. Like, huh? That shit is crazy!

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