The legendary radio show that launched Jay Z and Nas

Stretch and Bobbito are two goofball hip hop heads from New York City. In the 90s they hosted a legendary radio show called The Stretch Armstrong and Bobbito Show on WKCR. The show, which was completely one-of-a-kind at the dawn of that decade, changed many people’s lives, not least the rappers whose careers they helped jumpstart. Artists like Nas, Wu-Tang Clan, Big L and Jay Z were little known back then – some were even unsigned – so bringing this new music to so many ears played a monumental role in the genre’s continual reshaping. As Nas states in a clip promoting the documentary: “At that point in time your show was the most important show in the world.” The underground was headed for the mainstream.

In the new documentary Stretch and Bobbito: Radio That Changed Lives, both the DJs and the artists they helped propel to superstardom wax lyrical about the heyday of the show and the golden era of hip hop. We hear how Stretch and Bobbito had Method Man apologise on air to a girl he disrespected before a show; we hear how Stretch – the DJ of the two – would dash to the toilet in between cueing tracks; we hear how certain rappers weren’t as touch as they made out on their records. I recently sat down with the luminary DJs to talk about the show once named by The Source as the “Best Hip Hop Radio Show of All Time” in 1998 and to discuss the changing landscape of hip hop.

You guys basically had a conveyor belt of future rap stars coming in and out of the studio, and at the time most of them were unknown. Where would you discover them?

Stretch: I found myself spending a ridiculous amount of time in record shops. Four hours a day in one shop would not be an exaggeration. I got as close to working at downtown record stores as I could without actually being hired. I’d be behind the turntables and I’d play records for shoppers and tourists; they let me back there to DJ and play all the imports.

I just felt like there was a lot of music that I wasn’t hearing anywhere on other shows, so it was easy and it was fun. It was like, ‘Yo, it’s 5am and I didn’t play five new records that are incredible’, because we just ran out of time.

The craziest thing about the story of your show is that most of the artists were unsigned and went on to make heaps of cash, whereas you lost money. Did you ever feel bitter about that?

Stretch: No, we were proud of people if they succeeded. We didn’t want them to be held back.

Bobbito: The fact people graduated and made a lot of money, it was great, we applauded them. You know, Beastie Boys and Beatnuts sampled excerpts from our show for hooks on their songs and they never gave us anything. We were happy. We were like, ‘Oh shit, fucking Beastie Boys listen to our show! That’s cool.’

“Beastie Boys and Beatnuts sampled excerpts from our show and they never gave us anything. We were like, ‘Oh shit, fucking Beastie Boys listen to our show!’” – Bobbito

It was interesting to hear that Big L, one of the fiercest lyricists, was quiet and shy. Were rappers usually how you expected them to be in real life?

Stretch: I think rappers personas from records are often very different from who they really are. Like Biggie – he was 18 when he first came in – he just wanted to smoke blunts and tell jokes. He was this gregarious, fun-loving guy that just wanted to fucking kick it and laugh and snap on you. And Nas was also super quiet like L.

Bobbito: Another example of that is Big Pun. There’s a scene in the film where he exchanges snaps with another artist, it’s humorous, but you listen to his records and it’s all about guns and stuff. I think we also had that affect on people, we made them feel really comfortable. They knew that we were goofballs.

Stretch, how did you choose the backing tracks for the artists to freestyle over? That must’ve been insanely daunting.

Stretch: It was fun and it was like a puzzle. It’s funny because with the Big L/Jay Z freestyle – which is perhaps the most famous, most consumed moment from our show – they were rhyming for a long time, and I must’ve been tired that night because I wasn’t changing the beat for them; usually if they’re rhyming for more than three minutes I’ll change the instrumental. On that night either I was tired or it just felt good, but that was an instrumental from a Miilkbone record, super jazzy. On that same show Funk Dubious was up there, and the beat I gave him was “Who Shot Ya?” by Biggie. I was thinking, wow, if Big L and Jay Z had that beat it would’ve been a different night. I’m not saying it would’ve been better but it would’ve been a very different type of performance. It probably would’ve been more aggressive and they wouldn’t have been able to sustain that for nine minutes.

“I just felt like there was a lot of music that I wasn’t hearing anywhere on other shows, so it was easy and it was fun” – Stretch Armstrong

You famously premiered a song from Nas’ seminal record, Illmatic; were you aware of how important the record would become?

Bobbito: I think we sensed that clearly and I think everyone did. It was the most anticipated album of the decade. For anyone who was a hip hop head the build up for that was incredible. He came onto our show as an unsigned artist on February 1991 and again in early 1993, and in the Fall to promote the release of Illmatic he came on. And that’s the classic moment for me and Stretch: this phenomenal artist rhyming over Stretch’s beat that nobody’s heard of, in advance of this album that’s gonna completely change the fabric of hip hop. Illmatic is one of those albums that raised the bar of what rap could be.

How aware were you of your show’s impact on various subcultures in New York in the 90s?

Bobbito: We were friends with members of the Zoo York skate team, like Harold Hunter (starred in Kids), who has a cameo in the film, and Justin Pierce (also starred in Kids), so we were very aware of our impact on the skate community. They would come to Stretch’s gigs downtown; they were partying and taping us. Back then there was this whole community that cross-referenced, from basketball to skate to hip hop, it was always crossing.

Towards the end you speak about hip hop changing and losing the love. How do you feel about it today?

Stretch: I have enough friends that are in the hip hop world to know that there’s a lot of horrible shit and there’s some great stuff. The difference is you don’t have these concentrated shows where you have people sifting through everything and presenting the best of the best the way we did. That’s not to say there aren’t really good ready shows; there are, I just think it’s very spread out and there’s a lot of music being made; it’s a very schizophrenic world, there’s just so much music coming out that it’s hard to sift through it. It’s up to the individual to find it.

Do you miss the golden era?

Bobbito: I don’t miss it at all. Not even one bit. We experienced it to the fullest…

Stretch: Even when the music was great the show wasn’t a cakewalk; it was a lot of work, dealing with a lot of difficult people, difficult hours, and when it was over, in hindsight, we were just really appreciative that we were part of the scene and that we helped shape it. But I think we were both very happy when our radio careers came to an end.