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Interviewed by: Jesse Carr
Photography by: Kaitlyn Chow
Produced by: Dan Hwang

The Stretch Armstrong and Bobbito radio show defined what many consider to be the most impactful era of hip-hop. Their story is neatly compacted into Stretch and Bobbito: Radio that Changed Lives, a documentary which charts the rise of a college radio show on WKCR FM in New York City which blossomed into what is usually referred to as the best in hip-hop’s history. During the film, freestyles from the show were often augmented by live paintings of the lyrics from our very own Fresh + Creative subjects Eric Haze and Kevin Lyons. Besides being the first place audiences heard Jay-Z, Nas, The Notorious BIG, Eminem, and many more hip-hop stalwarts before they had record deals, the show had a loose format and freewheeling banter that shows still mimic today. In fact, the approaches of many popular podcasts have tangential connections to those classic, whimsical late-night mic breaks on the Stretch and Bobbito shows.


After the release of the film, the duo reunited for a limited run during the summer at the Samsung Space in New York City for 7 shows. Set within a large glass enclosure facing the street, the space at 837 Washington Street allowed both those in the store and pedestrians outside to see the famous duo at work redeveloping their chemistry. Before our interview, as our photographer shot them outside the space, there were at least five people who stopped to take selfies with them, many of whom thanked them for the documentary and their contributions to hip-hop. And, true to form, Stretch and Bob were happy to chop it up with each person while posing for the flicks in ways that make it clear that they don’t take themselves too seriously.


This recent run of shows happened live at the space on Mondays and were posted the next day on the Samsung 837 Soundcloud page, calling to mind the nature of their show in the 90s when many listeners would record the show and then fall asleep, awakening later to hear the exclusives and freestyles before the tape stopped. In the film, aside from interviews with many of the artists who grabbed the mic years ago, there are also appearances from fans who collected and archived the recorded shows. At a hilarious moment in the film, Busta Rhymes even joked that he made money from those tapes when he would sell them at school the next day. 

D-Nice, Pete Rock, and others stopped by to the show on the night of our meeting to chat in between music sets. Stretch and Bobbito took turns DJing, playing salsa, funk, and more. As the show progressed, to the delight of the many fans at the space whose heads were nodding along, Stretch Armstrong did eventually play some hip-hop. At one point, D-Nice discussed his photography, and it was just like the 90s, as the hosts traded jokes and pointed out tiny details in the photos that were projected throughout the Samsung space.


The two had obviously hit their stride, and during our interview even hinted at more joint ventures to come. Read on for their takes on the impact of their show, the sleight of hand involved in the production of the film, and even a rare comment or two from Stretch on the differences between the sound of the hip-hop that defined the show and the ways that the genre has shifted since they have been off the air. 

Left to right: Bobbito, Stretch Armstrong, and Jesse Carr

Left to right: Bobbito, Stretch Armstrong, and Jesse Carr

Can you contextualize for our readers the importance of The Stretch Armstrong and Bobbito Show? 

BOBBITO: The best way to capture it is to watch our documentary, Stretch and Bobbito: Radio that Changed Lives. It’s a transformative journey into an era that will never return in terms of visceral and aural experiences with radio. One of the reasons we made the film is to provide context for younger people to help understand what we represented in the 90s and what radio represented as well. The film can be seen on Showtime, Vimeo,, iTunes, and youtube. It’s also available on DVD. 

How does your return together compare to the way someone would have listened to your show years ago? 

STRETCH ARMSTRONG: If you listened to the show back in the day, you taped it yourself. Or maybe your boy taped it and your boy let you dub it or listen to it. That ritual meant a lot--the ritual of going to sleep and waking up and listening to what you recorded. 

BOBBITO: There was an awesome secret society of tapes. People may have taped it, only to find that the signal went out. It was kind of a crapshoot if you were on the border of where the signal traveled. 


Is there any genre of music today that reminds you of the excitement generated by the way hip-hop from the 90s? 

 STRETCH ARMSTRONG: No. There are underground scenes, and there are people in those scenes who are, perhaps, just as passionate as we were in the 90s, but we are also not 25 years old anymore and living our day to day existence just to be a part of a culture, which is what our lives were like back in the 90s. 

BOBBITO: Well said, Stretch. 

Did you have a hunch that you were on to something while the show was going on? Is that why you got people in there filming some of the footage that made its way into the documentary? 

BOBBITO: No, and if we had known, we would have had people in there filming every single week. 

STRETCH ARMSTRONG: There are video tapes from the first 6 months that a friend of mine recorded. If we knew that we needed to tape them then I would have asked for the tapes, but now those tapes are gone. 

BOBBITO: In terms of filmmaking, we took a lot of creative license. For the biggest moments of the film with Biggie, Jay-Z, Nas, Big L and Big Pun, we dressed the film with live painting and photos. Like with Nas, we had two photos of him at the studio, but the rest of the photos of Nas you see in the film are not at WKCR, but because you are hearing the freestyle and seeing the pictures of me and Stretch in the studio, it kind of lends to the moment that you automatically assume they were in the studio. A lot of people tell us about the great footage we got, but we didn’t have much live footage. 

STRETCH ARMSTRONG: It is a testament to the film that people think that we were these crazy archivers, which we really weren’t. 


What are the long term goals for your show? What happens after the run here at the Samsung space? 

BOBBITO: I’d like to be on forever, as long as we get the chance to play whatever we want, which is what the Samsung platform has allowed us to do in a very fun manner and still not take a complete departure from what we did in the 90s. We still bug out during the mic breaks, and it’s still us acting stupid and talking. We also have a show in development that will not be music based or a mix show and will feature a range of personalities. 

Many are wondering about the archives of your radio show. Is there a chance of seeing more episodes released? 

STRETCH ARMSTRONG: Right now they exist as reissue cassettes. We may release the Le Poisson Rouge reunion as a cassette box set as well. 

We could hear in the 20th Anniversary Reunion show that the chemistry was coming back. That scene in the movie was strong. Did you seem to snap right back into that chemistry when you got here to the Samsung space? 

STRETCH ARMSTRONG: Well this isn’t WKCR. You have people looking at you that you didn’t have there, and here people are looking at you, so there is a sense of self-awareness. Back in the day at WKCR, it was people there with us who were like family. 

It seems like there has been a gradual growth in these Samsung shows where you can hear you guys recapturing that rhythm. Is that a fair assessment? 

BOBBITO: That’s not even just fair, that’s spot on. 


How do you decide what you want to play here during this run at the Samsung space? 

BOBBITO: I want to play things that will open up some of our older, die-hard listeners to something that they may be interested in. I think that’s always been our purpose. I think that if me and Stretch had never parted ways in 1998, I think that what you are hearing now is what the show would have naturally developed into. 

STRETCH ARMSTRONG: Back in the 90s, there was a time when I was getting sick of hip-hop and I did consider using that show to play other music, but I had respect for what we were doing, but I was thinking about this shift in 1996 or 1997. 

What do you think the kids should check out after seeing the film? If the film is a bit of gateway to that era, where are some starting points?

STRETCH ARMSTRONG: One of the takeaways from the film is to have kids consider what hip-hop really is because right now you hear rap music which is made over synthesized beats. There’s no samples and there’s been a continuom. In the 80s, they were emulating old R&B and disco records to rap over, and when sampling came about, they were sourcing old music. That dynamic is gone. And for a young kid who may only know A$AP Ferg or whoever, they miss that whole genetics of a record. It’s a whole other world. For our peers who have become collectors, hip-hop was a way into the Latin records, Soul, or Funk or wherever else the samples came from. I’m not saying one is better than the other, it’s just that one has it’s place in history. 

How has your relationship grown?

BOBBITO: I’m loving this stage of me and Stretch’s relationship where we are talking every day again, traveling, and acting stupid. It’s like we’re kids all over again. I think about this a lot. I am so happy we made the film. We wouldn’t have the show, wouldn’t have toured, wouldn’t have done this as a gateway for people into the 90s.And it’s reconnected us with many people from back in the day. I hadn’t seen Nas or Jay-Z since we had them on the show. I hadn’t seen Nas since 1993 and we got to interview them for the film. 

STRETCH ARMSTRONG: Bob was called the director of the film, but really, he could have had many more titles because he was running around doing everything. What I was doing was wrangling rappers. It’s funny because after the show the reputaiton was that I was the one who was like “I’m done with rap.” But Bob doesn’t have that same reputaiton. There was never the same violent break with hip-hop that I had very publicly with the music, which I have humbly walked back several times. 

BOBBITO: Stretch saved the film, in many ways. We were waiting so long for the Nas, Jay-Z, and Eminem interviews. I was pushing the deadline saying we had to go and put it out to premier the film. And Stretch was telling me, “I’ll get them.” He was relentless. 


Last question: are there any other projects that you are working on?

BOBBITO: I have a basketball tournament called Full Court 21, played at the legendary Goat Park, as it's known to the basketball community. To the hip-hop community, it’s called Rocksteady park. I am happy to do that because that’s where I grew up. I’m also working on my next film, which is an autobiographical documentary.

STRETCH ARMSTRONG: I wish I could organize a hip-hop tennis tournament. That would be amazing. But, for real, I do have a book coming out this fall called No Sleep: NYC Nightlife Flyers 1988-1999 documenting NYC Nightlife culture.    


Instagram: @stretchandbobbito
Twitter: @stretchandbob