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During the 1980s, geographically speaking, rap fans had to stay awake for late night and weekend urban radio mixshows like New York’s Kool DJ Red Alert and Chuck Chillout on WRKS Kiss 98.7FM, Mr. Magic and Marley Marl on WBLS 107.5 FM, The Awesome 2 and The Zulu Beat Show on WHBI 105.9 FM, which fed the Tri-State area’s rap fix on the airwaves. The same came be said for Greg Mack on KDAY 1580 in L.A. during that decade. College radio station DJs with timeslots on their campus radio stations left of the dial were just as essential for listeners to create homemade cassette tape treasures.

In 1990, Columbia University freshman student Adrian Bartos (a.k.a. DJ Stretch Armstrong) pitched the idea for an early Friday morning 1am-to-5am radio show with former Def Jam-titled Alternative Promotions Manager, Bob Garcia, to the campus radio station WKCR 89.9 FM’s brass. As fate usually goes within legendary contexts, the idea was initially met with rejection. Luckily that station’s program director eventually acquiesced to green-light The Stretch and Bobbito Show. Ten years later, according to Hip Hop’s original “bible,” The Source Magazine, vote as “the greatest rap radio show of all-time.”

Nas, a former upstart guest of the show, stated to the duo in their riveting 2015 documentary film Stretch and Bobbito: Radio That Changed Lives, “At one point, your show was the most important in the world!” Together, Stretch and Bobbito were a two-man Dick Clark to Hip Hop’s version of American Bandstand through the most pivotal era in Hip Hop history. Fans attempting to record exclusive remixes of their favorite bangers and the hilarious snaps and inside jokes from co-host Lord Sear and the show’s guests during the twilight hours of Friday morning was fleeting.

The legendary DJ Stretch and Rocksteady Crew member-turned-venerable film director of Doin’ It in the Park and Radio That Changed Lives spoke with HipHopDX about their bond, the dogmatic approach to showcasing the 1990s underground Hip Hop canon on their monumental mixshow, Lastly, they discuss the show’s memorable freestyle sessions (i.e. Biggie Smalls, El-P of Run The Jewels’ original group Company Flow, MF Doom, Mobb Deep, Wu-Tang Clan, Hieroglyphics, Common, Eminem, Jay-Z with Big L, Boot Camp Clik to name a few out of the 300 others), plus why they opt not to listen to current Hip Hop radio.

The Integral Role of 3rd Bass for Stretch and Bobbito’s Connection

Stretch Armstrong: First off, much thanks to HipHopDX, and much love to you doing for us.

HipHopDX: It’s an honor to have you. Before your show initially aired on WKCR in 1990, Pete Nice of 3rd Bass was a Columbia student who had a radio show on that station from 1986 through 1988. That was actually the first Hip Hop show on that station.

Stretch Armstrong: Yes, he did. It was called We Could Do This Show, which had DJ Clark Kent and 3rd Bass’ DJ Daddy Rich.

Bobbito: Yup, that’s a very little known fact. Clark Kent was the DJ, and Daddy Rich, aka Richie Rich. So that was a fantastic show that not many people have heard or are aware of. But I mean, damn, Clark Kent and Rich? (Laughs) You got two of the top DJs of the whole decade, you know, and Pete Nice, a prominent MC of that decade as well. I actually never even heard the show (Laughs). Pete’s been keeping a hold of those tapes.

Stretch Armstrong: I never heard it at the time, but I actually have those tapes now.

HipHopDX: Were you both inspired by Pete’s show that preceded yours?

Bobbito: What Pete did was really a separate entity. Because Stretch and I weren’t aware of it, I mean, he definitely was the first Hip Hop show on ‘KCR. But it’s not like we took off where he left off. That show existed, it ended, and then we got on. It wasn’t a template for us because we had never even had heard it. But all praise due to Pete, and more honestly if it was not for him, Serch, and [legendary A&R and 3rd Bass co-founder] Dante Ross, I don’t have an entry point in [this industry] that got me the job at [Def Jam]. And if I’m not working at Def Jam, then I don’t meet Stretch. So even though his radio show wasn’t the jumping board for me and Stretch, like Pete, Serch, and Dante Ross, they’re kinda my stepping stones to being a radio personality.

The Funky Precedent of 1990s Hip Hop on NYC Rap Radio

HipHopDX: Around the time you started your radio show, New York City urban commercial radio stations didn’t play rap music all day like today. Did you feel that there wasn’t much competition to worry about on college radio?

Bobbito: Well, first of all, let me state that it wasn’t about competition for me and Stretch. We were just trying to do a fun radio show for us that we could listen to the next day. And because we weren’t on commercial radio, we didn’t see it as competition at all. Furthermore, I was working at Def Jam. So I was cool with Jeff Foss, Wildman Steve and (DJ) Riz, Red Alert, The Dirty Dozen. There were a lot of [shows]. And for those DJs who looked at it as competition, there was a lot of competition in New York. Me, personally, I kind of changed the tone in New York radio single-handedly. Because prior to that, a lot of shows were beefing with each other. You know, especially the commercial shows because they battled for advertisers, listenership, and just bragging rights because it’s Hip Hop, it’s competition. But because of my unique position as a dual radio personality as well as a radio show promotions rep at a premier like Def Jam, I got on the mic and started shouting out other shows. That was unheard of in New York. Like, what? Because to me, it was all about Hip Hop. I’m going to let the listeners know you can listen to Hip Hop every single day of the week. Because back then it wasn’t like could just listen to it anywhere, not like today where it’s like your could press the “search” button and then get what you want when you want it. Nah. You had to wait for the right time for the show and get the dial. A lot of people didn’t know about the shows to the left of the dial. I felt that my responsibility was when I got on the mic, I shared it. And other shows received it so well. You know, Funk Flex became our friend, even though he was a regular on ‘BLS with Chuck Chillout, Red Alert was our friend, Kid Capri was our friend. All these dudes were coming up to our show, they’re listening to the show, and Stretch had a bunch of exclusives, but they were tuning into the show, too, on some family vibes.

Stretch Armstrong: The great ‘80s show that were still on the radio in 1990 I think in some ways became a victim of their own insularity. As shows become more successful, I think DJ’s in general, and I think I’m guilty of this as well, when you first get on you reach out to music makers and creators to feed your show. And then when you get more popular, you get more passive because everyone’s sending you stuff, then you pick and choose the best of what you’re sent. Combine that with the way you that you clique up, especially the way you had it in New York City as far as KISS and ‘BLS and those guys. You know, Red and Marley would play records by artists that sort of transcended that cliquey-ness, but they both played records by Run-DMC, Public Enemy, and LL. But they would define themselves to play records by associated artists, and I think by 1990 that got really extreme. And the fact that 1990 was [all about] Hammer and whatnot really breaking through, showing that under the right circumstances you could make really popular records. Artists like [Big Daddy] Kane were making R&B records, and kind of making their big records in that way. That’s the setting where we got on the radio. And I think that’s why we were so effective at what we were doing because we were so hungry to find music that no one else is playing because almost by virtue, my attitude, and taste in music, people just soaked that up like sponges immediately. It was pretty dramatic.

Legacy Cemented: All the deets for the DJ duo’s film can be found right here.

HipHopDX: Once the show took off, and got more listenership, what were the other shows that were on your heels that you tuned into?

Stretch Armstrong: Once guys like Mark Moore and Mayhem at WNYU came through, I would say that it wasn’t a competition. It was more of a camaraderie. Certainly, I paid attention to what those dudes were playing. And the same can be said about them with me. But we really were extended family with everybody. So it was never about if you play this, I’m not going to play it. It was more like hmm, “I wanna play that too,” or “what else do they got?” That was a win-win for us on the radio, for the artists, and for [the community] as a whole.

HipHopDX: Who were the artists that you didn’t expect to become legendary?

Bobbito: I think everyone who became as large as they did, we couldn’t have anticipated that they were going to become that because there was no precedent. Back then, you know EPMD and Gang Starr was selling like 500,000 records and that was thought of as immensely successful, you know (Laughs). So to sell like 10 million records, you know, 75 million, 150 million, that was considered unfathomable in that era. So we had no idea that Eminem, Jay, Biggie were gonna sell that much because there was no precedent. And then, understand that we had 300 unsigned artists come up to our show in eight years. So some of them were phenomenal. It might possibly could’ve sold that many records if they were on the right label and came out at the right time. But that’s not for everybody. That lane is only for so many artists who could get that popular. So props to the ones who made it. There were at the right place at the right time and made some good decisions.

Stretch Armstrong: Big L was not a sure shot bet. He had made so much noise in the underground but remember he had a record on that came out on Columbia [Records] that didn’t do well. That was more like, “These are our artists that we love. Can they crossover to a more mainstream audience?” And honestly, that didn’t really matter to us. We didn’t pay attention to that. It was completely irrelevant to us and the community that tuned in every week.

Trapped in the Golden Era vs. Trap Music On-Air Today

HipHopDX: The fun that you guys had on the air was the greatest product of the show. When you hear a lot of Hip Hop radio today…

Bobbito: I don’t hear a lot of Hip Hop radio today. I don’t listen to the radio.

HipHopDX: It seems like much of Hip Hop radio show today rely on Twitter beefs, gossip, and some social issues that affect Hip Hop community, but more of the former than the latter. Does that turn you off from it?

Bobbito: No, it’s just that I stopped listening to Hip Hop radio back in the ‘90s (Laughs). Me and Stretch’s show was so strong that if I wanted one of my Hip Hop picks, I would just listen to our own tapes. It’s not a knock on anyone else’s show. When I was at Def Jam from ‘89 to ‘93, I listened to other people’s shows to see like “Okay, this person’s playing our records,” that was my job to keep the pulse. But after ‘93 when I stopped working at Def Jam, you know, I stopped listening to other show because my favorite Hip Hop was being played on me and Stretch. That’s because either because I was playing it myself, or because Stretch was playing it. I’m completely unaware of other shows and what they’ve done and more so in the last 15 years, unless I’m a guest on somebody else’s show. I can’t really speak on current Hip Hop. You’re better off talking to a lot of other people who brought a lot of attention to it. I can’t even fairly speak on it.

HipHopDX: So needless to say, trap music has no bearing on you at all.

Bobbito: I don’t even know what it is. I’ve heard of it, but I don’t really know a “trap” song. Or maybe I have and couldn’t tell you that that’s what it is. It’s over my head.

HipHopDX: Stretch, do you listen to much radio today, or check for any particular radio show?

Stretch Armstrong: I don’t listen to Hip Hop radio. I would say I don’t listen to SiriusXM, even though I’m going to get it soon so I can check out because I would like to hear [DJ] Premier, Eclipse, and Lord Sear, Statik [Selektah] once in awhile, and Tony Touch. I do listen to Combat Jack because I think his interviews are very compelling, and he goes about his interviews in a very smart way. Other than that, I don’t pay attention to Hip Hop Radio at all.

HipHopDX: In your documentary, you mentioned how between 1997 through 1999, you were turned off by a lot of what was coming out during what is dubbed as the “Jiggy Era.” Does today’s trap music that’s en vogue give you that same feeling?

Stretch Armstrong: I’m just not really interested in Hip Hop.

HipHopDX: What are you interested in now?

Stretch Armstrong: It’s funny because making this film with Bob, and then touring it over the last year has put me in the frame of mind for the first time in my life that I haven’t been compelled to learn about new music that much. But I know that will change, and when it changes it will happen naturally. But I’ve just been listening to old music. Whether it’s funk, soul, reggae, just what I would call “foundation” music for me, what shaped me growing up in the ‘80s and ‘90s. That’s what I’m listening to right now. And that doesn’t say that I’m just regurgitating stuff that I know. I’ve just been going deeper into areas that I’m already familiar with, which is sort of expanding my knowledge and having a great time doing it, and collecting records again.

HipHopDX: You had mentioned in the documentary that the about the rite of passage for artists to prove themselves on a platform like your show was for so many artists to gain credibility. Does it make you upset when you see today’s trap rappers like Lil Uzi Vert refuse to freestyle over a classic DJ Premier beat live on the radio?

Stretch Armstrong: You can’t blame them. You have to blame the teacher. It’s the teacher’s fault. That’s what he grew up thinking is dope versus me. I think the best years [in rap] were 1986-1988.

HipHopDX: Essentially, you can’t get mad at when this newer generation of rap artists were born.

Stretch Armstrong: Yeah. But also, I feel like there’s not much originality right now. Everything somewhat sounds derivative of trap. You know, the Tunes 808 bass tones, 808 snares and syncopated hi-hats. But people’s criteria for what is dope changes. I can’t be an authority on what you think is dope versus someone else’s thoughts on what is dope. As for New York artists like A$AP Mob, I like their records, and I like what those guys are doing. If I was 20, I’d probably be bumping their shit (Laughs).

HipHopDX: When you see artists like Joey Bada$$, or some of the Brooklyn artists of that element who are coming out today, do you think Hip Hop has come full circle?

Stretch Armstrong: I know like anything, things come full circle. I also know that recently Joey had a song that Hot 97 was starting to play. Aesthetically, it was a big leap from what Statik and Joey had traditionally been creating.

HipHopDX: You’re talking about “Devastated,” correct?

Stretch Armstrong: Yeah, exactly. So I don’t follow this deeply enough to speak on it in an informed way. But I do know that people were going at Ebro at Hot 97 for not playing certain artists. He was basically saying they haven’t earned it nor put in the work. Of course, that can be debatable because we see artists out the gate being played on radio that haven’t put in the time. That’s because record companies are throwing a lot of money at the system. So it’s a money game, and I do wish that local radio would be more supportive of whether they were making trap or making boom-bap Hip Hop. It’s sad that they don’t. The choices are to come out and sound like a Southern artist or to make records that sound like you’re in the 1990s. Whereas I think there should be a more wider variety of possibilities. If local radio stations were more supportive of their home talent, I think that kind of creativity could be more possible.

“You can’t blame [kids today]. You have to blame the teacher. It’s the teacher’s fault.” — Stretch on today’s youth not caring about lyrics and bars.

Cult Classic: The Legacy of The Stretch and Bobbito Show

HipHopDX: The greatest highlights of your show were the exclusive freestyles sessions. Who was your favorite artists to ever do that on your show?

Bobbito: Well, off the dome, I mean, there’s too many to mention. But in terms of written freestyle raps on our show, I would have to saw it was Nas and O.C. And if you watch our film, the longest verse of any in the entire film is O.C.’s from the night that he rhymed over Large Professor’s unreleased beat. And then Nas, they tried having him five months before Illmatic dropped, and the anticipation of the album with him rhyming over Stretch’s beat. Those are the things that really made our show special. You know had an unreleased verse, over an unreleased beat.

O.C.’s verse on our show never came out, and the beat that he rhymed over eventually came out two years later. Mad Skillz used it. Nas, his verse, nobody knew he could rhyme off the top of the head. And then he dropped the “Memory Lane” which became an anthem on the album, and it wasn’t even a single. And Stretch’s beat that he rhymed over, that never got released. You know, these are frozen moments. There wasn’t no easy like “Yo, we’re just gonna do a search for it on YouTube.” Nah, you either caught that moment and felt so honored and special to have heard it live, or you taped it. If you missed it, you hoped that somebody would’ve taped it, made you a dub, or shared the tape with you. It wasn’t an all-access thing. It was coveted.

HipHopDX: You both had a show on a Sunday night timeslot on Hot 97 in 1997 when the show was very popular, yet still kept your show going on college radio simultaneously. Did you keep the show WCKR consider that graveyard shift of 1am – 5am because you felt it was coveted as well?

God’s Son Flow: A rare Nas freestyle from the Stretch and Bobbito Show glory days.

Bobbito: No, that was never coveted. But it worked in our favor in the manner that it provided for our cult following that we developed, for people who were in the know, who were progressive compared to everybody else. Those people wore that like a badge. They knew about our show when the rest of the world didn’t. The people who knew about our show, the hundreds of thousands all felt special. You got like 300,000 to half a million feeling special that they were up on nobody else was up on. Then we started doing merchandise, and if you saw someone with a Stretch and Bobbito Show t-shirt, it’d be like “Oh, you know about that too?” It was a whisper tone, like, “Yeah I know about Stretch and Bobbito.” You know, it was the biggest shirt for Ecko Clothing that came out that season in 1996, so it was weird. It was like everybody knew about us, but everybody felt like it was their secret.

Follow Stretch and Bobbito on their Samsung 837 Soundcloud, Twitter and Facebook to keep up with their every move.