Stretch & Bobbito changed lives. Their 1990s New York City radio show (via Columbia University’s WKCR) had legions of fans staying up to all hours of the night, with fingers on tape recorders. On air (and off) DJ Stretch Armstrong and Bobbito The Barber were perhaps Hip-Hop’s greatest A&R men. Labels may have been taking a close listen, but it was the public and the burgeoning underground Hip-Hop community that they served. Those shows made headway in the careers of Biggie Smalls, Nas, JAY-Z, Big L, Eminem, Fat Joe, MF DOOM, O.C., Organized Konfusion, Kool Keith, The Artifacts, Large Professor, and Necro. That, of course, is just a sampling.

Today, Bob and Stretch are bridging the gap. At NPR, their What’s Good with Stretch & Bobbito show is a destination for cultural conversation. This time, music is less focus (but present), as the two personalities maintain their brand of humor and Hip-Hop, but cast a wider net to the public. Dave Chappelle, Stevie Wonder, and Run The Jewels have different kinds of chats here, and if it isn’t yet changing lives, it’s at least shaping unique perspectives.

Run The Jewels Discuss Homophobia In Hip-Hop With Stretch & Bobbito (Audio)

In the last week, Stretch and Bob’ spoke with Ambrosia For Heads. More than 10 episodes deep (today unveiled a chat with comedian Franchesca Ramsey), Bobbito reflected on the overall theme behind the interviewees. “I think the common thread [of all of our guests] is that we just want compelling narratives. Of course, the first season we wanted to hang out with people who might draw the most attention from the NPR mass audience. We both felt that our loyal followers from the ’90s are just gonna be happy to hear us back on the air, if we were known for having unsigned, unknown, and up-and-coming [guests], so we figured [that part of our audience] was good, no matter what. We could have the hot dog vendor from 17th Street, and they’d [be happy because of] Stretch and Bob’. For the NPR audience, which is vast; they have 200 million listeners across all platforms, and a lot of those people don’t know who we are, they don’t know what we’ve been, and they don’t know what we’ve really meant. So we had a Dave Chappelle and Stevie Wonder [to introduce ourselves to this audience]. Once we got them there, then we had a Mahershala Ali or a Linda Sarsour—people who are well known in their respective communities, but maybe not across-the-board super A-list superstars.”

Stretch adds, “There’s something about every one of our interviewees in the first season that relates to the things we’re interested in. There’s people that are from urban communities, whether they’re actors or musicians. Obviously, Bob and I are music fanatics, first and foremost. So naturally, having a Stevie Wonder is a dream come true, particularly for Bob. Run The Jewels just makes sense in that regard as well. Unlike Stretch & Bob of the ’90s, this is more concerned with looking outward into the world. Our interests have expanded into the realm of activism, so a Linda Sarsour makes complete sense. Then, you talk about somebody like Regina King, who—it actually would’ve made sense for Regina King to be on our show in the ’90s if we’d known her then. She’s been at our parties. Every one of our guests, I’d say with the exception of [political strategist/commentator] Anna Navarro, is somebody that we feel a certain kinship with, and a shared sensibility.”

Their 1990s radio show was revered for its freestyles and DJ selections—with many important premieres. While Stretch and Bob’s chatter was often humorous, there were messages at times not unlike the goals for What’s Good. “I remember one night when me and Stretch were talking about cereal, and Twinkies…,” jokes Bobbito, asked about any memorable talk segments. “—Were we talking about crappy breakfast foods?” interrupts Stretch, before a more serious reflection. “I don’t remember very many compelling conversations on WKCR. I just remember a lot of foolishness. [Laughs] But within the context of that foolishness, Bob would get serious if there was an issue or something that may have been mischaracterized or whatever. Bob would definitely interject with a serious manner, when appropriate. I think in that way, Bob, in some regards, was a leader within that ’90s Hip-Hop scene that we kind of helmed. It’s great if you can be funny all the time, but when you need to be serious and lead the way and show younger people that you might to look at something in a different way.”

Cucumber Slice (one of Bob’s monikers) saw a similar quality in his partner. “Let me say that Stretch—as an activist today on his social media is a lot different than his activism in the ’90s. However, while he may not have spoken about issues, when the L.A. Riots happened, we played an hour of really empowering, righteous music that spoke volumes. He didn’t have to say anything; he just played the music. Yo-Yo just happened to be in New York that night; she talked about Los Angeles. I never heard that show [as a recording] since. Stretch definitely had a way of speaking about stuff, with his hands.”

As hard-to-reach guests are frequently joining What’s Good in season 1, it’s noted that the duo collected participation from Jay, Nas, Em’, and others in documentary Stretch & Bobbito: Radio That Changed Lives. Major media companies are not often able to maneuver these MCs. Asked how they were able to, Stretch notes, “The time that we shared with these artists, back when they were starting out, it’s a mutually special time. It was incredibly special for me and Bob to be able to present the world, via our platform, such phenomenal talent—which would go on to really change the world, not just musically, but culturally. And I think those times were as important to these artists as well. A lot of those artists were very ambitious, and wanted to graduate out of the underground as soon as possible, and reach a wider audience.” Many artists appeared unsigned, or at times long before awards and plaques. “Some of them did not aspire to that, but a lot of the ones you just mentioned did. And I think in the course of their super-accelerated careers, a lot of them forgot about those early days. And in our film, we really brought them back to that. Of course, that’s not why they got in the film. Honestly, it took a lot of wrangling to get a lot of these guys in the film. It’s not really a reflection of them personally, it was the people around them that might not see a financial or career upside with them spending two hours with Stretch & Bob in 2015. But of course, once they did, many of these artists, we could’ve sat with for another hour or two, and I don’t think it would’ve been an issue.”

Stretch says that his partner made the moment a throwback. “It was Bob’s idea to walk into these interviews and actually sit down with a Sony Walkman cassette player, headphones, and a cassette of the episode they were featured on that we’d play for them. That whole tactile experience of putting the tape in, putting the headphones on, holding a cassette really took them back to that time. Look at Fat Joe’s face when he’s doing that. He becomes the 23-year-old again when he peers up. JAY-Z’s executive role just recedes into the background as he becomes JAY-Z, who used to f*ckin’ stand on the corner with Big L and just do it for the love.” For the viewer and the two radio juggernauts, it caused memorable scenes. “It was great to bring them back to that point. I think that just supports that whole idea of what a special time that was for all of us—and I think there’s an acknowledgment that says something really special about the venue that we created for the whole scene to come out of. I think that’s ultimately why these artists wanted to participate.” Stretch recently joined Up North Trips creator Evan “Ev Boogie” Auerbach in compiling and publishing No Sleep: NYC Nightlife Flyers 1988-1999. Whether radio, film, or text, Stretch is gifted at recreating a bygone era in New York City arts and culture.

With the film in mind, Bobbito is asked how What’s Good can change podcasts (and lives). “We’re always aiming at affecting people positively, whether it was music selections or compelling questions that we’re asking our interviewees in a way that they’re not getting asked [in] a comfort zone, or in a comedic manner. I feel like the interviews we’ve done so far, people are sharing stuff that they don’t just say in every other interview,” says the former publisher, label executive, and street ball documentarian. “It’s not really about, ‘Oh, I’ve got a film coming out, so I’ma do this interview.’ Like, Mahershala Ali, we asked about his [Hip-Hop career] and about being a Muslim and all these other things, and just about life. And that’s our goal: to get to the compelling narratives.”

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