“It might be a setup.”
The plan was to drive uptown to WKCR so that Eminem and Royce da 5’9” could make their debut on The Stretch Armstrong Show hosted by Bobbito the Barber, but Em was feeling a little Edward Leary about the whole thing. It was Thursday, Aug. 20, 1998—two days after Slim Shady made his NYC debut at the Tunnel, kicking off the Lyricist Lounge tour—and more history was about to be made. Still, the future rap god had some apprehensions about what he was walking into.
“Cage is they artist!” Em reasoned to Paul Rosenberg, his manager and business partner—along with myself, SKAM?, Marisa Pizarro, and Detroit rapper Invincible—as we stood on 14th St. outside a club called The Cooler. “How do we know we’re not gonna walk into the studio and he’s gonna be waiting there with writtens for us?” Em was far from a shook one—don’t get it twisted, battling is in his blood and felt himself the superior talent—but he didn’t want to walk into a situation unprepared.
Earlier that evening the Outsidaz had performed at the literally underground nightclub situated in Manhattan’s then bro-less and bridge-and-tunnel-less Meatpacking District, and had invited longtime friend Em to rock with them. The show was lit, to use the parlance of today. Newark, N.J.’s finest—Young Zee, Pace Won, Rah Digga, AzIz, DU, and Slang Ton (RIP)—tore down the micro venue, which probably had an audience of 50 people max, before introing Em and inviting him to perform “Just Don’t Give a Fuck.” The backpackers in attendance literally moshed. It was fucking nuts. Afterwards we regrouped outside the venue, and Paul explained that he’d hooked up a spot on Stretch and Bob.
This was a huge look for Em. Sure, by the summer of ’98 Marshall Mathers’ career was a rapidly growing snowball that was gaining velocity with each passing day, but success was still far from a foregone conclusion. In the previous nine months he’d released the Slim Shady EP regionally, signed to Dr. Dre’s Interscope-distributed Aftermath Records, and recorded his debut LP (though it wouldn’t be released until January of the next year). Those of us close to Em, who had heard the music, knew he had something incredibly special, but to the rest of the world there was still a litany of question marks around the project. Dr. Dre had been ice cold for a couple of years, thugged out NYC club music dominated the charts, and then, of course, there was the pale elephant in the room: Could any white rapper—even one as obviously gifted as Em—succeed on the scorched earth Vanilla Ice had left for them?
One thing was for sure, though, if Eminem was to succeed he was going to have to black out on Stretch and Bob first.
Launched in 1990 by then Columbia undergrad DJ Stretch Armstrong, née Adrian Bartos, and b-boy extraordinaire and Def Jam talent scout Bobbito Garcia, WKCR’s hip-hop show had become a rite of passage for aspiring rappers by 1998. The duo—armed with different, but impeccable ears—had made their lane premiering unreleased gems and breaking emerging talent. It was the perfect environment. Broadcasting from a small college radio studio on 114th Street between Broadway and Amsterdam, the Stretch and Bob show ran from 1 a.m. to 5 a.m. every Thursday night—four hours of uncensored and unscripted hip-hop gold every week. During that eight-year run, literally every East Coast rapper of significance cut their teeth on Stretch and Bob’s mic. Ay-yo!
Biggie destroyed it in ’91 (gotta watch their movie to hear this). Nas put a generation of rappers on notice the same year and then again twice in ’93. Mobb Deep made their debut as Poetical Prophets that year, and then showcased their hardened, mature Infamous sound later in ’94. Big L wrecked shop in ’92. Wu-Tang Clan debuted their criminology raps in ’91 and returned in ’93. Q-Tip introduced the world to Mad Skillz via 11 minutes of verbal intercourse in ’94. And then, at the end of that year Big L returned with an unknown named Jay Z and committed a lyrical exchange to the airwaves so epic that it would go on to become the most listened to radio freestyle on YouTube. Not to mention DMX (’91), Big Pun (’95), Capone-N-Noreaga (’95), Cam’ron (’95), MF Doom (’97), and the Fugees (’93), who all appeared as well.
Like I said, EVERYONE who mattered made their mark on 114th Street.
And Eminem, a student of hip-hop if ever there was one, knew this all too well. You couldn’t read The Source or RapPages without seeing references to the damage that had been done on Stretch and Bob. But, a battle rapper to the core, Em couldn’t get the X factor of Cage out of his head. And he had a right to be concerned. The Middletown, N.Y.-bred MC had shocked the underground in ’97 with his jarring, horrorcore-done-right 12” “Agent Orange,” and apparently felt a way when he heard the Slim Shady EP later that year. Cage was of the mind that the Slim Shady persona trod in familiar waters of white alienation and hyperbolic violence, and said as much when he called Eminem out, live on The Stretch Armstrong Show in the spring of ’98.
For his part Em felt blindsided, as he claimed to have never heard of, much less heard, Cage until word got back to him in Detroit that he was being slandered on NYC radio. He was even gracious enough to say that, upon finally hearing it, he was impressed by “Agent Orange” and thought it was crazy that the two were on such similar wave-lengths. But as everyone who would dis Eminem would learn, say his name once and it’s “bought Cage’s tape, opened it, and dubbed over it!”
In light of Cage’s modest career and Eminem going on to become the most successful rapper of all time, looking back at it now, it may be hard to wrap your mind around why this situation even bothered him. But you have to remember Eminem in August of 1998 was not the bleach-blond, two-hoop-earring-wearing TRL star who the world would meet six months later. This was still the brown-haired battle rapper who dressed in over-sized black Champion hoodies and sweats every day. Who still wore “that same damn NIKE hat.” The dude still coping with PTSD from crushing at the Rap Olympics and battles with Juice!
So when you consider that history, and the stakes of his appearance on the show, Em’s disquiet made total sense. This trip to Harlem—in which he imagined potentially being confronted by a prepared foe—could end in adulation or humiliation, and his ability to feed his family hung in the balance. Thankfully, the chorus of Paul, Marisa, and myself—all of whom had great working relationships with Stretch and Bobbito—were able to convince Em to get in the car. But things remained tense as we were escorted into the station. They wouldn’t let SKAM? in due to occupancy rules, and that only served to further spook dudes.
For my part, I was bugging, walking through those halls. I had been a faithful listener of Stretch and Bob since the fall of ’93, my freshmen year of high school, when Chances With Wolves DJ Kenan Juska, two years my senior, put me on to a tape of the show. Throughout high school, classmate Justin Monroe and I would alternate ruining our Friday mornings by staying up and recording the show for one another. This involved two 120-minute Maxells, and an alarm set for 3 a.m. Not to be on some “I-walked-to-school-in-six-feet-of-snow-with-no-shoes” shit, but back in the day we had to put in work for this.
And, as any Stretch and Bob acolyte—from Public School’s Dao Yi Chow to DJ Eli Escobar—will tell you, it was worth it. To listen to the show was to live on hip-hop’s bleeding edge, and we were all grateful. In a moment of peak fanboy-dom in ’95, I recall running into Stretch at Disc-O-Rama on West 4th Street and asking him—after we had discussed whether Blahzay Blahzay’s “Danger Pt.2” was really all that (it wasn’t)—to sign the bill of my hat. He obliged, awkwardly. At the time I just thought I was fanning out having met someone “famous,” but in retrospect I think there was something more going on. In a very real way Stretch—who was quite obviously, even to the most casual listener, at peace with his upper middle-class breeding and Ivy League education—validated my desire to participate in hip-hop in an authentic and organic way. Thanks to him, I felt like I didn’t have to be Milkbone to be down.
In any case, by the time I got out of high school I had actually interacted with both Stretch and Bob quite a bit thanks to “Bobbito’s Footwork,” dude’s sneaker and vinyl store on East 9th Street, and then later my internship at ego trip. To this day I know Bob remembers shutting me down when I begged to get on as a Fondle ’Em intern in ’96. And it was a major accomplishment a year later when I got a shout out as a result of ego trip’s Count Chocula appearing on the show! Big shit when you’re a senior in high school in Brooklyn. However, despite all that proximity, I had never been to a taping of the actual show. So, yeah, following Em and Paul into the place where all this history had happened, I was geeked.
Of course, when we walked into the studio all fears were alleviated, as Bobbito and Stretch warmly welcomed both Eminem and Royce and introduced them around the room to Lord Sear and Problemz, of Missing Linx fame. After that there was very little chit chat, as I recall. Within minutes of our arrival, Stretch’s music set finished and it was go time. Despite being on a pharmacopeia of drugs, Eminem and Royce were extremely focused.
The two sat down side by side (which always stuck me as a physically awkward way to make rappers perform), and Em lowered the brim of his hat and began bobbing his head. As soon as Stretch gestured to him to rap, Em raised his right arm and started counting 16th notes with his hand (a tic that took years for him to break). I sat in the corner with Sear and watched.
The next 12 minutes were nothing less than a workshop in multisyllabic rhyme juggling, acerbic metaphors, celebrity mud slinging, and hyperbolic violence. It was a blitzkrieg of wrought bars, over some of the best beats of the day, and it just kept going and going. In the words of Ninja Warrior, it was TOTAL VICTORY! When the dust settled, both Bobbito and Stretch dapped the two MCs, their respect earned. After that it was high fives all around and back to the DoubleTree on 47th Street, where Em and Royce were staying.
At the time we knew that this was a significant moment in the career of Eminem, his NYC baptism by fire, but I don’t think any of us had a sense of the significance it would have in story of The Stretch Armstrong Show. By 1996 it had become apparent to avid listeners such as myself that Stretch and Bob were heading in different directions, musically. For his part, Stretch was more interested in the thugged out sounds emanating from Queens (think Tragedy, C-N-N, etc.), while Bob gravitated to the thoughtful and quirky meditations bubbling up from the underground scene of Fat Beats and the Nuyorican Poets Cafe (think Company Flow and J-Live). When they both launched labels, Dolo and Fondle ’Em, respectively, the divergence became even more pronounced. This manifested at first in gentle ribbing—Thug Thursdays when Stretch was driving, they would joke—but as time passed it was clear that the two were grating on each other, unable to humor the other’s taste. Eventually it seemed that the tension extended beyond music.
That night was interesting because despite Eminem being decidedly more lyrical than most rappers he favored, Stretch had recently become a very vocal evangelist of Em’s—embracing his juxtaposition of punk rock attitude and pop aspiration. Bob’s interest appeared much more muted—perhaps due to Em’s beats, or maybe the shock-rap angle of his lyrics—but Bobbito knows when someone’s rapping their ass off, and that’s exactly what Em did. So, as a fan of the show, there was this really nice moment when the cipher finished and the two hosts shared in a moment of genuine exuberance. Eminem had killed it, and both Stretch and Bob knew that they had created another great radio moment.
Of course, a short four months later, in December of 1998, the two would go their separate ways and arguably the greatest hip-hop radio show of all time would come to an end. But when I think about that night, I really feel it was the informal finale of their oeuvre. In their near decade of broadcasting, Stretch and Bob broke every major ’90s rapper—BIG, Nas, and Jay—and the Aug. 20, 1998, show witnessed them breaking the last of the Mohicans—the final and biggest superstar of the decade—Eminem.
So as we approach almost 20 years from that night in August, it is with great pleasure that COMPLEX premieres the trailer to their incredible documentary feature, Stretch and Bobbito: A Film About Radio That Changed Lives. The movie could not be more aptly named. Whether it was Eminem or the countless other artists, myself or any of the other hundreds of thousands of other listeners, or just Stretch and Bob themselves, their show was indeed radio that changed lives.