Stretch and Bobbito sit on a couch in a Red Bull Academy studio.
© Lauren Crew/Red Bull Content Pool
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8 things you need to know about hip-hop pioneers Stretch and Bobbito
We meet up with hip-hop vanguards Bobbito and Stretch to discuss how they were present and responsible for a lot of seminal moments in rap history.
Ditulis oleh
9 min readPublished on
In every cultural movement there are people who drive things forward and create momentum for the scene. And when you talk about hip-hop music business, two names you can't miss are Stretch and Bobbito.
Adrian Bartos, who goes by the stage moniker Stretch Armstrong, is a musical tastemaker, producer and his staggering skills behind the decks have not only landed him spots spinning in over 20 countries but rocked radio from the break of the scene. Stretch produced Lil’ Kim’s first single from her platinum-selling debut album, he's worked with Jay-Z and Eminem and was the musical consultant for the award-winning film, Boiler Room.
Then there's Bobbito Garcia, whose also known as Kool Bob Love and DJ Cucumber Slice. He's been a Rock Steady Crew B-Boy, a top street ball player and coach, a pioneer of sneaker culture, and even an author and filmmaker, having published a book in 2003 and released the Rock Rubber 45s documentary in 2018.
While both have made seemingly endless moves within the culture, few would dispute that the duo’s most historic moment took place when Stretch hooked up with fellow hip-hop obsessed kid Bobbito at the Def Jam offices back in 1990 and convinced him to make a radio show, which introduced up-and-coming superstars like Wu-Tang Clan, Nas and The Notorious B.I.G. long before they were famous.
The story of this radio show made its way on the screens in the documentary Stretch and Bobbito: Radio That Changed Lives. Many years after the original show, the duo reunited for the podcast What's good with Stretch and Bobbito, which is praised as the underground source for stories from the dawn of hip-hop music.
Here are eight things about these two hip-hop heavyweights we learned during our in-depth conversation with them.
Bobbito and Stretch posing for the camera
Bobbito Garcia (left) and Stretch (right)© Brooklyn Wheeler/Red BullContent Pool

1. Bobbito battled Crazy Legs and was one of the original B-Boys of Rock Steady Crew

Rock Steady Crew is the most prestigious crew in the history of breaking. Crazy Legs is the president of the crew and Bobbito one of their DJs. Both are outstanding dancers.
I and Crazy Legs had a battle up rocking in Seattle that didn’t make my film ‘Rock Rubber 45’s’. I burnt ‘Legs’ in the battle. I destroyed him! His story of the battle might be different, haha, but that’s how I remember it.
Bobbito Garcia
If you go to Bobbito's Instagram @koolboblove you can find the deleted scene and check it out for yourself.

2. The Stretch & Bobbito Show broke hip-hop heavyweights such as Eminem, Ol’ Dirty Bastard, Wu-Tang and the Fugees

Definitive to the golden era of hip hop, the duo’s fusion of sharp wit, infectious passion, and remarkable ability to sniff out fresh talent not only put them on the map as hip hop pioneers but has yet to be duplicated.
"Some artists we broke, some artists we introduced to the world for the first time, some artists we played first so that other DJs like Funkmaster Flex on a much bigger station would then support them," says Stretch. "So there were different examples of us breaking artists, and there are also artists that to this day didn't get exposure outside of the show."
Nearly 350 different artists passed through the doors of the Stretch and Bobbito Show and most of them were either on their first single, a demo or unsigned. Collectively those artists to date have sold more than 300 million records.

3. They recorded everything but lost the tape of Biggie's first freestyle

Stretch and Bobbito have a big archive of freestyles from the Greatest. But on one occasion they missed to record, which led to a year-long search.
A tape that's marked Mobb Deep Freestyle
One of the legendary freestyle tapes© Bobbito Garcia
"One of us always taped the show on any given night," explains Stretch, "but one of the nights that neither of us taped for whatever reason was the night that Biggie came up. I think we just assumed at the time that someone would have a tape, but we never had a tape of it."
Stretch started a blog in 2007 where he posted things about hip-hop to attract listeners and create a forum of people that may have old tapes, in the hope of finding the Biggie tape. After two years, he gave up assuming that they'd never retrieve this recording.
But while they were making the film, Stretch and Bobbito: Radio That Changed Lives, they realised they'd never asked the one person who was in the studio that day, that really might have the tape: Biggie’s Dj, 50 Grand.
"We called him up and he said, 'Yeah sure, I’ve got the tape,'” says Stretch. "He was keeping it in a safe in his apartment in Brooklyn, so we went out there with a recorder and a digital converter and taped it that night."
Check it out below:

4. Bobbito wrote the first-ever article about sneaker culture for The Source magazine in 1991

When sneakers became popular in the scene, and people started recognising them as a lifestyle item, Bobbito was approached to write about sneaker culture.
"You know people customised sneakers before me, so I don’t want to take the credit for being a pioneer, but I certainly was recognised for it in a way that people before me doing it hadn’t been," says Bobbito.
"Because I was going downtown and because of who I was rolling with, hanging out with hip-hop legends, working at Def Jam and that scene, that sort of notoriety led me to be asked to write The Source article. I just happened to be in the right place at the right time and made that right moves, and the right effort to make things happen."
Bobbito did multiple brand collabs: the 50th Anniversary for Puma suede, the Nike Air Force One 25th anniversary in 2007 and a 35th Superstar Anniversary for Adidas in 2005.
Bobbito and Ramon shaking hands
Bobbito and actor Ramon Rodriguez meet on the basketball court© Imani Vidal

5. The Stretch & Bobbito Show was massively hyped across a wide range of fans

The show gained in popularity organically, but some unexpected support came from the inmates of federal prisons.
"When we first started on the radio, the most significant word of mouth that was initially spread came from the incarcerated population of the tri-state area," says Stretch, referring to the prisons in New York, New Jersey and Connecticut.
"The show played the 1am to 5am slot on Thursday nights – when people are either sleeping, or they’re going out. Some people stumbled across the show by mistake, got super excited and talked about it, but for the guys that were locked up in places like Rikers Island, the FM radios they were allowed in the cells where their only access to the outside world in real time."
Within weeks of debuting the show, Bobbito and Stretch received hundreds of letters from listeners – a quarter of which were from inmates.

6. Bobbito left stories out of his movie because he wanted to tell them the right way

Bobbito didn't talk about MF Doom and his album Operation:Doomsday because he wanted Doom to tell the story himself, which didn't work out.
"Doom and my time at Fondle ‘Em Records – that’s deep for me," says Bobbito. Doom and my time at Fondle ‘Em Records ... that’s deep for me. There’s a lot I wanted to include in Rock Rubber 45s that didn’t make it into the film.
"Had I had been able to interview Doom? That would have been different because I think Doom’s story is intense and emotional."

7. Bobbito has released a film called Doin It In the Park: Pick-Up Basketball NYC

Bobbito also made a movie about basketball and connected it to sneaker culture.
"When people ask me which of the three has made the biggest impact, for sure basketball would be the first primary influence," he says. "I just wanted to be the best ball player – and being in New York and being a hip-hop head and a stylish one at that, it was natural."
In Bobbito's opinion, sneaker culture wouldn’t exist without basketball. "It wasn’t going to happen with football cleats or cricket shoes," he says.
"Basketball was like the perfect primer to set it all up. They mixed with hip-hop and took it to a whole new level. If you look at all the iconic hip-hop shoes, they're all basketball shoes. Superstars, Chuck Taylors, Air Force Ones, even Pro-Keds. Running shoes come later, but in the beginning, it was all basketball shoes first."

8. They had no clue of the legends they were fronting or becoming

The pair say they could never know what was going to unfold for the people they met. "I was just living in the moment," says Stretch. "Living and breathing, and just doing what I loved to do – and that’s still what I'm doing now."
"We had absolutely no metrics in the '90s whatsoever for our show, and also you have to remember we were dealing with teenagers with no record contracts," adds Bobbito. "There was no way to know what the show was going to become, or what the artist’s who we were putting forward we’re going to become. No way!
"When I started writing a hip-hop column for VIBE, that’s when I had the sense that this was some big shit. When I started the sneaker shop, there was no precedence yet, so I didn't know that my idea for the sneaker boutique was going to become this huge force in the industry starting in the 2000s. Growing up, I don’t think any of us expected or could have imagined street ball and playground basketball would get to the place it has. But I’m not surprised by the huge global impact all three have had. They each have a powerful and passionate culture in their own right and because of each other."
Here's what Stretch has to say on the subject: "Looking back, I can’t say we knew anything. We were on long enough to see the cycles of artists coming through from unsigned to becoming really important and internationally recognised artists, and that happened many many times within the span of our show for sure.
"What I can say is being on the radio in the ’90s was some of the most fun I've had in my whole life. It’s easy to idealise things looking back, and even though the show was a lot of work, there were many moments, even years that it was just pure fun."
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