The Stretch & Bobbito Show: A Tale of Two Underground Pioneers

By: Adam Wells

It’s a Thursday evening on March 16th, 1995. You just came home from your job, school, or maybe even your grandma’s house after a family dinner. It’s around 8PM, but you’re mentally preparing to stay up past 1AM to tune into the Stretch & Bobbito Show on 89.9 WKCR FM; you might stay up until the show ends at 5AM, or maybe as long as possible to record the show on your Sony cassette player. The Roots and Smif-n-Wessun are special guests on the show that night, but you won’t know that until you tune in. Every week, you look forward to the show to get your fix of Hip-Hop that premiers new records, demos and exclusive freestyles. While the Stretch & Bobbito Show started for the love of Hip-Hop, the amount of 90’s Hip-Hop artistry that the show enabled to proliferate can never be replicated.


Stretch Armstrong and Bobbito Garcia both grew up in New York City, surrounded by a blooming Hip-Hop culture. While Stretch grew up on the border of the Upper East Side and Harlem, Bobbito grew up around the Upper West Side, living early-on in the Douglass Projects. Stretch was first exposed to Hip-Hop while going to Manhattan Country Day School, with classmates from a diverse array of neighborhoods that would repeat the lyrics to the the classic Sugarhill Gang record “Rapper’s Delight”. He eventually became interested in becoming a DJ in his senior year of high school, inspired by Brooklyn legend DJ Clark Kent. Bobbito attended Wesleyan University, playing on the varsity basketball team. Although he was cut from the squad a few times, he was able to play for Puerto Rico in his early 20’s. He eventually worked as an A&R representative at Def Jam Records, where he formally met Stretch.

Bobbito knew of Stretch before meeting him from seeing him DJ at gigs that Bobbito would attend. Once they met at Def Jam, the two clicked immediately and eventually became roommates. While hanging out, they would talk about wanting to do their own Hip-Hop radio show, where Stretch could DJ and Bobbito could be the host.


Although Stretch was initially denied having his own HipHop show at WKCR before his freshman year of attending Columbia University, the show eventually started in October of 1990, broadcasting on WKCR from 1AM to 5AM every Thursday night. Although Bobbito had no prior experience as a host, he had a natural knack for hosting with a dignified voice and a sparkling sense of humor. Stretch rarely let his voice be heard, sticking strictly to the music; many people were surprised that he was a white DJ once his face became unveiled due to the show’s growing popularity.

Quickly gaining a cult following, the Stretch & Bobbito Show was very different from the mainstream stations that played Hip-Hop at the time. The show was very free-form, which allowed for more leeway while broadcasting. Much of the Hip-Hop that was played on the show came from artists that sent their demos to the show; Stretch & Bobbito would listen to these demos, and play them if they sounded good. In an interview from 1994, Stretch proclaimed,

“…As a DJ, I’m extremely hard on the music, and won’t play anything if it’s all right. I mean, I hope that every record I play is a great record. If your shit ain’t happening, I’m not going to play it, and that’s the bottom line… I try to keep the integrity at an all-time high”. 

Since WKCR was a college radio station, they did not need to censor any of the lyrics from the music played. This meant that the listener would hear these deep cuts in their full, raw form. The show would bring many different guests from all over New York City. While the artists chosen had clear talent, some of the artists that went on the show would grow to be Hip-Hop legends. In 1993, a young Nas went on the show to spit verses from his then forthcoming album “Illmatic,” which many consider to be the best Hip-Hop album of all-time. In 1995, Jay-Z and Big L did the famous “10 Minute Freestyle,” which has generated over 6 million views on YouTube and is considered one of the best freestyles ever. While Jay-Z is now a Hip-Hop icon and entrepreneur, Big L was murdered four years later, creating one of the biggest “What if?” debates within the Hip-Hop community. Various artists that have headlined the Brooklyn Hip-Hop Festival in past years, including an artist from this years’ line-up, came up rapping on the show, such as DMX, Mobb Deep, Common, Talib Kweli, Raekwon, Ghostface Killah, Redman, Busta Rhymes, Brand Nubian, Q-Tip, KRS-One, Pete Rock, Buckshot, Smif-n-Wessun, and many more. 

Source: Screenshot from “Stretch & Bobbito: Radio That Changed Lives

For some, the Stretch & Bobbito Show was more than just a Hip-Hop radio station. Many fans wrote letters to the WKCR address with positive anecdotes regarding how much the show helped their lives. Some of these folks that wrote letters were prison inmates who listened to the show in their prison cells. According to Bobbito in an interview with Red Bull Music Academy,

“Our first audience was the incarcerated population of the Tri-State area. Within the second show we were getting letters from Rikers. People that would say, “Yo, you’re making my bid easier ’cause I have something to look forward to every Thursday night.” These are like dudes from Rahway Prison, life sentences. I would read their shout-outs and all of a sudden, their friends and their families could have a dialogue with their people inside”. 

In the recently-released documentary entitled “Stretch & Bobbito: Radio That Changed Lives”, Bobbito goes into detail about a Puerto Rican fan who looked up to Bobbito as a role model since he was a Puerto Rican who was able to graduate college, didn’t smoke or drink, and played basketball. This generated a realization that as a radio personality, Bobbito had a deep responsibility as a public figure that actually affected people in a positive way. Another resonant 


story in the documentary highlights someone who called the show after he had shot someone, seeking advice from Bobbito as someone who he could trust for help during this scary, spine-chilling situation. One guest on the documentary explained that during his time in the Army during the Gulf War in the early 1990’s, a Stretch & Bobbito Show tape that his brother sent him circulated around his unit, causing everyone to listen and enjoy it. After a very rough day where soldiers were injured and killed, he was able to go back to his room and zone out all of the horrors of war by listening to the tape.

Eventually, the show got so popular that in 1996, the two were offered to do a two-hour set on Hot-97 during a day-time slot every Sunday. While this meant that there would be more money and a wider audience, many of the cult fans were upset that this “underground secret” had gone commercial. They would continue to do their normal Thursday WKCR slot, but a lot of underground fans at the time did not have high opinions of commercial radio stations like Hot 97, and didn’t want to see the show get commercially exploited. A fan with the moniker Black Cloud wrote a letter to the station when they started on Hot 97 that was shown in the documentary, complaining,

“My anger was once again surfaced last night (Thursday, February 8th) when you announced that you were going to premier all of these new tracks on Hot 97. Personally I don’t think that it’s fair that all of these [people] that think that they are “hip hop heads” don’t know the first thing regarding the art of djaying, the struggle for those who work as independents (let alone support them) as well as their lack of interest in hip hop to such an extent that they are too lazy to stay up until 5am” 

Unfortunately, their additional show on Hot 97 in 1996 was the beginning of the demise of the show. Tension grew as the show became more popular. By the late-1990’s, the changes that Hip-Hop had gone through sonically made Stretch less passionate about finding and playing new Hip-Hop. The last official show was on Sunday, January 10th, 1999 on Hot 97 with Black Moon.


 The legacy that the show has left in Hip-Hop history is insurmountable. In 1998, Source Magazine voted the show as the greatest Hip-Hop show of all-time. The total record sales of artists that went on the show combined adds up to over 300 million dollars. The amount Hip-Hop legends that went on the show is awe-aspiring, especially considering that the majority of the show was done on a college radio platform. Stretch & Bobbito are a headlining act at Brooklyn Hip-Hop Festival 2017, which could not have came at a better time; in April of 2017, it was announced that Stretch & Bobbito will come back on the air to do their show on NPR, starting in the summer of 2017. This new version of the show will be in a podcast format, discussing art music, politics and sports. This year, many of the cult followers of Stretch & Bobbito can come out to the Brooklyn Hip-Hop Festival 2017 to see the rebirth of this distinguished duo.

Stretch & Bobbito: Radio That Changed Lives Trailer

Stretch & Bobbito Website