WKCR

In the late 1980s, DJ Stretch Armstrong was a club DJ in New York, and Bobbito worked as a Radio Show Promotions Rep for Def Jam. Armstrong had the idea to DJ his own hip hop radio show while attending Columbia University as a freshman, and recruited Bobbito to host the program. WKCR had already aired a hip hop radio show from 1986 to 1988 called "We Could Do This Show", hosted by Pete Nice from 3rd Bass and DJ Clark Kent with DJ Richie Rich filling in at times. Although Stretch and Bobbito reportedly weren't influenced by this predecessor show on their station, Bobbito has cited Pete Nice's 3rd Bass counterpart MC Serch as integral to his career trajectory.^[4]

The first episode of The Stretch Armstrong and Bobbito Show aired on October 25, 1990, from 1am to 5am, and featured guests Latee and Def Jeff. The first song played on the program was Ego Trippin' by Ultramagnetic MCs. Armstrong's connections as a club DJ, and Bobbito's connections at Def Jam, gave them access to some of their early guests like MC Serch who helped bolster the show's early reputation. The show continued to air on Thursdays from 1am to 5am on 89.9 and would become informally known as "89tec9" by the hosts and listeners.^[3]

Live freestyling became an element of the show on the second episode aired on November 8, 1990, with guests MC Serch, Two Kings in a Cipher, Kurious, and AJ Damane.^[5] From then on freestyling became an integral part of the show, and an unsigned emcee's freestyle could get them public recognition and in many instances record deals. Dante Ross, then Vice President of A&R at Elektra Records, signed Ol’ Dirty Bastard after hearing his Shimmy Shimmy Ya verses on the January 28, 1993 show. El Da Sensei and Tame One of the hip hop group Artifacts also claim to have been signed because label reps heard their freestyles on the show.^[6] Stretch and Bobbito were also able to air world premiers of songs like Nas' "It Aint Hard To Tell" which aired on October 28, 1993.^[3]

Due to the show's twilight hours time slot on WKCR Stretch and Bobbito were unaffected by the FCC's Safe Harbor law, which allowed them to air uncensored material and converse without any feeling of restriction. Lord Sear, who became a co-host of the show and served as comedic relief, took advantage of this with unabashed roasting of callers and guests, which contributed even more to the show's contrast with commercial radio.^[3] Celebrity guests like Rosie Perez, Rosario Dawson, and Quincy Jones also made appearances on the show.^[2]

As the show's popularity increased, DJ Stretch Armstrong grew uncomfortable with ownership of the show being attributed to Bobbito by fans and interviewers, and the show's name was changed to The Stretch Armstrong Show with Host Bobbito.^[3]

Hot 97

On February 11, 1996, Stretch and Bobbito began airing their show Sundays on Hot 97, the prominent commercial hip hop radio station in New York, while continuing to air late Thursdays on WKCR. The transition to Hot 97 resulted in new FCC restrictions on the hosts and guest lyricists who could no longer use profanity, which altered the show's overall vibe and created a schism in their core listenership. While the show had changed its time slot and demeanor for Hot 97, the artists who appeared on the show continued to be prominent and relevant. Guests on their Hot 97 show included DJ Premier, Black Star, De La Soul, Common, Xzibit, Noreaga, Brand Nubian, and more. Eminem and Royce da 5'9"'s October 11, 1998 appearance was on the Hot 97 Sunday show, which was considered his introduction to the New York City hip hop scene before the release of his debut LP in 1999.^[7] Stretch and Bobbito began developing creative differences, and Stretch experienced a loss of enthusiasm for contemporary hip hop from 1997 to 1998 which resulted in his frequent absence from the show, at which point Bobbito began DJing under the name DJ Cucumber Slice while hosting the show. The hosts' creative differences and ambivalence toward the work came to a head and the show eventually ended on January 10, 1999.^[2]