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Bobbito, formerly known as Bobbito the Barber and currently as DJ Cucumber Slice, has made significant contributions to the underground hip-hop scene over the years. In 1990, he partnered with DJ Stretch Armstrong to launch the renowned "Stretch Armstrong & Bobbito Radio Show" on WKCR-NY 89.9 FM, also known as 89 Tek-Nine. This show provided a platform for numerous underground artists and introduced future stars to listeners in New York City. In 1998, the show was recognized as the "best Hip Hop radio show of all time" by Source Magazine. Following Stretch's departure in 1998, the program was rebranded as "The C.M. Famalam Program," featuring DJ Lord Sear alongside Bobbito until 2002. Additionally, Bobbito founded and operated the influential underground hip-hop label "Fondle Em' Records" from 1995 to 2001 and ran "Bobbito's Footwork," a record, clothing, and sneaker store, from 1996 to 2000.