Although born in South Africa, Tsidi Ibrahim will always be a New Yorker by heart. The daughter of two jazz musicians, Ibrahim learned an appreciation for all genres of music at an early age giving her a good foundation on becoming a writer and producer. Then known as What? What?, she was recruited by a rapper named Ocean, who formed Natural Resource in the mid-90s. In 1997, they founded their own record label, Makin' Records, and released the single, "Negro League Baseball", which became an underground hip-hop classic. The group broke up due to creative differences, but the exposure worked towards her benefit. She changed her name to Jean Grae and appeared on a number of songs with artists such as Herbaliser, High & Mighty, the Mumia 911 Project, the Hip-Hop For Respect project, Mr. Len, Da Beatminerz and Masta Ace.

Pursuing new boundaries for hip-hop, Mr. Len brought forth a new vision for old school rap. One of the founders of the independent hip-hop trio Company Flow, Mr. Len remained with the crew for more than six years. By 1999, however, following its disbanding, Len decided to begin working on his own. After two years of constant work, including the single "This Morning," created with the Juggaknots, and "What the Fuck?," with Mr. Live, Mr. Len finally released his debut full-length album. Pity the Fool: Experiments in Therapy Behind the Mask of Music While Handing Out Dummys, issued in 2001, featured guest appearances by Jean Grae, Juggaknots, and Mass Influence.