Jean Grae

By her early teens, Grae had begun to hang out in New York's West Village, home to musicians, poets, and emcees. Grae recalled on her Web site that there were "beats everywhere," giving rise to some of rap's most respected performers, including Mos Def and Talib Kweli. In the early 1990s, Grae formed rap group Ground Zero and changed her name to What? What?. She left in 1996 to join Natural Resource. The group's self-produced 12-inch single "Negro League Baseball" went to number one on the college radio charts. The group also launched the record label Makin' Records and Grae produced tracks for local artists such as Pumpkinhead.

After Natural Resource broke up in 1999, Grae was determined to pursue a music career. "I wanted to start over and establish myself as a solo artist, and pretty much just as a grown woman," she told Eye Weekly. However Grae would not go solo just yet. Instead she earned the nickname "cameo queen." "I threw myself into any studio that I could get into for the next couple of years, doing appearances whenever asked," she wrote on her Web site. In 2001 she recorded three tracks for the album Pity the Fool by Mr. Len. Though a commercial flop, the album was critically acclaimed. It was also a turning point for Grae. "Len's album gave me the push to stop waiting for that perfect song in my mind and just put myself out there," she wrote on her Web site.

During the years of appearing on other people's albums, Grae earned praise for inserting uniquely female perspectives into the gritty realm of testosterone-driven rap. "She was a protective lover on Masta Ace's 'Hold U'; a covert assassin on Immortal Technique's 'The Illest'; a chillingly rendered molestation victim turned psychopathic schoolyard killer in Mr. Len's epic 'Taco Day,'" wrote a reviewer for the Minneapolis/St. Paul City Pages. "With these characters, Grae demonstrated her ability to tell stories male MCs couldn't, lending a voice to the heavier elements of the female psyche that hip hop rarely ventured into."