Williams began her career working for WVIS in the Virgin Islands. In 1989, Williams began at urban contemporary WRKS (now WEPN-FM) in New York City as a substitute disc jockey. WRKS hired her full-time for its morning show. A year later, Williams moved to an afternoon drive-time shift, eventually winning the Billboard Award for "Best On-Air Radio Personality" in 1993. In December 1994, Emmis Broadcasting purchased WRKS and switched Williams to the company's other New York property, hip-hop formatted WQHT ("Hot 97"), as WRKS was reformatted into an urban adult contemporary outlet. She was fired from Hot 97 in 1998.
Williams was hired by a Philadelphia urban station, WUSL ("Power 99FM"). Her husband, Kevin Hunter, became her agent. She was very open about her personal life on air, discussing her miscarriages, breast enhancement surgery, and former drug addiction, and helped the station move from 14th place in the ratings to 2nd.
In 2001, Williams returned to the New York airwaves when WBLS hired her full-time for a syndicated 26 p.m. time slot. Williams' friend, MC Spice of Boston, offered his voiceover services to the show, often adding short rap verses tailored specifically for Williams' show. The New York Times stated that her "show works best when its elements confessional paired with snarkiness are conflated," and cited a 2003 interview with Whitney Houston as an example. During the highly publicized interview that "went haywire" and included "a lot of bleeped language", Williams "asked [Houston], insistently, about her drug and spending habits".