1986–1994: Career beginnings, WQHT, and WRKS Two weeks after graduating from Northeastern, Williams began her career as a disc jockey working for the small,
calypso and
reggae-oriented
WVIS in
Frederiksted, U.S. Virgin Islands, but disliked the role because she did not learn as much about radio from her colleagues as she expected. and briefly worked overnight shifts at
WPLJ before being hired by
WRKS. Initially working as a fill-in, WRKS gave Williams a
non-compete clause and permanent morning position in May 1990 after
WBLS began poaching its employees. She joined Jeff Foxx and
Spider Webb as part of the station's "Wake-Up Club". By 1993, she was the highest-rated host in her time slot in the New York City market Williams co-hosted
American Urban Radio Networks' syndicated
Top 30 USA song countdown program in 1993 and
USA Music Magazine in 1994. By mid-1994, WRKS had suffered a ratings decline amid competition from
hip hop-oriented WQHT, which was owned by
Emmis Broadcasting. In an effort to reverse the trend, WRKS moved Williams back to mornings on September 26, 1994, where she hosted a program titled "Wendy and Company". However, Emmis purchased WRKS less than three months later and transferred Williams to WQHT, where she began hosting the evening drive time slot on December 12, 1994. As WRKS was reformatted into an
urban adult contemporary outlet geared toward older audiences, they believed Williams would better reflect WQHT's younger demographic.
1994–2001: WQHT, website, move to WUSL By this time, Williams attended parties to gain information which she would report on air in addition to reading
tabloid newspapers. Among her insinuations was that
Tupac Shakur was raped in prison, which he denied. Williams employed the term "
pinky's up" when alleging someone was gay and regularly used the slur
faggot, which she considered to be inoffensive. The station suspended Williams again in September 1997 for online comments insinuating that her colleague
Angie Martinez's boyfriend
Q-Tip was gay.