In the late 1980s, Berry went to Illinois to pursue a modeling career as well as acting. One of her first acting projects was a television series for local cable by Gordon Lake Productions called Chicago Force. In 1989, Berry landed the role of Emily Franklin in the short-lived ABC television series Living Dolls (a spin-off of Who's the Boss?). She went on to have a recurring role on the long running serial Knots Landing. In 1992, Berry was cast as the love interest in the video for R. Kelly's seminal single, "Honey Love".

Her breakthrough feature film role was in Spike Lee's Jungle Fever, in which she played a drug addict named Vivian. Her first co-starring role was in the 1991 film Strictly Business. In 1992, Berry portrayed a career woman who falls for Eddie Murphy in the romantic comedy Boomerang. That same year, she caught the public's attention as a headstrong biracial slave in the TV adaptation of Queen: The Story of an American Family, based on the book by Alex Haley.