After her debut in Kids, Dawson appeared in director Spike Lee's He Got Game and the episodic "New York life" comedy Side Streets, both from 1998. With the dawn of the 21st century, the young actress began to land more mature roles, including that of an unbridled stoner in Down to You (2000) and heroine Laura Vasquez in Men in Black II (2002).
Subsequent films for Dawson include the 2005 thriller Sin City, the musical Rent (in which she plays drug-addicted exotic dancer Mimi Marquez) and Clerks II (2006).