Although showing no interest in acting as a child, Rosario was discovered on her front porch step by photographer Larry Clark and Harmony Korine, where Harmony lauded her with praise as being perfect for a part he had written in his screenplay that would become the 1995 controversial film Kids. Since then Dawson's films have varied; ranging from independent films, to highly successful big budget blockbusters, and large scale box office bombs. Among her successes are Rent, He Got Game, opposite professional basketball player Ray Allen, and Men in Black II, which saw her sharing the screen with Will Smith and Tommy Lee Jones; among her failures are The Adventures of Pluto Nash (which was nominated for six Golden Raspberry Awards) and the live-action film adaptation of Josie and the Pussycats.

In 1999, Dawson teamed up with Prince for the re-release of his 1980s hit "1999". The new remixed version featured the actress in an introductory voice over, offering commentary on the stat