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At the same time, the young actor had begun to land small roles in television, making appearances on The Cosby Show, Law & Order, and I'll Fly Away. He also obtained minor roles in films, including Shakedown and King of New York. His first important screen role came in 1995, when he appeared in Wayne Wang's acclaimed drama Smoke. Perrineau played Rashid Cole, a young man searching for his absent father, played by Forest Whitaker. The performance earned Perrineau an Independent Spirit Award nomination for Best Supporting Actor.
In 1996 Perrineau was cast as Mercutio in Baz Luhrmann's idiosyncratic film adaptation, William Shakespeare's Romeo + Juliet, starring Leonardo Di Caprio and Clare Danes as the star-crossed young lovers. The film included many shocking elements—including Perrineau's portrayal of Mercutio as a black drag queen. "Mercutio was just buggin' out, you know what I mean?" the actor responded when asked about the role in a SPLICEDwire interview. "He was just high, crazy, stoned. In a society where macho is the thing, for Mercutio to come out in a dress, that's ballsy. Mercutio is just off his...rocker and doesn't care. Then there was that thing about him maybe loving Romeo or not, well I guess that changes things."
Perrineau next appeared in The Edge, opposite Anthony Hopkins and Alec Baldwin. Though the role was not large, he appreciated the opportunity to work with these acclaimed actors. In 1999 Perrineau's performance in The Best Man earned him an Image Award nomination for Outstanding Supporting Actor in a Motion Picture. He went on to take increasingly prominent roles, including another drag queen (in the 2000 film Woman on Top, co-starring Penelope Cruz) and the character Link in The Matrix Reloaded and The Matrix Revolutions.
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