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Guillermo Diaz first came to the attention of the film industry in Party Girl, with his comically conceived portrayal of a rookie Club DJ, whose carefully organized record collection is subjected to a Dewey Decimal system overhaul by his well-intentioned roommate, played by Parker Posey.

Next, in a complete about face, he won critical acclaim for his performance in Stonewall, which showcased him as the Drag Queen LaMiranda, the narrator in a film about the events leading up to the riot at the Stonewall Bar in New York in 1969.

In Lilli Taylor's Girls Town, Guillermo becomes its most visible male presence when he dramatically lectures his girlfriend, attacking her unfeminine-like behavior as a charter member of a hardened clique of high school girls.

In I'm Not Rappaport, he plays a vicious teenage skateboarding extortionist to Walter Mathau's and Ossie Davis' victimized but contentious old men. In Gregg Araki's Nowhere, he portrayed the concerned friend to James Duval's junkie. He then worked as Elizabeth Rodriguez's love interest in I Think I Do.

In his first studio film, High School High, for Tri-Star, Guillermo took a turn as the bumbling villain to John Lovitz's blundering hero.

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