He was the music director and house band member at the New York drag club Squeezebox, where he perfomed with stars like Debbie Harry, Lene Lovich and Joey Ramone, as well as various drag queens. Trask composed the music and lyrics for the off-Broadway stage musical and 2001 film Hedwig and the Angry Inch, about a transexual rock star named Hedwig. In the show, Trask's real-life band Cheater performed as Hedwig's band "The Angry Inch". He received an Obie Award for the play and a Grammy award nomination for the movie.

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