Milam began his career in Seattle working as an actor before moving to Chicago and getting work as an assistant director at the Victory Gardens, Remains, and Steppenwolf Theatre Companies. He directed the world premiere production of Killer Joe at the Next Theatre, which subsequently moved to the Traverse Theatre for the Edinburgh Festival, where it won a Fringe First Award, before transferring to London. A subsequent production of Lett's next play, Bug, transferred to The Gate Theatre in London and Milam began working on both sides of the Atlantic.
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