Skylar was born in Whitestone, New York and quickly moved to Knoxville, Tennessee at the ripe young age of one. He was surrounded by sports and masculinity until he stumbled into the theatre in an eighth grade production of Willy Wonka Jr. From then on, he lived as the supported artistic black sheep of the family.

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As a theatre graduate from Middle Tennessee State University, Skylar is a Chicago based theatre artist. In order to achieve a long term goal of artistic direction he has sought to understand the roles of his collaborators and study all areas of theatre to serve as the most effective leader he can. 

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Since moving to Chicago, Skylar has been peddling away at gig after gig working with Raven, Theatre, Writers Theatre, Improv Playhouse, Midsommer Flight, Underscore Theatre Company, Mudlark Theatre, and Haven Theatre.