Stashwick was born in Chicago and raised in the suburbs right outside of the city. As a child, he always loved making people laugh, and he aspired to one day perform at Chicago's famous The Second City. Soon after graduating from Illinois State University with a degree in Theatre, he began performing at several local improvisational theaters, and his dream came true when he was hired in 1992 to tour nationally with The Second City.Following productions at The Second City Detroit and The Second City Northwest, he moved to New York. There, he formed a company of improvisers and began staging the underground critically acclaimed "Burn Manhattan" all over the city. Other performers included Kate Walsh, Jeremy Piven and Spencer Kayden.Aside from his work in improvisational theatre, Stashwick worked for several years in late 1997 through Spring 2000 on "Late Night With Conan O'Brien," performing as part of their rotating stable of comedy actors.Work in television and film ultimately drew him