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Short joined at improv troupe The Second City in Toronto in 1977. Short came to public notice when the troupe produced a show for television, Second City Television or SCTV, which ran for several years in Canada, then the United States. At SCTV Short developed several characters before moving on to Saturday Night Live for the 1984–1985 season.
He had the lead role in the 1999 Broadway revival of the musical Little Me, for which he received a Tony Award and another Outer Critics Circle Award.
He is a judge on the upcoming Canadian reality show Canada's Got Talent.