In 2002, Wylie made his Broadway debut as Jack in the Tony Award-winning revival of Stephen Sondheim's musical Into the Woods. His role was meta-referenced on Gilmore Girls (2000) as having been done by his character ("Brad Langford") in that series. He also played Jack at the Ahmanson Theater production in Los Angeles. He has done regional theatre, including "Camelot" as Merlyn-Tom-Morgan, "Big River" as Huck Finn, "110 in the Shade" as Jimmy Curry, "On the Town" as Chip, "Footloose" as Willard, "Precious Sons" as Freddie Jr., "House Arrest" as Todd, and "Beauty and the Beast" as Chip. He played Leo Bloom in a regional production of the musical "The Producers" at the Gateway Playhouse.