In 1995, Wilson graduated with a B.F.A. in Drama from Carnegie Mellon University. Shortly after, in 1995, Wilson made his acting debut as an understudy in the role of Chris Scott in the national touring production of "Miss Saigon". The following year, he portrayed Billy Bigelow in the national tour of "Carousel". In 1999, he starred as Jamie Conway in the off-Broadway production of "Bright Lights, Big City", and Wilson later made his Broadway theatre debut in "The Full Monty" (2000), portraying Jerry Lukowski. For his performance in the role, he was nominated for the Tony Award for Best Actor in a Musical and the Drama Desk Award for Outstanding Actor in a Musical.