Osmond found success in musical theater through much of the 1990s when he starred as Joseph in "Joseph and the Amazing Technicolor Dreamcoat" for over 2,000 performances beginning in July 1992 in the Elgin Theatre's Toronto production. He relocated to Chicago where Joseph played for 16 months in 1993–94. During his performances for the musical, he suffered from social anxiety disorder, which caused him to feel light-headed and extremely nervous during his performances. In 1997, Osmond left his starring role in the tour to participate with his family in the cast of the Hill Cumorah Pageant. Creator Andrew Lloyd Webber later chose Osmond to star in the 1999 film version.