A gymnast while in his youth, Stea began dancing seriously while he was at college. A year after his first dance job, he was hired by Madonna as a dance captain, dancer and assistant choreographer on her 1990 Blond Ambition Tour. Stea appeared several times in the documentary "Truth or Dare", which was made about the tour. Along with Oliver Crumes and Gabriel Trupin who appeared in the documentary, Stea sued Madonna in the Los Angeles Superior Court for fraud and invasion of privacy, claiming that she had lied about the film and that they were not paid for their appearance in it. According to Stea, "Madonna told me she had a crush on me when we first started. And I thought she hated me.." Leslie C. Dunn and Nancy A. Jones in their book "Embodied Voices: Representing Female Vocality in Western Culture" (1997) argue that Stea and the other two dancers viewed Madonna as a motherly figure, a "mommy dearest".