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Stiefel was born in Tyrone, PA to his parents Alan and Mimi. He also has an older sister named Erin.
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Stiefel began taking ballet lessons when he was eight at a studio in Madison, Wisconsin. It was called the Monona Academy of Dance. He became involved because of his sister.
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Stiefel joined the corps de ballet of New York City Ballet at age sixteen.
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Stiefel took a leave of absence from the New York City Ballet to perform with the Zurich Ballet in Switzerland.
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After a year in Switzerland, Stiefel returned to the New York City Ballet as a soloist and became a principal dancer with the company until he ended his tenure two years later.
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Stiefel joined ABT as a principal dancer, which is where he also retired from fifteen years later.
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Stiefel made his screen debut in the film "Center Stage" directed by Nicholas Hytner.
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Stiefel created a four-week workshop for aspiring dance students to have the opportunity to train and perform with professional ballet dancers.
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Stiefel had his first appearance with the Australian Ballet in Nureyev's staging of Don Quixote. He took on the role of Basilio for its Melbourne and Sydney seasons.
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Stiefel and a few others were the recipients of the Dance Magazine Award for his role as a leader in the dance field.
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Stiefel also starred in "Center Stage: Turn It Up."
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Stiefel proposed to long time girlfriend, Gillian Murphy, who was also a principal dancer with ABT.
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In November 2010 Stiefel was announced as the next director of the Royal New Zealand Ballet and took that position less than a year later.
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Stiefel gave his final performance as an ABT principal dancer at the Metropolitan Opera House. He is said to be the "most advanced male dancer in the world."
