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In 1996 Macchio performed the lead role of J. Pierrepont Finch in the U. S. tour revival of the 1962 Tony Award winning musical How To Succeed In Business Without Really Trying, and received positive reviews.

Referring to his performance as a chorister in a high school production of the same musical, Macchio said, " I was known as the ' Dancing Kid ,' not that I was all that great.

But I had been dancing since the age of three, taking lessons at the June Claire School of Dance in Babylon, Long Island.