Esten was born in Pittsburgh, Pennsylvania but moved to Alexandria, Virginia at age 9.[2] He attended T.C. Williams High School and the College of William and Mary, where he was a brother of Theta Delta Chi. At William and Mary, he was the lead vocalist in the band N'est Pas from 1985 until 1988, one year after his graduation. After graduating from college and marrying his wife, Esten moved to the United Kingdom to make his theatrical debut, winning massive acclaim for his title role in the musical Buddy in the early 1990's.