Herrington was born in North Babylon, New York. Herrington grew up in Long Island learning karate from his father, a sensei. He had interests in boxing, wrestling and martial arts, but did not start bodybuilding until he was 24 years old, after moving to New York City.[4] Herrington began his erotic career when his then girlfriend surreptitiously submitted his nude pictures to Playgirl magazine. The photographs won him a "Real Men of the Month" contest and a $500 prize.[4] His appearance in the magazine caught the eye of famed photographer Jim French, but it was two years before Herrington posed for his first Colt calendars for French.[4] Soon after, Herrington was filming hardcore gay adult films for All Worlds Video, and appearing on mainstream TV programs such as Love Connection and the Ricki Lake talk show.[4][7] In 2002, Herrington said the adult film industry helped him to understand his bisexuality.[5] Among his starring roles is the Roman emperor in the Danish feature film HotMen CoolBoyz (2000). Herrington's scene in Conquered (2001) with Nino Bacci, Colton Ford, Blake Harper, and Jay Ross won the "Best Group Sex Scene" at the 2002 Adult Erotic Gay Video Awards ("Grabbys").[8] Occasionally, Herrington performed striptease acts at gay clubs in the United States.[9][10]