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.

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. 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. Soon after, Herrington was NSFW films and appearing on mainstream TV programs such as Love Connection and the Ricki Lake talk show. In 2002, Herrington said the adult film industry helped him to understand his bisexuality. In 2016, he responded to a Twitter comment identifying him as homosexual by stating that he was straight.

Herrington gained fame in Japan as an Internet meme, after a clip from one of his videos, Workout: Muscle Fantasies 3, was posted on Niconico, a Japanese video sharing website, on August 10, 2007. Thousands of mash-up parody videos of him have been made, many of which utilize deliberate mishearings (soramimi) of lines from his films. He is affectionately called "Aniki" (兄貴, lit. older brother) among the Nico Nico Douga community, and most of his videos are deliberately mistagged with "Wrestling Series" (レスリングシリーズ, resuringu shirīzu), "Forest Fairy" (森の妖精, mori no yōsei), "Philosophy" (哲学, tetsugaku), or all three. . In 2016, he responded to a Twitter comment identifying him as homosexual by stating that he was straight.

During the evening of March 1, 2018, Herrington was involved in a car accident on California State Route 111 in Rancho Mirage. He was found trapped in the wreckage and was brought to a Palm Springs hospital, where he died the next day. News broke of his death one day later. Fans responded with hundreds of tributes across video sharing sites and message boards. One tribute video uploaded on Niconico accumulated over 80,000 views in less than one week. Services for Herrington were held at the Forest Lawn Cemetery in Cathedral City, California.