David started in show business as a standup comedian in the early 80s, opening for acts ranging from Milton Berle to Robin Williams to Dana Carvey. As an actor, he appeared on Fresh Prince of Bel Air, Sister Sister, and the HBO/CTW show Encyclopedia, where he played characters ranging from George Washington and Napoleon Bonaparte to Leif Erikson and a leech enthusiast. He wwrote the movie script Army Dog for Disney. His one-man show, based on his memoir Chicken, debuted internationally at the Edinburgh fringe Festival. He is also an activist, a teacher, and a book doctor. He has taught at Stanford, University of New Orleans, University of Amsterdam, and ran a writing workshop for at risk teenagers and survivors of the sex industry for the United States Department of Justice in Washington DC in 2005. Sterry co-edited the Soft Skull anthology Hos, Hookers, Call Girls and Rant Boys: Professionals Writing on Life, Love, Money and Sex was featured on the front page of the Sunday New York Times Book Review on August 23, 2009. In the 1980s he was Emcee at Chippendales Male Strip Club in New York , the subject of Sterry's second memoir, Master of Ceremonies .He performs his show Sex Worker Literati all over the country. It consists of people from the sex industry reading and performing their work, and is based on an article which featured him, written by Alex Kuczynski in the New York Times. He is a regular contributor to the Huffington Post.

Sterry's 2002 memoir, Chicken: Self-Portrait of a Young Man for Rent, described by The New York Times as a "studiously wild souvenier" , details his experiences as a teenage hustler in 1970s Hollywood.

This same text was turned into a play called The Source of All The Evil by Hugh Allison, who directed it in April 2006.

David Henry Sterry has been featured in The New York Times, The Times, The Sunday Times, The Los Angeles Times, The Washington Post, New York Magazine, Penthouse. Details Magazine, nthWORD, BBC Radio, and NPR's Morning Edition, Weekend Edition and Talk of the Nation. Chicken was published by Judith Regan for HarperCollins in 2002, and by Canongate in the UK in April, 2003, and it has been translated into many languages.