[citation needed] In 1984, he moved to New York, where he appeared in commercials for McDonald's, AT&T, and Levi's, eventually becoming the spokesman for Publisher's Clearing House.
[citation needed] This would become the subject of his second memoir, Master of Ceremonies: A True Story of Love, Murder, Roller Skates & Chippendales.
He became a regular on the HBO/CTW show Encyclopedia, where he played characters ranging from George Washington to Napoleon Bonaparte to Leif Erikson.
He began writing books in 2001, with the publication of Satchel Sez: The World, Wit & Wisdom of Leroy Sawtchel Paige (Random House).
Sterry 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.