At 14, Ron Palillo (born Ronald Gabriel Paolillo) started his own summer theater in Cheshire, Connecticut. His parents, Gabriel and Carmel Paolillo, were surprised when the summer theater actually made money. After graduating from high school, Ron went to the University of Connecticut at Storrs, where he majored in drama. He appeared in many school plays in college. After graduation, Ron got a job with a touring company which performed in Shakespearean plays. He claimed to have received invaluable drama training during that tour, acting in Shakespearean masterpieces like "Macbeth", "The Taming of the Shrew" and "A Midsummer Night's Dream".

After his Shakespearean tour, Ron became a member of a repertory company in Miami, Florida. Shortly after arriving in New York, Ron got a role in the off-Broadway success "Hot l Baltimore." He stayed with the show for over a year. Because of his work in "Hot L Baltimore". Ron was given a lead role in a musical special, "The Last Sweet Days of Isaac", on television. After Isaac, he once again went on tour and appeared with Mickey Rooney in "A Midsummer Night's Dream" and with Jan Sterling in a serious play, "Summer Brave". He has two brothers and a sister. His elder brother, Richard Paolillo, is an eye surgeon, his brother Robert Paolillo, is a salesman and his sister Ann, became a teacher.