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.