Ryan began his political career by serving on the Kankakee County Board from 1968 to 1973 (his brother Tom J. Ryan was Mayor of Kankakee for 20 years from 1965 to 1985). He was then elected to the Illinois House of Representatives, where he served from 1973 to 1983, including two terms as Minority Leader and one term as Speaker. He then spent 20 years in statewide office, as Lieutenant Governor under Governor James R. Thompson (1983–91), Secretary of State from 1991 to 1999, and as governor from 1999 to 2003. During his first term as Secretary of State, then–State Treasurer Pat Quinn was publicly critical of Ryan. Specifically, he drew attention to special vanity license plates that Ryan's office provided for clout-heavy motorists. This rivalry led Quinn in a failed bid to challenge Ryan in the 1994 general election for Secretary of State.