Raoul Cunningham began his civil rights activities when he joined the Louisville NAACP Youth Council in 1957 at the age of 14.
He experienced his first direct nonviolent action campaign with the Youth Council on Christmas Day 1959 when the Brown Theater would not admit blacks with mail-ordered tickets to see the all-black movie Porgy and Bess.
As college students across the south began to sit in and protest to end segregation, there was a growing interest to tackle segregation in Louisville. With no black college in Louisville, Cunningham and others had to convince the adult NAACP Branch that high school students could fill the void. In January of 1961, the NAACP Youth Council and the Congress of Racial Equality (CORE) started demonstrating in downtown Louisville. Raoul was the first of the many students arrested. The demonstrations along with negotiations, an economic boycott, and voter participation ended segregation in Louisville.
As a Howard University student, Cunningham continued his civil rights activities by affiliating with the college chapter of the NAACP and Student Non-Violent Coordination Committee. He organized the university's first Young Democratic Club and became a volunteer working for the 1963 March on Washington.
When he returned to Louisville, Cunningham managed the successful campaign to elect Georgia Davis Powers as the first African American and the first woman to the Kentucky Senate
He served as Senior Assistant for Legislation and Community Relations for U. S. Senator Walter D. Huddleston in Washington for twelve years – working on a variety of issues including civil rights legislation, immigration issues, and legislation, school desegregation issues and legislation, community action legislation, and the Martin Luther King Holiday Bill.
He was appointed by two governors as Deputy Commissioner of the Department of Personnel where he directed the Affirmative Action Plan for the state.
In 2000, Raoul joined the National Staff of the NAACP in the Voter Empowerment Program as a state and regional coordinator. In 2002 he was named National Deputy Director of the Program.
Raoul Cunningham was elected President of the Louisville Branch NAACP in 2004 and President of the Kentucky State Conference of the NAACP in 2014. He serves on the Kentucky Advisory Committee for Help America Vote (HAVA) and was inducted into the Kentucky Civil Rights Hall of Fame in 2003. He was awarded the 2006 Dr. Martin Luther King, Jr. Freedom Award by the city of Louisville and in 2015 was awarded the Honorary Doctor of Humanities Degree from Simmons College of Kentucky.