Dooley's political career began with part-time positions in the village of Northwoods, where he and his family reside. Dooley was elected as an Alderman in Northwoods in 1978, and in 1983 he was elected mayor. He served as mayor until he was elected to the St. Louis County Council in 1994. He was the first African-American elected to the council, and was re-elected in 1998 and 2002. In 2000, Dooley was an unsuccessful candidate for election to Congress. He lost the Democratic primary to Lacy Clay in a race to succeed Clay's father, Bill Clay.