He was raised on a farm near Providence, Kentucky and came to Louisville at age 21 to take a job in a tobacco warehouse.

With the support of the John Henry Whallen's Democratic machine, he defeated James F. Grinstead to be elected mayor of Louisville in 1909.

Local newspapers ran stories intended to scare white voters into voting for Head, exploiting fears of the growing black community in Louisville.

After his term as mayor, he served as a delegate to the Democratic National Committee and as president of the Louisville Water Company.

He died on April 19, 1931, in Clearwater, Florida, and was buried in Cave Hill Cemetery in Louisville.