Country Singer served in the US Navy from 1993-1999 and was an ESWS-qualified Electronic Warfare Technician aboard an FFG-7 class frigate homeported in San Diego. During this time he deployed once to the Western Pacific for CARAT-95/MALABAR and twice to Central and South America in support of Counter Narcotics Operations.

Within two weeks of leaving the Navy he enlisted in the California Army National Guard as a 97B. After tiring of life in Southern California, he returned to his native Tennessee and subsequently rejoined the Army National Guard, and has served there since 2005 as a 98J, an 11B, and currently as a 35H.