b. 28 December 1958, Brownwood, Texas, USA. As a small child Dillingham sang on stage with family members, an impromptu performance that led to his becoming a part of his sisters’ act. He was then aged eight. While in his mid-teens and still attending school, he began working with Ray Price, whom he credits as being a major influence in both his singing style and his approach to his songs and his audience. After leaving school, Dillingham joined The Louisiana Hayride and also wrote several songs in the hope of securing a recording contract. He signed a contract with MCA Records but despite a string of minor country hit singles in the early 80s, including ‘Have You Ever Loved Your Woman Today’ and ‘Honky Tonk Women Make Honky Tonk Men’, changes in the company meant that an album never appeared.
Nevertheless, Dillingham, who was by now based in Nashville, Tennessee, continued writing songs and performing whenever the opportunity arose. Over 20 years after his initial chart success, he was heard by chance by a Decca Records A&R man and another contract was offered; this time, the result was his debut album. Most of the songs on 2004’s Almost Yesterday were written or co-written by Dillingham and the album received critical praise for its honest appreciation of the more traditional elements of country music, especially that corner reserved for honky tonk.