He rather reminds me of Boxcar Willie:

Boxcar Willie was perhaps the most successful invented character in the history of country music. With his kitschy persona and stage act -- highlighted by his amazingly accurate impersonation of a train whistle -- Willie played into the stereotype of the lovable, good-natured hobo who spent his life riding the rails and singing songs. Since his popularity had more to do with his image than his music, it makes sense that he was massively successful in England, where he personified Americana...