Earle began learning the guitar at the age of 11 and entered a school talent contest at age 13. He ran away from home at age 14 to search for his idol, singer-songwriter Townes Van Zandt. Earle was "rebellious" as a youngster and dropped out of school at the age of 16. He moved to Houston with his 19-year-old uncle, who was also a musician. While in Houston, Earle finally met Van Zandt.