At 15, Earle ran away from home in search of his musical hero, Townes Van Zandt, a country and folk icon known for his heavy drinking (via Magnet magazine). Earle ended up in Nashville, where he worked for years before he got his big break with his song “Guitar Town” (posted on YouTube) in 1986. Earle soon had his first brush with the law. According to the Dallas Observer, he was charged with assaulting a police officer in 1987 after fighting with an off-duty officer who was working security at his New Year’s Eve show.

Unfortunately, Earle’s success only fueled his growing drug problem. He amassed an impressive guitar collection, but he ended up selling them to support his habit. As Earle explained to Magnet magazine, his need for drugs and alcohol eventually surpassed his commitment to his music. And though he wasn’t charged for some of his actions, he admitted that he carried a gun and hung around criminals. Earle even said that “I robbed a couple of drug dealers.”