Earle first encountered Van Zandt in a Houston dive when he was only 17.
"I knew who he was, and he was stinking drunk," Earle says. "It was pretty irritating actually."
Earle knew who he had been dealing with. "It's a bummer to get heckled by your hero, but it was also embarrassing that I didn't know 'Wabash Cannonball.'"
But when Earle responded with "Mr. Mudd & Mr. Gold," a song penned by Van Zandt, that was end of the jousting.
"It sort of established our ground rules for our relationships which were that we would probably like the only moments with real intimacy when there was no audience at all. When there was an audience, we would abuse the fuck out of each other."
Earle later played bass with Guy Clark, another hero. Eventually, Earle earned his own turn.
Earle, 42, has been putting out records since 1983 with his major label debut on Sony. He eventually was dropped and ended up with a long stint on MCA where he gained most of his acclaim starting off with his label debut, "Guitar Town" in 1986. He was part of the new renaissance of country at the same time as Dwight Yoakam and Lyle Lovett were taking country different places than the pop-oriented sound which afflicted the genre earlier in the '80's.
Earle mixed gritty vocals, a keenly sharp songwriting style often telling stories within his songs and edgy music where guitars sometimes reigned supreme though within a country context.
He faced the difficulty of being labelled as too rock for country and too country for rock. While his second album, "Exit O" was certainly country oriented, his 1988 follow-up, "Copperhead Road" was more rock influenced with country stations generally steering clear.
Earle's career spiralled downhill as he continued using drugs. MCA eventually dropped Earle, who developed a reputation as being extremely difficult to work with.
And a headstrong attitude in the go-along, get-along city of Nashville didn't earn him many friends there either. "I sort of slipped in through the cracks and had a number one country album. A lot of people made damn sure it didn't happen again."
Earle eventually found himself in jail for almost a year due to heroin possession. With his life in turmoil, Earle managed to put out "Train a Comin'," a very spare sounding disc receiving much critical praise.
Despite his problems, he maintained a core following.
While certainly affable and in good spirits throughout the interview, Earle still is not one to mince words. And that includes his attitudes towards the music coming out of Nashville these days.
"I haven't heard anything the least bit encouraging that I can think of off hand," Earle says. "In fairness, I don't listen to country radio very much. "
Sometimes Earle says he will sit on the porch outside his record company with a young country singer with a cowboy sauntering boy, telling him that he was a great influence on his work. Earle sometimes will listen to the end result.
"It makes me not want to sit on the porch for a long time. I hear their music and hope to God I didn't have anything to do with it." One artist he did clearly influence was Texan Jack Ingram, whose recent album Earle produced.
Earle, who plans to hit the road in the States in January, hopes changes are on the horizon. "I am hopeful because sales have plummeted, which means they're going to do something. They're panicking so they have to do something. That's what happened when "Guitar Town" came out. That shit nearly caught on. It scared the hell out of everybody."
In addition to his own career, Earle spends much time on his E Squared label, the home of The V-Roys and Cheri Knight.
The record company was almost an afterthought. "We made 'I Feel Alright' basically on Jack's (Emerson)," Earle says. "We started to protect ourselves legally. That really wasn't a conscious decision to start anything to do anything. It sort of happened organically. Now, it's this. I'm sitting here trying to make like it's exactly like I wanted it."
Earle made no such claims about "El Corazon."
And he's not complaining.