Cyrus told Rolling Stone Country of their first meeting.
"I sat across the kitchen table in my house in Tennessee looking at my hero Waylon Jennings," Cyrus said. "Waylon looked at me and said, 'Son, do you know what the definition of an outlaw is?' I said, 'No, sir, what is that?' And he said, 'One who has been outlawed.' He winked and said, 'Welcome to the club.'"
Jennings introduced Cyrus to his son, Shooter's style of country music, which is a mix of rock and country. Jennings described Shooter's music as "full-fledged rock & roll, but it has southern roots".
A friendship formed between Shooter and Cyrus and they have both proven time and time again that their relationship goes beyond the music.
"The times I was probably most lost in my life, he would randomly show up," Shooter said.
Shooter was performing a series of shows in Los Angeles, and Cyrus happened to be in the audience, so of course they performed a duet together.
In this particular duet, they sang Waylon's classic song "I've Always Been Crazy" for an adoring crowd at Loaded in Hollywood, California.
The reunion got them thinking about actually recording a song together, which they did a few months later. Their song "Killing The Blues" was born, and they recorded "I've Always Been Crazy" for the B-side.
The performance that inspired the recording is a must-see for any Jennings or Cyrus fan. Shooter kicked things off with a gritty solo, and Cyrus joined in with the harmonies in the next verse.
They vibe so well together; it's as if they've been playing together for years and years.
Watch their rockin' performance below.
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