Meaning Behind Waylon Jennings’ Self-Aware No. 1 “I’ve Always Been Crazy”

In 1978, Waylon Jennings earned his sixth No. 1 on the Billboard Hot Country Songs chart with a very honest portrayal of himself, in his song, “I’ve Always Been Crazy.” The title track of his 1978 album, “I’ve Always Been Crazy” spent three weeks at the top of the chart.

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The song remained on the chart for 13 weeks and became one of the more revelatory songs for Jennings, who comes to terms with all his past mistakes, mishaps, regrets, and more, all linked to his drug addiction.

The Meaning: Self-Reflections and Regrets

At the start, “I’ve Always Been Crazy” is a succinct narrative of Jennings’ life on drugs, and how he never meant to intentionally hurt anyone along the way.

I’ve always been crazy, and the trouble that it’s put me through
Been busted for things that I did, and I didn’t do
I can’t say I’m proud of all of the things that I’ve done
But I can say I’ve never intentionally hurt anyone

“I wasted a lot of years,” said Jennings in a 1988 interview. “I wish a lot of things. I could have been a lot more creative. You know, I spent the last five years that I was on drugs. I withdrew completely from people. I spent more time alone, sitting in my room, with that cocaine bottle in my hand, when I could have been very creative.”

He added, “The thing I am sorry about the most is … and I don’t know if anybody’s reading this who’s a drug addict … There is something you don’t think about, but if you do think about it, if you ever have a chance to sit and think about what you’re doin’, it’s your life, you can destroy it if you want to. But look at the people around you, that care about you. Think about what it’s doin’ to them. You don’t have to destroy their lives too. And that’s what it does. I actually think it’s worse on them than it is on yourself because they have to sit and watch someone they love and care about destroy themselves. That was one of the reasons why I was able to pull out of it because I saw it on my wife Jessi’s [Jessi Colter] face.” 

Drug Use

Always honest about his drug habit, Jennings, who once lived in an apartment with Johnny Cash in Nashville, even admitted to $1,000-a-day cocaine habit, which he was eventually able to kick, cold turkey, in 1984. Prior to that, his drug of choice was pills, which he stopped taking following Elvis Presley’s death at 42 in 1997. Jennings’ heavy drug also contributed to, and exacerbated, his health problems later in life, and he died on Feb. 13, 2002, at the age of 64, from complications of diabetes.

“I wasn’t just doing a little drugs,” said Jennings. “I was doing them constantly. I’d do them until I collapsed, then I’d get up and start right doing them again. I was killing myself. I’d definitely hit bottom with it. I would never sleep. I’d stay up six or seven days or nights at a time, and I wouldn’t go home.”

He continued, “My health was bad, I had dizzy spells where I could hardly drive, I had cars strewed all over this town, because I’d get somewhere, and I’d have to leave ’em and have somebody else take me home.”

I’ve always been different with one foot over the line
Winding up somewhere one step ahead or behind
It ain’t been so easy, but I guess I shouldn’t complain
I’ve always been crazy, but it’s kept me from going insane

Cocaine Bust

A year before the release of “I’ve Always Been Crazy,” Jennings was busted by police on Aug. 23, 1977, for possession of cocaine, while he was at American Sound Studios in Nashville recording “Storms Never Last.” The song was later released on his 1980 album Music Man, which also include his famous Dukes of Hazzard theme song “Good Ol’ Boys.”

The incident left Jennings shaken, and he also recounted the incident on his I’ve Always Been Crazy track “Don’t You Think This Outlaw Bit’s Done Got Out of Hand,” which was also posthumously released under the title “Outlaw Shit” in 2008.

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