12 righteous weed songs from the world of Americana

Captain – The Red-Headed Stranger

Americana and its associate members may have a certain advantage when it comes to this particular type of music. Folk was a protest movement, and Outlaw Country was a protest movement. They weren’t merely comfortable discussing taboo subjects; they were celebrated for it.

Even when they weren’t protesting anything, Americana and bluegrass tended to focus on the personal stories of people living far from big-city politics. People who might like to light up in the privacy of their homes after a hard day at work. Of course, such an unfussy demonstration of personal freedom is an enormously political statement, but the songs didn’t feel the need to belabor the point.

Whether political or personal, Americana songs of weed tended to feature more humor than other genres. That is not to say they couldn’t explore darker areas of drug abuse. But the best of them tended to use humor as an entry point, even if the appraisal turned dark.

And they had one of the greatest champions of recreational smoking as their spiritual leader. Sometimes known as the Ambassador to Weedville, Willie Nelson just turned 91 and is burning as bright as ever. He will be well-represented in the following list.

“ILLEGAL SMILE” by John Prine (1971)

But we’ll save Willie for a bit later. We have a dynamite lead-off hitter in John Prine, who wrote about the downtrodden on his self-titled debut album in 1971 with more compassion than most songwriters could muster in an entire lifetime. Though that debut would feature a heart-breaking song about the tragedy of drug addiction (“Sam Stone”), he opens the album with a lighter touch.

Back in the day, Prine would never say that “Illegal Smile” was about the wonders of marijuana. It would have been professional suicide to do so. He attributed his illegal smile to his off-center way of seeing the world. True enough – but “fortunately – I have the key – to escape reality” told a different story. At the very least, that illegal smile was being aided and abetted by external substances.

“BURN ONE WITH JOHN PRINE” by Kacey Musgraves (unreleased)

About 35 years after Prine’s debut, he wasn’t as concerned about keeping his weed use from going public. Kacey Musgraves, one of many artists who were inspired by and helped along by Prine, wrote him this touching, funny tribute, which she performed live for him back in 2015.

Prine introduces the song by recalling a chance meeting with Musgraves shortly after she arrived in Nashville and then asked her to sing the song she wrote as a result of said meeting. Roger Harvey recorded a nice version in 2019, but if possible, find Kacey’s live performance. “I ain’t good at being careful – I just say what’s on my mind – Like my idea of heaven – Is to burn one with John Prine.”