As April 20 approached, I thought it seemed appropriate to pen a brief homage to the myriad musical paeans to pot. After all, from ganja to wacky tobacky, weed, dope, and grass have been a continual source of inspiration for artists across many genres. Often, they sing its praises. But sometimes, they caution against its darker sides. It can be used for humor or escape. It can be, and often is, political. It can be, though not as often, spiritual.
Then, I thought printing such a piece on April 20 felt far too paint-by-numbers for such an outside-the-lines topic. Those in the know have led me to believe that marijuana use can lead to procrastination. Thus, my 4/20 essay is ready to go by early June.
I also decided that simply listing a bunch of songs, as engaging as it may be, couldn’t do the topic justice. There are too many sub-genres with their own style and point-of-view. So I took inspiration from Shel Silverstein, author of one of the legendary songs in the world of weed. Better known as a writer of children’s books, Silverstein was also a prolific songwriter. He wrote several major hits for Dr. Hook, as well as Johnny Cash’s iconic “Boy Named Sue.” He also wrote pot songs.
The Americana team of weed songs
“I Got Stoned and I Missed It” came from Freakin’ at the Freaker’s Ball in 1972. A few years later, he adapted his epic poem “The Smoke-Off” on his 1978 album Songs and Stories. It told the story of a showdown between Pearly Sweetcake – who could smoke more joints than anyone on the planet, and the Calistoga Kid, who could roll them faster than the speed of light. Silverstein put the two of them together in front of a sell-out crowd in Yankee Stadium to see if she could smoke ‘em faster than he could roll ‘em. I won’t spoil the outcome.
I will not be including “The Smoke-Off” on the following lists. Just remember it as inspiration. What I have decided to do here is put together teams in order to determine which genre has the best songs about pot. I’m choosing a dozen songs from four different genres. Each team has a captain. (Well, I don’t know if the last one does yet, but I'm still deciding on that.) Each team has a batting order. We’ll examine one team each day, and at the end of it all, you, the reader, can choose which you like best.
Up first, we have Americana – with the affiliate genres of folk, bluegrass, and outlaw country.
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.”
“WEED WITH WILLIE” by Toby Keith and Scotty Emerick (2003)
Well, it didn’t take long to get Willie, now did it? Keith and Emerick released a live version of this story song as a bonus track from his 2003 album Shock’n Y’all.” It recalls a trip to Willie’s Honeysuckle Rose tour bus – a trip that many a musician has made. Keith says he has heard many of them echo the refrain of this song: “I’ll never smoke weed with Willie again.” And, SPOILER ALERT, that vow would be broken on many occasions.
“ROLL ME UP AND SMOKE ME WHEN I DIE” by Willie Nelson (2012)
I’m only going to choose one song from any artist for this list (Eric Church fans, be warned). So, this is his only entry. But what a glorious song it is. From his 2012 album Heroes, it is an unapologetically feel-good tribute. He does a solo version, but the best version is the upbeat collab he performs with outlaw brother Kris Kristofferson, country giant Jamey Johnson, and one more vocalist who I hesitate to mention because he is on another team. He is actually the captain of one of the other teams.
Then again, fans of weed will tell you that when used by responsible adults in the right frame of mind, recreational use can lead to amazing fellowship between men. Perhaps that’s what Willie has been trying to tell us.
“SMOKE A LITTLE SMOKE” by Eric Church (2008)
Church has been one of many artists who seem to have inherited Willie’s passion for promoting the positive attributes of marijuana. “Smoke a Little Smoke” isn’t the only time he has sung about the subject. But it was the first major public proclamation. He has since explained that “smoke” is a bit of a misstatement. He prefers edibles, which are not as hard on his vocal cords.
“DOWN HOME DISPENSARY” by Molly Tuttle (2023)
Bluegrass artists are no strangers to weed and wine. Molly Tuttle has multiple tracks on her Grammy-winning album City of Gold, covering assorted angles on the subject of grass. This is her most overtly political. But it’s not angry politics. It’s just a happy, upbeat plea for politicians to stop living in the distant past and make it legal. This is a theme that one of the other teams will focus on a lot more. For Molly, it’s pretty simple. “Hello legislator, the voters have spoken – There’s too much politickin’ and not enough tokin’.”
"WORRY B GONE” by Chris Stapleton (2020)
Is this a murderer’s row, or what? Batting seventh, you’ve got one of the biggest stars in modern country doing a song by Guy Clark, one of the most celebrated songwriters from the world of the outlaw. A classic blues rocker states its intentions right up front. “Oh, gimme just one more puff of that worry be gone.” The song takes down virtually everyone and everything that is causing trouble in the world, and then – you can probably guess the solution.
“KEEP OFF THE GRASS” by Todd Snider (2000)
Snider, one of the wittiest performers in American music today, tells a great story about how he created this song, essentially stealing it from Bob Dylan. He didn’t release it for years because he thought such thievery was somehow improper. Once he began touring more and hanging out with other musicians, he realized that it was just SOP.
Snider makes drug references in many of his songs, going so far as self-identifying as a “tree-huggin’, peace-lovin’, pot-smokin’, porn-watchin’, lazy-ass hippie” in one of his most beloved songs. But I’m using this sly complaint about how society keeps telling him what he can and can’t do – complete with a double entendre in the title.
“I ALMOST STOLE SOME WEED FROM TODD SNIDER” by John Craigie (2013)
And thus, the legacy continues. The way Willie inspired others, Snider now inspires Craigie to write just about the funniest song you will ever hear on the subject. Told in true Snider fashion – I mean, Craigie is a virtual sound-alike to begin with – this song has the added bonus of referencing several of the performers already discussed, such as John Prine and Kris Kristofferson. Snider, in a show of good fellowship, has given his approval to the larceny.
“SEEDS AND STEMS (AGAIN)” by Commander Cody (1971)
From the debut album by Commander Cody and His Lost Planet Airmen, most known for the band’s biggest hit, “Hot Rod Lincoln,” comes this somber song about a love gone wrong. Whereas many of the songs here have championed weed and put it in a positive light, this one uses it as a metaphor for deprivation.
Of course, it is all done with a touch of overly dramatic tongue-in-cheekiness, as the final verse suggests – “Well, my dog died just yesterday and left me all alone – The finance company dropped by today and repossessed my home – But that’s just a drop in the bucket, gal, compared to losing you – And I’m down to seeds and stems again too.”
“HOLDING” by John Hartford (1971)
The third song on our list from 1971. I wonder if that means anything. “Holding” is a brief piece of happy-go-lucky scat bluegrass, which sounds happy but really explores the disaster that occurs when no one you know has got anything to light up.
But, in the can-do attitude associated with the topic at hand, Hartford ends his two-minute ditty on a note of optimism… “But if you ain’t got none, and if I ain’t got none – Let’s go find some other head – Find out if they’re holding, get down and start rolling – And smoke what they’re holding instead.” Talk about your rose-colored glasses.
“THE WEED SMOKER’S BLUES” by Sad Daddy (2016)
Sad Daddy’s unique American brand of neo-swing bluegrass is in full flower on their 2016 album Fresh Catch. I’m closing this lineup with their song because I fear I may have been a tad too flippant with the bulk of this list. The catchy, finger-snapping rhythm of this song does not hide the fact that, unlike the other songs mentioned here, this is a genuine warning about how too much weed can cause absolute devastation. Great song. Important reminder.
And that ends our first list. Tune back shortly for team number 2. (“Shortly,” as anyone conversant on this topic surely knows, is a relative term.)