And if you see me tonight
With an illegal smile
It don’t cost very much
And it lasts a long while
Won’t you please tell the man
I didn’t kill anyone
I was just trying to have me some fun.
— John Prine 1971
John Prine insisted that “Illegal Smile” is not about cannabis.
Of course, it is. What else could it be about?
“I have to confess, the song was not about smokin’ dope,” Prine, who died at age 73 of complications from COVID-19, told Performing Songwriter magazine. “It was more about how, ever since I was a child, I had this view of the world where I can find myself smiling at stuff nobody else was smiling at. But it was such a good anthem for dope smokers that I didn’t want to stop every time I played it and make a disclaimer.”
I believe Prine, who was honest to a fault during interviews. But for so many of us, getting the debut album and hearing the opening track, “Illegal Smile” was about pot.
It was a different time. The Controlled Substances Act, the legislation that jump-started the Drug War and put cannabis in the same Schedule-One category as heroin, came into effect on May 1, 1971. John Prine was released on June 1, exactly a month later. It was a period when, for some reason, everybody seemed to be looking for the “new Bob Dylan.” It’s true that Prine played acoustic guitar and had a raspy voice, but beyond that, like so many others stuck with the “new Dylan” tag, there was little resemblance. Yet an early Atlantic Records promotional piece included a photo and headline: “In the tradition of Brando, Dean and Dylan.”
John Prine wasn’t a hit. In spring of 1972, Frank Kresen and I began following the local heroes in a burgeoning scene—Prine, Steve Goodman, Bonnie Koloc and Fred and Ed Holstein—and trying to make a living on Chicago stages. We failed, at least in part because there was no way I would write anything remotely as good as “Angel from Montgomery,” “Paradise” or “Illegal Smile.” But Prine’s songs were ripe for the taking—lyrically vivacious and simple to reproduce because they were mostly written around the three chords (G, C and D) that every folksinger knows.
“Illegal” was an anthem. To so many Americans, the Drug War already seemed ridiculous. Spending millions of dollars to jail people for something lawyer and civil-rights advocate Judd Golden, who joined NORML at its inception, once explained: “Life is a series of encounters. Cannabis makes the next one just a little more fun.”
“Illegal Smile,” whatever its origin, suggests the same thing.
Prine continued to release albums, and while they never really translated into sales, individual songs were being picked up by people like Bonnie Raitt, who did sell lots of records. I once called him a “word-of-mouth” artist. “Between word of mouth and anybody who works as a solo at a Ramada Inn lounge or wherever they end up,” he told me, “even if they’re supposed to do covers of Top 40 stuff, they end up doing two or three of my songs ’cause they’re made for one person with a guitar, and they tell people who wrote the song.”
I never burned one with John Prine. But like many involved in the music industry back in the late 1970s and early 1980s, I felt a connection. He was popular in the Denver/Boulder area from the beginning. “I started out in Boulder when Tulagi was still open. I used to play Marvelous Marv’s in Denver—zebra-skin on the walls with waitresses dressed like they were cave girls,” he told me in 1985 from a Dallas hotel.
“Me and George Carlin played there, and George said it was like the Playboy Club—called it the Beehives and the Bowties. For some reason there was a lot of Chicago people who settled in Boulder and around Colorado Springs. It seemed they’d migrate west, go to Boulder and just stay around.” He referenced the Hotel Boulderado in an early song, “Come Back to Us Barbara Lewis (Hare Krishna Beauregard).”
Prine left the major labels, and with Al Bunetta and Dan Einstein started Oh Boy Records in 1986. He became even more accessible—he gave interviews to anyone who asked—and he was soooo much fun to talk with: “There ain’t no middle man. People are giving their money to me,” he explained about starting his own label. “Instead of getting 12 cents per record, you get between four and six dollars. So about 50,000 records would be gold on Oh Boy. And the president of the record label comes to see me at every concert. I’m going to send everybody a picture of the boat I’m going to buy with all their money.” You could see him smiling even over the phone.
And, as with almost everything about Prine, there was no ill will. “It’s not like I got anything against them. If I sat down and wrote something that sounded like something I heard on the radio last night or that sounded like Prince or something, I might go to one of the companies,” he explained. “I don’t hold it against them. It’s just that what I’m doing ain’t got nothing to do with selling blue jeans and cars.”
As he got older, more and more people caught on, and over the last couple of decades songwriters have (rightly) praised him to the sky. It’s been really heartening to read the tributes posted by so many of them in the last few days.
“’Angel from Montgomery’ opens with the line, ’I am an old woman/named after my mother.’ I remember hearing his 1971 recording of this song for the first time and thinking, ‘No, you’re not,’” wrote Jason Isbell in a New York Times column. “Then a light bulb went on, and I realized that songwriting allows you to be anybody you want to be, so long as you get the details right. John always got the details right. If the artist’s job is to hold a mirror up to society, John had the cleanest mirror of anyone I have ever known. Sometimes it seemed like he had a window, and he would climb right through.”
That’s about it. That mirror was spotless. The light bulb Isbell mentions went on for so many others after hearing Prine. But it’s his essential kindness and complete lack of ego I will remember. I treasure the hour Billie and I spent with him just shooting the shit after a show at the Uptown Theater in KC in 1982—the first time I ever heard mention of Phil Spector and guns. Or listening to the late guitarist Michael Hedges rave on about Prine’s genius as we headed to a show on the CU campus in the early ’90s. Or after a set he played in the early ’80s with a full band—the best show I ever heard him do. When I asked afterwards why he didn’t use a band all the time, he looked at me, smiled and said, “I can’t afford it.” Duh.
“Illegal Smile” is the first song on his first album. The last song on his final record, a bookend to his career, is titled “When I Get to Heaven.” It’s a wonderful, eternally charming piece in which Prine claims he’s going to forgive “everybody that done me any harm,” which is in keeping with his attitude from the beginning (and good advice for anyone, right?)
He also says he’s going to shake God’s hand, get a cocktail made of vodka and ginger ale and “smoke a cigarette that’s nine miles long.” Prine was a heavy smoker, which no doubt contributed to his death, and I don’t want to make light of that, or of his family’s grief. But if there is an after-life, I sincerely hope he’s still “smiling at stuff nobody else is smiling at,” drinking that vodka and ginger and sucking on that butt right now. He deserves every inch and then some.
Leland Rucker has been addicted to music for as long as he can remember. He spent 30 years as a music and pop culture critic, reporter and editor for dozens of publications. Today he writes mostly about cannabis and has been known for the occasional illegal smile.