Classic Americana: John Prine's (sort of) 'Illegal Smile'
by Mike Pengra and Luke Taylor
October 17, 2025

Every Friday around 11 a.m. Central, it’s time for Classic Americana on Radio Heartland. We pull a special track from the archives or from deep in the shelves to spotlight a particular artist or song.
For this week’s Classic Americana pick, we’re honoring, somewhat belatedly, the birthdate of the great John Prine and the release of his debut album.
The Chicago-raised singer-songwriter was born October 10, 1946, and he left us a treasure trove of songs before we lost him to COVID back in 2020.
Prine’s self-titled debut album released in October 1971 on Atlantic Records. The very first track on the record is a funny little song called “Illegal Smile.” Ever since its release, the song has been embraced by marijuana users … although the “illegal” part is much less so now that 24 U.S. states (including Minnesota), and all of Canada and at least seven other countries permit recreational use of marijuana for people who are of age.
But here’s the big surprise: Prine wasn’t writing about marijuana. “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,” Prine wrote in the liner notes to his 1993 compilation album, Great Days: The John Prine Anthology.
“But it was such a good anthem for dope smokers,” Prine continued, “that I didn’t want to stop every time I played it and make a disclaimer.”
In whatever way you think of the song, it’s a delightful opening track to Prine’s debut album. And it concludes with a risible, seemingly improvised rhyming quatrain: “I’m just trying to have me some fun / Well done / Hot dog bun / My sister’s a nun.”
Certainly Prine and his many fans have enjoyed plenty of fully sanctioned smiles over that.
External Links
John Prine – official site
