Behind the Mysterious Meaning of John Prine’s “Illegal Smile”

John Prine has been and always will be a songwriter’s songwriter. His catalog is littered with witty jokes, existential tropes, and a philosophical depth matched with a sublime simplicity. In other words, the man and all of his songs contain multitudes. And while he can be ever-so clear, he can also be ever-so confusing, and he utilized his talent for ambiguity on the song “Illegal Smile”.

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Released on his 1971 debut album, Prine’s “Illegal Smile” has remained a staple in his catalog. Despite people’s familiarity with the song, its true meaning has yet to be completely understood. Some folks associate the song with marijuana usage and the joyful effects it entails. Others believe it is a tune harping on the internal happiness or comedy one experiences when getting enthralled by their pleasant thoughts.

Of course, the song can be interpreted in any way you’d like it to be, and John Prine seemingly agreed with that notion, as he never strictly declared what the song was truly about. Although he once did make some comments surrounding the connotation of it. While they are insightfully revealing, Prine, being Prine, didn’t flash his cards.

John Prine Just Liked To Smile

John Prine was seemingly a pretty happy guy. Now, did the artist have his ups and downs, yes, of course, who doesn’t? However, Prine, being the comedically absurdist writer he was, somehow seemed to find a way to smile through it all and look at the world through a healthy yet detached lens. And in a general sense, that is the foundation of this song.

Concerning the song’s meaning, John Prine once divulged, “The song soon got a reputation for smoking marijuana, but at first that’s what it was about. I’d just be walking down the street with a kind of a half grin on my face cause my little world was fine. And I called it an “illegal smile,” per Life Of The Record.

Contrary to what that comment implies, Prine also stated, “This is a song about smiling. It’s an old song, I wrote about four years ago. Around the time I wrote it, I was writing a whole bunch of songs about death. You know, just knocking them out, one right after another, death death death death death. So I figured this might be a challenge. This is about smiling illegally because that’s as close as I could get to smiling at all right at the time.”

So, per those comments, what do you think Prine’s “Illegal Smile” is about? A gleeful internal being or a baked perspective on the world? Regardless, this conversation is a testament to Prine’s comedic and philosophical wit.

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