Pretty Good — a wry smile at life’s crooked road, told with tenderness and truth
There’s a certain warmth that washes over you the moment John Prine begins to sing “Pretty Good.” It’s the warmth of an old friend settling into a story — not a grand tale, not a sorrowful confession, just one of those everyday reflections that somehow say more about life than any solemn sermon ever could. Released on his landmark 1971 debut album John Prine, the song never climbed the charts, yet it has lived for decades in the quiet corners of memory, cherished by those who understand the magic of simplicity.
That debut album was a revelation. While the world was busy chasing rock anthems and electric revolutions, Prine arrived with an acoustic guitar, a poet’s heart, and a gift for turning ordinary life into unforgettable truth. “Pretty Good” sits early in that collection like a wink, a reminder that wisdom often hides beneath humor, and that a man who can laugh at the world can also see straight through it.
Written by Prine himself, the song is carried by his unmistakable storytelling — that blend of Midwestern plain-spoken charm and gentle melancholy. He sings about small misadventures, awkward choices, narrow escapes, and the strange comfort of realizing that everything turned out, well… “pretty good.” And in that phrase lies the entire spirit of John Prine: humble, human, and profoundly honest.
Behind the lighthearted tone lies a deeper story. Prine had spent his early twenties delivering mail in suburban Chicago, writing songs in the quiet hours, observing people with the kind of patience that only comes from walking the same streets day after day. His debut album — and this song in particular — reflects that time in his life: grounded, unhurried, shaped by the small wonders and small disappointments of everyday existence.
When he sings each line, there’s no attempt to impress, no flourish meant to dazzle. Instead, he offers a shrug, a grin, a soft sigh — the emotional language of someone who has lived enough to know that perfection is a myth and that surviving with your sense of humor intact is its own kind of victory. For listeners who have walked long roads themselves, that attitude feels like a comforting hand on the shoulder.
What makes “Pretty Good” so endearing is how it gently mirrors our own memories. We all have those stories — the ones that are neither tragic nor triumphant, yet somehow linger as markers of who we were. A strange encounter, a questionable choice, a moment that makes sense only years later. Prine captures that feeling with the ease of a man flipping through a well-worn scrapbook, chuckling to himself as he turns each page.
And beneath the humor lies Prine’s quiet philosophy: life doesn’t need to be spectacular to be meaningful. Sometimes the most important thing is simply that we made it through — bruised maybe, wiser hopefully — and can look back with a smile that says, “It wasn’t perfect, but it was pretty good.”
Listening to the song today, especially for those who lived through the era when Prine first strummed his way onto the scene, feels like returning to a familiar porch at dusk, the air warm, the world unhurried. His voice — gentle, worn, wonderfully human — reminds us that it’s okay to laugh at ourselves, to let go of regret, and to find beauty in the crooked paths we’ve taken.
Oldies Songs