A crooked little love song that reminds us real devotion is rarely polished—but it endures anyway.
When John Prine released In Spite of Ourselves in 1999, it did not arrive with the thunder of a chart-dominating hit. Instead, it slipped gently into the world—much like many of Prine’s finest songs—carrying humor, humility, and a startling truth about love that only grows clearer with time. The song served as the title track of In Spite of Ourselves, an album of classic country duets released in September 1999. The record reached No. 21 on the Billboard Top Country Albums chart, a respectable position that reflected the quiet but loyal following Prine had cultivated over decades.
Yet chart numbers never fully explained Prine’s influence. What mattered more was the way his songs found permanent homes in people’s memories.
“In Spite of Ourselves” is perhaps one of the most charmingly unpolished love songs ever written. The original recording paired Prine with Iris DeMent, whose bright, slightly mischievous voice created the perfect counterbalance to Prine’s relaxed, conversational delivery. Together they sang a duet that sounded less like a performance and more like two lifelong companions teasing each other across the kitchen table.
The song’s lyrics are full of playful imperfections. The couple described in the song bickers, drinks too much, watches television, and occasionally behaves like teenagers. Yet the chorus delivers the gentle revelation at the heart of the song: somehow, despite all their flaws and stubborn habits, they remain deeply devoted.
It is love in spite of ourselves.
Prine once explained that he wanted the song to capture the feeling of couples who had spent years together—people who understood that romance does not always look glamorous. Instead, it survives in shared routines, private jokes, and the quiet knowledge that someone knows every one of your shortcomings and stays anyway.
That honesty is what has allowed the song to live far beyond its original release.
In later years, a particularly moving interpretation emerged through the voices of Jason Isbell and Amanda Shires. Unlike many cover versions that attempt to reshape a classic, their performances leaned into the song’s warmth and humor. The fact that Isbell and Shires are partners in real life added an extra layer of authenticity. When they sing the teasing lines back and forth, it feels less like a tribute and more like a continuation of the story Prine began.
Their version gained particular attention in the years surrounding Prine’s passing in 2020. During live shows and intimate performances, the couple often delivered the song with a mixture of laughter and tenderness—honoring not only the songwriter but also the spirit of long relationships that weather time’s unpredictable turns.
Listening to “In Spite of Ourselves” today, one hears more than a witty country duet. One hears a philosophy of love that runs counter to the polished fairy tales often celebrated in popular music.
Prine’s characters are messy.
They argue.
They make mistakes.
They watch too much television and occasionally say the wrong thing.
And still, the bond holds.
That idea sits at the core of Prine’s songwriting legacy. Unlike many artists who sought grand poetic gestures, he specialized in the beauty of ordinary lives. A Prine song could begin with a joke and end with something quietly profound, leaving the listener smiling and thinking at the same time.
“In Spite of Ourselves” embodies that rare balance perfectly. The melody carries the easy sway of traditional country music, echoing the classic duet era of George Jones and Tammy Wynette, while the lyrics reveal Prine’s unmistakable storytelling voice—sharp, compassionate, and gently amused by human nature.
Over the years, the song has become a favorite at concerts, weddings, and informal jam sessions. It is the kind of tune that people sing together rather than simply listen to. Perhaps that is why it has endured so gracefully: it belongs not only to its writer, but to everyone who recognizes themselves in its crooked, affectionate portrait of love.
And long after its modest chart debut in 1999, the song continues to travel—passed from one pair of voices to another, each new performance quietly reaffirming the same truth.
Love rarely arrives perfectly arranged.
But sometimes, in spite of ourselves, it lasts.
Oldies Songs