An Ode to Imperfect Love: How John Prine and Iris DeMent Found Heaven in a Messy Duet

This classic duet is a hilarious, heartfelt testament to enduring love that flourishes despite—and because of—all of life’s charming imperfections.

There are certain songs that, the minute they drift from the speakers, don’t just fill a room—they fill a lifetime. For those of us who came up listening to the wry wit and profound empathy of an artist like John Prine, the 1999 title track, “In Spite of Ourselves,” featuring Iris DeMent, is one such track. It arrived at the turn of the millennium like a gentle, knowing wink, reminding us that the best love stories are usually the messiest ones, full of bad habits, questionable tastes, and a whole lot of enduring affection.

The song’s origins are as beautifully homespun as its melody. John Prine was in recovery from a serious bout with throat cancer, a period of uncertainty where he wasn’t sure if his voice, that magnificent, sandpaper-and-honey instrument, would ever fully return. During this time, the actor and filmmaker Billy Bob Thornton asked Prine to write a song for the end credits of his movie, Daddy and Them. This request became the catalyst for one of the most beloved duets in modern folk and Americana history. “In Spite of Ourselves” was the very first piece of original writing Prine completed after his cancer battle, a true sign of his creative spirit rekindling.

The song was the cornerstone of the album, also titled “In Spite of Ourselves,” released on September 28, 1999, on Prine’s independent label, Oh Boy Records. The album, which was mostly a collection of classic country duets with a rotating cast of incredible female singers like Lucinda Williams and Emmylou Harris, found moderate but respectable commercial success, especially considering Prine was never a Billboard darling. The album peaked at No. 21 on the U.S. Billboard Top Country Albums chart and No. 197 on the all-genre Billboard 200, but its cultural impact, spearheaded by the title track, far outpaced its chart position.

What sets “In Spite of Ourselves” apart is its unflinching, yet deeply affectionate, honesty. It’s structured as a playful “he said, she said” between two partners who clearly drive each other absolutely mad. Prine’s character is the beer-drinking, “wacked-out weirdo” whose corny jokes are endured by a woman who is “pure as the driven snow,” except for her fondness for “convict movies” that “make her horny.” DeMent, in turn, sings about his less-than-stellar looks and habits, even confessing she “caught him once and he was sniffin’ my undies.” The humor is direct, unvarnished, and instantly relatable—a picture of a long marriage where all the little secrets and flaws are not just known, but embraced.

The true heart of the song, however, lies in its soaring, optimistic chorus: “In spite of ourselves / We’ll end up a-sittin’ on a rainbow / Against all odds / Honey, we’re the big door prize.” It’s a powerful acknowledgment that genuine, lasting love isn’t about finding a perfect partner; it’s about two imperfect people choosing, day after day, to love each other in spite of their flaws. It speaks to the quiet, enduring miracle of connection that many of us who have walked this life for a while recognize—the simple, magnificent fact of finding someone who not only tolerates your baggage but helps you carry it. It’s why, despite its cheeky lyrics, the song has become an unconventional, beloved choice for a wedding dance, proving that a dose of reality can make a romantic gesture all the more profound. It is quintessential John Prine: finding the extraordinary in the ordinary, the sacred in the mundane, and an eternity of truth in a good, earthy laugh.

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