INTRODUCTION

Sometimes the best musical partnerships begin in the most unexpected ways.

For John Prine and Iris DeMent, it started with a recording, an old red Ford, and a voice that immediately stopped Prine in his tracks.

In the 1990s, record producer Jim Rooney introduced the two artists. Rooney shared Iris DeMent’s first record with Prine, who listened to the tape for the first time while sitting inside his old red Ford.

What happened next became part of the story of their friendship.

Prine was so moved by what he heard that he reportedly became emotional—so emotional that he was said to have “cried into his pork chops.”

It wasn’t simply admiration for another singer.

Prine recognized something special in DeMent’s voice.

There was honesty in it. There was humor. There was toughness. And beneath all of that was a kind of emotional vulnerability that made even simple words sound deeply personal.

Not long afterward, Prine invited DeMent to open for him on tour.

That decision would lead to one of the most memorable musical friendships of their careers.

The two artists came from different generations and had different musical personalities, but they shared something important: neither needed to pretend.

Their songs could be funny without becoming shallow, heartbreaking without becoming overly dramatic, and ordinary without losing their beauty.

And that connection would become especially important when Prine began writing one of his most recognizable songs.

THE SONG WAS WRITTEN WITH IRIS IN MIND

When John Prine wrote In Spite of Ourselves, he already knew who he wanted beside him.

Iris DeMent.

The song was unusual in many ways.

Rather than presenting love as perfect or glamorous, Prine wrote about two people who know each other’s flaws, habits, contradictions, and imperfections—and somehow love each other anyway.

It was funny.

It was affectionate.

It was slightly mischievous.

And it was filled with lines that required a singer who could deliver them with just the right combination of sincerity and attitude.

Prine knew DeMent could do exactly that.

As he later explained in an interview with KPBS, he had Iris’s voice in his mind while writing the song.

He imagined the way she could approach the character.

He knew she could be “a little sassy.”

More importantly, he believed she could push back against the male character in the song.

That dynamic was essential.

In Spite of Ourselves works because it feels like a conversation between two people who have been together long enough to know exactly how ridiculous the other person can be.

They tease each other.

They criticize each other.

They expose each other’s quirks.

But underneath the jokes is something much warmer.

They love each other.

That was precisely why Prine wanted DeMent.

So he called her.

And instead of simply sending her the song and waiting for an answer, Prine warned her about what she was about to hear.

There were some questionable lines.

Some things she might not want to sing.

He told her to listen and decide for herself.

If she didn’t want to do it, that was perfectly fine.

Then Prine waited.

And waited.

And waited.

THREE WEEKS OF SILENCE

According to Prine’s recollection, Iris DeMent didn’t respond for three weeks.

Nothing.

No phone call.

No answer.

No decision.

For three weeks, Prine apparently had no idea whether she had rejected the song or simply hadn’t decided what to do with it.

Eventually, he called her himself.

“Iris?”

“Yes?”

“Well?”

And then came the answer.

“Not while my mother’s alive!”

It was classic Iris DeMent.

The joke perfectly captured the personality Prine admired in her.

She understood exactly what kind of song it was.

She knew some of the lyrics might make her mother uncomfortable.

And she wasn’t going to pretend otherwise.

But the story didn’t end there.

Because despite her initial reaction, DeMent eventually agreed to sing the song.

And that decision gave In Spite of Ourselves the chemistry Prine had imagined from the beginning.

WHY THEIR VOICES WORKED SO WELL TOGETHER

There was something almost magical about the contrast between John Prine and Iris DeMent.

Prine’s voice had a weathered, conversational quality.

He could sound like he was telling a story across a kitchen table rather than performing on a stage.

DeMent brought a different energy.

Her voice could be warm and vulnerable, but it also carried an unmistakable edge.

That edge mattered.

In Spite of Ourselves needed someone who could meet Prine’s humor instead of simply following it.

DeMent didn’t sound like a guest vocalist who had been brought in to decorate the song.

She sounded like the other half of the relationship.

She challenged him.

She answered him.

She made the song feel like two real people talking.

And that is one reason the recording has remained so memorable.

The song isn’t really about a perfect couple.

It is about an imperfect couple.

Two people who know exactly what is wrong with each other and somehow keep choosing one another anyway.

That idea is both hilarious and deeply romantic.

A DIFFERENT KIND OF LOVE SONG

At first glance, In Spite of Ourselves can sound like a novelty song.

The lyrics are funny.

The characters are eccentric.

The situations are intentionally awkward.

But listen more closely and something deeper appears.

The song understands that long-term love isn’t always poetic.

Sometimes love is knowing someone’s strangest habits.

Sometimes it is remembering the things that drive you crazy.

Sometimes it is laughing at the same ridiculous argument you’ve had a hundred times.

And sometimes it is simply staying.

Prine understood that kind of love better than most songwriters.

He didn’t need to describe romance as perfection.

He could find romance in imperfection.

That made the song feel unusually human.

And DeMent’s presence made that humanity even stronger.

Her delivery gave the female character a personality of her own.

She wasn’t simply reacting to Prine.

She was holding her own.

That balance made the duet unforgettable.

THE FRIENDSHIP BEHIND THE RECORDING

What makes the story even more meaningful is that Prine and DeMent already had a genuine friendship before recording the song.

Their relationship wasn’t created in a studio.

It grew through touring, conversation, music, and mutual respect.

Prine had become an admirer of DeMent from the moment he heard her early recording.

He didn’t simply hear a talented newcomer.

He heard an artist whose voice had something difficult to manufacture: authenticity.

DeMent, meanwhile, became part of Prine’s musical world.

Opening for an established songwriter like Prine could have been intimidating, but their shared sense of humor and musical sensibility helped create a natural connection.

By the time In Spite of Ourselves came along, Prine already knew what DeMent could bring to the song.

He knew her personality.

He knew her voice.

He knew her timing.

And he knew she wasn’t afraid to tell him exactly what she thought.

Even if that meant telling him she wouldn’t sing the song while her mother was still alive.

That honesty was part of the magic.

MORE THAN A FUNNY STORY

The story of DeMent almost refusing the song is funny.

But it also reveals something important about John Prine.

He didn’t write songs in isolation from the people around him.

He wrote with voices in mind.

He understood that the right singer could transform a song.

When he imagined In Spite of Ourselves, he didn’t just hear a melody.

He heard Iris DeMent.

He imagined her attitude.

He imagined her timing.

He imagined the way she would deliver the lines.

And he was right.

Her performance became an essential part of the song’s identity.

Without her, the recording would have been different.

With her, it became a genuine musical conversation.

THE BEAUTY OF TWO IMPERFECT PEOPLE

Perhaps the greatest reason the song continues to connect with listeners is that it doesn’t promise a perfect kind of love.

It celebrates the opposite.

It says, in effect, that two imperfect people can build something meaningful together.

They can annoy each other.

They can embarrass each other.

They can laugh at each other.

They can know every flaw and still remain deeply connected.

That is a much more believable kind of romance.

And perhaps that is why Prine knew DeMent was the right person for it.

She understood the humor.

She understood the humanity.

And most importantly, she understood that beneath all the jokes was genuine affection.

When John Prine first heard Iris DeMent’s voice in his old red Ford, he couldn’t have known exactly where that moment would lead.

He couldn’t have known that the young singer whose recording moved him so deeply would eventually become the voice he imagined while writing one of his most beloved duets.

And he certainly couldn’t have known that when he finally called her about the song, her response would become one of the funniest stories surrounding its creation.

“Not while my mother’s alive!”

She eventually did it anyway.

And perhaps that is the perfect ending.

Because In Spite of Ourselves was never supposed to be a perfect love song.

It was supposed to be honest.

Funny.

A little outrageous.

A little uncomfortable.

And completely human.

Just like the friendship between John Prine and Iris DeMent.

Sometimes the most unforgettable songs aren’t born from perfect circumstances.

Sometimes they begin with a songwriter hearing a remarkable voice in an old car.

Sometimes they require three weeks of silence.

And sometimes, before a singer agrees to make musical history, she simply has to make sure her mother won’t be listening.

In the end, Iris DeMent said yes.

And John Prine got exactly what he had imagined when he wrote the song:

two wonderfully imperfect voices, singing about two wonderfully imperfect people who, somehow, couldn’t help loving each other.