INTRODUCTION:

There is something wonderfully deceptive about The Jet Set. On the surface, it sounds like a lighthearted country song about glamorous people, expensive places, and the strange world of those who seem to live far above ordinary life. But in the hands of John Prine and Iris DeMent, the song becomes something warmer and far more revealing.

Written by Bobby Braddock, The Jet Set was the second song covered on Prine’s 1999 duet album In Spite of Ourselves, with Iris DeMent joining him at the microphone. The pairing was almost perfect: Prine’s dry, conversational wit met DeMent’s unmistakably earthy voice, creating the kind of musical chemistry that cannot be manufactured by studio polish alone.

Their version does not chase glamour. It quietly laughs at it.

That is part of what made In Spite of Ourselves such a memorable record. Instead of trying to reinvent country music, Prine returned to songs that understood human beings in all their contradictions—lonely, funny, romantic, foolish, hopeful, and sometimes completely out of their element.

And The Jet Set fits that world beautifully.

A SONG ABOUT PEOPLE WHO DON’T QUITE BELONG

Bobby Braddock had a remarkable gift for finding humor in ordinary human behavior. His songs often carried a deceptively simple surface while revealing something sharper underneath.

The Jet Set works in much the same way.

The title immediately suggests glamour. “Jet set” evokes celebrities, first-class travel, sophisticated parties, expensive clothes, and a lifestyle far removed from everyday working people. Yet the song’s real appeal comes from the contrast between that world and the people observing it.

That contrast gives the song its comic heart.

Rather than treating the jet set with complete admiration, the song looks at that glamorous universe with a knowing country-music smile. There is distance between the narrator and the people being described, but there is also curiosity. Perhaps even a little envy.

Country music has always understood that tension.

For generations, country songs have placed ordinary people beside wealth, fame, sophistication, and social status. Sometimes the rich world looks attractive. Sometimes it looks ridiculous. Often, it looks like both at once.

That ambiguity is exactly where The Jet Set finds its charm.

WHY JOHN PRINE WAS THE PERFECT INTERPRETER

By 1999, John Prine had already spent decades proving that a country song did not need grand production or dramatic vocal theatrics to leave a lasting impression.

His greatest strength was his ability to sound as though he were simply sitting across the table from you, telling a story.

That quality matters enormously in The Jet Set.

The song is not built around vocal fireworks. It depends on personality, timing, observation, and the ability to let the humor breathe. Prine understood all of those things instinctively.

His delivery could make an absurd situation feel completely believable. He could sing about disappointment without becoming sentimental, and he could find humor in human weakness without becoming cruel.

That was one of his greatest gifts.

When Prine approached older material, he rarely treated it like a museum piece. He made it feel alive again.

And on In Spite of Ourselves, that approach became especially powerful because he was not singing these songs alone.

He was sharing them with women whose voices brought entirely different emotional colors into the music.

IRIS DEMENT CHANGES THE TEMPERATURE OF THE SONG

Then comes Iris DeMent.

Her voice was never anonymous. It carried personality from the very first phrase. There was something homespun and emotionally direct about her singing, but there was also intelligence behind it.

That made her an ideal counterpart for Prine.

The magic of their duet was not that their voices sounded identical. Quite the opposite.

They sounded like two distinct people.

Prine brought his relaxed, sly, slightly mischievous presence. DeMent brought a more openly expressive quality that could make even a humorous lyric feel emotionally grounded.

Together, they created conversation.

That is perhaps the most important thing to understand about their recording of The Jet Set. It does not simply sound like two singers taking turns.

It feels like two personalities inhabiting the same little world.

That distinction is crucial.

The finest country duets often work because listeners believe the singers are reacting to one another rather than merely sharing a microphone. Prine and DeMent possessed that rare chemistry.

THE GENIUS OF IN SPITE OF OURSELVES

The 1999 album In Spite of Ourselves was built around a deceptively simple concept: John Prine revisiting classic country songs with female duet partners.

But the emotional result was much larger than the premise suggested.

Prine had always been fascinated by the strange intersection of humor and sadness. His songwriting could make people laugh at something that, underneath the joke, was painfully human.

The album embraced that philosophy.

Instead of presenting the songs as untouchable classics, Prine treated them as living pieces of country culture.

That made The Jet Set especially interesting as the second track.

It established an important part of the album’s personality early. This was not going to be a solemn exercise in nostalgia.

There would be laughter.

There would be eccentric characters.

There would be romantic disasters.

There would be people making questionable decisions and somehow remaining lovable.

Most importantly, there would be humanity.

THE WEST 54TH PERFORMANCE ADDS ANOTHER DIMENSION

The Live From Sessions at West 54th performance provides another fascinating way to appreciate the song.

Live performance changes the relationship between singer and listener. Studio recordings can be polished, carefully balanced, and constructed one element at a time. A live session exposes timing, interaction, body language, and the natural rhythm between performers.

For a song like The Jet Set, that intimacy is particularly valuable.

The humor becomes more immediate.

The pauses matter.

The expressions matter.

The chemistry matters.

And that is where Prine’s understated performance style becomes such an advantage. He never needed to oversell a joke. Often, the less he appeared to be trying, the funnier the moment became.

DeMent’s presence complements that perfectly.

Their musical conversation gives the song an almost theatrical quality without turning it into a stage performance in the exaggerated sense. It remains grounded in country storytelling.

COUNTRY MUSIC HAS ALWAYS LOVED THE OUTSIDER

Perhaps the deeper reason The Jet Set works so well is that country music has always had an affection for outsiders.

The genre is filled with characters who are looking through windows rather than walking through the front door.

People who are broke.

People who are heartbroken.

People who dream of somewhere else.

People who have tasted success and discovered that it did not solve everything.

People who laugh because crying would be too easy.

The jet set may represent everything distant from those characters, but the song does not simply create a wall between the two worlds.

Instead, it invites us to look.

And maybe to wonder.

What would it be like to live that way?

Would we actually be happier?

Would all that glamour make love easier?

Would expensive surroundings change the basic problems that follow human beings everywhere?

Those questions are never hammered home. That is what makes the song effective.

The humor leaves room for the listener to think.

WHY THE SONG STILL FEELS SO REFRESHING

Modern music can sometimes become obsessed with making everything bigger.

Bigger production.

Bigger vocals.

Bigger emotional declarations.

But The Jet Set, particularly through the personalities of John Prine and Iris DeMent, reminds us of another tradition.

Sometimes a song becomes memorable because it is small.

A clever lyric.

Two distinctive voices.

A little irony.

A little affection.

And a story about people being imperfect.

That was one of Prine’s great artistic strengths. He trusted the song.

He trusted the listener.

He understood that country music did not always need to announce its emotional meaning. Sometimes the listener could discover it gradually, underneath the laughter.

A MEMORABLE CHAPTER IN PRINE’S DUET LEGACY

Looking back at In Spite of Ourselves, it is easy to focus on the title track or the album’s broader collection of memorable collaborations.

But The Jet Set deserves attention for another reason.

It demonstrates what happened when John Prine encountered material perfectly suited to his personality and paired it with a singer as distinctive as Iris DeMent.

The result was neither a simple revival nor an attempt to imitate an earlier era.

It was a conversation between generations of country music.

Bobby Braddock’s songwriting supplied the foundation. Prine’s interpretation supplied the wit. DeMent’s presence supplied another emotional perspective. Together, they turned an amusing country song into something that feels personal.

And perhaps that is the greatest compliment that can be paid to a recording like this.

It makes an old idea feel new without pretending the past never happened.

It allows humor and nostalgia to coexist.

Most of all, it reminds us why country music has survived so many changes: because underneath the clothes, the cars, the fame, the money, and the changing fashions, country songs have always been about people.

People trying to find love.

People trying to make sense of the world.

People laughing at lives that rarely go according to plan.

And sometimes, people looking toward the glamorous world of The Jet Set and realizing that being ordinary might not be such a bad thing after all.