The Greatest Oldies Music

Country

LEE ANN WOMACK DIDN’T COME TO THE STADIUM TO ENTERTAIN; SHE CAME TO TESTIFY TO THE DEPTH OF ALAN JACKSON’S LEGACY. While other stars lined up to perform the radio-ready anthems that filled the rafters, Womack bypassed the easy hits. She chose “Between the Devil and Me”—a song that strips away the shine and stares directly at the wreckage of a life caught between redemption and ruin. For Lee Ann, that choice was a statement of purpose. Just as she stood against the tide in the late 90s to keep the steel guitar and the ache of “real” country music alive, she used Alan’s farewell to remind us why he mattered. She wasn’t interested in the fireworks; she was interested in the honesty that occurs when the music stops and the trouble begins. In a night celebrating a legend, she chose to honor the dark, messy, and deeply human heart of the genre. She didn’t just sing a song for Alan Jackson—she sang a song for the kind of country music he fought to preserve: the kind that doesn’t just sound good, but cuts deep.

LEE ANN WOMACK DID NOT COME TO ALAN JACKSON’S FINAL SHOW TO SING THE EASY HIT. SHE CHOSE “BETWEEN THE DEVIL AND ME.”

By the time Lee Ann Womack walked onto the Nissan Stadium stage, Alan Jackson’s last full-length concert had already become a night of giants.

George Strait had come.

Carrie Underwood had come.

Luke Combs.

Miranda Lambert.

Eric Church.

Lainey Wilson.

A stadium full of fans had gathered to honor the man who spent more than three decades keeping fiddle, steel  guitar, small-town stories, and old-country heartbreak alive on the radio.

Lee Ann did not choose “Chattahoochee.”

She did not choose “Gone Country.”

She chose “Between the Devil and Me.”

It Was Not The Easy Song

“Between the Devil and Me” was one of Alan Jackson’s darker records.

A song about a man caught between the life he knows is right and the trouble he cannot stop reaching for.

When Alan released it in 1997, it went to No. 2 on the country chart.

It did not need fireworks.

It did not need a giant singalong chorus built for a stadium.

It needed a singer who knew how to let a hard line sit in the room.

Lee Ann Womack knew how to do that.

She Came From The Same Side Of Country Music

When country music was getting brighter and smoother in the late 1990s, Lee Ann came in carrying something older.

Fiddle.

Steel guitar.

Women who were angry.

Ashamed.

Lonely.

Stubborn.

Women who did not need heartbreak to be pretty before they could sing about it.

Then “I Hope You Dance” made her a crossover star.

But she never let that song become the whole story.

She Kept Choosing The Harder Songs

In 2005, Lee Ann made There’s More Where That Came From.

It was full of the kind of country hurt Nashville had started treating like old furniture.

Cheating songs.

Crying steel guitar.

Women who did not solve their lives before the final chorus.

It won CMA Album of the Year because it did not try to make traditional country sound fashionable.

It made it sound necessary.

That is why “Between the Devil and Me” made sense for Alan Jackson’s final show.

She Was Singing More Than A Deep Cut

Lee Ann was not simply picking an unusual Alan Jackson song.

She was choosing one of the records that explained why he mattered.

Not just because he gave people summer songs and fishing songs and family songs.

But because he still believed  country music could look directly at temptation, regret, damage, and the mess a person makes of his own life.

That was always part of Alan Jackson’s gift.

He could make a whole stadium smile.

Then turn around and make one quiet line feel like a confession.

What That Moment Really Left Behind

The deepest part of this story is not only that Lee Ann Womack sang at Alan Jackson’s farewell.

It is what she chose to sing.

A stadium full of country stars.

A man nearing the end of the road.

One dark song from 1997.

A singer who had spent her own career protecting the same old-country ache.

And a tribute that did not reach for the easiest memory.

Lee Ann Womack sang “Between the Devil and Me” because Alan Jackson was never only the man who made country music feel good.

He was also the man who kept it honest when the song had nowhere easy to go.

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