5 Timeless Alan Jackson Songs That Aren’t “Chattahoochee”

Sure, “Chattahoochee” is a killer tune that really encapsulates all that was cool about country music in the 90s. But if we’re being honest, it’s nowhere near the best song Alan Jackson ever released. He has a downright impressive discography full of songs that will no doubt stand the test of time to be enjoyed by future generations of country fans.

These songs aren’t necessarily Alan Jackson’s biggest hits or award-winning songs. At the end of the day, chart positions and trophies aren’t what give great songs their longevity. It all boils down to how close they can get to the human experience that allows them to resonate with generations of listeners.

“Midnight in Montgomery” (Alan Jackson, Don Sampson)

There is just so much here to love. It’s a ghost story and a tribute to Hank Williams. More than that, Alan Jackson’s somber delivery over the song’s sparse arrangement captures the reverence of the moment at the center of the narrative. Then, the pedal steel ties the whole package together.

This song will continue to haunt playlists as long as stellar songwriting, immaculate steel guitar work, and ghost stories remain popular.

“Tall, Tall Trees” (George Jones, Roger Miller)

Alan Jackson’s rendition of “Tall, Tall Trees” is the result of three masters of their craft coming together for one song. George Jones and Roger Miller wrote and recorded the song decades before Jackson. Jones released it as a B-side in 1957. Miller’s rendition was an album cut on A Trip in the Country (1970).

Jackson’s cover struck the perfect balance between Miller’s Cajun-infused arrangement and Jones’ vocal delivery to create a bona fide classic. More importantly, though, he injected enough of his personality into the song to make it his own.

As long as love makes people briefly lose their grip on common sense, this heartfelt toe-tapper will remain in rotation.

“Chasin’ That Neon Rainbow” (Alan Jackson, Jim McBride)

Storytelling has long been part of what sets country music apart from other genres. Some of Alan Jackson’s best songs tell great stories. “Chasin’ That Neon Rainbow” is a perfect example of how well he spins a musical yarn.

As long as songs still inspire people to chase the dream of making it in the music business, this single from Jackson’s debut album will be relatable. “Chasin’ That Neon Rainbow” is the story of his early years trying to find his big break.

“Drive (For Daddy Gene)” (Jackson)

Great songwriters have a way of taking a set of personal lyrics and making them relatable to wide sections of the music-loving public. This is one of the most personal songs in Alan Jackson’s discography. At the same time, you don’t have to have the same experiences to feel the emotion behind this tribute to his late father in your bones. Unfortunately, songs like this will never stop being relevant.

“She Just Started Liking Cheatin’ Songs” (Kent Robbins)

Alan Jackson released “She Just Started Liking Cheatin’ Songs” as an album cut from Under the Influence in 1999. That was nearly 20 years after John Anderson recorded the original version in 1980. So, the song has already proven to have some longevity.

This is another one that will unfortunately never stop being relatable. As long as infidelity and suspicion exist, songs like this one will resonate.

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