It was the only single from its album that failed to reach No. 1, yet its black and white cemetery video won CMA Video of the Year and the song became one of the recordings most closely tied to Alan Jackson’s traditional country identity.
I’m So Lonesome I Could Cry.
By 1991 Alan Jackson had already proved traditional country could still sell. Here in the Real World produced four Top 5 hits and Don’t Rock the Jukebox pushed him even further with four No. 1 singles.
But hidden among those radio hits was something much darker. Jackson had visited Hank Williams’ grave in Montgomery, Alabama on what he later described as a stormy night around midnight. That real visit became the seed for a song he wrote with Don Sampson.
They Imagined A Meeting Instead Of A Tribute
They did not write a conventional tribute. They imagined a meeting.
In “Midnight in Montgomery” the narrator is traveling toward Mobile for a New Year’s Eve show when he stops at Hank’s grave. The wind dies down, a mysterious man in cowboy clothes appears, thanks him for remembering, then disappears.
The fiction was built around real history. Williams is buried in Montgomery and he died on January 1, 1953 while traveling toward a New Year’s Day performance. As Jackson’s narrator leaves the cemetery, a distant train whistle leads into that famous Hank line.
A No. 3 Single With An Impact Beyond The Chart
Jackson recorded “Midnight in Montgomery” for Don’t Rock the Jukebox. Released in April 1992 it reached No. 3 on Billboard’s country chart as the only one of the album’s five singles that failed to reach No. 1.
But its impact lasted far beyond the chart position. The black and white video deepened the cemetery atmosphere and won CMA Video of the Year.
A Chain Stretching Across Three Generations
That connection to the past ran through much of his career. His music repeatedly reached back toward the artists who built the genre before him, from George Jones to Merle Haggard and Charley Pride.
Nearly three decades later “Midnight in Montgomery” found another life when Josh Turner recorded it for Country State of Mind in 2020.
The chain had stretched across three generations with Hank Williams supplying the history, Alan Jackson turning it into a ghost story and another traditional country singer carrying it forward.