Midnight in Montgomery

"Midnight in Montgomery" was written by Jackson and Don Sampson, recorded on August 21, 1990, produced by Hendricks and Stegall, and released as the fourth single on April 20, 1992 (Arista 12418) with "Working Class Hero" on the B-side. It is a mid-tempo, largely acoustic ballad in D minor, and a tribute to Hank Williams: the singer, driving to Mobile for a New Year's Eve show, visits Williams's grave in Montgomery, meets his ghost, who thanks him and vanishes, and the lyric refers to Williams songs including "I'm So Lonesome I Could Cry". Williams died on January 1, 1953. American Songwriter quotes Jackson saying Williams has always been such a big part of what real country music is, and a poet, and that he showed how simply you can write; a search summary, which could not be checked, says Jackson wrote in the booklet of The Complete Hank Williams that he and Sampson wrote it after visiting the grave.

It debuted on the country chart the week of April 25, 1992, peaked at number three, the album's only single not to reach number one, was number three in Canada, year-end number 12 on RPM and 27 on Billboard, and is certified gold. The video, directed by Jim Shea, is black and white under a full moon among headstones in an empty cemetery, was reshot once because of an unintended shadow, and won the CMA's music video of the year for 1992. Country Universe's Leeann Ward graded it A in 2011, calling it a genuinely spooky song for the Halloween season, with eerie steel guitar and a haunting vocal. Josh Turner covered it on Country State of Mind (August 2020).

A report on the farewell show puts it fifth in the set, after "Summertime Blues", on June 27, 2026 at Nissan Stadium; the report cites no source. The upload we hold is titled as the official music video.