Alan Jackson's 5 most underrated songs
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Alan Jackson has had a whopping 26 No. 1 singles in his hall of fame worthy career that has seen him win numerous CMA, ACM and Grammy Awards. However, Jackson still has some releases in his illustrious career that haven’t gotten the reception or topped the charts like they should have.

Here are Alan Jackson’s five most underrated songs …

1. “Here In the Real World”

“Here in the Real World” was Alan Jackson’s first successful single of his 25-plus year career and the one that essentially put him on a path to greatness. The 1990 release, which hit No. 3 on the Billboard country chart, is also potentially the greatest song ever recorded in his discography. The fact that it wasn’t a chart topper and isn’t very well remembered today of his greatest hits is the reason why it’s truly the most underrated song of his career. “Here in the Real World,” from Jackson’s album of the same name, is certainly one of the best country music weepers of all-time.

2. “Little Man”

“Little Man,” from Alan Jackson’s 1999 album High Mileage, is the story of small mom and pop businesses struggling to survive in a world that’s being overrun by huge corporations and how things used to be better in the good old days. It’s about as political as Jackson will ever get in his career and a truly remarkable song about respecting and remembering those who worked hard to get where they are. “Little Man” topped out at No. 3 on the Billboard country chart in 1999.

3. “Midnight in Montgomery”

“Midnight in Montgomery” is without a doubt one of the greatest releases in Alan Jackson’s 25-plus year career, but the fact that it failed to top the Billboard country chart upon its release in 1992 is what truly makes it underrated. “Midnight in Montgomery,” from Jackson’s sophomore album Don’t Rock the Jukebox, tells of a struggling country singer who one night after playing a show in Mobile, Ala. makes his way through Montgomery and makes a stop at the gravesite of Hank Williams to pay his respects to the man who pretty much turned the genre into a mainstay. Here he encounters Williams’ ghost, in a theme that’s appeared multiple times in country songs throughout the years. “Midnight in Montgomery” made it to No. 3 on the charts in 1992.

4. “Small Town Southern Man”

“Small Town Southern Man,” from Alan Jackson’s 2008 album Good Time, is one of Jackson’s most recent No. 1 hits from late 2007, but the fact that you’d likely never see it on a list of his 10 greatest hits is what truly makes it underrated. The song was likely the best release in the entirety of country music in 2007 and tells of a man, no doubt inspired by Jackson’s own father, who worked hard despite the struggles of life to provide for his wife and family. It’s certainly one of the most memorable vocal performances of Jackson’s great career.

5. “So You Don’t Have to Love Me Anymore”

For some reason country music of today isn’t very kind to the legends of the recent past. All-time greats like George Strait and Alan Jackson are now struggling to put out even top 25 singles in these days of young (mostly untalented) bucks like Luke Bryan and Sam Hunt topping the charts. It has nothing to do with the caliber of their current releases either, as these living legends are turning out singles that sound like their hits of the past. It’s just that country’s pop infusion has completely altered the genre. Jackson’s 2012 single “So You Don’t Have to Love Me Anymore” is a perfect example of this trend. The song, which only made it to No. 25 on the Billboard country chart, would’ve certainly been at least a top five hit for Jackson had it been released five to 10 years earlier, but the heartbreaker simply couldn’t go anywhere in today’s country climate.