Top 10 Alan Jackson: Most Underrated Songs

by Matthew Wilson

Everyone has a favorite Alan Jackson song. The singer has been a part of country music for three decades now, with over 20 albums. That’s a lot of music to sift through. Jackson’s various No. 1 hits rank among the singer’s greatest. But some tunes didn’t get the appreciation they deserved.

You won’t find awards or heaps of praise for some of these tunes. But they’re often Jackson at his best and deserve a little recognition. Here are Alan Jackson’s Top 10 Underrated Songs.

10. ‘Job Description’ Explores Alan Jackson’s Life on the Road

Alan Jackson is at his most powerful when he’s singing about himself. Similar to “Drive (For Daddy Gene),” Jackson borrows from his own past for this look at life on the road. The tune featured on the album “Who Am I,” in 1994. It’s not easy being away from home, even if you’re a country singer. This tune focuses on all those lonesome miles between concert venues and home.

The song plays very much like Jackson’s own longings for home as well as an apology to his family for all those moments he’s missed.

Lyrics include, “And I sure don’t like to leave you/ Couldn’t stand for you to think that I don’t care/ So I wrote this job description/ Just to tell you what I do when I’m not there.”

9. ‘The Sounds’ Was Included Among His Greatest

Technically one of Jackson’s greatest hits, “The Sounds” never got the credit that it deserved. The tune first appeared on 2002’s “Drive” album before later appearing on Jackson’s “Greatest Hits Volume II.”

The tune was overshadowed by some of Jackson’s other biggest hits. But the song is a powerful portrayal of a break up, as told through the sense of sound. Jackson offers a poignant look of a man not realizing the tell-tale sounds around him until its too late and there’s only silence.

Jackson sings, “Those are the sounds of a woman leaving/ Stronger then the wind in a willow tree/ Those are the sounds of a heart breaking/ You can’t hear it/ But the noise is killing me.”

8. Jackson Sings the ‘Three Minute Positive Not Too Country Up-Tempo Love Song

Well, try saying that title three times really fast. What the tune didn’t win in awards, it more that made up in being one of the singer’s trickiest song titles ever. Featured on 2000’s “When Somebody Loves You,” up-tempo loved songs weren’t exactly in vogue. But was never one to adhere strictly to convention.

The tune functions as much as a meta-commentary of the country music industry as it does a rip-roaring love ballad. Lyrics include: “Yeah, it’s a three minute positive, not too country up-tempo love song/ It’s a way for me to tell her that I love her but it can’t be too long/ There’ll be no drinkin’, no cheatin’, no lyin’, no leavin’/ That stuff it just don’t belong/ In a three minute positive not too county up-tempo love song.

7. Alan Jackson Mourns a Loved One in ‘Monday Morning Church

Alan Jackson brought his listeners to church. It says a lot about the power of Jackson’s catalog that a No. 5 hit could be considered underrated. But there’s a reason why Jackson is one of the most celebrated names in country music. He built his career on little gems like this.

Featured on 2004’s “What I Do,” the tune is a meditation on loss and grief. The song explores moving on with one’s life after losing someone important.

Jackson tugs at the heartstrings with, “You left my heart as empty/ As a Monday morning church/ It used to be so full of faith and now it only hurts/ And I can hear the devil whisper/ ‘Things are only getting worse’/ You left my heart as empty/ As a Monday morning church.

6. ‘Every Now And Then‘ Is a Throwback

Every musician has their heyday, and Jackson’s lasted longer than most. But country music tastes aren’t the same as they were during the 1990s. Jackson stands out among his peers as a traditionalist even amid the changing tide. “Murder on Music Row” will attest to that.

So while “Every Now and Then” should have been a sure-fire hit, it didn’t receive the respect and love that deserved. Even in 2010, Jackson remained at the top of his form. The tune features all the makings of a great Jackson song.

Lyrics include, “And every now and then that old feeling comes around/ Every now and then I see your face in another cloud/ And every now and then some old something takes me right back again.

5. Alan Jackson Sings of Nostalgia in ‘Blacktop’

Forget dirty roads, get Jackson some asphalt and highway. Released in 2013 on “The Bluegrass Album,” Jackson’s tune is an ode to simpler times. But unlike other country songs, the country singer doesn’t rail against progress but actually supports it. Jackson sings of how a blacktop changed his life and opened the world for him.

Like many of Jackson’s best, the song is also a meta-commentary on the industry. It pokes fun at those singers who lament the country dirt roads of their youth.

I was glad to see the blacktop/ When they laid it down in ’65/ Yeah I was glad to see the blacktop/ No more dust in my eyes,” Jackson sings.

4. ‘That’s All I Need to Know‘ Is Alan Jackson at His Most Vulnerable

“That’s All I Need to Know” ranks among Jackson’s most tender and poignant songs. While it doesn’t get the recognization it deserves, the tune is Jackson at his most poetic. The country singer sings of both love and heartbreak intermixed in a relationship that wants to end but also refuses to die.

The song hinges on Jackson’s performance on the mic. And he shows his range hitting all the notes in this hidden-gem classic.

Jackson sings, “That’s all I need to know/ Do you want to stay together/ Just say let’s don’t let go/ And I’ll keep holdin’ on forever/ Have the teardrops that you’ve cried/ Drowned the fire in your eyes.”

3. ‘Tropical Depression‘ Is a Jimmy Buffett-Inspired Hit

Jackson channels his best Jimmy Buffett in this tune from his album “A Lot About Livin’ (And A Little ‘Bout Love).”

The tune features a tropical vibe perfect for its subject matter. But Jackson never goes as light and as care-free as Buffett might if he was in charge. The “Margaritaville” singer always hid the darkness of his songs within his lyrics. Meanwhile, Jackson’s a little more mournful and morose during this tune.

Jackson sings, “I’m in a tropical depression/ I’ve got the blue water blues/ Can’t shake this loving you obsession/ Can’t stand this sand in my shoes/ This forgetting you vacation.

2. ‘Just Playin’ Possum‘: An Ode to George Jones

Alan Jackson and George Jones were quite the pair. For instance, Jones was the creator behind Jackson’s “Tall Tall Trees.” Also who can forget that infamous CMA moment? But Jackson’s ode to one of country music’s greatest doesn’t get the love that it should. “Don’t Rock the Jukebox” stole all of its thunder on the album of the same name. But after all, how many times can listeners hear Jackson and Jones play together?

The late great musician lend his helping hand in the final line to bring the whole tune to a close.

Lyrics include, “And just playin’ possum/ Laying low/ I’ve got a hundred watts of hurtin’/ Coming through the speakers of my stereo.”

1. Alan Jackson Mesmerizes in ‘Rainy Day In June

Jackson has fun songs, then he has sad songs. And “Rainy Day in June” ranks among his saddest. Released by an older Jackson in 2004, the singer puts his age and experience into every line. This is a musician who’s sure of himself, his craft, and how to squeeze the maximum amount of emotion out of every lyric.

That may seem like a facade, but Jackson sounds incredibly convincing in this rainy blues. Put this song on, get some tissues, and have a good cry.

Jackson sings, “It’s a rainy day in June/ The sky is grey and I am blue/ Tryin’ to make it without you/ On this rainy day in June.”