Favorite Songs by Favorite Artists: Alan Jackson (2020 Edition)

As part of my introduction to Country Universe, I’d like to revive of my personal favorite features here and talk about one of the artists who shaped my early love for the country music genre. Warm, charismatic, personality-driven and touched with a dash of wisdom and experience, Jackson’s material is oddly timeless to me. He emerged with the other members of the class of ‘89 and proved to have the greatest longevity of its four members, notching hits for three decades – all while staying true to a familiar neotraditional sound.

Now, that comes with the inevitable criticism that he stuck with what worked. I plan on challenging that criticism, but regardless, it’s one of few one could levy at him, I think. Either way, too, consistency is a valuable trait, which is why he’s remained a favorite of mine ever since I was a child. Narrowing down a list of his best songs wasn’t easy, but I hope you enjoy my ramblings. Feel free to share your own selections in the comments below, of course. Also, I turned to Leeann’s own list for inspiration when compiling my own on more than one occasion.

 

#25

I’ll Try

The Greatest Hits Collection (1995)

Written by Alan Jackson

A love song without the cornball cheese? Yes, please. I will say, though, this character’s going to have do a lot more than just “try” in the long run. Still, the sentiment captures that relatable, scary feeling of first entering into a relationship and not quite knowing if it will work out for the better, but hoping it does. Take out the “I’m not perfect, just another man” line and I’d have it a few spots higher.

 

#24

Job Description

Who I Am (1994)

Written by Alan Jackson

One of my favorite touring songs, where Jackson frames it as a conversation between him and his wife, acknowledging the underlying sadness that comes with being a performer. He’s, of course, grateful for the opportunity and finds pleasure in the live setting watching his fans’ reactions, but there’s a blunt honesty in the framing, where he rips away any veneer of glamour of what goes on in between shows.

 

#23

Small Town Southern Man

Good Time (2008)

Written by Alan Jackson

One aspect of Jackson’s talent that will show up quite frequently on this list is his knack for humanizing his characters. It’s a simple story, but also one that’s a bit of a slow-burn. It could have easily been cloying, but Jackson effectively downplays his performance to honor, in a nutshell, a simple man who put his family before him and worked hard to provide for them with no complaints. It’s not Jackson’s greatest tribute to his father – we’ll get to that later – but it’s touching all the same.

 

#22

There is a Time

The Bluegrass Album (2013)

Written by Rodney Dillard and Mitch Jayne

Dark bluegrass is my favorite kind of bluegrass, and with Jackson’s deeper, weathered tone handling this old, well-known tune, there’s a ton of sincerity added to a song, ultimately, about the journey through life itself. Jackson’s slightly faster take on the song remains my favorite version, and one of many examples why The Bluegrass Album added to a secure legacy.

 

#21

Gone Before You Met Me

Angels & Alcohol (2015)

Written by Michael White and Michael P. Heeney

The Roger Miller influence has always been evident in some form in Jackson’s approach to songwriting, and this may the most obvious example in his discography he didn’t write himself. It’s there in the composition, too – especially in the interplay between the harmonica and rickety rollick of the song overall. But the ultimate setup is a dream he had, where he’s hanging around with Tom Sawyer and Jack Kerouac before waking up and realizing he made the right choice to stay with his wife instead of endlessly rambling on. The best kind of quirky, really.

 

 

#20

Where Were You (When the World Stopped Turning)

Drive (2002)

Written by Alan Jackson

I’m likely either to surprise you for having this on here at all or for having it this low on this list. As a tribute to the fallen victims of the 9/11 terrorist attacks, this works as an honest reaction from a self-regarded simple person who isn’t sure what to think in the moment, even if certain lines haven’t aged well. That’s the important context, I think – it’s the only way Jackson knew how to make sense of the world around him at the time, drawing out genuine empathy and unity for a nation struck by grief and loss.

 

#19

I’ll Go On Loving You

High Mileage (1998)

Written by Kieran Kane

I consider this a precursor to Jackson’s Like Red On A Rose album, where he trades in his cornball humor and witty reflections for something … sensual. For a self-regarded staunch traditionalist, Jackson wasn’t afraid to show his versatility as a writer and performer, and while this – for whatever reason – is regarded as a polarizing moment in his discography, my God, it just works. The combination of his low recitation and the simmering acoustics provides the right mood, showing a completely new side to Jackson’s performance capabilities.

 

#18

So You Don’t Have To Love Me Anymore

Thirty Miles West (2012)

Written by Jay Knowles and Adam Wright

I’ve never cared for songs that sound whiny, clingy or – even worse – angry over the fact that someone might want to move on from a relationship. Jackson’s “So You Don’t Have To Love Me Anymore” was a welcome return to form anyway, but it’s also one of his most brutal – acknowledging a love that’s truly dead while he does his best to give his significant other the space she desires, even if it means having to be the bad guy to make sure any lingering feelings die too. It’s a mature, complex outlook on an ending that benefits from Jackson’s broad perspective.

 

#17

The Talkin’ Song Repair Blues

What I Do (2004)

Written by Dennis Linde

Dennis freakin’ Linde, am I right? Combine some of his zaniest, most hilarious lyrics with Jackson’s straight-laced, half-spoken delivery of this tale of a repairman and a songwriter, and you have an oddball pairing that shouldn’t work as well as it really does. It’s the one entry on this list that’s endlessly quotable.

 

#16

Here in the Real World

Here in the Real World (1989)

Written by Mark Irwin and Alan Jackson

Whereas “Blue-Blooded Woman” showed Jackson’s humorous side that could err on the side of cheesy and corny, “Here in the Real World” was the better showcase of his talents – and his first big hit. In hindsight, this almost feels like a meta cut for Jackson to record, where, in a career marked by painstakingly real stories and personal reflections, his first hit was all about ripping away the veneer and cutting to the heart of the matter.

 

#15

Let It Be Christmas

Let It Be Christmas (2002)

Written by Alan Jackson

I originally thought of starting off the list with this … and then I revisited it and felt a reason for the season in the sweltering heat of June. I mean, this just feels like Christmas, and while I’ve already commended Jackson’s naturally warm charisma (and will continue doing so for this list), this wouldn’t have worked as well with anyone else. Not even the child choir can ruin this!

 

#14

Three Minute Positive Not Too Country Up-Tempo Love Song

When Somebody Loves You (2000)

Written by Alan Jackson

Ah, 2000 – when the traditionalist boom had long died out, Garth Brooks was set to retire, newcomers like Keith Urban and Kenny Chesney had set out to take over where the class of ‘89 left off, and when Alan Jackson responded to it all like the sly smart-ass he was with this selection. Country music’s response to the turn of the century was to sound somewhere between traditional and adult-contemporary, meaning that intended progress for the genre just sounded boring, instead. Jackson would be fine, of course, thanks to possessing a greater versatility as a performer than peers like Clint Black or Travis Tritt had. It wasn’t quite as subtle as “Gone Country,” but “Three Minute Positive Not Too Country Up-Tempo Love Song” is Jackson’s other great protest song (and for what it’s worth, “Murder On Music Row” just barely missed the cut for this list).

 

#13

Song For the Life

Who I Am (1994)

Written by Rodney Crowell

One can tell Rodney Crowell penned this song, but that it blends in so seamlessly with the rest of Jackson’s own discography speaks volumes for his own standards of quality. As a song that acts as a reflection on the journey so far and optimism for the journey ahead, its time of recording was fitting, too, for what then was an artist settling in for the long haul of his career.

 

#12

Chattahoochee

A Lot About Livin’ (and a Little ‘Bout Love) (1992)

Written by Alan Jackson and Jim McBride

I say this with love – part of Jackson’s appeal is his corniness and self-awareness of it. His fun-loving side is much subtler than his reflective side, enough to where, as previously mentioned, it makes his humor come across with the same dry wit as, say, Roger Miller … “I Still Like Bologna” not withstanding, that is. At this point, more people likely remember this for the “burger/grape snow cone” line that’s been memed to death, but there is something to admire about a rapid-fire summer story song that’s lightweight in a good way.

 

#11

Monday Morning Church

What I Do (2004)

Written by Brent Baxter and Erin Enderlin

It’s bad enough the significant other in question here dies rather than, you know, just leaves this character (as these songs typically go), but what’s further soul-crushing about “Monday Morning Church” is the fallout of it all. The depiction left by the hook is strong enough, but the admittance of a loss of faith by this man makes it more than just a sobering metaphor. The subtext suggests an imminent downward spiral, but there’s enough aching sadness here in detailing the events leading up to it.

 

#10

The Sounds

Drive (2002)

Written by Alan Jackson

Jackson can pen a great sad song, no doubt. But beyond the strong vocal performance here, “The Sounds” is a creative exercise in showing how this character walks back through the steps that led to his significant other’s departure, enough to where it haunts him and he shows plenty of remorse and regret for ignoring those “sounds” earlier. “You can’t hear it, but the noise is killing me” – that says it better than my words about it ever could.

 

#9

Gone Country

Who I Am (1994)

Written by Bob McDill

Subtlety is the greatest asset to both humor and protest songs – case in point. Granted, while “Gone Country” is out to prove a point, it never bogs itself down by being too overly self-righteous or serious. It’s a fun jab that, sadly, is way more applicable now than it was then, though it is worth mentioning the context for this song’s release: In a sea of new hat acts that entered country during its boom period of the early ‘90s, Jackson stood out as the real deal.

 

#8

The Older I Get

Single (2017)

Written by Adam Wright, Hailey Whitters, and Sarah Allison Turner

One thing I’ve noticed about Alan Jackson’s 2010s output is that his voice is a shade deeper than before. Ultimately, it’s just a tiny feature, though it does seem to grant his newer performances a rugged, lived-in sincerity. Case in point – a reflection on mortality that, while thematically familiar, is bolstered by Jackson’s warmth and grace. Even when Jackson recalls his past, it’s never filled with regret. Not that he hasn’t carried his own burdens, mind you; he’s just not content to dwell on them. There’s always an honesty to Jackson’s reflections, and “The Older I Get” is, as of this writing, his latest example.

 

#7
The Blues Man

Under the Influence (1999)

Written by Hank Williams Jr.

Under The Influence is a cool little project anyway, but its best moment may be this song – a take on a Hank Williams Jr. song, where Jackson shapes the original first-person narrative into a third-person one. It works as a simple love song, painting an honest picture of the ups and downs of a relationship that would later frame Jackson’s own “Remember When,” but as a tribute to the side of Hank Williams Jr. most fans didn’t know much about, it’s brilliant in any capacity.

 

#6

Drive (For Daddy Gene)

Drive (2002)

Written by Alan Jackson

Leave it to Jackson to deftly present a personal childhood memory with so much earnest joy that it ends up feeling wonderfully relatable. And for as much as that child-like innocence shines through in this trip down memory lane, it’s equally a song about the people in Jackson’s life who helped form those memories. Nostalgia never shined with so radiance as it did here.

 

#5

Remember When

Greatest Hits Volume II (2003)

Written by Alan Jackson

Perhaps the most obvious pick for this list, but that doesn’t make it wrong. “Remember When” isn’t just a love song; it’s a beautiful tribute to Jackson’s marriage to wife Denise, going beyond the basic “we made it” cliché by actually delving into the relationship’s highs and lows along the way. It may even be a bit too descriptive at points, which makes it personal, of course, but is also filled with subtle lessons learned that feel relatable for any couple lucky enough to make it that far. Jackson was already a bona fide superstar when he released this; it just helped secure his legacy as one of country music’s most thoughtful songwriters.

 

#4

Little Man

High Mileage (1998)

Written by Alan Jackson

I’m not sure I’ve ever heard Alan Jackson get angry. I mean, he’s peppered in subtle hints of social commentary every now and then, but never to the full extent of this song. With that said, I wouldn’t call it an isolated moment in his discography, either. His portrayals of small town life have never felt sugarcoated, especially given how this is a cry for a loss of personality within a community as gentrification sweeps its way in. It’s a Merle Haggard-esque commentary that gets its point across through empathy above all else.

 

#3

Walk On the Rocks

Everything I Love (1996)

Written by John E. Swaim

I love that hook – “take a walk on the rocks that I stumbled on.” It’s an admission of regrets and failures from a convict to his son, yet there’s no moral judgment cast on either side. Jackson does his best to cast sympathy toward someone who’s owned up to whatever mistakes he made, and the son – while lacking his perspective in the narrative – still, at least, sees enough good in his father to visit him. Whether it’s through characters like these or through his own personal perspective, Jackson’s discussions of lessons learned always feel – dare I use this word in a country music discussion – authentic, and “Walk On the Rocks,” next to “Remember When,” is one of his most purely beautiful cuts.

 

#2

Blue Ridge Mountain Song

The Bluegrass Album (2013)

Written by Alan Jackson

This is the ultimate test of Jackson’s strength as a performer, detailing an incredibly rich and dark love story that ends up being much more lonely than any song like this should ever be. It’s simple, yes, but sold with Jackson’s usual grace and warmth to hook listeners on every word of this six-minute-story. By 2013, Jackson’s time at radio had ended; this proved he had moved past trying to make a hit and just wanted to add to an incredibly rich legacy.

 

#1

Midnight in Montgomery

Don’t Rock the Jukebox (1991)

Written by Alan Jackson and Don Sampson

It’s one thing to just namedrop Hank Williams; it’s another to craft an entire story about meeting his ghost. Granted, “The Ride” operates in similar fashion, but whereas that one is bombastic enough to lose itself in the tension of the moment, “Midnight in Montgomery” always feels uneasy. It’s a literal ghost tale with an ominous presence, and Jackson – though just a young performer at the time – was the perfect artist to play the role of the bright-eyed dreamer honoring his influences. As this list suggests, Jackson is adept at penning thoughtful, reflective material – some of which even comes with a humorous twist; “Midnight in Montgomery,” however, is not only Jackson’s coolest-sounding song in his discography, but also one of his most boldly creative.