Alan Jackson by Russ Harrington

The Best Alan Jackson Songs

October 15, 2021 7:00 am GMT
Last Edited June 15, 2023 3:26 pm GMT

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“My goal and motive was just to do what George Jones had always told me, and that’s just to keep it country,” Alan Jackson once said.

For a little over 30 years, that’s exactly what he’s done, with a down-home honesty, humour, integrity, unpretentiousness and personal warmth that’s made country music fans all over the world connect with his earthy baritone.

Holler takes a look back at the highlights from an incredible career in country music. Time to put a little AJ in your day:

Arista Records | 1991

Don’t Rock The Jukebox

You probably know it best from the Alvin and The Chipmunks album Chipmunks In Low Places, but it had actually already been a huge country no. 1 for Jackson on his own.

Sung from the perspective of a “heartbroken hillbilly” who waits by the jukebox in a bar, telling the other customers not to interrupt the queue of country break-up songs he’s got lined up, the video features a cameo from the one and only George Jones.

Sadly the original doesn’t include the bit where he argues with a chipmunk at the end though.

Arista Records | 1996

Little Bitty

Written by legendary songwriter Tom T Hall, it’s a perky paean to the smaller things in life.

While Alan Jackson isn’t actually the tallest singer in country music - Charles Kelley from Lady A and Trace Adkins are both 6’6” – he’s still pretty damn tall at 6’4”.

So, to be fair, most things are going to look fairly Lilliputian to him.

Sony Music Entertainment | 2015

Tall, Tall Trees

Jackson inhabits a world more suited to a man of his size with this breezy cajun cut from 1995, promising his romantic interest whatever outsized object of her desire she wishes for.

Whether it be a "big limousine", a "great big mansion", or rather less logistically possible, "tall, tall trees and all the water in the seas", you can’t fault him for trying.

Written by Roger Miller and George Jones in the late 50s, Jones actually forgot he’d co-written it, until Jackson covered it nearly 40 years later for one of his many Greatest Hits collections.

Arista Records | 1992

Livin' On Love

Maybe it’s the moustache, or his gentle, fatherly smile.

No other male singer in country is capable of taking an overly sentimental love song and making it sound like the most matter of fact and unabashedly down to earth song you’ve ever heard.

Somehow pressing all our emotional buttons at the same time, this single from Who I Am tells the story of "two young people without a thing”, who finish the song as “two old people without a thing”.

Swinging on a porch swing after their children have moved out of home, their still “livin’ on love”.

Is anyone else’s hay fever really playing up? Pass me a tissue.

Arista Records | 1999

Pop a Top

Alan Jackson just loves a bar.

So much so, that he opened one of his own last year on Nashville’s Broadway, suitably calling it A.J.’s Good Time Bar.

‘Pop A Top’ was written by Nat Stuckey. It had previously been a hit in the 60s for Jim Ed Brown, but Jackson revived this honky-tonk classic - complete with novelty bottle opener sound effects - for Under The Influence, his covers album of songs that had inspired him.

Arista Records | 1991

Midnight in Montgomery

Hank Williams is often manifesting as a ghost in country songs, and Alan Jackson had his own encounter with him in the fourth single from Don’t Rock The Jukebox.

It tells the story of how Jackson stopped off in Montgomery one New Years Eve, on the way to play a gig, to visit Hank Williams’ grave, only for the country legend himself to pop up and thank him for visiting.

Rather spookily, the music video had to be rerecorded after they noticed a shadow that wasn't supposed to be there when they watched the first take back.

Sony Music Entertainment | 2015

Remember When

In this achingly poignant tribute to married life, Jackson looks back on his life with his wife, Denise.

Tracing the narrative arc of their love from their first time together, through to raising a family and watching their children grow up – Jackson has three daughters – he ponders on how he and his wife will reminisce about it all when they’re old.

We’re going to need those tissues again. How does he do it?!

MCA Records | 2000

Murder on Music Row

Alan Jackson teamed up with George Strait as unlikely country music detectives investigating a “murder” case, to try and discover out who “killed country music and cut out its heart and soul”.

It’s safe to say they lamented the decline of traditional and neotraditional country music being played on the radio, in the face of bro-country and pop-country crossover acts.

Sony Music Entertainment | 2015

I'll Try

Jackson stopped promising the moon and the stars - as well as all the “tall, tall trees and all the water in the seas" - for a moment with this simple, honest and refreshingly realistic love song.

"I'm not perfect, just another man / but I will give you all that I am / and I'll try to love only you / and I'll try my best to be true”, he sings and… oh for goodness sake, just hand us the whole box of tissues, please.

BMG Entertainment | 2002

Drive ( For Daddy Gene)

With tissues at the ready for this one, Jackson turns a simple car song into a nostalgic through-the-ages emotional blockbuster.

Dedicated to his own father, the song begins by looking back at the cars and boats that he remembers growing up with, and how those vehicles related to his own memories and his relationship with his father.

From there, he travels forward to his own daughters’ reminiscing about the cars they’ll remember Alan letting them drive.

His three daughters, Matti, Alexandra and Dani, all starred in the video.

BMG Entertainment | 2002

Where Were You (When The World Stopped Turning)

Two months after the September 11 attacks, Alan Jackson debuted his honest and thoughtful tribute at the CMA Awards in Nashville.

“I'm just a singer of simple songs / I'm not a real political man / I watch CNN, but I'm not sure I can tell you the difference in Iraq and Iran”, he sang, opening up questions rather than pushing for answers.

Thought-provoking without ever feeling judgemental, it was a rare foray into political commentary, which he approached with the same straightforward everydayness that he would any other subject, only adding to its poignancy.

Arista Records | 1992

Gone Country

As a genre, country music has always been joyfully self-referential, and Alan Jackson has sung about the ins and outs of country music more than most.

This no. 1 single from 1994 takes an affectionate sideswipe at all the artists from other genres.

In this case, it’s a lounge singer, a folk-rocker, and a serious composer that end up carpetbagging over to country, when they fail to find commercial success in their own native genres.

Arista Records | 1989

Chasin' That Neon Rainbow

Alan Jackson looks back on growing up, listening to country shows on the radio and hearing the songs his mother used to sing to him, as his parents tried in vain to steer him away from the possible disappointments of a career as a musician.

Fortunately, for the rest of us, the lure of the bright lights was too much for little Alan, and he chased that neon rainbow all the way to Nashville; becoming one of country music’s greatest living legends.

Arista Nashville | 2003

It's Five O'Clock Somewhere

It seems fitting that just across Broadway from A.J.’s Good Time Bar you’ll find the legendary Margaritaville, the Nashville branch of Jimmy Buffett’s cocktail restaurant chain.

Jackson and Buffett are responsible for one of country music’s most effervescent drinking songs. An anti-authority anthem and high spirited celebration of happy hours the world over, the song is an answer to the perennial question, “what would Jimmy Buffet do?”

Arista Records | 1992


This up-tempo summer smash is ostensibly just a song about having fun, growing up, and coming of age in a small town.

Jackson delivers it all with affection and charm that won it the CMA awards for Song and Single of the Year.

Strangely, it’s not remembered for its video; Jackson surprised us all with his water-skiing skills in it, bouncing around in a dingy on a lake in just his red cowboy boots, aviators and life jacket.


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Written by Jof Owen
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