25 Best Alan Jackson Songs: Classics from a Country Legend

Last updated on June 1st, 2023 at 09:24 pm

Alan Jackson has been dominating our radio waves for 40 years now, and throughout, he has given us classic love songs, genuine southern feel-good songs, and some party hits that we love to dance to.

He’s been known to make us laugh and cry with his beloved hits while showing off his superb songwriting skills right along with them.

What are the 25 best Alan Jackson songs? Find out below.

Best Alan Jackson Songs

25. “Livin’ on Love”

There’s nothing impossible as long as you’re in love, or so Alan Jackson makes us believe in the 1994 single “Livin’ on Love.”

Called catchy, charming, and full of funny details by Kevin John Coyne of Country Universe, how could we not include this uplifting hit on our best Alan Jackson songs list?

24. “First Love”

While not one of his singles, Alan Jackson’s “First Love” makes us smile with glee every time.

We can’t help but laugh every time it’s made clear that that “first love” was a car.

We all know that man who feels that way about a car, and we think it’s brilliantly written.

23. “I Don’t Even Know Your Name”

This song is the original, funnier version of Carrie Underwood’s 2008 hit single, “Last Name.”

“I Don’t Even Know Your Name” is a hilarious twist on love at first sight gone wrong that’s made even funnier and more memorable in the music video starring comedian Jeff Foxworthy.

We hope we don’t end up in this situation, but we’ll happily laugh whenever we hear it.

22. “Murder on Music Row”

If there’s one thing that earns “Murder on Music Row” a spot on our list of the best Alan Jackson songs, it’s this.

It brings together the current kings of country music – Alan Jackson and George Straight.

These true-blue country boys remember when country music was what it was under the leadership of Hank Williams, George Jones, and Merle Haggard instead of the current country-pop wave.

It’s a theme seen in many of Alan Jackson’s biggest hits, which is why we love him.

21. “www.memory”

Released when the internet was starting to get big, “www.memory” cleverly plays on the internet terminology as the narrator tells the story of waiting for his lover to return, saying, “if you feel the need, just click on me.”

We love a clever pun to put the icing on the cake of a great song.

20. “Where Have You Gone”

One of the most recent Alan Jackson songs to grace our list, “Where Have You Gone” off his 21st studio album of the same name, is yet another one of his nods to what country music used to be in comparison to the country-pop vibe of the day.

This 2021 single brings a tear to our eye every time we mourn “sweet country music” right along with him.

19. “She’s Got the Rhythm (And I’ve Got the Blues)”

Alan Jackson went slightly R&B with this country tune, but we’re not complaining.

“She’s Got the Rhythm (And I’ve Got the Blues),” which Jackson co-wrote with Randy Travis, was initially meant for the legendary B.B. King, but we can’t hear anyone else bringing this upbeat song to life.

It secured Jackson another number-one hit, and it’s safe to say he doesn’t have the blues over that!

18. “Little Bitty”

Get reminded of the simplistic small things in life with the 1996 single “Little Bitty” off Alan Jackson’s sixth studio album, Everything I Love.

Just because something is small doesn’t mean it can’t be one of the greatest joys in our lives, and that’s what Jackson reminds us of in this up-tempo number, which peaked at the number one spot on the Hot Country Songs Chart.

17. “Gone Country”

One of the few Alan Jackson songs on our list that doesn’t include a songwriting credit for the singer, “Gone Country,” was written by one of Jackson’s self-proclaimed favorite writers of all time, Bob McDill.

Jackson said, “When I first heard this song, I fell in love with it. I wish that I’d written it cause it says a lot of things that I’d like to say.”

The song is a commentary on the current country music scene in the 90s, particularly the story of three different singers whose careers were failing in other genres, and they’d “Gone Country” instead.

16. “When Somebody Loves You”

Alan Jackson knows how to write a love ballad. There is no doubt about that.

“When Somebody Loves You” was released in 2001 as the second single from his ninth studio album of the same name.

Jackson’s smooth vocals on the track are a “treasure,” according to Billboard magazine’s Deborah Evans Price.

They certainly translate into a treasure amongst all the best Alan Jackson songs.

15. “Where I Come From”

It’s always nice to remember your roots like Alan Jackson in the 2001 number-one hit single, “Where I Come From.”

The moderate up-tempo song hears the narrator proudly claim his southern accent, boldly make it known that the chicken at the diner isn’t like his mom would make, and more.

This critically called “redneck anthem” is always one of the most fun Alan Jackson songs to bop around in the car to, and we’re not one bit ashamed.

14. “I’ll Go on Loving You”

Alan Jackson gives a new vibe in his 1998 single, “I’ll Go on Loving You.”

Along with his classic vocals, as he sings the song’s title repeatedly for the chorus, the listener also hears him passionately promising to remain faithful to his wife “long after the pleasures of the flesh” through spoken word verses as a steel-string acoustic guitar and entire string section accompany him.

13. “Little Man”

We can’t help but get nostalgic over “Little Man” considering the events of the world in the last few years that saw the exact thing that Alan Jackson sings about in this 1999 hit single.

In the song, the narrator tells the story of small businesses, “the little man,” that lost out to the competition of the large corporations, as he sadly recalls the memories in the now abandoned storefronts.

To all those small businesses that experienced the same after COVID-19, “God bless the little man.”

12. “Good Time”

It’s the song that inspired the “longest line dance” in the world, or at least that was the concept of the music video.

“Good Time” was released in 2008 and is an up-tempo party song that tells the story of just wanting to have a great time after a long work week. Who couldn’t relate to it?

Like many Alan Jackson songs, we’ll never get tired of listening to this one.

11. “Small Town Southern Man”

“Small Town Southern Man” is a classic song driven by a fiddle and steel guitar, as Alan Jackson seems to tell the story of his late father and how Jackson and his siblings were “raised on the ways and gentle kindness of a small-town Southern man.”

A classic tribute for any Southern gentleman with a rural upbringing, Jackson said of the 2007 song, “Wherever you go, there are rural people that are working for a living and raising families. They all have the same qualities and goals as a small-town Southern man.”

The song earned Jackson his 23rd number-one hit and marked his first since releasing “Remember When” three years earlier.

10. “Chasin’ That Neon Rainbow”

“Chasin’ That Neon Rainbow,” the fourth release from Alan Jackson’s debut studio album, Here in the Real World, is the singer’s story of finally making it to the big stage of country music and is now “living that honky-tonk dream.”

This memorable song, the first songwriting collaboration between Jackson and Jim McBride, represents anyone who will do anything to go “Chasin’ That Neon Rainbow” toward their dreams.

9. “Don’t Rock the Jukebox”

This is the perfect anthem for those who love country music at its very core and know that only a country song is the best remedy for heartbreak when you’re sitting in a bar, ordering another drink.

So, “Don’t Rock the Jukebox!”

Described by critics as “honky-tonk heaven,” this upbeat classic hit peaked at No. 1 on the US Hot Country Songs, Canada Country Tracks, and US Country Songs charts in 1991, and we can’t get enough of it.

8. “Here in the Real World”

Alan Jackson was still new on the country music scene when he released “Here in the Real World” in 1990, but he immediately proved how much of a legend he was bound to become.

He’s the king of the classic country song that is relatable to everyone, and this one is no exception. It’s become such a classic that it was even covered by the likes of Glen Campbell, George Jones, and Charley Pride.

7. “Mercury Blues”

One of the few covers that Alan Jackson has done, “Mercury Blues,” was originally recorded by the K.C. Douglas Trio in the 1940s.

Despite this, Jackson’s version, released in 1993, remains the more notable, peaking at number two on the Hot Country Songs chart that year.

The song was such a huge hit that it was even used in a Ford Motor Company commercial for the Ford pickup truck, changing the hook line from “crazy ’bout a Mercury” to “crazy ’bout a Ford truck.”

He also sang the song during a 1996 episode of the hit sitcom Home Improvement starring Tim Allen.

6. “It’s Five O’Clock Somewhere”

“Margaritaville” singer Jimmy Buffett joins Alan Jackson for this 2003 hit that answers the question: what was Alan Jackson’s most successful song?

“It’s Five O’Clock Somewhere,” which topped the charts for eight straight weeks, is the song that workers everywhere are blasting when they’re bogged down by the grind, counting the hours until it’s time to go home and pour a drink.

Don’t worry, as the narrator boldly declares: “It’s only half-past 12, but I don’t care. It’s five o’clock somewhere.” Now, let’s find a happy hour, shall we?!

5. “Midnight in Montgomery”

“Midnight in Montgomery” is a mid-tempo, albeit spooky, acoustic ballad telling the story of Hank Williams’ death in the early morning of New Year’s Day 1953.

As the narrator walks through a Montgomery graveyard, where Williams is buried, the ghost of the late singer appears to give his appreciation for the singer honoring him before disappearing again.

As he does, the song ends with the shiver-inducing line, “Hank’s always singing there.”

Peaking at number three on multiple charts, it received an “A” from critics saying, “along with the ominous production and chilling story, Jackson’s performance strays from its usual smooth reliability and picks up its own haunting quality, which perfectly adds to the overall darkness of the song.”

4. “Drive (For Daddy Gene)”

Who else remembers the first time they drove with their dad beside them, teaching them the ropes? We do, and so does Alan Jackson in this 2002 single “Drive (For Daddy Gene),” dedicated to his father, Eugene Jackson, who died two years earlier.

Once again, Alan Jackson shows off his writing skills as he paints a vivid picture of driving around an old beat-up truck that he and his dad restored together, floating on the water in a boat with him, and then bringing it around full circle as he teaches his own daughters to drive.

This song brings up all the memories for the beloved singer and us, and that’s why it had to be included on our best Alan Jackson songs list.

3. “Chattahoochee”

Described by Alan Jackson as a “song about having fun, growing up, and coming of age in a small town,” the 1993 single “Chattahoochee” became an even bigger phenomenon than even he saw coming.

It goes to show how much the world occasionally craves an upbeat, feel-good, no-worries song about the goodness of adolescent days to put on the radio and escape the craziness of the real world.

Plus, who didn’t love Jackson water-skiing in his cowboy hat, red cowboy boots, and red life vest in the accompanying music video?

2. “Remember When”

Alan Jackson’s 2003 single “Remember When” made us believe in love as the song looks back on his life with his beautiful wife, from their first intimate encounter to being sure they’ll remember their children once they’re grown and gone.

If that weren’t enough, the music video is beautifully intimate as he and his wife, Denise, dance. The video also features Jackson sitting on a stool while pictures and home videos of their life together surround him.

This is easily one of our list’s most beautiful Alan Jackson songs. We agreed entirely with Billboard when they called it “the most poignant, well-written country song to hit the format in a long time.” It’s no wonder it hit number one on the charts within just a little over a week of its release.

1. “Where Were You (When the World Stopped Turning)”

It was the “Where were you when Kennedy was shot” of the 2000s. When the twin towers were struck, and the towers fell on 9/11, the “world stopped turning,” and everyone wondered, “where were you.”

Alan Jackson left the arena silent when he debuted this powerful song two months later at the Country Music Association Awards on November 7, 2001, and there wasn’t a dry eye in the house.

The beautifully written song, which would go on to top the Hot Country Single & Tracks chart for five weeks and win two Song of the Year Awards and a Best Country Song Grammy Award, was Jackson’s way of remembering the feelings he felt that day as he pushed us to think about our own emotions surrounding the tragic event.

“Faith, hope, and love are some good things [God] gave us, and the greatest is love.”

This is, without a doubt, the greatest song that the beloved superstar has ever delivered, and that’s why it had to take the number one spot on our list of the best Alan Jackson songs.

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