After the release of his debut album, Here in the Real World, in 1990, Alan Jackson spent the next two decades largely dominating the country music charts. Nearly 40% of the singles he’s released in his career have topped the charts as he had been one of the biggest flag fliers for traditional country music in the mainstream.
In the 32 years that have followed his debut, Jackson has released 18 studio albums chock-full of good ol’ country tunes, ranging from good timing anthems to tear in your beer gems that will live for the rest of eternity amongst some of country music’s best.
To celebrate Jackson, we asked Thomas Fountain, Sadie Self and John Ruiz to sift through Jackson’s impressive catalog to choose some of their favorites, and they didn’t disappoint!
Thomas Fountain
First, I combed through his catalog of songs and it was extremely hard for me to pick five. Alan Jackson is probably my favorite country singer/songwriter of all time. Of course his resumé speaks for itself, but what is even more impressive is how many number one songs he actually wrote. To me, besides Merle Haggard, he is the greatest country singer/songwriter that we’ve seen.
- Between The Devil and Me
- Actually written by Harley Allen and Carson Chamberlin. The intro is very daunting from the beginning. I love the driving rhythm of the song with almost a bluegrass feel. Makes sense because Harley Allen is most known as a bluegrasser himself. The dynamic of the song is what makes it. The continuous build and just the right taste of each instrument at just the right time. It’s one of those songs that doesn’t sound like a lot is going on, but in the studio, there was a ton. It has a huge warm rhythmic section, not to mention the songwriting is phenomenal.
- Wanted
- It may be his best work as a songwriter to me. An entire song about a wanted ad, twisted into a heartbreak song. I love how the title is so emphasized throughout the song. I love the line “no ma’am, tomorrow may be too late, I’d like to have it started right away.” Again, the mix and production is great and allows the song to tell the story.
- Chasin’ That Neon Rainbow
- I will forever have memories of singing this song to the top of my lungs to my dad in his ’86 two tone Chevy Silverado. We’d have the windows down, radio up, and he’d just give an ol’ country grin. I knew every word and didn’t even really know at the time what I was singing about, but I knew I wanted to chase that neon rainbow.
- Home
- I have four sisters like Alan. The way of life he sings about in “Home” is exactly how a lot of people grew up in my small hometown. This song always reminds me so much of my grandparents. They were teenagers when they got married, had absolutely nothing but love and a little piece of land. They were very self sufficient and raised a family on the same ground.
- Don’t Rock The Jukebox
- It’s just an absolute monster honky tonk song. It’s been pretty consistent as a cover in my live show for years. The musicianship in this song is just next level country. Every solo is so tasty and so much fun to play live. It’s always a crowd favorite.
Sadie Self
- Remember When
- “Remember When” is one of those songs that reminds me why I fell in love with country music in the first place. You can really just feel the heart and soul that Alan puts into this one as he reflects back on love and life. This song truly is a masterpiece, and I feel that it is one of the best songs ever written in country music history.
- Chasing That Neon Rainbow
- This is another song that Alan Jackson actually wrote with Jim McBride based from his experiences playing in the honky tonk circuit. It’s one of his first songs I ever heard and it’s really what got me hooked on Alan’s music. It is definitely one of my favorite honky tonk tunes, and without a doubt everything that country music should be.
- Murder On Music Row
- This classic song was written by Larry Cordle and Larry Shell, but I couldn’t imagine a more iconic duet recording and releasing it than Alan Jackson and George Strait. I find myself relating to this song more and more with time because it’s so relevant with what is happening in the music industry today. This song has always been one of my favorites because it reminds me of all the country legends that left behind their heart and soul in the sound of real country music. As Alan sings, “The almighty dollar, and lust for worldwide fame, slowly killed tradition.” It tears my heart out because slowly, traditional country music is becoming harder and harder to find.
- Things That Matter
- My grandpa has always been Alan Jackson’s biggest fan, and we share many memories of singing and listening to his music together. This song, titled “Things That Matter,” came from the latest album that Alan released, and it has a way of tugging on my heartstrings, because it makes one stop and think about what’s really important in life. I will always love this one because it reminds me of my family, and especially my grandpa.
John Ruiz
- So You Don’t Have To Love Me Anymore
- We have all from time to time realized that we were the one to cause the relationship to run off the rails. Sometimes the last thing we can do is to fall on the sword and let the other move on with grace and dignity. Alan captured that perfectly here.
- Where Have You Gone
- What seems at first as a lover’s lament song quickly materializes as a statement to the current state of Nashville country. George Strait may be the King of Country, but Alan is the Prince, and he rolled into Nashville with a royal decree on how real country should be!
- Where Were You (When The World Stopped Turning)
- While several of his peers took the chest-beating “Boot in your ass” (I’m talking to you, Toby Keith) approach to the tragedy of Sept. 11, 2001, Alan put together a wonderfully introspective song that was realistic and encompassed what I think most of us felt that day.
- I Don’t Even Know You Name
- What could be typically written off as another comedy country tune. Alan Jackson has a distinct way of adding authenticity to his songs with his perfect Georgia drawl. The real aspect that sets this song apart is the absolute barn burning musicianship on the track. Fiddle, steel and chickin’ pickin’ guitar bring this one to a whole other level!
- Midnight in Montgomery
- While many artists have name dropped Hank Williams Sr. in songs. No track since DAC’s “The Ride” has been able to fully realize the mystique and ghostly presence that Hank has in country music, until “Midnight in Montgomery.” Throughout the tune, you can feel the indelible mark that Mr. Williams left on Alan. Alan understood the gravity of writing a song about the patron saint of country, and it permeates every line he sings here.
Justin Loretangeli (Pro Country)
I’m breaking my own rule here by including more than five songs. I never participate in these, but Alan Jackson is my favorite artist of all time, and I will always take the opportunity to show some love and respect to the man.
- Everything But The Wings
- One thing I love about Alan Jackson is that even though he has a catalog that spans three decades, the quality of the music he’s released hasn’t diminished in the slightest. This one was released in 2012, and Alan’s voice sound as good, if not better, than it ever had to that point. The production is perfect, and the lyrics are absolutely beautiful.
- Dancin’ All Around It
- Two of my favorite types of country songs are those that tell a story and those that incorporate wordplay or have a double meaning. This one has both. It tells a beautiful story of finding love at a dancehall. Even though both sides are a bit guarded at first, they ignite a flame sparked by the music. Coupled with the song dripping with steel and fiddle, this one is an underrated piece of country gold.
- Remember When
- Alan described himself perfectly as a “singer of simple songs.” “Remember When” is one of his simplest, but it is undeniably one of his best. A solo-written love letter to his wife, Denise, this was one of the songs that made me fall in love with country music. The Paul Franklin steel solo and the key change are so well done. In my opinion, this is the best-written country song of the 21st century.
- Chasin’ That Neon Rainbow
- Something I’ve always loved and admired about Alan’s songwriting is how he writes about things that are personal to him, and those songs end up relating to millions of listeners around the world. Several of those songs went on to become hits, but “Chasin’ That Neon Rainbow” has since turned into an anthem for aspiring musicians and dream chasers alike.
- Here In The Real World
- Imagine turning on the radio in 1989 and hearing that opening Rob Hajacos fiddle lick and a new artist named Alan Jackson singing those opening lines. It’s undeniably, unashamedly country, and set in motion a legendary, hall of fame career. And who doesn’t love a good ol’ sad song?
- Monday Morning Church
- Speaking of sad songs, Erin Enderlin sure can write them. What an opening line this song has, and as usual, Alan can make you believe he’s as heartbroken as the song he’s singing. Alan is one of those rare artists where many of his singles are his best songs on each album The lyrics and performance are dripping with emotion, and the instrumentation does a great job of staying subdued and letting the lyric do the talking, all the while, becoming more prominent when necessary.
Pro Country 
Leave a Reply