Top Ten Best Alan Jackson Songs

There is very little in the world that makes me as happy as an Alan Jackson song blasting on a truck radio.  I firmly believe that if everyone in the world sat down and listened to their daily dose of Alan Jackson that the world would be a much better place.  Seriously, doctors should start prescribing folks the mustached country legend’s music as medicine for any and all ailments, the stuff is that good.  When picking my brain for a new country article idea, it dawned on me that no self-respecting website that covers country music should be without an article on Alan Jackson.  Narrowing his music down to a list of ten was about as difficult as passing by a Chick-Fil-A without stopping, but I soldiered on so I could share the good word of Alan Jackson with the world.  Without further ado, here is Honky Tonk Haven’s top ten favorite Alan Jackson songs.

  1. Remember When

Remember When, in this one man’s humble opinion, is not only Alan Jackson’s best song but one of the best country music songs of all time.  Penned by Jackson himself, the highly personal song serves as a love letter to Jackson’s long time wife Denise, and reflects on their life journey together.  Love, like life, is filled with ups and downs, and Jackson perfectly captures this theme throughout the song.  It’s the precious memories spent with loved ones that allow us to weather the storms we face in life; always appreciate the little things that cause us to look back and “Remember When”.  Filled with fiddle and the wail of a cryin’ steel guitar, Remember When is the kind of tune that makes you wanna grab your lady and hold her tight.  Best Line: “Remember when, I was young and so were you, and time stood still and love was all we knew.” (Listen Here).

  1. Blue Ridge Mountain Song

There are few things in life that sound as good as a banjo and fiddle played together in perfect harmony.  Throw in the soothing voice of Alan Jackson and a heartbreaking country tale, and you’ve reached musical heaven, which is exactly what listeners get with the bluegrass tune Blue Ridge Mountain Song.  The song tells a beautiful yet heartbreaking story that we won’t spoil here, and is the type of tune that you’ll listen to over and over again when taking your truck out on a relaxing moonlight drive.  Best Line: “They were young and they were free, like a mountain melody, in love as they could be, singing that blue ridge song.” (Listen Here).

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

The tragedy of 9/11 has been covered in numerous movies, books, documentaries, and songs.  However, I would argue that none do so as respectfully and beautifully as this tribute penned by Alan Jackson.  The song doesn’t make any bold political statements, but instead focuses on what millions of everyday Americans felt in the aftermath of the tragedy.  Prayer, family, anger, remorse, unity, all are powerful themes woven throughout the story of that fateful September day, and Jackson sings about each of them masterfully.  Best Line: “Did you go to a church and hold hands with some strangers, stand in line to give your own blood? Did you just stay home and cling tight to your family, thank God you had somebody to love?” (Listen here).

  1. Small Town Southern Man

Alan Jackson has a unique knack for crafting honest and relatable stories of the everyday man from middle America.  Perhaps the best example of this is the song Small Town Southern Man.  Traditional family values are celebrated in this song, which tells the tale of a man growing up in small town USA.  God, family, and honest, hard work are the three greatest values for millions across this great nation, and Jackson sings about each of them in a relatable way.  Best Line: “And he bowed his head to Jesus, and he stood for Uncle Sam.” (Listen Here).

  1. I Still Like Bologna

Sometimes the best way to make an important point is with a little bit of good ol’ fashioned country humor, and that’s exactly what Jackson does in I Still Like Bologna.  The world is constantly changing, with a flashy, new technology seemingly being introduced to America every other day.  Grumbling and complaining about change won’t stop the world from changing, and folks need to embrace new opportunities and technologies in order to make the most out of life.  However, on the flip side, it would be extremely unwise to forget to appreciate life’s simple things by throwing out everything that is “old and outdated.” Jackson advocates a middle ground in this catchy and humorous tune, admitting that while the new digital world has made life better in a lot of ways, folks can still appreciate the simple things like the grass between our toes and a bologna sandwich.  Best Line: “The grass between my toes, and that sunset sinking low, and a good woman’s love, to hold me close.” (Listen Here).  

  1. Amazing Grace

The songs an all-time classic, so I won’t waste time by writing long winded sentences about it.  I will say however, that Alan Jackson’s rendition of the gospel classic is as beautiful and moving as I’ve ever heard.  If y’all haven’t done so yet be sure to listen to all of the songs of his two gospel albums.  Power, moving, and beloved by millions worldwide, Amazing Grace is arguably the most popular hymn every written.  Be sure to give this amazing rendition a listen.  Best Line: “Amazing Grace, how sweet the sound, that saved a wretch like me.” (Listen Here).

  1. Midnight in Montgomery

If I had to describe this song in a few words it would probably be along the lines of chilling, haunting, or just plain old spooky!  Midnight in Montgomery tells the chilling tale of a visit to the grave of country great Hank Williams, and after one listen you’ll probably be looking over your shoulder just to make sure that the ghost of old Hank isn’t right behind you!  It’s fitting that a song paying tribute to Hank is so haunting, as the country great passed away tragically at the young age of 29.  The tune is best listened to during a dark, stormy night, in between spins of Hank’s own country classics.  Best Line: “And off somewhere a midnight train is slowly passin’ by, I can hear that whistle moanin’, I’m so lonesome I could cry.”

  1. Drive (For Daddy Gene)

Think back to the first time you’re Grampa or Dad let you drive the family boat or truck… what do you remember?  For me, few things in life were as magical as that feeling of freedom I got when sitting on my Grampa’s lap as a kid and getting to drive.  That’s the feeling that Alan Jackson capture’s in his song Drive.  Timeless childhood memories are things we hold on to forever, and something as simple as driving an old truck down a country road with your childhood hero can be a highlight of an entire life.  Best Line: “A young boy two hands on the wheel, I can’t replace the way it made me feel.” (Listen Here).

  1. It’s Five O’Clock Somewhere

There are some days when we feel like we can take on the entire world, days that are super productive and filled with hard work.  And then there are some days where we just wanna throw our hands up in the air and a scream, “I NEED A DRINK!!!.” It’s Five O’clock Somewhere is about that second kind of day.  Whether the boss has you down or you just haven’t relaxed in forever, everyone has those days where they just wish they were away on a Mexican vacation.  Relaxing, fun, and a great reminder that there is never a bad time to have a drink, this tune is the perfect song to put on the juke box at the end of long hard week (or in the middle of a work day while you play hooky…).  Best Line: “An’ pour me somethin’ tall an’ strong, make it a “Hurricane” before I go insane.” (Listen here.)

  1. Chattahoochee

This song perfectly captures that magical feeling of lazy summer days spent swimming with buddies and crushing on your high school sweetheart.  For a teenage boy, there are few things more pressing on a hot summer night than drinking cold beers with a buddy and making memories with friends.  Alan Jackson struck gold with this song, and it remains a staple of summer time party playlists across America.  Best Line: “Down by the river on a Friday Night, a pyramid of cans in the pale moonlight.” (Listen Here.)

  1. Gone Country

That’s right I’m breaking my own rules.  I know I said I was giving y’all the top ten best Alan Jackson songs, but the simple truth is I couldn’t narrow the list down that far!  After a fight almost broke out in the Honky Tonk Haven boardroom over what songs would make the list, I made the executive decision that an unprecedented eleventh song would be included, in the interest of public safety and to prevent riots.  Gone Country is a humorous song, and pokes fun at the growing trend of non-country fans who jump in on the country lifestyle.  Catchy, memorable, and a great sing along song, Gone Country should be in every Alan Jackson fan’s rotation.  Best Line: “He’s gone country, look at them boots, He’s gone country, oh, back to his roots.” (Listen Here.)


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