Favorite Songs By Favorite Artists: Alan Jackson

TWIN LAKES, WI - JULY 17: Singer/Songwriter Alan Jackson performs at the 17th Annual Country Thunder USA music festival on July 17, 2009 in Twin Lakes, Wisconsin. (Photo by Rick Diamond/Getty Images) *** Local Caption *** Alan Jackson

In CMT’s recent Nashville Skyline column, Chet Flippo said it best when he wrote: “In some ways, Jackson has become the Ernest Hemingway of country music. In writing, that is. Not necessarily in lifestyle. At Hemingway’s best, he told stories very simply, getting directly to the point. He knew his subject inside out, whether it was bullfighting or deep-sea fishing and could brilliantly tell a vivid story about it in as few words as needed. Similarly, Jackson, has staked out his turf and can write and sing about it in a simple and direct style.”

In great anticipation of Alan Jackson’s forthcoming album called Good Time”, set for a March 4 release, I will be counting down 25 of my favorite Jackson songs. With this list, I am sure that we will discover Flippo’s Hemingway analogy to be quite accurate. Hopefully, his new album will leave me wishing that I could update this list.



“I’ll Go On Loving You”

High Mileage (1998)

Whew! Many times, talking songs don’t quite work for me, but this one certainly does. It’s raw and hot! Jackson is able to use his deep speaking voice to make us forget that he hardly sings.



“It’s All About Him”

It’s All About Him: Finding the Love of My Life (2007) – Denise Jackson book

This is one of two songs recorded for his wife’s book, “It’s All About Him: Finding the Love of My Life.” The title was kind of clever because it made the average tabloid reader think it was referring directly to Alan. In reality, the title refers to a Greater Power. Inspired by the book’s title and premise, this is not another love song for his wife, but a song that focuses on God, the One who is credited for saving their once faltering relationship.



“Let it Be Christmas”

Let it Be Christmas (2002)

This is the first of two Christmas songs on this countdown. It’s simple, but captures the spirit of Christmas. In all actuality, the words may be somewhat cheesy, but it sounds like a classic coming from Jackson. It’s one of the few times that a children’s choir works.



“Rainy Day in June”

What I Do (2004)

This song captures the essence of loneliness very well. It uses the gloominess of a rainy day in June to paint the picture of the singer’s feeling of loneliness since his significant other has left him. “The sky is grey and {he} is blue and Jackson’s performance compliments this sad proclamation.



“It Must Be Love”

Under the Influence (1999)

Alan Jackson proves his ability to interpret a song. This already good Don Williams song is expertly covered by Jackson on this album of cover songs. While he doesn’t necessarily reinvent the sound, he updates it so that it would reemerge as a hit with his own signature sound.



“Chasin’ That Neon Rainbow”

Here in the Real World (1989)

This early Jackson song is infectiously catchy. With a sound of innocence, it takes us through the journey of his musical history up to the point of the realization of his “honky tonk dream.”



“That’d Be Alright”

Drive (2002)

With its upbeat Cajun feel, the singer tells us that all he really needs is the basic things in life in order to truly be alright (You know, practical things like money growing on hackberry trees…). It even has a little social commentary: “If everybody, everywhere/Had a lighter load to bear/And a little bigger piece of the pie/We’d be livin’ us a pretty good life/And that’d be alright.”



“Tonight I Climbed the Wall”

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

In this song, Alan puts some verbs in his sentences, as Dr. Phil would say. The singer acknowledges that there is a symbolic wall between him and his lover. He doesn’t just lament the decline of their relationship, he does something about it. He crosses the divide and “climbed the wall” in order to take steps toward the repair of their marriage because they’ve “come too far to fall.”



“A Good Year For the Roses” (with George Jones)

The Bradley Barn Sessions (1994) – George Jones album

I love this George Jones collaborations album that covers many of George’s classics with the help of some of my favorite artists of the time. One of the stand out performances on it is this duet with Alan Jackson. The opening line clearly sets the tone for the song: “And a lip print on a half filled cup of coffee/That you poured and didn’t drink/But at least you thought you wanted it/That’s so much more than I can say for me.” The self deprecation is right on the surface here.



“You Can’t Give Up On Love”

Who I Am (1994)

In the first verse of this song, the singer is encouraging a friend to keep working on his relationship and telling him that he “can’t give up on love.” The singer acknowledges that love doesn’t always come easy, but it’s worth it when you have it. In the second verse, the singer looks out his window and sees what he assumes to be a broken family and maintains his point that we “can’t give up on love.” The bridge is practical and admits that “every day can’t be a honeymoon.” A simple melody with a conventional, but poignant, message.



“That’s the Way”

It’s All About Him: Finding the Love of My Life (2007) – Denise Jackson book

This is the second of the two songs that Alan Jackson recorded for his wife’s book about their marriage. He sang this song at their wedding ceremony and then at their vow renewal ceremony. It’s a nice cover of a wedding song with Alan’s signature touch.



“It’s Five O’clock Somewhere” (with Jimmy Buffett)

Greatest Hits Volume II (2003)

As Kevin has already pointed out in his review of this song, the hook isn’t technically plausible, but it’s Another fun way of saying “take this job and shove it” Hey, it even subtly promotes responsible drinking: “I could pay off my tab/pour myself in a cab/An’ be back to work before two.”



“Monday Morning Church”

What I Do (2004)

What an achingly sad song! This poor man’s wife has died and his “heart is empty as a Monday morning church.”—that’s pretty empty. if you need to find someone to accentuate the feeling of sadness in a song, Patty Loveless is just the right person to fit the part.



“Here in the Real World”

Here in the Real World (1989)

This is a reality check. The singer is taught, by an assumed ex, that life isn’t always like the movies because the “the boy don’t always get the girl/here in the real world.” This a cool way to sing a true country song, isn’t it?



“Right On the Money”

High Mileage (1998)

This Phil Vassar-penned song, put in Alan Jackson’s capable hands, is fun. The first person character defines himself as a “good old boy” and proceeds to prove it throughout the song. He uses “good old boy” imagery to tout the perfection of his girl. She must be pretty perfect, since after all, she is “the best cook that’s ever melted cheese!”



“Song For the Life”

Who I Am (1994)

Alan Jackson sings this Rodney Crowell song beautifully. It is a tribute to a woman who has settled her man down. In fact, she keeps his feet on the ground. I like a good love song and this is among the best.



“The Blues Man (a Tribute to Hank Williams Jr.)”

Under the Influence (1999)

On one of Alan’s best albums, he covers this Hank Williams Jr. song with class. Not only does he cover it, but he turns it into a tribute to Bocephus himself.



“I’ll Try”

The Greatest Hits Collection (1995)

This song is stingingly honest! Perhaps too honest. He’s not vowing to always love her, as love songs usually go, but he’s pledging to try to always love her. There’s a difference, I think.



“Let’s Get Back to Me and You”

Who I Am (1994)

This autobiographical song is an up-tempo number that appeals for some marriage rejuvenation. He sings “I’m always on the road/You’re always all alone/And I’m not always there when I’m at home.” As a concession, he allows, “I’m ready for a little change/I’m ready to accept some blame…”




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

This song about a carefree teenager is one of the first country songs that caught my ear. It has a catchy melody with a guitar pattern that sticks in your head.



“(Who Says) You Can’t Have it All”

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

This lonely man sure is the king of his castle. He has no possessions and nobody to love, just memories and old love letters, but at least he’s the “Lord and master” of it all.



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

Drive (2002)

This is a fine example of Chet Flippo’s eloquent comparison of Alan Jackson to Ernest Hemingway. Like so many other people in the United States, this song deeply resonates with me. How can it not. Alan does such a good job of capturing the mood of Americans at the time of “that September day.” He asks “Where were you when the world stopped turning?” At the beginning of each stanza, he asks us about our physical location and then moves onto our emotional “location” of that day, which are both things we will, without a doubt remember for the rest of our lives.

“Did you turn off that violent old movie you’re watching/And turn on “I Love Lucy” reruns?” is the line that proves, to me, that Alan really intuited the impact that that day had on so many people. In fact, I remember that my college roommate and I had been watching the news coverage throughout the day. Finally, that night, she asked if we could just turn off the news and watch Nick at Night for a while, which was an idea that I welcomed with much relief.

While this line may not be the specific line that captured everybody’s emotion of that day, this “singer of simple songs” surely provided an outlet for all of us to mourn the heartbreaking tragedy that we cannot truly understand to this day. This is a testament to a truly brilliant songwriter.



“Midnight in Montgomery”

Don’t Rock the Jukebox (1991)

When I was a kid, I remember that this song scared the hell out of me. To put it simply, it’s creepy! Clearly, Alan reveres the Hanks. This haunting song describes a fictional vision that he had of Hank Williams Sr.



“The Angels Cried” (with Alison Krauss)

Honky Tonk Christmas (1993)

This is, unapologetically, the second Christmas song on this countdown list. It is probably one of my favorite original Christmas songs that exist. Alan’s and Alison’s pure voices blend perfectly together. Furthermore, the bluegrass feel only adds to this song’s perfection.



“Remember When”

Greatest Hits Volume II (2003)

This song is an eloquent tribute to Alan’s marriage to his wife, Denise. It is one of the few songs that stand strong without a chorus.

It takes us through the highs and lows of their relationship. He may even have given us too much information with, “You were the first/so was I/We made love and then you cried/Remember when?”

Because my mother defines her life and self worth by her children, I think she can’t imagine the time when there will be no children in her house. As a result, my parents have adopted many children in order to fill the void that she is afraid of facing. In reaction to this, I have always told myself that such would not be the case for me. So, even though I am not yet a parent, I plan to adopt my favorite line of this song as a promise to myself and my marriage: “Remember when we said when we turned gray/When the children grow up and move away/We won’t be sad, we’ll be glad/For all the life we’ve had/And we’ll remember when.”




  1. I don’t know if I agree with all of your choices (everyone’s personal favs are different), but I’ve always loved Remember When. That might be my favorite Alan Jackson song too.

  2. Vince Gill was right when he said at the 2001 CMA Awards that “Alan Jackson conveys simple truths that come from the heart.” Alan Jackson is one of the greatest singer – songwriters in country music history.

    Some of my favorites are “Chasin’ That Neon Rainbow”, “Midnight in Montgomery”, “The Sounds”, “Chattahoochee”, “Dallas”, “Livin’ On Love,” and “Here in the Real World”.

    It has been 19 years since Alan debuted. He is still making great music, and perhaps more amazingly remains popular – still getting played on country radio and selling albums. I think that speaks volumes about Alan Jackson and his music.

    Like LeAnn, I look forward to hearing more great Alan Jackson music on his forth coming new album “Good Time”.

  3. Alan Jackson is an ordinary man with an extraordinary knack for plaintive, heartfelt lyrics and melodies that speak directly to the soul. He tells the truth no matter how painful, and finds the simple joys that are all around us, if we’d only stop long enough to appreciate them. He is hardworking, humble, and quick to admit he’s not perfect, which for my money, makes him THE perfect country singer/songwriter. From the moment I first heard “Here In The Real World” I have been a fan and I continue to appreciate what a great artist he is. Your list may not match mine exactly, but you have shown a good cross-section of songs that show the depth of a deceptively complex “simple man.”

  4. Alan is definitely one of my favorite artists, so I’m glad you chose him. Some songs I would have put would be “Drive (For Daddy Gene)” and “Small Town Southern Man”, but other than that great list.

  5. I definitely concede that Drive was a strong contender. I like Small Town Southern Man, but I don’t love it. I was happy, however, that it returned to form.

  6. Pretty good list. I really like ‘Blues Man’ and ‘A Song For The Life’ so nice to see them included. Wouldn’t have chosen ‘Remember When’ as the no.1, because it drags on that song.

  7. “Where Were You (When the World Stopped Turning)?” is probably my choice for classic Alan Jackson. He really pegged the day and the emotions of 9-11. Where others took on the anger, Alan went with the confusion so many of us were truly feeling. Still gives me chills when I hear it.

    I really appreciate Alan for staying true to country music. Where so many others give into the seduction of “cross-over”, Alan writes and plays what he knows… and that’s why people still relate to him 20 yrs later.

  8. My favorite is definitely “The Blues Man”. It was also nice to see “Monday Morning Church” and “Song for the Life” mentioned. I would also add (I know, I know. It’s tough to limit the list to 25) “Gone Country”, “Like Red on a Rose” and “Between the Devil and Me”. :) Thanks again!

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