Alan Jackson is one of my favorite artists. The first time I remember really getting into Alan’s music was a Saturday back at home with my folks. I was still just in the single digits in age, but I found a copy of Alan’s first greatest hits collection in my parents’ CD case. I took out the disc and put it in the player and we listened to the songs all day through and through. From that point on I’ve been an Alan Jackson fan. Here is a list of Alan Jackson’s best country songs with descriptions by me of why they belong on this list. Please share your own thoughts in the comments.
Alan Jackson Songs
50. Freight Train
I really wish this one would have been released as a single. It’s rocking and rolling and Alan is singing perfect on the fast paced track. The album Freight Train was released at a time when Alan and his label seemed to be on the outs. There wasn’t much excitement with the album and the title track never saw the light of day on radio. I think it could have been a big hit thought. It’s one of my all time favorite Alan Jackson songs.
49. I’ll Fly Away
In 2006, Alan Jackson released a gospel album. Originally recorded only as a gift for his Mom, the set was released to the general country and Christian audience and it really caught on in a big way. The set sold a million copies. It’s a great collection of all the classics including I’ll Fly Away. The song is a perfect example of how Alan does well by the original song while still adding his own stamp.
48. Santa’s Gonna Come In A Pickup Truck
Alan’s Christmas songs still get some good play on radio every holiday season. I get a smile on my face each when I hear Alan team up with the Chipmunks for this Christmas classic. The Chipmunks are ready for their presents while Alan is trying to get through to them about the true meaning of the holiday season. It’s just a fun song with plenty of laughs and smiles for the kids and for the adults.
47. Where I Come From
During the summer of 2001 I was working at a local golf course on the maintenance crew. In the early mornings it was my job to cruise around cutting grass. During that time I enjoyed listening to the hit country music of the time on my headphones. One of the biggest songs that summer was Where I Come From by Alan Jackson. The song is full of great hooks including the rhyming of salsa and Tulsa. It doesn’t get anymore country that that right there.
46. Mercury Blues
It’s hard to follow up a huge single like Chattahoochee, but Alan was able to do just that in ’93 when he came out with the classic Mercury Blues. The song dates back all the way to 1949, but Alan’s version is well remembered in the country world. It’s an ode to the great Mercury cars of past and present. Alan is a well known car buff and this song fits him just fine. It raced up the charts to #2 and remains a fan favorite today. It’s a classic example of how Alan can crank up the beat on a good traditional country song.
45. Buicks To The Moon
This is the kind of music I like from Alan the most. It’s just a good song with a catchy melody and lyrics about love. Buicks To The Moon was a simple album cut on Everything I Love, but I’ve heard it every once and a while on the classic country stations. It’s that simple melody that Alan really knew how to get across to the country audience. The simple country charm of a good Southern man is what made Alan famous and he’s still the best at it and at his own best when singing like this.
44. I Don’t Even Know Your Name
The story behind this song is Alan’s brother in law and nephew gave him the title. Alan let it sit around a while until finally entertained the pair of co-writers by finishing the song. The tune became a big hit for Alan and even the video was fun. Jeff Foxworthy lent a hand to his good buddy and the song went to a new level. Country fans like to have fun once and a while and so does one of their favorite artists Alan Jackson. Before there was The Hangover there was I Don’t Even Know Your Name.
43. From A Distance
I may get a few of you with this song. It wasn’t a single in Alan’s career, but I love the song. I hear it every once and a while on AOL ’90s Country Music station. It’s a throwback to Alan’s early career. From A Distance is a song about not being able to be with someone you love. You love them from a distance, but can’t be with them. It’s a great song Alan co-wrote with Randy Travis. Talk about two heavyweights coming together for a song most country fans haven’t even heard before.
42. Designated Drinker
Alan’s Drive record was packed with great country songs. One song on the set that wasn’t released as a single was a great duet with George Strait. Designated Drinker is a little play with words on the typical meaning of designating someone to drive when you’re out having a few drinks. Here we have two of country’s biggest names getting together again for a great country drinking song. It really doesn’t get better than Alan and George on record together and with a great song it makes for something special.
41. Pop A Top
In 1999, Alan released his cleverly titled Under The Influence album. The set was a collection of songs made famous from some of Alan’s heroes. It was his ode to the influence they had on his career. The first single from the set was Pop A Top. The song has the classic country drinking song theme. Fools sitting down to drink their sorrows away has been a popular country theme over the years. With so many drinking songs and so many good drinking songs it’s really tough to stand out as one of the best, but I think Alan was able to take Jim Ed Brown classic and make it a classic of his own.
Everything is always a little more fun with controversy. Two country legends teamed up for Murder on Music Row. The year was 2000 and Alan Jackson and George Strait didn’t officially release the song, but they performed it at an award show and some people in the industry were offended. Country had gone a bit back to the pop ways with a few new acts and the traditional guys felt they needed to say something. The two didn’t write it, but the song had an impact and probably always will each time the pop influences find their way back into country music.
39. Blue Blooded Woman
I always have a soft spot in my heart for artists’ first singles. Blue Blooded Woman didn’t become Alan’s first hit yet I think it’s a great song. I’m not sure why this one didn’t race up the charts. It’s hard for new artists to break through even when they have good material. The country world just wasn’t ready for Alan when he came out with this one, but it worked out in the end. If you haven’t heard this song before be sure to check it out. It’s classic AJ.
38. I’ll Go On Loving You
It seemed to be interesting times for Alan Jackson in the late ’90s. The rumor was he was having troubles with his marriage as his wife later described in her memoirs. I’ll Go On Loving You seemed to have a bit of darkness to it. It still charted high on the singles charts yet the entire album it was on had this dark side as Alan admitted later on. It was still a great song though. Alan is one of the best at capturing emotion even on songs he didn’t write himself.
37. Where Were You (When The World Stopped Turning)
Some people will put this song higher on the charts. I remember watching the CMAs when Alan first performed this song after 9/11. The song soon captured the emotions of the nation and it became a huge hit song. It was quite the accomplishment for Alan. He knows how to get his feelings down on paper and the story that he had heard the melody in his head one night was great.
36. The Talkin’ Song Repair Blues
Alan Jackson took this song to number 18 on the charts back in 2005. It wasn’t his biggest hit by any means, but I thought it was a classic. It’s a fun song written by the legendary Dennis Linde. The song is about a guy that runs down on his luck and needs his car fixed. The two try to hustle each other and it makes for some fun back and forth. It’s a great song that deserved to charts higher, but even so it stands tall on its own.
35. Tall, Tall Trees
On Alan Jackson’s ’95 Greatest Hits release he nailed it with this new single. The song was actually a cover of a song co-written by two country greats – George Jones and Roger Miller. I think I remember reading a quote from George about the song where he had forgotten he had even written it. I’m sure he was kidding, but I think it’s pretty cool that Alan was able to dig up this old classic, make it his own, and turn it into a great country hit.
34. Midnight In Montgomery
On Alan’s second album he really came into his own and became a country star. On that record was a different kind of song from Alan Jackson. Midnight In Montgomery was Alan’s tribute to the great Hank Williams. Alan always paid tribute to those that came before him. It was one of Alan’s humble traits that probably contributed to much of his success. This song was never really one of my favorite Alan tunes until years after it was released. Now I see it for the great tribute it is.
33. That’d Be Alright
Alan did a little reflecting on life and people over the years. With this song he thought that it’d probably be a little better if everyone didn’t have so much to worry about. And all he asked for himself was half a ham sandwich in his lunch pale. Alan always seemed to be the soft spoken humble type, but every once and a while he let out his feelings about the world with great songs like this hit from 2002.
32. I’d Love You All Over Again
Beginning in 1991 Alan Jackson started a run of many many number one hits on the country charts. This was the first number one for AJ. It’s a great love song about knowing all the things you have gone through with someone and be willing to do it all over again without question. I still hear this song on the radio from time to time. It’s a classic Alan song from his very first album. Alan was really hitting it with country fans when this one came out and it’s no wonder it’s still a huge hit with fans even today.
31. Small Town Southern Man
At the end of 2007 Alan Jackson kicked off a great run of hits with Small Town Southern Man. The song was kind of a throwback to the tunes Alan made famous back in the early ’90s. It was a simple song about good southern folks. Alan was always at his best singing about the things he knew from his family and friends back in the simple southern life. The song hit the top spot on the charts and started another run of three straight top hits. Not a bad feat for a guy nearing his twentieth year at the top of the country world.
This was Alan’s tribute to his Dad. The song is about what every kid loves to do growing up: Drive. The song tells the story of Alan growing up and being able to drive what his dad would let him. Then things move into Alan’s new life where he lets his own kids drive the Jeep around their property. I remember the first time my dad let me drive the truck. It was back in the field on my Uncle’s farm. It’s funny how that’s the exciting stuff you remember from your days as a kid.
29. Tonight I Climbed The Wall
What a great way to sing about love and devotion. Alan wrote this song about a couple that had been fighting. They had built a wall between them will all the argument and disagreement. Now the guy in the song climbed that wall. He put all the indifference behind him and went to his wife. After he made the climb and admitted his faults he realized the things they were fighting over were so small.
28. I Only Want You For Christmas
Alan released his first Christmas single back in 1991. The song – I Only Want You For Christmas – was a snappy little number about being in love on Christmas Day. The song nearly cracked the top 40 back during its initial release and now it makes an appearance on radio every holiday season. I always look forward to hearing this one during Christmas. It’s a great song period no matter what the season.
27. Monday Morning Church
At the tail end of 2004 Alan released this sad country song about a guy losing the love of his life. The loss was apparently sudden and tragic, but that’s beside the point. Here we have the story of a guy suffering an enormous loss. Now he’s wondering how something so bad could happen. He’s done all the good things he’s been asked to do. Why would he be shown such pain for his good life? This is a powerful and emotional song about faith. I love songs like this even though they don’t usually make a huge impact. Some people just don’t want to hear it. For others, these songs make you think.
26. Summertime Blues
This song was original recorded and and made famous by Eddie Cochran way back in 1958. It was later covered by the Beach Boys and The Who, but it was in 1994 that Alan Jackson made the song his own and took it to number one on the country charts. It’s a story about coming of age in the summer and going through various things boys go through during the summer months. Cars, work, and trying to get by. The classic story made the song. That and the cool deep voice hook in the chorus.
25. Little Bitty
Tom T. Hall wrote this fun little track. Alan took it to number one on the country singles charts in 1996-1997. The song takes a look at the busy life people were leading back in the ’90s. The internet was just about to boom and life was getting fast paced. Alan took Tom’s song and made people realize that living the simple, little country life is still not a bad way to go about it. People agreed with them and the song remains a hit even today.
24. Who’s Cheating Who
Alan took this song to number two on the charts in 1997. It was actually a cover of Charly McClain’s number one hit from 1980. The song is a simple one about cheating and the people we live our lives with. There’s nothing special to it except for a great melody and great lyrics. It’s interesting to listen to the original version after hearing Alan’s. Both are great, but I’ll always side with Alan on his songs. It would be interesting one day to see Alan’s songs covered by others. Someone like Chris Young maybe.
23. She’s Got The Rhythm (And I Got The Blues)
Alan’s album A Lot About Livin’ (And Little ‘Bout Love) was a huge, huge success in 1992. The set sold something like 6 million copies. The first song released as a single was She’s Got The Rhythm (And I Got The Blues). It was yet another co-write with Alan and Randy Travis (those two really need to get together again for a session). It’s a groovy little song that shot up the charts to number one. A good old country song about loving and leaving from Alan Jackson. It really doesn’t get any better.
22. Right On The Money
I’m not sure why, but this song has a special place in my heart. In 1998 I really took a strong liking to country music and the songs on the radio at that time were a big part of my growing obsession. Right On The Money peaked at the top spot that year, but seems to be overlooked in some instances among the greats in Alan’s collection. Phil Vassar had a hand in writing the tune. It’s a good old song about loving a good woman. She’s even the best cook that’s ever melted cheese. A classic country line.
21. Little Man
In 1999, Alan released Little Man as the final single from his High Mileage album. It’s a great track and I think it’s too often overlooked in his collection. The song is about how things have changed in the late 20th century and beyond. Local events, businesses, and community were left behind in favor of connecting with the outside world. I don’t think Alan was trying to say either way is wrong or right. I think he was simply acknowledging that times were changing and he captures that emotion well.
I was close to listing this song in the top ten. It’s probably in my top 3 favorite Alan Jackson songs. I probably should have put it in the top 3, but I’m happy with it here. Someday is another simple yet awesome country song. The guy in the song is seeing the life he knows end. The woman he’s with is fed up with him. She’s finally moving on. The guy was always saying he’d get his act together someday, but someday never came around and she got sick of waiting. Women put their faith in love and the ambitions of their man. Sometimes it doesn’t work out and someday never comes. It can make for some sad times…and good country songs.
19. Good Time
Old Alan brought back line dancing 2008 with the title track to his hugely successful album. Good Time had the line dancing beat and country fans took to the song as fast as you can two step. The track hit the top of the charts that year and Alan kept things rolling in his big career. This song was a throwback for me to the days when Alan would take a great melody and pair it with some simple lyrics about the good country life. I really liked where hew as heading when this song was released.
18. Remember When
Alan Jackson’s second greatest hits album became a must have because of its two huge hit singles. The first single you’ll read about in two spots, but the second was also a huge hit. Remember When is an apparent autobiographical song about Alan and his wife. It’s a sweet ballad about their life together. Alan gives fans a little peek into their lives over the years. There were through some ups and downs, but through it all they were able to still love each other and look back fondly at the good times they have had together.
17. I’ll Try
Alan took this song to number one back in 1996. The song was off his first collection of hits. I’ll Try is about a guy and the love of his life. They’re talking about their worries and dreams for the future. They’ve both been in difficult situations and they’re not sure if they can make each other happy. The guy sits back and says that he will only promise to try and do the best he can to make things work. Sometimes that’s what you have to go with in a relationship. It takes a bit of a risk in order to experience something great.
16. It’s Five O’Clock Somewhere
There aren’t many country songs that hit multiple week number one status. In the summer of ’03 that’s just what Alan Jackson did though. The first single from his second greatest hits collection was It’s Five O’Clock Somewhere. The song became a huge, huge country hit that year and remains popular every time the sun shines on the beach somewhere in the country world. Alan called in Jimmy Buffett to help him out with the island themed song. It made for a great combo and both artists had a huge boost in their careers not that either needed it.
15. Gone Crazy
Gone Crazy was released on 1998’s High Mileage album. The song peaked in the top five on the country charts. It’s a great country breakup song. The guy is at home going crazy out of his mind thinking about what he could have done differently to make his ex stay with him. Now she’s gone though and she’s not coming back. She’s gone and he’s gone crazy. If you’ve ever really screwed up with a girl you know what this song is about. You don’t realize the mistakes you’re making until it’s too late.
This was an interesting song. Alan Jackson sat down and wrote the first person story of a guy calling in to the local paper to place a wanted ad. The man isn’t looking for new love. He is looking for forgiveness with the woman he blew it with. She left and now he’s missing her something bad. He calls up the paper and wants to place the ad. It’s a really interesting take on what a country song can be. It’s a great song with a good melody and even the spoken words are great. I’ve always loved hearing this song on the radio.
13. (Who Says) You Can’t Have It All
Alan Jackson is probably the best at taking a simple melody and a short set of simple lyrics and making it memorable. This song is the perfect example. Alan laid out a catchy yet simple melody and put it to the heartbreak lyrics and created a country classic. It’s the song about a guy that is almost laughing looking at his sad bachelor life and wishing he was back with his woman. He laughs about the things he doesn’t have now that she’s gone. He does have a light bulb without a shade. Who says you can’t have it all?
12. Everything I Love
Cigarettes, Jack Daniels and caffeine have had their grasp on a few people. Everything I Love was a song from Alan Jackson that told the story of a guy watching his life fall apart. Everything in the guy’s life is falling apart. Everything he loves is literally killing him. He loves those cigarettes, those shots of JD, and those cups of coffee in the morning. He also loves his good woman, but she left and now the life he’s leading without her is killing him. It seems the guy doesn’t stand a chance.
11. Gone Country
Something I love about Alan Jackson is he always had the best way for being subtle in the way he let everyone know his feelings toward something a little controversial. I think it all started way back in 1994 with Gone Country. The song was not written by AJ, but he sang the hell out of the song – a story about the rush to country music in the ’90s by music execs and every kind of singer there was out there. Alan used this song to share his feelings on how country music became saturated. He later used the same subtle tactic in 1999 when he stopped his own song at the CMA’s and performed George Jones’ Choices as a tribute to his hero after George had been denied the opportunity to perform the entire song. AJ is awesome.
It’s a heartbreak song about a gal heading out of town for a new life. She’s heading out the door because there is no common ground anymore. She’s leaving the marriage in Tennessee and heading for Texas. All the guy can do is wish he could move Dallas back to Tennessee, but his thoughts are hopeless. There is no getting her back and there’s probably part of him that realizes it. That’s the tough part about breakups sometimes – they catch you by surprise.
9. Livin’ On Love
These songs about the simple country life from Alan get me every time. Here we have the love story of two people barely getting by on life with the common means of money and possessions. What the couple has though is love and that’s all they need to make their lives happy and full. Alan has the right kind of charm to tell these kinds of stories. And that’s really what I think Alan Jackson is best at – telling the stories of the simple, good country life people still lead today.
8. Love’s Got A Hold On You
It was the fifth and final single from the Don’t Rock The Jukebox album, but this song became another number one hit for Alan and probably one of his more remembered songs. It’s got the groovy, upbeat melody and the catchy, fun lyrics. The great image of a guy falling in love and not knowing why he’s acting weird is fun and energizes. If you’ve ever fallen head over heels for someone you know that it can make you a little crazy. You may not need to go to the doctor though. Love’s just got a hold on you.
7. There Goes
I love the emotion in this song. It’s so upbeat and fun. Sure it’s not the snappy uptempo number, but I love this kind of laid back good time feeling kind of song. The song went number one back in 1997, which was just about the time I really became interested in country music. This was the kind of music that really got me interested in country. It’s the simple kind of love song that sees a guy falling for a woman. It’s nothing tricky or surprising about the lyrics and that’s the charming appeal that made people fall for the song. I still think Alan writes the best melodies and lyrics when he solo writes and this is a perfect example.
6. Here In The Real World
Without Here In The Real World we may not even know who Alan Jackson is. Ok, I’m sure AJ would have made it big at some point, but this was the song that broke his career through to the mainstream. The song compared real life with that of the old movies Alan would watch. He seemed to have a love for the westerns. In real life, though, it’s real people that get hurt when hearts are broken. People cry real tears and things really aren’t easy. It’s a unique topic for a song and it was just the right track to break Alan into the top 3 on the charts for the first time back in 1990.
Alan was always at his best when he was singing about the simple life he grew up in. With the aptly titled Home he had to wait for it to see the light of day on radio. The song was cut for his first record, but never made it out as a single. Later on his greatest hits collection the song was released and became a huge hit. I love the line about his granddaddy rolling down an old tool shed on two logs. It’s a great image and a great country hook that just about everyone sings along with when it comes on the radio. It doesn’t take too much to make a happy home for a family and that’s just what Alan sang about in this classic.
4. Don’t Rock The Jukebox
Alan kicked off his second album with a major hit. Don’t Rock The Jukebox is a genius use of wording to create one of the best country songs of all time. The song is an ode to traditional country music. The idea for the song actually caught Alan a bit by surprise. He was playing a show one night in a little honky tonk. He was hanging out over in the corner by an old wobbly jukebox. A guy in his band walked over to chat and leaned against the old music player and it rocked over a bit. Alan looked at him and said… The rest was history and the double meaning song became a huge hit. I don’t need too much rock on my jukebox. Plenty of Alan Jackson will do just fine.
3. Chasin’ That Neon Rainbow
If you pressed me for my all time favorite Alan Jackson song it would be Chasin’ That Neon Rainbow. I love the image of Alan Jackson working the small time shows while trying to make it big in Nashville. He was chasing his dreams when everyone around him thought he would never make it anywhere doing what he loved. He fell in love with country music while listening to his daddy’s radio. I think the dreaming in the song and the hope for a better life is what connected with so many fans. I love, love, love this song and it makes me feel good each time I hear it.
2. A House With No Curtains
This song is going to catch a few people off guard. It wasn’t even a top 15 hit for Alan. The song is one of my favorites though and since this is my list I had to give it a little unfair advantage. I just think the lyrics are so clever and the song so…so country. A House With No Curtains is about a couple that stays together even though they are not happy. They still put on the show, but they both know that everyone sees things are falling apart. Well…maybe not falling apart, but the couple just can’t come to terms that they really aren’t meant for each other and everybody can see through the windows of their relationship.
It’s almost an iconic image. Alan Jackson (and his stunt double) bare footing on the water behind the ski boat on a lake in the summer. Chattahoochee became a huge hit for Alan Jackson and really became the signature song in a collection of legendary songs. It’s a simple song about growing up as a young boy down south. Learning about the way things are and just trying to live the good life is what the song is about. It’s simple yet the story rang true with fans. And the fast melody had everybody singing along nonstop for years and years.