Alan Jackson has definitely produced some of the all-time best songs in the country music songbook. He is one of the greatest singer-songwriters in country music history; no questions asked. After all, he has scored over thirty No. 1 hit singles in a career that spans three decades and counting.

Here are our top picks of Alan Jackson songs.

15. Remember When

Alan Jackson looks back about the ups and downs of relationships as a tribute to his wife, Denise. In the song, he described their love from their first time together, through raising their children, and described how he and his wife would “remember when” the children were young after they are grown. 

“Remember When” debuted at No. 45 on the U.S. Billboard Hot Country Singles & Tracks and reached No. 1 on the chart.

14. Where Were You

“Where Were You (When the World Stopped Turning)” was the lead single from Alan Jackson’s tenth studio album, Drive. The lyrics of the song center on reactions to the September 11 terrorist attacks on New York City and Washington D.C., written in the form of questions. 

He debuted the song publicly at the 2001 Country Music Association’s Annual Awards Show. The song spent five weeks at No. 1 and earned Jackson a Grammy award, along with numerous country music accolades.

13. Drive

“Drive (For Daddy Gene)” was a song dedicated to Jackson’s father, Eugene Jackson, who died in January 2000. In the song, Alan recalled the moments how he and his Daddy Gene would drive around the countryside when he was a child on their old beat-up truck that they fixed up together and the boat they would drive around the lake. 

In the song’s final verse, Jackson talked about sharing his childhood experiences with his daughters and letting them drive his Jeep around their pasture.

12. Gone Country

The song served as a commentary on the country music scene which Jackson illustrated through three other singers: a folk-rocker in Greenwich Village, a lounge singer in Las Vegas from Long Island, New York, and a “serious composer schooled in voice and composition” living in the San Fernando Valley. 

The three found that their careers are failing, and as a result, they decided to begin performing country music instead. “I think it’s just a fun song actually, celebrating how country music has become more widespread and accepted by all types of people all over the country,” Jackson said.

11. Chattahoochee

“Chattahoochee,” co-written with Jim McBride, did not only claim the No. 1 spot on the year-end Billboard Country Songs chart but also earned CMA Awards for Single of the Year and Song of the Year. “We never thought it would be as big as it’s become,” Jackson said.

The song is about having fun, growing up, and coming of age in a small town – which anyone across the country can totally relate, not just by the Chattahoochee. 

10. Here in the Real World

Some of the best country songs deal with real-life emotions and consequences, just like “Here In The Real World,” the title track of Alan Jackson’s debut album. In the song, Jackson pointed out the glaring differences between make-believe movies and the truth in his lyrics. 

In the chorus, Jackson observed that “Here in the real world, it’s not that easy at all/’Cause when hearts get broken, it’s real tears that fall.” The song reached a peak of No. 3 on the U.S. Billboard Hot Country Singles & Tracks charts.

9. Livin’ on Love

The song described a couple who are “livin’ on love.” In the song’s first verse, there are “Two young people without a thing/Say some vows and spread their wings/Settle down with just what they need Livin’ on love.” Throughout the song, the couple stayed in love with each other as they aged. 

“Livin’ on Love” became his ninth No. 1 hit on the Billboard country charts.

8. It’s Five O’Clock Somewhere

In 2003, “It’s Five O’Clock Somewhere” became a career song not only for Alan Jackson but also for his collaborator Jimmy Buffett. Both the CMA Awards and the ACM Awards named the song as Vocal Event of the Year. It also topped the country singles charts.

A working-man’s anthem, the song’s title referred to a popular expression used to justify drinking at any time of day, given that somewhere in the world, it’s 5:00 PM, which is typically the start of ‘Happy-Hour’ at most restaurants and bars.

7. Between the Devil and Me

Written by Harley Allen and Carson Chamberlain, “Between the Devil and Me” is a song about a man describing the sexual temptation of an extramarital affair by saying that “She’s all I see/Between the devil and me.”

The mid-tempo ballad peaked at No. 2 on the U.S. Billboard country singles charts.

6. Midnight in Montgomery

Another country star inspired this song. While Allan Jackson was heading to Mobile for a New Year’s Eve show, he paid a visit to Hank Williams’ grave in Oakwood Annex Cemetery after performing a concert in Montgomery. He said he had encountered the ghost of Williams, who thanked him for paying tribute before disappearing. 

The song also referenced several hits of Williams, including “I’m So Lonesome I Could Cry.” The song ended with the words “Hank’s always singing there.”

5. Amazing Grace

There are definitely some songs that can just wrap their arms around you. The moment you hear the song, you automatically close your eyes, feel better, and just feel at home. “Amazing Grace” is one of those songs.

The song was penned by John Newton after renouncing his role as a slave trader, converted to Christianity, and became an abolitionist. It dates back to 1773 and has been recorded countless times over several musical styles. You could say Jackson’s version is one of the best as he sings with every fiber of his heart and being.

4. Home

In this moderate up-tempo song, Alan Jackson recalled his parents’ upbringing as a child in the state of Georgia. It’s a loving tribute to his parents and the home they provided. 

Jackson penned this song the first month he moved to Nashville because he was feeling homesick.

3. In the Garden

Alan Jackson is very open about his Christian faith, and he is praising the Almighty One for all the world to hear in his song “In the Garden.”

The song’s lyrics are comforting enough and will guide you to the better future that’s waiting for you. It has the power to ease the feeling of loneliness within you while its melody will make you realize how beautiful life is.

2. Summertime Blues

“Summertime Blues,” a song about the struggle between a teenager and his parents, his boss and his congressman, was originally recorded by American rockabilly artist Eddie Cochran in 1958.

It has been covered by many artists throughout the years. Alan Jackson released his own version in 1994 and gave “the oft-covered Eddie Cochran oldie the full, twangy ‘Chattahoochee’ treatment.”

1. The Older I Get

Released in October 2017, “The Older I Get” marked his induction two days later into the Country Music Hall of Fame. 

“This song reflects a lot of how I feel these days,” Jackson said. “It’s a good song. I really liked it, but the message was a little different when I first heard it. I thought maybe it could be a little more positive about being older and wiser and more content, so they rewrote a few things, and this is how it ended up.”

Chasin’ That Neon Rainbow, Don’t Rock the Jukebox, Gone Country are just some of other Alan Jackson’s songs that worth mentioning. We definitely couldn’t get enough of this great artist.