Alan Jackson is not your typical country star. He doesn’t only make country songs that you will love. He doesn’t change his style of music to a completely different one to become famous. No, Alan Jackson is one of a kind country artist, and that is why people enjoy listening to his music.

In an industry where most people try to chase fame, this Georgian native is different. He writes and performs songs because it’s what he’s passionate about. He doesn’t care about the business side of the industry. In his website, there is a statement by Alan where he talks about the music business.

“I never really liked the whole star part of the music business,” Jackson said. “I like the singing and the writing and all that goes with that. That’s the part that drew me into it. I wanted to make good country music, and I never wanted to venture too far from that.”

Now that’s amazing! He never goes after fame, but he is too incredible not to be noticed.

The Early Days of Alan Jackson

Alan Jackson was born in Newnan Georgia on October 17, 1958. He was born to Joseph Eugene Jackson, a mechanic at a Ford Motor Company, and Ruth Musick Jackson, a dietitian, and school cafeteria manager. Alan was the last child. He has four older sisters. None of Alan’s family members were inclined to music. Therefore how did Alan fell in love with writing and singing country songs?

Country Music Inspiration

His love of music happened when his friend introduced to him certain artists in the country music genre. His love of music therefore grew, and he finally knew what he wanted to become.

Moving to Nashville

When Alan met his wife, Denise, at the age of seventeen, they fell in love and got married in 1979. Alan was lucky enough to marry Denise because she supported him in his dream to pursue a career in music.

One day, Denise met Glen Campbell and asked him for some advice on what her husband must do about his career. Campbell suggested that she and her husband must move to Nashville. Hence, they listened to Campbell, and they moved to Nashville.

His Music Career

Alan is known to have released a total of sixteen studio albums. In addition, he has sixty-six singles that have entered the chart, and in that sixty-six singles, twenty-six songs reached number one on the US Billboard Hot Country chart.

He signed his first contract at KayTeeKay Music as a songwriter. He only began recording the songs he wrote in 1988. Because of his demos, he was able to sign a contract with his first record label Artista Records. The following year Alan released his first single “Blue Blooded Woman.” This became his first song to enter the Billboard chart. It reached number forty-five.

He released his first album Here in the Real World in 1990. The album contained five songs that entered the country chart. Furthermore, his album included his first number one song on the chart (“I’d Love You All Over Again”). After the success of Here in the Real World,  Alan continuously released songs and albums that made him successful in his career.

Alan Jackson’s Top Ten Singles

There are a lot of Alan Jackson songs that we all love. But, we are going to list here the ten songs that became the highlight in his career. The songs are not arranged in particular order.

“Chattahoochee”

“Chattahoochee” is an up-tempo country song that sold half a million copies. Therefore, it was gold-certified by RIAA. With this song, Alan took home an award for CMA’s Single and Song of the Year.

Alan’s single is about life growing up in a town near the Chattahoochee River. Moreover, the song also mentions about falling in love.

A lot about livin’ and a little ’bout love

“Chattahoochee” became part of his third studio album A Lot About Livin’ (And a Little ‘Bout Love).

“It’s Five O’clock Somewhere”

Another hit single of Alan came out in 2003. Alan collaborated with Jimmy Buffet for this single. The song was part of his compilation album Greatest Hits Volume II. “It’s Five O’clock Somewhere” gave him his twenty-first number one song on the country chart. Furthermore, his single placed at number seventeen on the Hot 100 chart.

The song was written by Jim Brown and Don Rollins. On an interview with The Boot, Rollins said that he was asked to write a song that has kind of a Jimmy Buffet style of music. When he told Brown about his idea, they began writing the song down. It was first given to Colt Prather’s producer, but he turned it down. Alan took the song because he said that he wanted to record something with Jimmy Buffet.

“It’s Five O’clock Somewhere,” tells the story of a man who is tired of his work. He doesn’t care if it’s too early because of somewhere out there, in another country, its already five o’clock. Hence, he started drinking beer at twelve noon.

Pour me somethin’ tall an’ strong,
Make it a “Hurricane” before I go insane.
It’s only half-past twelve but I don’t care.
It’s five o’clock somewhere.

Alan won the CMA’ s Vocal Event of the Year with his single.

“Where Were You (When The World Stopped Turning)”

This perhaps is the most powerful and emotional song Alan Jackson has written in his entire career. The words came to him one day on a quiet Sunday morning. It was a well-written song about the 9/11 attack. Many people were moved by the words of Alan’s single. Therefore, it was able to reach number one on the Billboard country chart. Furthermore, the song place at number twenty-eight on the Hot 100 chart.

Where were you when the world stopped turnin’
That September day?

His song made him won multiple awards. He won the ACM and CMA’s Song of the Year and Single of the Year. Moreover, Alan won his very first Grammy Award.

“Drive (For Daddy Gene)”

Alan immortalized one of his memories from his childhood days into a song. “Drive (For Daddy Gene)” is a single penned by Alan that tells the story of a young boy who remembers his father teaching him how to drive an old boat and car. Moreover, the narrator of the song says that he will let his daughters drive on his old jeep and let them make their own memories with it.

“Drive (For Daddy Gene)” is a nostalgic song that captivated a lot of people’s heart. It reached number one on the Billboard Hot Country Songs chart. Thus, making this his twentieth number one on the chart. Furthermore, Alan’s single crossover to the pop chart at number twenty-eight.

The single was part of his tenth studio album, Drive. Furthermore, it was performed by Taylor Swift in 2008 as a tribute to him.

“Chasin’ That Neon Rainbow”

Before Alan and Jim McBride wrote “Chattahoochee” their first collaboration was Alan’s single “Chasin’ That Neon Rainbow.” The song was about a man who performs in bars to earn money and trying to get record deal, but he can’t sign a deal, and the money he earned will be spent on paying for gas and his band. The song was based on Jackson’s younger days. Furthermore, the radio mentioned in the song is real. It is now displayed at the Country Music Hall of Fame.

Daddy’s got a radio, he won it thirty years ago

This was one of the recordings of Alan Jackson during his early days as a singer. The song appeared on his first studio album Here in the Real World. It entered the chart and reached number two. Furthermore, “Chasin’ That Neon Rainbow” secured a spot on the Canadian chart.

“Little Bitty”

The greatest pleasures in life are seen in the simplest of things. This is the message of Alan Jackson’s single “Little Bitty.” The song was written by Tom T. Hall in 1996. It became part of Alan’s album Everything I Love. This up-tempo single became his fourteenth number one song on the chart. In addition, his track crossed over to the pop chart and also entered the Canadian chart.

“Here in the Real World”

Alan’s single “Here in the Real World” was his first top-five single on the chart. In addition, it was also his first number one song to enter the Canadian chart. “Here in the Real World” reached number three on the Billboard country chart.

The sad song about the reality of life was written by Mark Irwin and Alan Jackson. The story is about a man feeling sad that he didn’t end up with the woman he loves. He mentions that in this world we are living some stories don’t end happily like in the movies.

But here in the real world
It’s not that easy at all
‘Cause when hearts get broken
It’s real tears that fall
And darlin’ it’s sad but true
But the one thing I’ve learned from you
Is how the boy don’t always get the girl
Here in the real world

“Gone Country”

Country music is one of the oldest and greatest genres of music. This has been emphasized in Alan’s song “Gone Country.” His single talks about three different singers who are professionals in their own style of music. However, their career began to fade. Therefore, they tried to begin their individual careers in country music.

“Gone Country” is a song penned by Bob McDill in 1994. Alan Jackson recorded the single on the same year and released it as one of the tracks from his album Who I Am. He earned another number one with this single. Alan also made his song enter the Canadian chart at number two.

“Remember When”

“Remember When” is a nostalgic song about Alan’s love story. At the beginning of the song, he talked about how he and his wife first fell in love. The song transitioned to the day they vow that they will love each other, and finally until they have kids and grow old together. Some considered this to be one of his emotional songs, together with his 9/11 tribute single “Where Were You (When The World Stopped Turning).”

The song was written by Alan and included in his album Greatest Hits Volume II. This song together with his single “It’s Five O’clock Somewhere” were two of his new tracks from his compilation album. The single “Remember When” reached number one on the Billboard Country Chart.

“Midnight in Montgomery”

This is the last but certainly not the least in our list of Alan Jackson’s hit songs. Alan Jackson’s single “Midnight in Montgomery” is all about Hank Williams. The narrator in the song was going to Mobile to perform on a New Year’s Eve show. However, he stopped at Montgomery, where Hank Williams was buried. While visiting the grave, he saw a man in a cowboy hat. The mysterious man thanked the narrator and suddenly disappeared.

And a drunk man in a cowboy hat,
Took me by surprise,
Wearin’ shiny boots, a nudie suit, and haunted, haunted eyes,
He said: “Friend, it’s good to see you,
It’s nice to know you care

There were some parts of the song that mentioned details about Hank, such as

I’m so lonesome I could cry…
Well, Hank’s always singin’ there…

Alan Jackson and Don Sampson wrote the song in 1992. It became a track from his album Don’t Rock the Jukebox. The song reached number three on the US Billboard Country chart. It also placed at number three on the Canadian chart.

There you have it, folks! The ten best songs of Alan Jackson.

What’s New?

The last single to enter the chart was released in 2017. The song is known as “The Older I Get.” In addition, he was inducted into the Country Music Hall of Fame in 2017. This year, Alan became part of the Nashville Songwriters Hall of Fame. Furthermore, his son-in-law died due to a traumatic head injury after helping a woman get into a boat last September.