Top 10 Alan Jackson Songs

By: Kevin Richards/TasteofCounty.com

Alan Jackson is the voice of 35 No. 1 hit songs — and counting. From singalong classics like ‘Chattahoochee’ and ‘Don’t Rock the Jukebox’ to emotional standards like ‘Remember When’ and ‘Where Were You (When the World Stopped Turning),’ this list of the best Alan Jackson songs captures the best songs that represent this ‘modern’ legend’s catalog of hits. Known as one of the greatest songwriters in country music history, many of Jackson's massive hits were inspired by simple everyday stories and experiences — from an influential dad to reminiscing about life and love — something every country fan can relate to. With this amazing talent, it’s no wonder that he’s often listed as one of the top singer/songwriters in the genre.

'Chasin’ That Neon Rainbow'
From ‘Here in the Real World’ (1990)

This is a three-minute version of Alan Jackson’s biography. ‘Chasin’ That Neon Rainbow’ is a great example of how the singer turns his own life stories into monster hits. From his debut album, this song song became the Georgia native’s third Top 10 hit. Meanwhile, the ‘radio’ he references in the beginning of the song is still on display at the Country Music Hall of Fame and Museum.

'Gone Country'
From ‘Who I Am’ (1994)

In 1994, it seemed that everyone was ‘going’ country! From Garthmania to line dancing, coast to coast people were wearing boots and discovering the lyrics to country music songs by the masses. To capture this spirit in pop culture, Bob McDill wrote the story of ‘Gone Country.’ McDill was also responsible for the country classics ‘Baby’s Got Her Blue Jeans On,’ ‘Amanda,’ ‘Song of the South’ and ‘It Must Be Love,’ which was also a hit for Jackson.

'Good Time'
From ‘Good Time’ (2008)

Just when everyone thought that the line dance craze was over, Alan Jackson lined up dancers for the illusion of the world’s longest line dance in the video for ‘Good Time.’ Featuring a cameo from his idol George Jones, the song also became a favorite on country radio, scooting its way to No. 1. The country party anthem was also featured in a comical TV commercial for General Electric.

'Remember When'
From ‘Greatest Hits (Vol. 2)’ (2003)

By the time ‘Remember When’ came along, Alan Jackson already had 14 years of hits under his belt. A popular selection for anniversary celebrations, the song hit No. 1 in 2003, while Jackson dominated the CMA Awards with another Entertainer of the Year and Male Vocalist of the Year win. Like many of the songs on this list of the Top 10 Alan Jackson Songs, the tune was self-penned and inspired by his own life.

'Sissy’s Song'
From ‘Good Time’ (2008)

Once again we find Alan Jackson with another hit, also based on a real life experience. When Jackson’s housekeeper, Leslie Fitzgerald, perished in a motorcycle accident, he wanted to honor his 26-year-old employee and friend, known as Sissy, with a musical eulogy. ‘Sissy’s Song’ has helped many people cope with the loss of their own loved ones time and time again. Another self-penned emotional ballad finds its way to our list of the Top 10 Alan Jackson Songs.

'Don’t Rock the Jukebox'
From ‘Don’t Rock the Jukebox’ (1991)

In 1991, Alan Jackson soared to No. 1 with a song that was inspired by an incident that took place at a little truck stop lounge in Virginia. In the liner notes to his ‘Greatest Hits’ collection, Jackson explained that ‘Don’t Rock the Jukebox’ was inspired by a real jukebox. “Roger, my bass player, was already over there reading the records. I leaned on the corner of it and one of the legs was broken off – the jukebox was kind of wobbling around,” he wrote. “Roger looked over at me and said…”

'Drive (For Daddy Gene)'
From ‘Drive’ (2002)

After Alan Jackon’s father, Eugene, passed in 2000, the singer wanted to write a song to honor his memory in an uplifting and positive way, rather than in a slow, somber ballad. The result was a fun song about learning how to drive with dad, fixing up trucks and spending quality time together on a boat. The song comes full circle as Jackson concludes with a line about taking his own daughters for a ‘Drive.’

'Chattahoochee'
From ‘A Lot About Livin’ (And a Little ‘Bout Love)' (1993)

This 1993 CMA winner for Single of the Year, ‘Chattahoochee,’ spoke directly to the generation of high school and college students who were making memories of their own, while giving ‘grown-ups’ a chance to reminisce about their own younger years. Inspired by the Chattahoochee River on the Alabama/Georgia border, the song applied to anyone, anywhere, along any river bank. ‘Chattahoochee’ is a must on our list of the Top 10 Alan Jackson Songs.

'Where Were You (When the World Stopped Turning)'
From ‘Drive’ (2001)

Alan Jackson is easily considered one of the greatest country music songwriters in history. Described as the 'master of simplicity,' he has a talent for taking everyday emotions and experiences and putting them into a song that most everyone can relate to. ‘Where Were You (When the World Stopped Turning)’ was one of those masterpieces that flowed from his heart and mind, onto a piece of paper, and into the ears of people who needed to hear the story.

'It’s Five O’Clock Somewhere' (with Jimmy Buffett)
From ‘Greatest Hits Vol. 2’ (2003)

In 1999, Alan Jackson released an album of his favorite country classics called ‘Under the Influence.’ On that project, he teamed with Jimmy Buffett for a new take on ‘Margaritaville.’ In 2003, the musical icons reunited for a new party smash titled ‘It’s Five O’Clock Somewhere.’ The song stayed at No. 1 for an impressive eight weeks and created a popular saying that is painted all over the walls at Margaritaville restaurants. Billboard lists this song as the biggest charting hit of Jackson's career, and we can't help but agree that it deserves the top spot on our list of the Top 10 Alan Jackson Songs.

What Is Your Favorite Alan Jackson Song?

As you can imagine, we had a tough time picking just 10 Alan Jackson songs, so now it’s your turn to weigh in. Would you have included his holiday original ‘Let It Be Christmas’ or one of his newer recordings like ‘So You Don’t Have to Love Me Anymore'? How about the classic covers of ‘Who’s Cheatin’ Who’ or ‘Summertime Blues'? Perhaps the songs he recorded written by the legends — like 'Tall, Tall Trees' penned by George Jones and Roger Miller, or 'Little Bitty' written by Tom T. Hall? Please leave your suggestions below.