’90s Country: Top 10 Alan Jackson Songs

by Matthew Wilson

Alan Jackson was one of the biggest artists around in the 1990s. When he released his debut album in 1990, Jackson took the country music genre by storm. Over the next decade, he released some of his most iconic songs. It doesn’t get more 90s country music than Alan Jackson.

Outsider put together some of Jackson’s most iconic songs. Here’s his Top 10 classics.

10. ‘I’ll Try’ by Alan Jackson

Alan Jackson is at his most poignant in this heartbreaking if honest look at love. Songs often promise grandiose visions of pulling down the moon or some other larger than life act. But Jackson’s promise is a lot more down to earth and realistic. He promises to try to love his wife to the best of his ability. That’s all anyone can really do in the grand scheme of things.

Lyrics included, “We’ve both felt love/ We’ve both felt pain/ I’ll take the sunshine over the rain/ And I’ll try to love only you.

Jackson included the song on his 1996’s album “The Greatest Hits Collection,” and upon release, the singer had another hit on his hands. Audiences connected with the song’s sentimental and honest outlook.

9. ‘I’d Love You All Over Again

If “I Try” is realistic, then “I’d Love You All Over Again” is sentimental and optimistic. For all those wanting to stay in their spouses’ good graces, don’t worry. Because Jackson has you covered with this 1991 hit. Featured on his debut album “Here in the Real World,” the tune explores a husband reflecting on his marriage on their 10th anniversary.

With lyrics like, “The preacher man said till death do us part/ That seemed like forever to a young man’s heart/ Now the days seem much shorter/ The longer we love,” the tune became Jackson’s first No.1 hit. In 1998, Jackson renewed his vows to his own wife, proving some lyrics inspire reality.

8. ‘Little Bitty’ by Alan Jackson

Jackson reminds listeners that the best things in life often start in the smallest places with this hit song. The tune proved to be more than a little bitty hit when it topped the charts in 1996. The song featured on his “Everything I Love” album, and it’s uptempo energy shows Jackson is more than just love ballads. Though, there is a little bit of that thrown in there as well with a relationship starting from a first glance.

Jackson sings, “Well, it’s alright to be little bitty/ A little hometown or a big old city/ Might as well share, might as well smile/ Life goes on for a little bitty while.”

7. ‘Chattahoochee’

Ah to be young again. Jackson’s singing about small-town living and youthful reckless abandonment in this revving country song. The song’s title is inspired by the river that separates Alabama from Georgia. But you’ll have a tough time separating these lyrics from your mind after a listen. The singer sings about being young and having fun in this 1993 single to “A Lot About Livin’ (and a Little ’bout Love).”

Way down yonder on the Chattahoochee/ It gets hotter than a hoochie coochie/ We laid rubber on the Georgia asphalt/ We got a little crazy but we never got caught,” Jackson sings.

6. ‘Murder on Music Row

George Strait and Alan Jackson? Now that’s an iconic duo. The two country artists joined forces for a noble cause, to figure out who killed country music. Now, video may have killed the radio star. But according to Jackson and Strait, no one bat an eye when country music died.

Both Strait and Jackson are country music traditionalist. Their song decried the amount of pop country overloading the airwaves. Upon release, the song broke into the Top 40.

Nobody saw him running from sixteenth avenue/ They never found the fingerprint or the weapon that was used/ But someone killed country music, cut out its heart and soul/ They got away with murder down on music row,” they sing.

5. ‘Don’t Rock the Jukebox’ by Alan Jackson

Jackson recorded the second greatest song to ever feature Jukebox in the title. (The first will always belong to the late Joe Diffie and his “Prop Me Up Beside the Juke Box If I Die”). Similar to “Murder on Music Row,” Jackson is commenting on the music industry. This time he has his sights set on rock music and The Rolling Stones.

The song was apparently inspired by true events. Jackson accidentally literally rocked a jukebox at a dive bar by leaning against it.

Lyrics include, “Don’t rock the jukebox/ I want to hear some Jones/ Cause my heart ain’t ready/ For the Rolling Stones/ I don’t feel like rockin/ Since my baby’s gone/ So don’t rock the jukebox.”

4. ‘Chasing That Neon Rainbow’

Alan Jackson certainly chased that neon rainbow all the way to the pot of gold at the end. Jackson, with a little help from Jim McBride, wrote the song based on his own autobiographical experiences. For instance, Jackson’s father really did win a radio. The tune, which featured on “Here in the Real World,” is for all those dream chasers out there.

Upon release, it shot to No. 2 on the charts with lyrics like “Mama used to sing to me/ She taught me that sweet harmony/ Now she worries cause never thought/ I’d ever really take it this far/ Singin’ in the bars and/ Chasin’ That Neon Rainbow/ Livin’ that honky-tonk dream.

3. ‘Midnight in Montgomery

Alan Jackson’s ode to the capital of Alabama is a little creepy but definitely iconic. This will probably the closest the country singer ever gets to writing a Halloween song. In the tune, Jackson comes across the ghost of country music pioneer Hank Williams on his way to Mobile for a concert. The music video won Jackson a CMA award in 1992

The tune is a haunting ode to country music’s past, with lyrics like “And a drunk man in a cowboy hat took me by surprise/ Wearing shiny boots, a Nudi suit, and haunting haunted eyes/ He said friend it’s good to see you, it’s nice to know you care/ Then the wind picked up and he was gone, was he ever really there.”

2. ‘Here in the Real World

Alan Jackson imagines if life was like the movies in this classic song from his debut album. One of his earliest was also one of his best works. In the tune, Jackson breaks down the iconic imagery of westerns and cowboys. This song will definitely have audiences weeping with its sad, mournful melody and Jackson at his best.

Jackson sings, “Cowboys don’t cry, and heroes don’t die/ Good always wins, again and again/ And love is a sweet dream that always comes true/ Oh, if life were like the movies, I’d never be blue.

1. ‘Gone Country‘ by Alan Jackson

This tune became a rallying cry for country music fans everywhere. Released in 1994 on Jackson’s “Who I Am” album, the country star had a hit on his hands. Despite its catchy nature, the tune is actually a critique of all those would-be singers who think they could be country music stars. Jackson examines what he views as phonies or bandwagon performers in the industry. And he does so with some of the catchiest lyrics around.

Well the folk scene’s dead, but he’s holding out in the Village/ He’s been writing songs, speaking out against wealth and privilege/ He says, I don’t believe in money, but a man could make him a killin’/ ‘Cause some of that stuff don’t sound much different than Dylan,” he sings.