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The 10 Best Alan Jackson Songs

Alan Jackson arrived on the Nashville scene in 1989 with a mullet and perfectly ripped Levis. Although his debut single “Blue Blooded Woman” didn’t break the Top 40, in just a few short years Jackson would be known as a keeper of the classic country flame and a leader in the neo-traditional movement of the genre.

With 35 No. 1 hits, it’s tough to narrow down Jackson’s almost 30 year career to only 10 songs. There are his covers of Nashville legends like Tom T. Hall and Roger Miller (“Little Bitty,” “Tall Tall Trees”), rollicking “blues” numbers (“Summertime Blues,” “Mercury Blues”), tender love songs (“Blues Man,” “I’d Love You All Over Again”) and spot-on explorations of rural life (“Small Town Southern Man,” “Little Man,” “Drive (For Daddy Gene).”) Then there are his irresistible party songs, like the collaboration with the king of Margaritaville Jimmy Buffett on “It’s Five O’Clock Somewhere.”

But since we can’t choose all of ’em, here are our picks for the 10 best Alan Jackson songs.

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10. “Dallas”

Released in 1991, “Dallas” is about a Tennessee country boy who loses his lady to her one true love–Texas. Written by Jackson and Keith Stegall, the track went to No. 1 on the country charts. Jackson has said he was inspired to write the song after playing a show in Dallas. After making the remark that he wished “Dallas was in Tennessee,” he knew he had a song on his hands.

9. “Here in the Real World”

Written by Jackson and Mark Irwin, “Here in the Real World” was the title track of Jackson’s debut album. The song, which compares real life love with the picture perfect endings of classic Hollywood films, cemented Jackson as a neo-traditional troubadour.

8. “Midnight in Montgomery”

Co-written by Jackson and Don Sampson, “Midnight in Montgomery” follows a young singer who has an encounter with the ghost of Hank Williams while visiting the country legend’s grave in Montgomery. The chilling song rose to No. 4 on the Billboard Hot Country Singles chart.

7. “Chattahoochee”

One of Jackson’s most enduring and beloved hits, “Chattahooche” embodies the spirit of coming of age in a small town. Jackson hits all the rural livin’ touch points, but the song’s universal message of learning “a lot about livin’ and a little ’bout love” remains as fresh as ever. The infectious song went to No. 1 on the country charts in 1993.

6. “Murder on Music Row”

“Murder on Music Row,” written by Larry Cordle and Larry Shell, is a blistering take down of Music Row politics and disposable pop country that was creeping onto airwaves in the late 90s. Jackson teamed up with George Strait to record the song, which surely echoed the two traditionalists’ own concerns about the direction of country music. The song won the CMA award for Vocal Event of the Year and Song of the Year.

5. “Remember When”

“Remember When,” a love song Jackson wrote about life with his wife, looks back at the ups and downs of a lifetime love with gratitude. The song went to No. 1 on the country charts in 2003.

4. “Chasin’ That Neon Rainbow”

Jackson has come a long way since playing dive bars for tips, but he never forgot the long road to success. “Chasin’ That Neon Rainbow,” written by Jackson and Jim McBride, follows Jackson’s career trajectory from honky tonks all the way to Music Row. The song peaked at No. 2 on the charts in 1990.

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3. “Gone Country”

“Gone Country” was written by songwriting legend Bob McDill as a response to performers from other genres–lounge singers on the Vegas circuit, folk singers– turning to country music to save a fledgling career. Is it a criticism of Music City carpetbaggers or a celebration of the genre’s widespread appeal? Either way, it’s one of the best country songs of the 90s.

2. “Don’t Rock the Jukebox”

In the liner notes of Jackson’s Greatest Hits Collection, the singer explains that the song came about when Jackson bumped into a wobbly jukebox in a Virginia truck stop lounge. Jackson’s bass player told him “don’t rock the jukebox” and country music history was made. Written by Alan Jackson, Keith Stegall and Roger Murrah, “Don’t Rock the Jukebox” hit the No. 1 spot in 1991.

1. “Where Were You (When the World Stopped Turning)”

Alan Jackson debuted “Where Were You (When the World Stopped Turning)” on the 2001 CMA Awards broadcast. The song is a response to the Sept. 11, 2001 terrorist attacks. “Where Were You” went on to become one of Jackson’s greatest hits and won a Grammy for Best Country Song in 2002. More importantly, the song, which focused on shared experiences and coming together in a time of tragedy, offered solace for listeners across the country.

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The 10 Best Alan Jackson Songs