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Top 10 Alan Jackson Songs

Alan Jackson
Terry Wyatt, Getty Images

Alan Jackson songs are some of the essential country songs of the last two decades. The singer-songwriter is widely acknowledged as one of the best songwriters in modern country music.

With more than 60 singles to his credit — nearly half of which have reached No. 1 — narrowing this list down to just 10 songs is difficult. Jackson is one of the very few superstars of the modern era who built his career almost entirely on true traditional country, and his songs are so strong that he doesn’t need anything else. There aren’t a lot of lights, moving parts and explosions at an Alan Jackson concert — just one of the greatest singers in country music history singing some of the best-written songs in the history of the genre.

Our list of the Top 10 Alan Jackson Songs takes in the top tracks from his entire stellar career.

Alan Jackson Chattahoochee


From: ‘A Lot About Livin’ (and a Little ‘Bout Love)’ (1993)

Inspired by the Chattahoochee River on the Alabama/Georgia border, the third single from Jackson’s third studio album is a fun look back at times and coming of age experiences that are universal for nearly everyone. Written by Jackson and Jim McBride, the uptempo track reached No. 1 on the country charts and received CMA Awards for both Single and Song of the Year.

Alan Jackson Its Five O Clock Somewhere

“It’s Five O’Clock Somewhere” (with Jimmy Buffett)

From: ‘Greatest Hits Vol. 2’ (2003)

Jackson scored one of the biggest hits of his entire career with this collaboration with Jimmy Buffett. Released as the new single from Jackson’s second hits collection, the song — which was written by Jim “Moose” Brown and Don Rollins — became a phenomenon, landing at No. 1 on the country charts and crossing over to land at No. 17 on the pop charts. The fun track, which used a play on words to justify drinking at any time of the day or night, also won a CMA Award for Vocal Event of the Year.

Alan Jackson Don't Rock the Jukebox

“Don’t Rock the Jukebox”

From: ‘Don’t Rock the Jukebox’ (1991)

The lead single from Jackson’s second album is a perfect example of his appeal. The lyrics tell of a man who wants to hear country music on the jukebox to ease his heartache, as he implores other patrons not to play rock music. Written by Jackson with Roger Murrah and Keith Stegall, the song derived from a real-life incident that happened when Jackson walked over to the jukebox in a dive he and his band were playing in. His bass player was looking at the titles, and when Jackson leaned against the machine, which was missing a leg, he said, “Don’t rock the jukebox,” thereby inspiring the song.

Alan Jackson Drive single

“Drive (for Daddy Gene)”

From: ‘Drive’ (2002)

Jackson’s father, Eugene, passed away in 2000. The singer wanted to pay tribute to him, but not with a slow, somber ballad. The title song and second single from “Drive” told yet another simple, universal story, with the singer reminiscing about times he shared with his father in a pickup truck or on their boat, and then tying it together at the end with times he shares with his own daughters. Delivered with the deceptive, disarming ease that characterizes most of Jackson’s best work, the song reached No. 1 on the country charts and crossed over to hit No. 28 on the Billboard Hot 100.

Alan Jackson Here in the Real World Album

“Chasin’ That Neon Rainbow”

From: ‘Here in the Real World’ (1990)

Jackson demonstrated his penchant for turning his real-life experiences into hits with this early song, which was the fourth single from his debut album. The song tells of a radio his father won many years ago, on which the young Jackson first heard country music, then ties it into his life as a struggling musician who is “Chasing that neon rainbow / Livin’ that honky-tonk dream.” The uptempo track’s alluring melody and tight arrangement helped it reach No. 2, making it Jackson’s third Top 10 hit.

Alan Jackson Little Bitty

“Little Bitty”

From: ‘Everything I Love’ (1996)

Simplicty is at the heart of much of Jackson’s success. His ability to translate the seemingly mundane details of life into profound, sweeping truths about people is one of the things that most sets him apart from other country artists. “Little Bitty” is another deceptively simple song that extols the everyday joys of the simple life. Written by country legend Tom T. Hall, Jackson’s delivery is so disarmingly convincing that he makes it seem like the song could have come from his own pen. “Little Bitty” was yet another No. 1 country hit for the superstar.

Alan Jackson Here in the Real World Album

“Here in the Real World”

From: ‘Here in the Real World’ (1990)

Jackson’s broken our hearts numerous times with his sincere approach to songs that could, in another’s hands, come off as cloying or silly. After his first single failed, the title song and second single from his debut album rocketed to No. 3 in the country charts, kicking off a chart run that few have matched in country music history. The song describes the difference between movies and real life: “Here in the real world, it’s not that easy at all / ‘Cause when hearts get broken, it’s real tears that fall.”

Alan Jackson Who I Am

“Gone Country”

From: ‘Who I Am’ (1994)

Jackson scored one of the defining hits of his career with “Gone Country.” Written by Bob McDill, the song was both an ode to the commercial explosion of country music at the outset of the ’90s and a satire of those who came to Nashville specifically to cash in, including a struggling folk singer: “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.'” The song reached No. 1 in the country charts and became a Jackson staple.

Alan Jackson Greatest Hits Vol. 2

“Remember When”

From: ‘Greatest Hits (Vol. 2)’ (2003)

Another stellar example of Jackson’s ability to turn his own life experiences into universal songs, “Remember When” was inspired by a difficult period in his marriage when he and his wife separated, then reconciled. Jackson uses that framework to provide a timeline of important life events, then once again ties it all back to his children and the continuance of the family line. The staggeringly simple, perfectly written song is not only one of Jackson’s best, it is an all-time country classic.

Alan Jackson Where Were You When the World Stopped Turning

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

From: ‘Drive’ (2002)

No other Jackson song captures his unique talent for capturing the common sentiment in song as much as this track, which was inspired by the 9/11 terrorist attacks. Calling himself “a singer of simple songs, I’m not a real political man,” Jackson perfectly sums up the feelings of fear, uncertainty, patriotism and faith that most Americans felt in the wake of the attacks. He debuted the single live at the CMA Awards that November to a standing ovation, and the subsequent single release became not only a No. 1 hit, but a career-defining moment for Jackson.


NEXT: What’s YOUR Favorite Alan Jackson Song?

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