Alan Jackson’s 10 Best Songs

Alan Jackson is one of the true greats . As part of the neo-traditionalist era, the singer-songwriter came up at a time when country music was shifting away from the shimmer of countrypolitan and the rough exterior of outlaw country for something far more grounded in the roots of the genre.

From country to gospel , Jackson has covered it all. Across 21 studio records, including two Christmas sets, he has mastered the craft of real, authentic storytelling. From such hits as “Litty Bitty” to even “Chattahoochee” and “Chasin’ that Neon Rainbow,” he has demonstrated a great knack for delivering down-home stories.

Off the success of 35 No. 1 hits, Jackson has won a slew of industry hardware, including two Grammy Awards and 16 CMA trophies. But his legacy is far more than accolades. His influence can still be felt today, through such artists as Jon Pardi , Justin Moore , and Brothers Osborne, among many others who have brought neo-traditionalism back into the spotlight .

To celebrate his ongoing impact , we’ve compiled Alan Jackson’s 10 best songs, from sensitive ballads to uptempo toe-tappers. Our list spans his entire career, a perfect mosaic of one of the greatest country singers to ever live.

“Here in the Real World”

“I gave you my love / But that wasn’t enough,” sings Alan Jackson. He holds his tattered heart in his hands. Despite everything, he wouldn’t give up that love for the world. The real world, he surmises isn’t like those movies you see on the silver screen. “It’s not that easy at all,” he weeps.

“Remember When”

Jackson gazes back into the past. “Remember When” laments the passage of time, every curveball that came his way. There’s still a sorrowful element to the song that grips you tightly and won’t let go. “Life was changed, disassembled, rearranged,” he sings. Once in love, he fell out with his lover, so the heartache informs the soul-crushing aspect of the song.

“Midnight in Montgomery”

One of Jackson’s darker, southern gothic-inspired songs, “Midnight in Montgomery” pays tribute to Hank Williams, who hailed from Montgomery, Alabama. “Feel that lonesome chill,” sings Jackson. It’s both a sensitive ode and a darkly-laced, wonderfully creepy song about death and ghosts.

“Livin’ on Love”

Sometimes, love is all you need. “She don’t care ‘bout what’s in style / She just likes the way he smiles,” he sings. The world might say something different, but it doesn’t matter. “Without somebody, nothing ain’t worth a dime,” muses Jackson. A steady rhythm, “Livin’ on Love” is as feel-good as they come. It’s not about what you don’t have when what you have before you is so good.

“I Don’t Even Know Your Name”

A raucous little ditty, “I Don’t Even Know Your Name” sees Jackson locking eyes with someone across the bar. “I’m in love with you baby / I don’t even know your name,” he sings over a steady gallop. It’s as a honky tonk number as there ever was one. There’s no mistaking what the song is: a straight-up hook-up song.

“Home”

Home is where the heart is, as they say. With “Home,” Alan Jackson muses upon the meanings of life and home. Delicate guitar and pedal steel decorate the production, leaving Jackson’s voice to carry the emotional thread line with great care. “They made that house a home,” he sings. Despite the weight of the world, home will always be a refuge.

“Who’s Cheatin’ Who”

Electric guitar storms the song, gluing it together with a honky tonk spirit. “Who’s Cheatin’ Who” is Jackson’s open book on the “trouble with a woman and a man.” A little bit of bark goes along way, as he struggles to know “who’s cheatin’ who, and who’s being true, and who don’t even care anymore,” he sings.

“Drive (for Daddy Gene)”

Perhaps Jackson’s best song on this list, “Drive (For Daddy Gene)” sees Jackson contemplating life, death, and the passage of time. He relates these themes to a truck and how one’s memory leaves an indelible imprint on our lives. “It was just an old hand-me-down Ford,” he sings. The words fall like pebbles, weighted but somehow light in the same breath.

“Small Town Southern Man”

There’s nothing like small towns. The lineage of the family comes into clear focus with “Small Town Southern Man,” as the narrator grows up, gets married, and has kids of his very own. It’s the cycle of life in a small town. It’s nothing fancy, but there’s satisfaction in the simple life you can’t get anywhere else. “He’s always proud of what he had,” he sings.

“Little Man”

“Little Man” explores the very real problem of mom ‘n pop shops closing down as big businesses move into small towns. It’s a difficult pill to swallow; it’s a stark, brutal reality that happens every single day. “Forget about that little man,” he laments. As shop after shop shutters their window displays, concrete grows in its place. “They don’t know they’re killing the little man,” sings Jackson.