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Readers’ Poll: The 20 Best Alan Jackson Songs

See which of the Georgian’s classics managed to top “Gone Country” and “Drive”

Alan Jackson

Our readers' picks for best Alan Jackson songs span 20 years.

Daniel Boczarski/Getty Images

If anyone has proved staying power in country music — without caving to trends — it’s Alan Jackson, the long, tall Georgian who burst onto the Nashville scene in 1989 and hasn’t gone a year since without having a hit. Among his laundry list of accolades are 60 million albums sold, 50 Top 10 songs (35 of them reaching Number One) and 16 CMA Awards, along with numerous other trophies on his crowded mantel.

On November 6th, the country traditionalist will release his first-ever box set, the aptly titled Genuine: The Alan Jackson Story, featuring 59 tracks that span 25 years. In celebration of the three-disc compilation, we asked our readers to vote on their favorite Alan Jackson songs and the response was tremendous. Here are your picks, which range from drinking songs to weepers to dances with the devil — with all of them sporting Jackson’s genuine lyrical stamp.

Alan Jackson

“Murder on Music Row”

You hear a lot these days about “real” country music getting squeezed out by the pernicious forces of bro-country and pop-country, but it’s not a new debate. A full decade before Florida Georgia Line came to be, this 2000 duet between Alan Jackson and George Strait was decrying the fact that Old Hank, the Hag and the Possum “wouldn’t have a chance on today’s radio” because of “the almighty dollar and the lust for worldwide fame.” True to its spirit, the arrangement is pure tear-in-your-beer with mournful fiddles and pedal steel to go with Strait and Jackson’s anguished yelps. Never officially released as a single (it was the B-side to “Go On” from the Latest Greatest Straitest Hits album), “Murder on Music Row” still picked up enough airplay to crack the country Top 40 – making it the exception that proved the rule. D.M.

Alan Jackson

“Little Bitty”

Contrary to the title, this whimsical ditty with a Cajun fiddle flavor was a big ol' hit for Jackson, topping the charts in 1996 as the first single from his Everything I Love album. It's one of the few big hits that the singer didn't have a hand in writing, instead throwing himself cheerfully into the charmer by the legendary Tom T. Hall, the man behind hits like Jeannie C. Riley's "Harper Valley PTA ." The brisk tune imparts a big lesson in a small package: that the most important things in life can start from a tiny place, like a single glance that becomes a lifelong love affair. Or a less than three minute song that reminds you that life's short and to enjoy what you have. S.R.

Alan Jackson

Alan Jackson

Jim Steinfeldt/Michael Ochs Archives/Getty Images


“I’ll Try”

An honest love song, "I'll Try" steers clear of the gooey optimism that filled many mid-Nineties ballads and, instead, focuses on a more realistic pledge. "I'll try to love only you," Jackson sings during the chorus, promising his wife not the moon, but a simple attempt to do his best.  Released as one of two newly-recorded tracks on 1996's The Greatest Hits Collection, "I'll Try" became something of a greatest hit itself, topping the charts that same year. A.L.

Alan Jackson

“Pop a Top”

This Nat Stuckey original was no hidden gem — Opry legend Jim Ed Brown also released a version in 1967 that climbed its way onto the Billboard country charts, putting that whooshing sound of a cracking can deep into the genre's iconography. When Jackson recorded it for his eighth studio album, Under the Influence, he left the cadence and western swing completely intact; nor did he edit out that top-a-poppin'. The result was more of a sweet tribute to Nashville's fading honky-tonk innocence than a silly rehash, and paved the way for songs like Toby Keith's "Red Solo Cup" to make barroom noises as useful as fiddle pulls. It also bred a delightfully bizarre video that blended speakeasy and hillbilly through the magic of an enchanted beer: we all dream, and we all drink. M.M.

Alan Jackson

“I’ll Go on Loving You”

Mr. Denise Jackson certainly has a knack for keeping romance alive through music and could easily put together a multi-disc greatest hits package of nothing but love songs. Still, 1998's "I'll Go on Loving You" was a bit of a departure for the singer-songwriter, as he starts the track with a sensuous spoken word introduction about "pleasures of the flesh." An even bigger of a step outside his country borders was a second, Portuguese version of the track, "Vou Seguir Te Amando," sung as a duet with Brazilian musician Leonardo.

Alan Jackson

“I’d Love You All Over Again”

The kind of sentiment that any spouse would be happy to hear on their 10th anniversary, this ballad, co-written by Jim McBride, finds Jackson vowing that if given another chance he'd still take the plunge because "you're looking better than you did back then, you still make this old heart give in." Swoon.  In 1998, Jackson put his money where his mouth was and renewed his vows with wife Denise. Fittingly, the timeless ballad was his first Number One hit, the final single off his debut album, Here in the Real World, and he did that all over again more than 30 times. S.R.

Alan Jackson


Nowadays you might post to Reddit or Tumblr, but back in 1990 when your woman finally had enough of your crap, took off and couldn't be found, there was only one thing left to do: Place a clever romantic ad in the local newspaper's classified section begging for forgiveness. That's the unlikely-but-heartwarming premise of Jackson’s "Wanted," co-written by the country star with Charlie Craig. With a slow build to the chorus and Jackson casually conversing with newspaper staff in the verses, "Wanted" was Jackson's third-ever single and had that classic, golden-era feel of country from the Sixties and Seventies, helping to cement his status as a traditionalist early on. He'd build on that formula (simple, heartfelt messages and an unapologetic country sound) for the rest of his career. C.P.

Alan Jackson

“Country Boy”

In 2008, bro-country was still in its early stages. Every day seemed to bring new songs about trucks, beers and girls, but Florida Georgia Line and "Cruise" were still a few years off. Into this environment stepped Jackson with "Country Boy," a song that presented the trendy new subject material in a different light. There’s nothing complicated about "Country Boy" – Jackson wrote the song about a girl who needs a ride and a good ol' boy with a 4×4 – but there's also none of the muscle flexing or locker-room aggression. Calming and breezy rather than densely packed with beats and effects, this is bro-country for bros at a more settled stage of life. Rising to Number One on Billboard's country airplay chart, it was also a reminder to a new generation of country stars that they still had to compete with the legends. C.P.

Alan Jackson

“Chasin’ That Neon Rainbow”

The fourth of five hit singles from Jackson's debut LP, Here in the Real World, the singer penned this with Jim McBride and based the upbeat tune on his real-life experience playing a number of honky-tonks. His daddy really did win a radio, and his mama really did sing to Jackson and his sisters, as the lyrics suggest. The radio was eventually donated to the Country Music Hall of Fame, on display as inspiration for other neon-rainbow chasers dreaming of a honky-tonk existence. In spite of its memorable melody and knowing lyrics, the single stalled at Number Two. His next, "I'd Love You All Over Again," would start Jackson's streak of chart-toppers. S.B.

Alan Jackson

Alan Jackson

Rick Diamond/WireImage


“Sissy’s Song”

Leslie "Sissy" Fitzergerald was a longtime housekeeper for the Jackson family. When she died in a motorcycle accident in May 2007, a grieving Jackson wrote this stripped-down ballad to deal with her passing. Featuring little more than steel-string acoustic guitar, gospel harmonies and a melody worthy of Sunday morning church service, "Sissy's Song" was recorded quickly and simply, just in time to make its debut at Fitzgerald's funeral. Jackson's record label convinced him to include it on 2008's Good Time,  too, but they couldn't convince him to change the song's production, whose uncomplicated arrangement still packs a serious punch. A.L.

Alan Jackson

“Midnight in Montgomery”

The capital of Alabama is well-known for its art scene and was also home to singers Nat King Cole and Big Mama Thornton. But it's the city's Hillbilly Shakespeare, Hank Williams, who haunts this chilling tale as Jackson encounters the ghost of the country legend while stopping to visit his gravesite on the way to a New Year's Eve show in Mobile. Williams died in the early hours of New Year's Day, 1953, on his way to a show he would never perform. The spooky 1992 CMA Music Video of the Year beautifully captures the singer's incredulity regarding the ghostly presence, but by this time in Jackson's stellar career there was no doubting that Williams' indelible mark was stamped firmly on the honky-tonk troubadour. S.B.

Alan Jackson

“Between the Devil and Me”

Jackson brings serious depth and complexity to this track off 1996’s Everything I Love, written by Harley Allen and Carson Chamberlain. Led in by devilish licks that linger like thunderclouds, it’s a song that dips sweetness (“I hold her in my arms tonight/So safe and warm, I close my eyes”) into poison (“The gates of hell swing open wide/inviting me to step inside”), made digestible thanks to Jackson’s smooth, tender tone. He’s singing about the temptation of one woman when you’re betrothed to another – in the hands of lesser artist, this could come across as ugly or shallow. But Jackson somehow spins it as a sincere, if not ominous, confession about the lure of infidelity that finds virtue in its honesty. M.M.

Alan Jackson

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

You'd be forgiven for initially listening to this rowdy, let's-ditch-work-and-drink anthem and mistake it for a Jimmy Buffett glass-raiser. It's no accident: Jackson was looking for a song to cut with Mr. Margaritaville, and this Jim "Moose" Brown and Don Rollins-written tune was just the ticket. Spending eight consecutive weeks at Number One on the Billboard Hot Country chart, "It's Five O'Clock Somewhere" is a pure workingman's kiss-off. "It's only half past 12. But I don't care/It's five o'clock somewhere." Bottoms up. D.H.

Alan Jackson

“Livin’ on Love”

Suffused with the sweet, simple charms that are Jackson's trademark, this winsome, fiddle-infused Number One hit from 1994's Who I Am painted a picture of a couple that understands what's important. From the newlyweds crossing the threshold short on cash but long on affection to the elderly couple enjoying their empty nest twilight years, Jackson crams a lifetime into a couple of verses. Sentimental but never cloying, the song reminds listeners, in Jackson's folksy fashion, that "without somebody nothing ain't worth a dime." S.R.

Alan Jackson

“Here in the Real World”

The loose ends of life rarely tie up as neatly as they do on the big screen, where cowboys are always stoic and heroes narrowly save the day. No song better personifies that sentiment than this classic weeper, Jackson's first Top Five hit. Co-written with Mark Irwin, the title track from the country singer's debut album put the world on notice that the Georgia native was a traditional sort who preferred his fiddles to evoke longing, his tempos ambling, and his sentiments straightforwardly delivered. "If life were like the movies I'd never be blue," croons Jackson before conceding with resignation that in the real world, "the boy don't always get the girl." The perfect song to accompany a last call spent alone. S.R.

Alan Jackson


If country music does one thing particularly well, it puts the listener right there: smack-dab in a particular setting, time and mood. You didn't need to grow up in small-town America to know that easy-going vibe Jackson was channeling when he roared, "Never knew how much that muddy water meant to me/But I learned how to swim and I learned who I was/A lot about livin' and a little 'bout love." The third single off 1993’s A Lot About Livin’ (and a Little 'bout Love), "Chattahoochee," all dance-floor shuffle and whiskey-soaked bounce, is the quintessential tale of living carefree and cutting loose. D.H.

Alan Jackson

“Gone Country”

In the years "After Garth" (Brooks), country music became the gold-rush promised land for crossover attempts, a phenomenon that continues to the present day (see: Steven Tyler). "Gone Country," a chart-topping single from the Who I Am album, finds Jackson poking gentle fun at three interlopers: a Vegas lounge singer, Grennwich Village protest folk singer and classical composer "schooled in voice and composition" who all decide to get in touch with their inner carpetbagger. So, they twang it on up: "Lord it sounds so easy, this shouldn't take long/Be back in the money in no time at all," the phonies muse, but we're spared hearing about their inevitable failures. Jackson's easy-going glide has just enough edge to suggest that it’s a lot harder than it looks. D.M.

Alan Jackson

“Drive (for Daddy Gene)”

Before truck songs became a worn cliché, Jackson wrote this heartfelt tribute to his father, Eugene "Gene" Jackson, who passed away in 2000."I was king of the ocean when daddy let me drive," he sings on the track off of 2002's Drive, recalling a youth spent toiling around the countryside and stealing a turn behind the wheel of his dad's "old plywood boat." In the last verse, Jackson really goes for the waterworks, when he brings the lyrics to present day and lets his little daughter take the controls. It's proof that the automobile can be used as a delicate metaphor for the powerful nostalgia of childhood – and not always just the size of one's manhood. M.M.

Alan Jackson

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

Debuted just shy of two months after the tragedies of September 11th, 2001, "Where Were You (When the World Stopped Turning)" is without question the most risk-taking single the singer has released to date. He's admitted to initial hesitation when releasing it, not wanting to capitalize on a horrific event. However, in listening to the tender tune's heartfelt, sentimental message of shock, grief, and ultimately love and compassion in the wake of so many senseless deaths, Jackson comes across not as opportunist but rather refreshingly raw. "I'm just a singer of simple songs," he confessed, but Jackson's voice, if only for a short time, undoubtedly alleviated some of our collective pain. D.H.

Alan Jackson

“Remember When”

Country music has had a long love affair with nostalgia. But for pure lump-in-your-throat beauty it’s hard to top this wistful love letter from Jackson to his wife Denise. From the sepia-toned steel guitar solo to the lyrics detailing the joys and hardships of long-term relationships, it is a song that makes you look forward to looking back. If you really want to get verklempt, check out the tender slow dance between Jackson and his wife in the video. The ballad was a single from his second greatest hits collection in 2003 that ended up being one of his greatest hits, going to number one in 2004. S.R.