Alan Jackson: 20 Best Songs
It’s been six years since Alan Jackson, one of country music’s modern-day legends, put out an album of all new songs. That drought comes to an end on May 14th with the release of Where Have You Gone, a sprawling 21-track compilation that finds the Country Music Hall of Fame member reflecting on the state of his beloved genre, paying tribute to his late mother, and, in some songs, simply having a honky-tonking good time.
Ahead of Where Have You Gone, we’ve been revisiting the Newnan, Georgia, native’s catalog and listening with fresh ears. In the end, we put together this chronological list of Jackson’s essential songs, from the free-spirited “Chattahoochee” to the national healing anthem “Where Were You (When the World Stopped Turning).”
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“Here in the Real World” (1990)
Image Credit: David Corio/Redferns/Getty Images When pop giant Arista Records opened their Nashville offices in late 1989, Alan Jackson was designated as the label’s flagship “hard country” act. Although his good looks and muscular baritone were instantly front and center, his — and the label’s — first single, “Blue Blooded Woman,” peaked just outside country’s Top 40. It took this collaboration with songwriter Mark Irwin, a Bronx-born movie fan who was tending bar at the Bluebird Cafe, to turn a cinematic scenario into a true-life success story. Hungover from their first meeting the night before, the two crafted this genuine country classic in just over 30 minutes. Originally cut by another fledgling artist whose album was never released, the song hit Number Three and got a Hollywood ending, even if its brokenhearted cowboy narrator didn’t. — S.B.
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“Chasin’ That Neon Rainbow” (1990)
Image Credit: Beth Gwinn/Redferns/Getty Images By the time this exhilarating single was released, Jackson had earned four CMA nominations and a gold album for Here in the Real World. He was also inching closer to his first chart-topping single, “Don’t Rock the Jukebox,” which was heard briefly at the end of the video for this tune. His first song co-written with future frequent collaborator Jim McBride, its memorable first line was drawn from real life (“Daddy won a radio/he tuned it to a country show.”) Once the song hit, Jackson donated his dad’s prized radio to the Country Music Hall of Fame and Museum for an exhibit. Songs about pursuing a country-music career may be fairly common, and Jackson’s days of piling five pickers into an old Dodge truck are long behind him, but this one still inspires generations of rainbow-chasing hopefuls. — S.B.
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“I’d Love You All Over Again” (1991)
Image Credit: Tim Mosenfelder/ImageDirect/Getty Images Brimming with heartfelt emotion, this steel guitar-drenched tune represented a pair of significant firsts for Jackson as songwriter and artist. It was his first single release to credit him as a solo songwriter and, more importantly, would be his first in a long string of Number One hits. Penned as a 10th anniversary gift to his wife Denise on a rainy night in a Pine Bluff, Arkansas, hotel room, “I’d Love You All Over Again” was also the first public display of Jackson’s romantic (and decidedly mature) side. It wouldn’t be his last. — S.B.
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“Don’t Rock the Jukebox” (1991)
Image Credit: Rick Diamond/Getty Images Name-checking other artists in country music is commonplace and even predictable these days, but Jackson, who references honky-tonk royalty George Jones and the Rolling Stones in this infectious, now-classic tune, was one of the practice’s earliest adopters. He then went one better in the video, with Jones popping up beside the jukebox in the clip and also appearing on the album track “Playing Possum.” Their mutual admiration society would continue, perhaps reaching its zenith in Jackson’s touching and defiant 1999 CMA Awards show performance of Jones’ “Choices,” precipitated by the organization’s invitation to Jones to perform a truncated version of the nominated song on the program — an invite the Hall of Fame legend declined. — S.B.
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“Midnight in Montgomery” (1992)
Image Credit: Time Life Pictures/DMI/The LIFE Picture Collection/Getty Images Speaking of name-checks, this song doesn’t even mention its large-looming subject by name until the very last line, but from the offset there’s no mistaking who it’s about. A chilling, whiskey-tinged ghost story co-written with Don Sampson before Jackson even had his record deal, “Midnight in Montgomery” just missed the top spot on the country chart but has since become more iconic than the two Number One hits that preceded it (“Someday” and “Dallas”). And although the accompanying video was responsible for an uptick in pilgrimages to Williams’ Montgomery burial site, Jackson’s schedule and financial logistics prevented the crew from filming there. The headstone in the clip is actually a Styrofoam replica, but the song remains a stone-country classic. — S.B.
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“Chattahoochee” (1993)
Image Credit: Beth Gwinn/Redferns/Getty Images While he didn’t originate it, another trend Jackson seized on early in his career was the quintessential summer party anthem. This aquatic earworm, which includes the line that gave his third LP its title A Lot About Livin’ (and a Little ʼbout Love), was another songwriting collaboration with Jim McBride. But the song is often best-remembered for its video, in which Jackson goes waterskiing in ripped jeans and red cowboy boots before emerging from the water in his trademark white cowboy hat. A multiple award winner, the song’s most unique honor came from Mrs. Jackson and Mrs. McBride, who presented their husbands with a plaque noting the “Best Use of the Word ‘Hoochie Coochie’ in Song Since 1937.” — S.B.
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“Livin’ on Love” (1994)
Image Credit: Tim Mosenfelder/Getty Images Jackson’s ninth Number One single and second from Who I Am relies on two of his most dependable themes: nostalgia and lasting romance. Written for his parents, Eugene and Ruth Jackson, the lyrics could also apply to Jackson and his high school sweetheart Denise, whom he wed in 1979. The song acknowledges that while the sentiments might sound simple, there’s complexity beneath the surface, especially in the line “love can walk through fire without blinkin’.” The couple’s publicly shared struggles bear that out, but the song offers hope that fairytale romances do exist, even if the real-life setting shifts from a quaint front porch swing to a sprawling mansion. — S.B.
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“Gone Country” (1994)
Image Credit: James Schnepf/Getty Images Jackson’s fifth album Who I Am found him reconciling his touring life as a Nineties superstar with the down-home family obligations. But he also delivered a buzzed-about dose of biting wit through the Bob McDill-penned “Gone Country,” which topped the chart early in 1995. A wryly observant poke at a trio of country-music hopefuls — a Las Vegas lounge singer from Long Island, a Greenwich Village folkie, and a “serious” L.A. composer — Jackson delivers this with the same Southern backhand that morphs the genial “bless your heart” into a withering putdown. The upshot being that Nashville would gain a reputation as a place where big, easy bucks were to be made by blurring genre lines and embracing the Music City zeitgeist. Right… as if that would ever happen. — S.B.
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“I’ll Try” (1996)
Image Credit: James Crump/WireImage By 1996, only seven years after his debut, Jackson had already racked up enough massive hits to justify a greatest hits package. Among the 20 tracks included on The Greatest Hits Collection was the previously unreleased “I’ll Try,” which found Jackson tapping into his unabashed romantic side for a love song about two people committing to one another. Jackson, who usually tempered his sentiment with a dose of realism, made sure his narrator remained grounded and honest about his shortcomings. “I’m not perfect/Just another man/But I’ll give you all that I am,” he sings. It went on to reach Number One on Billboard’s Hot Country Songs chart. — J.F.
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“Little Bitty” (1996)
Image Credit: Chris Pizzello/AP Tom T. Hall’s 1973 single “I Love,” his sole pop Top 40 as an artist, was based on the principle that the simple things in life are worth celebrating, a theme he explored again in the song “Little Bitty.” Hall tried to retire from the music business, but was coaxed into making the 1996 LP Songs From Sopchoppy, which contained his original version of “Little Bitty.” Producer Keith Stegall brought the song to Jackson and its message resonated with country singer, who imbued the colorful tune with a Cajun feel and enough energy to bring a big ol’ smile to a whole lot of little bitty faces. — S.B.
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“Who’s Cheatin’ Who” (1997)
Image Credit: Tim Mosenfelder/Getty Images Pop-country singer Charly McClain had her first Number One hit with this guitar-driven gem in 1981. The track remained just as irresistible 16 years later when Jackson included it on his Everything I Love album, switching the lyrics to male pronouns and amping up the rocking guitar parts with driving fiddle. The second instrumental break spotlighting steel guitar is a real treat and the track continues with extended guitar and piano solos before fading out. Sure, cranky grammarians (we know who we are) might bristle at the song’s use of that second “who” in the title, but when cheatin’ and speculating about who’s doing it with whom (see, we can’t help ourselves) kicks up as much hillbilly dust as this rousing country rocker, all is forgiven. — S.B.
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“Where I Come From” (2001)
Image Credit: Paul Natkin/Getty Images The biggest hit from Jackson’s When Somebody Loves You album would go on to become his 18th Number One single in the summer of 2001. With a tantalizing array of Southern food references that rival a Waffle House menu, Jackson’s road stops take him far from his Georgia home and find him encountering hostile New Jersey law enforcement as well as Michigan barbecue and biscuits that just don’t compare to Mama’s. A verse about an encounter with a deep-voiced woman in California is an unfortunate relic of the time period, but “Where I Come From” succeeds in casting the narrator as a Southern gentleman, even if his worldview is one filtered through his small town. — S.B.
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“Where Were You (When the World Stopped Turning)” (2001)
Image Credit: Bill Steber/Getty Images Rarely has the debut performance of a country song made as monumental an impact as this one when it was introduced on the CMA Awards telecast just eight weeks after the tragic events that inspired it. The terrorist attacks of September 11th were still fresh in the minds of millions of Americans, including Jackson, who was awakened in the middle of the night with a melody that he sang softly into a tape recorder before going back to bed. He finished it in the morning and recorded it just two weeks before the CMAs. As fresh and vital to our collective healing as the song was then, it remains a powerful reminder and a soothing balm today, particularly after the tumultuous year that was 2020. That’s Jackson’s gift: crafting a simple melody, marrying it to raw, insightful lyrics, and in the end showcasing country music’s ability to connect to real people and real life. — S.B.
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“Drive (For Daddy Gene)” (2002)
Image Credit: John Russell/AP From age 15 when he bought a 1955 Ford Thunderbird to his early days of stardom in 1990, Jackson owned and sold some 300 boats, cars, and motorcycles. With a mother whose maiden name was Musick and a father who worked as a mechanic, Jackson was perhaps predestined to write and record one of country’s quintessential driving songs. But even though “Drive (for Daddy Gene)” pays tribute to his motor-mania, it’s really a loving homage to his father, who passed away in 2000. The sweet, sleek tune helped propel the singer-songwriter into the record books months after its release when he earned 10 CMA Award nominations, and took home five trophies, including Entertainer of the Year and Album of the Year for Drive. — S.B.
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“It’s Five O’Clock Somewhere” (2003)
Image Credit: L. Busacca/WireImage Only Alan Jackson could take a shopworn barfly cliché and turn it into something as bracing as a gin & tonic. Written by Jim “Moose” Brown and Don Rollins, “It’s Five O’Clock Somewhere” hits right in Jackson’s sweet spot — he’s all cheeky charm and an aw-shucks grin rhyming “workday passes” with “like molasses.” He gets a famous assist from Jimmy Buffett near the song’s end and the two trade goofy ad-libs about where they park their boats, but Buffett’s cameo isn’t even necessary. Jackson sells this multi-week Number One right from the jump, proving that after a pair of more poignant chart-toppers (“Drive” and “Where Were You (When the World Stopped Turning),” he could still have fun and hit Number One with a song about letting loose. — J.H.
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“Remember When” (2003)
Image Credit: Tim Mosenfelder/Getty Images Jackson’s 21st chart-topper and a new cut from his second greatest-hits compilation, “Remember When” is an achingly honest reflection of a couple’s romantic journey. While it offers a nostalgic look back at their courtship, marriage, and the birth of their children, the lyrics acknowledge that the path to the present hasn’t always been sunshine and roses. As Jackson ponders what will be his and his wife’s golden years, with their children grown up and moved away, there’s an unmistakable tinge of melancholy conveyed beneath his tough exterior. While the soft-spoken singer has always been willing to express his emotions on record, this one captures him at his most vulnerable. — S.B.
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“Monday Morning Church” (2004)
Image Credit: John Bazemore/AP As mournful a melody and heart-wrenching a story as has ever graced country music, this slowly revealed tale of a couple’s separation finds the man grieving his loss by turning his back on God. The key line — “as empty as a Monday morning church” — was inspired by a line in a poem penned by lyricist Brent Baxter’s English teacher mother, written to her students. The tear-stained melody was devised by songwriter Erin Enderlin, who has had songs cut by other heavyweights like Reba McEntire, Lee Ann Womack, Terri Clark, and Randy Travis. Jackson has never sounded more crestfallen and the harmony vocal from Patty Loveless compounds the grief. Still, it never strays into mawkish territory. — S.B.
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“Like Red on a Rose” (2006)
Image Credit: Ralph Notaro/Getty Images As staunchly country as Jackson has always been, the 2006 LP Like Red on a Rose, produced by Alison Krauss, had to be a shock for his most ardent supporters. Here the honky-tonk traditionalist exudes a smoother pop/AC vibe. He gives up space on the album to other songwriters, including Krauss favorite Robert Lee Castleman, who penned the elegantly compelling title track. Sure, Jackson has been laidback before, but he’s never been quite this mellow, and it works beautifully. Those stunned by the album’s change of pace at the time should revisit it today. Like fine wine it has aged gracefully, ranking among the artist’s best works of all time. — S.B.
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“Small Town Southern Man” (2007)
Image Credit: Jennifer Soliz/The Desert Sun/AP One of Jackson’s finest singles of the last 20 years, “Small Town Southern Man” was the lead offering from 2008’s Good Time and his 23rd Number One. In classic country-music fashion, it’s a story of an entire life in three verses, set to lively fiddle and a two-stepping rhythm. Jackson’s lyrics aren’t strictly autobiographical here (his Southern man is more of an archetype), but he sings of finding fulfillment in an honest life of hard work and family, making sure to pass those lessons on to the next generation. “He said his greatest contribution is the ones you leave behind,” he sings. “Raised on the ways and gentle kindness of a small-town Southern man.” — J.F.
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“Where Have You Gone” (2021)
Image Credit: Amy Harris/Invision/AP Jackson and George Strait jabbed at Nashville’s pop takeover in their 2000 duet “Murder on Music Row,” a song that, while a true collaboration, remains more identified with Strait. In the devastating “Where Have You Gone,” Jackson makes his own feelings known on the Nashville scene, writing and recording a song that laments the absence of steel guitar, fiddle, and heartfelt lyricism on today’s radio playlists. “Sounds from the soul, fiddle I need you,” he sings, his voice aching. “The airwaves are waiting/please come back home.” There’s a little disappointment in Jackson’s tone too, which keeps the ballad from veering into old-man-yells-at-bros territory. Because nothing stings worse than disappointment. — J.H.
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