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15 Rare Gems from Alan Jackson

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Despite being on the top of the charts throughout the ’90s, Alan Jackson still feels like one of the decade’s most underrated talents. While most think of the neo-traditional country boom in the ’90s as being George vs. Garth, Jackson held the title as the leader in the clubhouse for his fair share amount of time as well. In many respects, Jackson’s efforts were rooted in old-school honky-tonk, Bakersfield Sound grit and hillbilly charm more so than anyone else outside Dwight Yoakam. Still, Jackson was more refined and polished than Yoakam and even Brooks.

Songs like “Dallas,” “Don’t Rock the Jukebox” and “Chasin’ That Neon Rainbow” set a high mark as both radio hits and dancehall staples. Love ballads like “Wanted,” “Here in the Real World” and “Someday” helped establish him as a go-to for when you were down and out and love was on the rocks. In many respects, it’s those heartaches that made Jackson feel like a genuine throwback to ’60s and ’70s country and not another smooth voice pretending to play cowboy.

Still, it was songs like “Drive (For Daddy Gene),” “Remember When” and the ever so poignant “Where Were You (When the World Stopped Turning)” that made Jackson a guiding reassurance in humanity. While “Chattahoochee” and “That’d Be Alright” may have established him as a blue-collar everyman, it was songs like “Where Were You (When the World Stopped Turning)” that drove that point home as a comforting and consoling voice.

With 20 studio albums under his belt, Jackson’s been one of the most consistent voices in country music. And while he certainly has one of the most soothing, soaring and rich vocals ever heard, what helps set Jackson apart from most is his lyrical efforts. Unlike most, Jackson has routinely written the vast majority of his albums. They aren’t just filler either. He’s been the guiding voice behind some of his biggest hits. Still, the deep cuts within Jackson’s catalog could have been hits for others.

Here are 15 of the best deep cuts in the Alan Jackson discography.

15. “Job Description”

“Job Description” is one of those moments that helped set Jackson apart from some of his contemporaries. Like “Drive (For Daddy Gene)” or “Where Were You (When The World Stopped Turning),” “Job Description” comes from a slice of Jackson’s home life and actual first-person point of view. In many ways, it finds an even more laidback and serene Jackson than usual. It pays off by never feeling like a song, but rather, a late night conversation with his family.

14. “Wait A Minute”

Found on Like Red On A Rose, “Wait A Minute” is prime Jackson in love ballad mode. Built around a powerful piano movement, Jackson doesn’t ever throw his fastball vocally. Rather, he opts for quieter, softer tones that pull you in rather than blow you away. After many years working with Keith Stegall, Alison Krauss stepped in as the producer on Like Red On A Rose. But rather than creating an expected bluegrass album, Krauss and Jackson created intimate moments that a felt smokey, smoldering and robust. In turn, it made “Wait A Minute” one of Jackson’s best exhales in his catalog.

13. “If I Had You”

“If I Had You” is another deep cut found on Who I Am. In many respects, it’s a hint at Jackson’s fondness for bluegrass that’d come 20 years later when he recorded the aptly-titled The Bluegrass Album. Now, “If I Had You” isn’t a full-blown bluegrass number, but the subtleties of the soft fiddle and earthy acoustic slide guitar create a perfect back porch confession.

12. “If Love Was a River”

The country duo The Wrights, Adam and Shannon Wright, wrote “If Love Was a River.” Adam, a nephew of Jackson, would go on to collaborate with Jackson on that The Bluegrass Album. Here though, The Wrights provide some refreshing and clean harmony vocals. Again, the number hints at future Jackson projects, namely his gospel albums Precious Memories. Jackson and company aren’t so much a forceful river as they are a gently flowing creek. It’s laidback, cooling and invigorating.

11. “Just Playin’ Possum”

“Just Playin’ Possum” has one of the best Easter eggs in the Jackson catalog. What makes the obvious George Jones ode that much better is when Jones shows up to sing final line of the honky-tonker. Found on Don’t Rock the Jukebox, With greasy guitar lines and a classic earworm hook, “Just Playin’ Possum” would have been a surefire single had it been released on any of Jackson’s other ’90s albums. Instead, it helped create one of country music’s defining records of the ’90s.

10. “Angels And Alcohol”

Jackson’s songwriting fingerprints have always been on the vast majority of his records. But as he’s aged, more solo cuts have made it onto albums. On his twentieth studio album, the title cut “Angels And Alcohol” is one of Jackson’s best. Though his vocals aren’t as piercing as they once were, his lyrics cut deeper and with more precision than ever before.

9. “Three Minute Positive Not Too Country Up-Tempo Love Song”

“Three Minute Positive Not Too Country Up-Tempo Love Song” is one of the first examples of Jackson thumbing his nose at the industry. As the final track on 2000’s When Somebody Loves You, it almost acts as an explanation and apology for the minor offense of “www.memory.” Though it’s a great song, it’s remarkable that it found its way onto a record at all.

8. “Every Now And Then”

Jackson’s Freight Train is really around the time Jackson began losing traction on the radio. While trends started going towards bro country and pop-tinged stadium anthems, Jackson has been one of country’s honky-tonk and traditionalist holdouts. Despite this, few can deliver a love ballad like Jackson. Had it been released in the mid-’90s, “Every Now And Then” would have easily been a contender for radio gold.

7. “Blue Blooded Woman”

Technically, “Blue Blooded Woman” is Jackson’s first single. Released in ’89 to jumpstart Here in the Real World, it peaked at 45 on the Billboard U.S. Country charts. Still, it set the pace for Jackson’s national debut. It’s Jackson in prime honky-tonk form with sharp and crisp fiddle, guitar and a healthy dose of attitude. And despite being nearly 30 years old, “Blue Blooded Woman” has an anti-aging quality to it. It could have just as easily been a George Jones hit in the ’60s as it could be one for one of Country’s neo-traditional revivalists today.

6. “Talk Is Cheap”

“Talk Is Cheap” was written by songwriting legend Guy Clark and a relatively unknown Chris and Morgane Stapleton back around 2010. Once you know that, you can see how easy it’d fit on one of Clark or Stapleton’s solo albums. Still, it fits perfectly within Jackson’s straightforward and to the point style.

5. “Rainy Day In June”

“Rainy Day In June” is as heartbreaking as any of Jackson’s best. And while it’d have probably been a hit during the ’90s, I’m not sure ’90s Jackson could have delivered the aching ballad as perfectly as 2004 model does. Vocally, Jackson isn’t as young and lean, but he’s more believable with the slight tears. The opening lines “I need some sunshine on my face to help me dry my eyes,” are delivered with a tender conviction. A pat on the back won’t suffice for Jackson on the lonesome ballad. He needs something to help him go on living. By the end, your heart is breaking right along Jackson’s.

4. “Blacktop”

As mentioned before, by the time The Bluegrass Album came along in 2013, Jackson wasn’t as interested in radio success just for the sake of being on the radio. Rather, he began recording passion pieces on his own accord. With Keith Stegall and Adam Wright at the producing helm, Jackson delivered one of his best albums of the decade. And as another tongue-in-cheek jab at the Bro-Country trends, “Blacktop” delivers a mighty punch at those infatuated with songs about dirt roads.

3. “Tropical Depression”

While it’s easy to see the influence of bluegrass, George Jones and Merle Haggard on Jackson’s version of country, one of the more slight influences is Jimmy Buffett. Found on A Lot About Livin’ (And A Little ‘Bout Love), “Tropical Depression” fits the bill perfectly as a Buffett-esque cool beach bum number. It doesn’t go full on “Margaritaville” since it has a healthy dose of pedal steel licks, but it does come with one of Jackson’s best hooks with lines like “I’ve got the blue water blues” and “can’t stand the sand in my shoes.”

2. “Hurtin’ Comes Easy”

It’s easy to pick out a handful of songs in Jackson’s catalog and wonder why they were never released as singles. Much like “Tropical Depression” before it and “That’s All I Need to Know” after, “Hurtin’ Comes Easy” checks all the boxes as one of Jackson’s biggest radio what ifs. It’s not as personal and could even be classified as one of his more generic efforts, but “Hurtin’ Comes Easy” still finds Jackson running in perfect stride.

1. “That’s All I Need to Know”

“That’s All I Need to Know” is one of Jackson’s most perfect songs. There’s a warbling pedal steel buried deep and has Jackson delivering some of his most dynamic vocals. He hits the high singalong hooks and captivates you with his soft and refined touches. Again, Jackson opens up the song with a vivid scene setup with the lines “I had to look through our old pictures to see the way we used to smile.” From the jump, Jackson is ready to lay it all out on the line. Sure, it’s intimate, but more so, it’s Jackson exposed and vulnerable.

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15 Rare Gems from Alan Jackson