Five Times Alan Jackson Proved He Was The King Of ’90s Country Music Videos

Alan Jackson Chattahoochee
Alan Jackson

What a legacy he’s leaving in country music.

We’re just a day away from Last Call: One More For the Road – The Finale, Alan Jackson‘s final concert of his legendary career.

It’s a career that’s included nearly 60 million albums sold, 35 #1 hits, 22 ACM awards, 17 CMA awards, two Grammy awards, and induction into the Country Music Hall of Fame back in 2017.

Alan’s easily in my top 5 favorite country artists of all time, and it’s hard to even know where to start when going back over his catalog with hits like “Don’t Rock the Jukebox,” “Chasin’ That Neon Rainbow,” “Livin’ On Love,” “Drive (For Daddy Gene),” “It’s Five O’Clock Somewhere,” “Gone Country,” and of course, “Chattahoochee.”

Of course I grew up listening to Alan Jackson so his music was the soundtrack to my childhood. But aside from his music, one thing that always stood out to me was his music videos.

The ’90s were the golden age for country music videos. There are so many classics that I still remember to this day, from Tracy Byrd’s “Watermelon Crawl” and Sammy Kershaw’s “Queen of My Double Wide Trailer” to Garth Brooks getting splattered with paint in the video for “The Red Strokes.”

But among all of the artists who were pumping out incredible music videos, Alan stood firmly at the top of the list.

Here’s a look at 5 times Alan Jackson proved he was the ultimate king of ’90s country music videos:

1. “Chattahoochee”

Everybody still remembers his classic music video for “Chattahoochee,” which featured the country singer water skiing in jeans and a cowboy hat. It’s maybe THE defining country music videos of the ’90s, and may go down as the greatest country music video of all time – especially after artists largely turned their focus away from videos in the 2000s.

In the 2017 documentary Alan Jackson – Small Town Southern Man, Sony label exec Gary Overton recalled that Alan was the only one who believed in the song, and he was the one who came up with the idea for the now-iconic video:

“He came up with the idea of the water-skiing with his boots on video. And everybody was like, ‘Oh my gosh, what are we doing?’ This guy was taking off, are we going to mess up?

And Alan said, ‘No man, this is going to work.'”

Spoiler alert: It worked.

2. “Midnight In Montgomery”

While this video is the polar opposite from the rowdy, colorful party scene in “Chattahoochee,” it was still a cinematic masterpiece that proved Alan’s range far beyond the summer anthems and honky tonk twangers.

Shot in black-and-white, the video shows a late-night encounter with the ghost of Hank Williams in a foggy graveyard. It’s a visually stunning example of the power of storytelling in a music video, yet understated enough to serve as the perfect complement to the haunting ballad.

3. “Mercury Blues”

This video is peak ’90s: The fashion, the lighting, the at-times seizure-inducing jump cuts between scenes – and to top it all off, a then-unknown guitar player named Keith Urban in the background.

As Keith recalled:

“They needed a guy, a long-haired guitar player, to come in and be in this video… I signed with this publishing company, and the guy who ran the company was Alan’s manager, so they just went, ‘Oh, we got the guy for you.'”

And when he got the details of the video shoot, he assumed he would get some up close and personal time with AJ:

“We had a scene where I had a very tiny stage… and it was going to be basically me playing the solo, kind of silhouette, with a bit of lightning and stuff, and Alan right there singing the song. 

I’m like, ‘Wow, it’s going to be great. Just him and me. Fantastic.'”

But that’s not exactly how it went on the set:

“So they shot my stuff a few times and then they said, ‘Alright, we’re going to bring out Alan.’ So here he comes, Alan walks out, stands right there, and he sorta looks at me, and looked back at the camera and they go, ‘And action!’ 

I went, ‘Well ok.’ Played the song a few more times. He never said anything to me. Nothing. I kept waiting to introduce myself. Nothing. Just a look to me and then just, ok back to the camera again.

And then he walked away and that was the end of it.”

Of course that wasn’t REALLY the end of it. Keith and Alan would cross paths again a few years later, and he says that the two are good friends now – and that Alan even apologized for that music video:

“He’s like, ‘Man, I’m so sorry, I hated that video.'”

Sorry Alan, we still love it.

4. “Gone Country”

An at-times satirical look at the country boom of the ’90s, the video for “Gone Country” highlights the culture shock between the big city and rural America, with scenes from New York and Las Vegas along with Alan even singing from atop Grand Central Plaza in the Big Apple – after opening with a scene that looks straight out of Hee Haw. 

5. “I Don’t Even Know Your Name”

This one may be my favorite of them all. It’s so ridiculous, so over-the-top, that it will no doubt go down in history as one of the greatest country music videos of the ’90s – even if it’s not as well-known as some of his other masterpieces.

The video features comedian Jeff Foxworthy as the main character in the story, who falls in love with the waitress serving him drinks at a bar. As it goes on, it gets even more ridiculous (in the best possible way) as Foxworthy snaps out of his bender and finds himself in the middle of a wedding with a woman who…well, doesn’t look exactly like he thought she did when he was throwin’ back shots of tequila.

Oh, and the video also features a tribute to Alan’s now-infamous 1994 ACM Awards protest, when he was asked to perform to a backing track so he sent his drummer out without drumsticks to prove a point.

It’s an all-around masterpiece, one that perfectly sums up how ridiculously amazing the ’90s were for country music videos.

And among all the incredible artists who were making country music videos at the time, Alan Jackson was the ultimate king.

Enjoy your time off the road Alan, you deserve it for all that you’ve given us over the past 40 years.

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