During an interview with Holler, prolific songwriter Mac McAnally shares how he ended up re-recording his 1990 single, ’Down the Road’, with Kenny Chesney in 2008. The revamped duet version ended up becoming a major hit for both Chesney and McAnally, rising to No. 1 on the Billboard Hot Country Songs chart the following year.

The song tells the moving story of a young boy and girl who live on the same street and fall in love, with the listener being shown the perspective of both the boy and the girl's father.

McAnally's original is a beautifully intricate offering, but there's no question that the addition of the harmonies and the cleaner production on Chesney's version brings a whole new life to the song, accentuating the emotionality and sweet, rose-tinted ambience.

When chatting to Holler about the song, which remains a fan-favourite among both McAnally and Chesney's respective fanbases, the former explains how he initially came up with the idea for ’Down the Road’ after assembling toys early one Christmas morning.

He explains, “Sometimes young dads, or dads of young children, are in the wee hours of Christmas morning doing some assembly that they're not necessarily adept at. And that's what was going on with me. I was trying to put some stuff together and make some bells ring and some whistles whistle and lights flash like they were supposed to, and I had to go out and chase down some batteries that I did not know I needed in the middle of the night. And I got back and got everything working like it was supposed to, and I was excited about my kids waking up and looking under the Christmas tree in a couple of hours. I only had maybe 90 minutes before the sun was going to come up, and my kids are early risers on Christmas, so I decided to forego sleep and just pick up the guitar and noodle around”.

The ‘Back Where I Come From’ singer-songwriter goes on, “I started thinking about family and how proud I am of my family from Mississippi...and my kids and all the hope and love I got for wherever they wind up in the world. It was just a really good family feeling, and that song just fell out really easily. It was written in about 20 minutes. As I told Kenny, I put it out on one of my unintentional collector's item albums!...That song sat around for 21 years, and and Kenny just calls me out of the blue, and we're friends, and I'm always happy to hear anything from Kenny. But he said, ‘Can you come to the studio tomorrow?’”

McAnally continues, “And I said, ‘Sure. What are we going to do?’ And he says, ‘Well, we're going to cut one of your songs, and I don't care which one’. And as a songwriter, for 50 years, nobody has ever said that to me, ever, except Kenny. And if you're going to hear that, Kenny's a great guy to hear it from. So I get up and go to the studio that the next day, and I say, ‘What are we going to do?’ He says, ‘What song do you want to sing? I know a whole bunch of your songs’ And I said, ‘It doesn't matter to me, Kenny, I know a whole bunch of my songs too! You can pick’”.

He shares how Chesney felt as though ’Down the Road’ always struck a chord with him, “He said, ‘Well, I don't have any children yet, but if and when I do, I would love to say to my kids what you said to your kids in that song, ‘Down the Road’. Let's do that. You sing the second verse, and we'll make it a duet’. And we played it about three times through on two guitars. My buddy Eric Darken that I play my shows with on a cajon, it's just the three of us sitting in a studio. That's all that's on that record, and it was magical...It was written in less than an hour, and it was recorded in less than an hour, and we had a No. 1 record and a GRAMMY [nod]”.

McAnally fondly concludes, “I remember backing out the studio that day, thinking to myself, ‘That sounds pretty good. I think maybe if you didn't have me on it, it might be a hit’. But it turns out I was underestimating Kenny, because he was able to drag me all the way up the charts to No. 1, like I was an ankle weight or something, and we had a No. 1, and we had a GRAMMY nomination, and we got to sing it in NFL stadiums and SEC football stadiums, and just so many blessings came from that song. But my favourite one of all those blessings is the way it made me feel on Christmas morning right before the sun came up, and that I got an exactly correct picture of family, and what that means”.

Of course, McAnally, humble as ever, is tremendously underplaying how crucial he was to the success of ’Down the Road’. Yes, Chesney introduced the song to his legions of fans and shaped the fantastic new version, but ultimately, the tenderness of the storytelling and the understated yet enchanting melody is courtesy of McAnally.

McAnally remains a cornerstone of the island-inspired, Gulf and Western sound that Chesney, Jimmy Buffett and so many others have been flag-bearers of. Thanks to him, we have songs like ’Two Dozen Roses’ by Shenandoah and countless Buffett earworms. He's a songsmith in the truest sense, and we're still keeping our fingers crossed that he has another album en route soon after 2020's Once in a Lifetime.