The Best Hit Songs Of 1985

The Highwaymen

In 1985, The New York Times published an article declaring country music’s death. While the genre was caught in a weird area after the decline of the Urban Cowboy era, the article failed to take into account certain factors. Yes, older artists were generally faring worse during this time, and sales were down overall. But it failed to take into account the plans set in motion to combat this decline. One of those plans was to introduce an entirely new generation of country artists to the format – ones who had greater creative control and stronger artistic identities (in other words, when you’ve hit rock bottom, you may as well start taking risks).

And with three exceptions, the following list reflects those changes. Today, the idea of ushering out older artists in favor of newer artists has mostly brought destruction and chaos to the format, but this was a different time in country music.

As always, this is the only feature where Wikipedia is a handy source, as I’m counting down the best “hit” songs of 1996 (basically top 20 or close to it). Also, these are of course only my personal picks and preferences. I invite you share yours down below!


Let’s start with some honorable mentions!

Further honorable mentions can be found here.


No. 10 – John Anderson, “Eye Of A Hurricane”

Sadly, John Anderson’s chart success was waning by 1985, and Eye Of A Hurricane is certainly not one of his better known albums. Even the title track showed a different direction for him. Still, the odd upbeat, lively country-rock number backed by saxophone fit his demeanor at least. The song isn’t anything special lyrically, but its infectious atmosphere and Anderson’s unique charisma still manage to make it one of his more underrated hits.

No. 9 – The Judds, “Love Is Alive”

You know, this song could almost be labeled cheesy if it weren’t for the sincerity packed behind the performance. Beyond that, though, there is admittedly something simplistically true about the song’s sentiment. Backed by warm acoustics and piano, this is one of those songs that’s a good reminder of why country music is at its best when it’s kept simple.

No. 8 – George Strait, “Does Fort Worth Ever Cross Your Mind”

One of Reba McEntire’s musical regrets is passing on “Does Fort Worth Ever Cross Your Mind.” Indeed, while George Strait’s younger vocal could work against him in terms of a confident performance, this song is one of those songs that just manages to stick out in his loaded catalog. In a nutshell, this is a simple tale of regret that sticks out for its great opening line.

No. 7 – Ricky Skaggs, “Country Boy”

This song is obviously not here for its lyrical content. In truth, “Country Boy” just may be one of the most infectious songs in country music, showcasing bluegrass picking in a way that was cool to mainstream audiences. The technical playing is of course great, but it’s those phenomenal solos that start around the middle and end of the track that really make this stand out in a great way, especially for 1985. I just love when the drums kick in during the verses. The Looney Tunes reference is really just the icing on the cake.

No. 6 – Reba McEntire, “Somebody Should Leave”

As I’ve said before with this particular feature, one of Reba McEntire’s key aspects of her material is her approach to them. There’s a frank, refreshing honesty with which she approaches her best songs, and in this case, she finds herself approaching the end of a line. Neither party loves each other, but they hang on for the sake of their children, and the reality of that situation cuts deep when you consider her blunt confession that there’s nothing left between the two lovers.

No. 5 – Ray Charles and Willie Nelson, “Seven Spanish Angels”

Hey, let’s make some room for the veterans why don’t we? Ray Charles wasn’t the most familiar face on the country charts in 1985, but his huge impact on country music in the early 1960s can’t be understated. He introduced a soulful country style that still surfaces today. On paper, this song is a western love saga that Willie Nelson himself could have tackled in his sleep at this point. Somehow, though, the two have a rare chemistry that simply makes the track convincing. As a result, the two men issued a classic.

No. 4 – George Strait, “The Cowboy Rides Away”

Speaking of old western tropes, George Strait somehow reinvented the concept of “riding off into the sunset” with this song. Today, the song is looked as Strait’s farewell to stadium tours, but the actual song itself remains a highlight in his career. This cowboy didn’t get a choice in the matter when it came to leaving, unlike what tradition would tell us. Instead, the power is in his lover’s hands, and Strait’s delivery is an aching exercise in conviction.

No. 3 – George Jones, “Who’s Gonna Fill Their Shoes”

There’s very few artists who care about country music and its meaning more than George Jones. As previously mentioned, country music was caught in a state of disarray in 1985. As much as some didn’t want to admit it, it was time to start planning for the future. The title is ironic, as we all know no one can fill the shoes of the legends before, including Jones himself. But we’re always going to need at least one artist who cares about the beating heart of country music, and thankfully, the artists filling those shoes included Dwight Yoakam, Kathy Mattea, Randy Travis and so many more. It’s safe to say it was in pretty good hands. This is one of those songs that’s never going to go out of style, because we constantly need to ask this question to keep country music’s fire burning.

No. 2 – George Strait, “The Chair”

Was George Strait on fire this year or what? This has all the makings of a classic – a delivery that no one could ever emulate, a clever story that comes with its own twist at the end, and a captivating atmosphere to keep the listener coming back when it’s over. There’s no chorus or refrain, so it’s amazing how good the song is at keeping the listener tuned in. When the song is this good, though, that’s not exactly hard.

No. 1 – The Highwaymen, “Highwayman”

Ironically, in a year filled with big transitions for country music, it took one last hurrah from some of country music’s best to take this No. 1 spot. This song is so good that it made Glen Campbell, who wanted to record the song and was denied the chance, storm out of Capitol Records, never to return. There’s no doubt that Jimmy Webb is one of the finest songwriters ever, and this philosophical tale of reincarnation really did fit multiple voices best. Thankfully, the voices enlisted to tackle this were among country music’s best. Beyond the pure magnificence and scope of the song, the pure magnitude of this union can’t be overstated. Johnny Cash, Kris Kristofferson, Waylon Jennings and Willie Nelson formed the country super group, and they sounded like a polished group – not just some people thrown together as a marketing gimmick.

And despite the obvious lapses in time between the character’s numerous times on earth, the verses all fit the singers perfectly. Nelson is the wild western cowboy who winds up paying a heavy price for his ways. Kristofferson is the dreamy-eyed sailor never content with letting the journey end. Jennings takes on the dangerous, reckless job because … well, someone has to, just as someone had to fight for artistic rights for all not long ago. And then there’s Cash just trying to find a place to rest his soul, especially with how many adventures he had in his time. And like they all say, they’ll be gone eventually (two of them already are). But they’ll be back again and again and again and again, if not in body or spirit, then certainly in the music they leave behind for all of us.

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