Top Fifty CMA Single of the Year Winners, Part One: #50-#41

As the 51st Annual CMA Awards approach, what better time to look back at the fifty years that came before?

For five days, we will be counting down the fifty winners of the CMA Single of the Year, ten a day, worst to best, as voted on by Country Universe writers Kevin John Coyne, Leeann Ward, Jonathan Keefe, and Sam Gazdziak.

We kick things off today with the first ten entries in our countdown, which we collectively view as the least significant winners of this prestigious award.

Top Fifty CMA Single of the Year Winners

Part One: #50-41 | Part Two: #40-#31 | Part Three: #30-#21

Part Four: #20-#11 | Part Five #10-#1


Florida Georgia Line


Sometimes one can listen to a song after a long layoff and gain a new appreciation for it, to discover a layer of nuance or subtlety that may have been overlooked. Then there’s “Cruise,” which remains a terrible, terrible song and helped usher in one of the least artistically satisfying periods in country music’s long and storied history. Thanks for nothing, guys. – Sam Gazdziak

“I Run to You”

Lady Antebellum


Lady Antebellum’s descent into endless tedium can be traced back to their having been over-rewarded early in their career for work that showed potential but wasn’t necessarily great on its own merits. “I Run To You” isn’t as memorably awful as “Cruise” or “Achy Breaky Heart,” but that’s precisely its problem: There isn’t a single thing memorable about it. – Jonathan Keefe

“Holes in the Floor of Heaven”

Steve Wariner


It was emotionally rewarding to see Steve Wariner finally celebrated at the CMA Awards after two decades on the country charts. But as this list will prove repeatedly, maudlin sentiments, topical songs, and novelty records rarely age well.  This old tearjerker has lost its potency over time. – Kevin John Coyne


Little Big Town


“Pontoon” was a song that people either loved to hate or hated to love. The production is delightfully quirky and the melody catchy, but the witless attempts at innuendos made it a controversial choice for Single of the Year in 2012, especially up against decidedly stronger singles like Dierks Bentley’s “Home” or Eric Church’s “Springsteen”. – Leeann Ward

“Achy Breaky Heart”

Billy Ray Cyrus


Country’s equivalent of Los Del Rio’s “Macarena,” “Achy Breaky Heart” was an obvious novelty track married to an easy-for-drunks-to-do-at-a-wedding-reception line dance. It wouldn’t ever have been great, but I’ve long felt that the single wouldn’t be *quite* so derided had it been “Achin’, Breakin’ Heart,” which would have still fit with the song’s meter and rhyme scheme. – JK

“Die a Happy Man”

Thomas Rhett


Like most Thomas Rhett songs, “Die a Happy Man” is an inoffensive, listenable pop-centric tune. It’s a fine romantic ballad, but calling it a “Song of the Year” would seem a bit of an overreach. – SG

“Country Bumpkin”

Cal Smith


Cal Smith would probably be higher on this list if he’d won the trophy for “The Lord Knows I’m Drinking,” but alas, it’s the emotionally manipulative “Country Bumpkin” that earned him his biggest industry award. He does his best to sell it, but repeatedly rhyming “bumpkin” with “pumpkin” while marking a woman falling in love, and then giving birth, and then dying is hard to take seriously. – KJC

“The Happiest Girl in the Whole U.S.A.”

Donna Fargo


To hear such exuberance in a song is a bit jarring in these times. There’s no cynicism in it, just pure joy and gratitude. As much as we need that now, a song with such expressions of happiness would seem too silly today, but still somehow managed to resonate during the unrest of the early seventies.- LW

“I Swear”

John Michael Montgomery


He’s local, so I’m supposed to root for John Michael Montgomery, but he’s one of the 90s’ more baffling success stories: Literally any other Hat Act— let’s say Ty England, because why JMM and not him?— could have turned the cloying, gauzy “I Swear” into a hit and a wedding standard just as competently. – JK



Miranda Lambert


In a perfect world, Miranda Lambert would be competing in 2017 with “Vice” instead of “Tin Man,” and then she’d have a shot at winning this again with a song worthy of her talent. “Automatic” is a bizarre exercise in nostalgia for things that weren’t as good, like Rand McNally maps and having to wait in line to pay for gas. I know country music is supposed to glorify the good old days, but we never heard Loretta Lynn pining for iceboxes and outhouses. – KJC


  1. Interesting that you guys find “Holes In The Floor of Heaven” to have lost its shine. As someone who has next to no stomach for sappy, formulaic songs (see “I Swear,” for instance…), “Holes…” is actually one of the few songs that gets me every time and it’s definitely my favorite song of this batch.

  2. I agree with the comments on most of these. However, I love Country Bumpkin and consider it a stellar song. Very relatable about the stages in life. It’s become a common theme in country (example: Patty Loveless-How Can I Help You Say Goodbye), but I still think Country Bumpkin is one of the best.

  3. Awesome idea! This is the kind of out-of-the-box content that had me hooked on Country Universe all those years ago. These types of countdowns are some of my favorite things you’ve ever done.

    I’m having some trouble with the placement of “Cruise” at the bottom of this list. The track’s significance lies in what you said – the song ushered in Bro Country. But it also shows the CMA embracing Bro Country. I’d say the song is very significant for those reasons. The song is as important as “On The Other Hand” or “Any Man of Mine.” I would’ve ranked it much higher, under those parameters. Creatively? You placed it perfectly.

    I totally agree with the placement of “I Swear,” “Pontoon” and “I Run To You.” I probably would’ve added “I Saw God Today” to this grouping.

  4. I would’ve definitely put Happiest Girl In The Whole USA much higher. It’s hard not to smile when you hear that song, even today. But I am biased since Donna Fargo is one of my all time favorite female country singers.

    As for the others here, I’m shocked that most of them were even nominated, much less won the award. Some really forgettable songs here with the exception of Country Bumpkin and Automatic.

  5. Aww, I love “Holes In The Floor Of Heaven.” It sure hasn’t lost any of its emotional impact for me, since I still get teary eyed and reach for the tissues when I hear it. I also think Steve gives it a great emotional performance. I still really like “I Swear,” too, and I’ve always been pretty fond of “Country Bumpkin.” Guess I’m just a sucker for sentimental songs. :)

    As for the others, I totally agree with “Cruise” being at the bottom. It deserves that ranking simply for kicking off one of the worst trends in country music history, imo. I would’ve put “Pontoon” closer to the bottom, as well. I did like it when it first came out, but it hasn’t aged well for me at all. Now it just grates on my nerves when I hear it, especially if someone plays it during the friggin’ wintertime, lol. I think the placement of “Achy Breaky Heart” is just about right. It’s pure fluff for sure, but it’s also a guilty pleasure for mostly nostalgic reasons. The rest I can either take or leave.

  6. Cool feature!

    I admit that “Holes in the Floor of Heaven” is pure ’90s sap, but I’d be lying if I said it didn’t get to me.

  7. Interestingly enough “Achy Breaky Heart” was a cover of a Marcy Brothers recording from the year before. The Marcy Brothers used the title “Don’t Tell My Heart” with essentially the same arrangement as Billy Ray’s cover.

    “Achin’, Breakin’ Heart” was the title of a George Jones hit from 1962. Perhaps Billy Ray’s producer didn’t want this song confused with the earlier George Jones hit

  8. “Holes” still holds up.
    “Cruise” is better than what people say. It is the epitome of a great escapist song.

    What is wrong with Rand McNally maps?! Geez. Maps are magical.

  9. @ Paul,

    I knew about the “Achy Breaky Heart” version From the year before Billy Ray’s, but, for whatever reason, I’d only ever seen it given the same title. I wonder if, somewhere along the line, the Marcey Brothers’ label may have re-tagged their version to capitalize on the popularity of the Cyrus Virus. Or if the mp3 I found ages ago simply had the title wrong. Either way, that’s an interesting bit of trivia.

    Song titles get recycled so often— there wasn’t a single song title on Lady Antebellum’s debut that wasn’t shared with another relatively well-known song— that I doubt the Jones connection would have stopped anyone. I think everyone was just content with writing a novelty song!

  10. You guys have been busy. I can understand your characterization of this group of songs as the “least significant winners” although I may find a few that follow that I like even less.

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