A Country Music Conversation: Sirius Top 1000 Country Songs of All Time, #350-#341

Merle Haggard’s B-sides continue to outshine most of the A-sides on this list.



Montgomery Gentry, “Where I Come From”

#8 | 2011

JK: Baffling that this is ranked ahead of “My Town,” which is obviously the superior cut in every way. With so many artists not represented on this list at all, there’s no way this copy-of-a-copy-of-a-copy single should’ve been here. So Wrong (Doesn’t Belong)

ZK: It’s too bad this was their last top 10 hit, a poor retread of their numerous other songs in this vein. So Wrong (Doesn’t Belong)

KJC: The formula was wearing thin well before this was released.  As Jonathan and Zack note, there are earlier and better tracks to represent them.  So Wrong (Doesn’t Belong)



Dwight Yoakam, “Guitars, Cadillacs”

#4 | 1986

ZK: One of the defining records of its time, especially as country music shifted away from some of the more boring traits of the Urban Cowboy era. 1986 was an important year for the genre, and it’s a single like this that shot some life into it. Far, far Too Low. 

KJC: As perfect a country record as exists.  If I had to distill the entire genre down to a single CD, this would be on it.  Too Low

JK: When we did our Best Singles of the 1980s lists for Slant some years ago, I knew I’d be the only vote for anything country, so I culled the country singles from my ballot, except for the ones that I’d ranked in my top 10. This is one of those singles I kept. It’s a stone classic, and this ranking is entirely Too Low.



Jake Owen, “Barefoot Blue Jean Night”

#1 | 2011

KJC:  A pleasant enough record that shouldn’t be able to view the top four hundred in the distance from its proper location.  Too High

JK: The only one of Owen’s uptempos I’ve ever liked was “Yee Haw,” of all things, but I can at least understand why this one would be included on this list… like 600 entries back and certainly not ahead of “Guitars, Cadillacs.” Too High

ZK: A bit too early for its time to be called “bro,” and what can I say? There are very few modern mainstream artists who can pull off lightweight, breezy material effectively, and I’d say Jake Owen is one of them. Certainly not a cut I’d place right here, but I can’t quibble with it actually being here at all, though maybe more in the lower 900s than anywhere else. Too High 



Merle Haggard and the Strangers, “Silver Wings”

B-Side | 1969

JK: The one thing that I’ve actually learned from this list is that there are some classic Haggard tracks that I honestly had just assumed were massive chart hits but were actually B-sides. In terms of stature, this one would be like if “Tennessee Mountain Home” had been a B-side or “The Grand Tour” had been an album track. I legit did a double-take when I read that. Too Low

ZK: Look, they did a surprisingly decent job with the Haggard selections overall, but this stands next to “Sing Me Back Home” in the what-the-fuck-were-y’all-thinking-with-this-placement department. Too Low

KJC: I first heard this song on the Mama’s Hungry Eyes tribute album, which was a last minute addition because they realized, “Nobody’s done ‘Silver Wings!’”  Pam Tillis did the honors, which is why I bought that album in the first place. So my shock that it wasn’t a proper A-side dates back 26 years. Too Low



Dierks Bentley, “Sideways”

#1 | 2009

ZK: I’m looking at the fine folks over at Sirius a bit sideways for putting this just ahead of “Silver Wings.” And “Jolene.” And “Seven Year Ache.” And … So Wrong (Doesn’t Belong)

KJC: I’d be totally fine if the only thing on this list that resembled bro country was Dierks Bentley’s indulgences in it.  But I’d get them out of the way early on like a veteran act dropping new songs into their set list.  Too High

JK: I like Dierks Bentley quite a lot, but come the entire way on with this inclusion and ranking. Swap it for “Bourbon in Kentucky” or “Say You Do” or “Up on the Ridge” and drop it 300 places back. So Wrong (This Song)



Shania Twain, “Whose Bed Have Your Boots Been Under”

#11 | 1995

KJC:  Shania Twain’s big three albums worked because of two critical elements: Twain’s clever and distinctively female point of view as a songwriter, and “Mutt” Lange’s decision to structure her songs like pop records recorded with country instruments.  It’s a testament to the high bar set by The Woman in Me that this was only the third or fourth most impactful release from that landmark record.  Out of all of the album’s eight singles, though, this one was not just the first. It was also the best.  About Right

JK: I’d swap the ranking of this one with “No One Needs to Know,” which we covered ages ago, to represent what are easily Shania’s two finest singles. The production on this has aged remarkably well, and it says so much about country radio that this missed the top 10. Too High

ZK: Her most conventionally country song to date, the one that started a commercial hot streak rivaled only by Garth Brooks … and yet one that feels forgotten in the larger conversations surrounding Twain’s discography. I might not have it quite *this* high, but I’d definitely have it in the upper half. I’m glad it was included. Too High 



Bobby Bare, “500 Miles Away From Home”

#5 | 1963

JK: I mean, yes, this is one of his bigger chart hits, but it’s almost like they just looked at Bare’s singles discography entry on Wikipedia to make and rank their picks for him. I’d have this in the first quarter of the list somewhere and would have cut a lot of nonsense in between to make room for some of his less conventional work. Too High

ZK: They really didn’t try that hard with the Bobby Bare selections, and while it’s a good song and his version is the most commercially successful and likely the best, his 2nd highest song here? For real? Too High 

KJC:  It’s impossible not to measure this against “Detroit City,” which has a similar theme but far more lyrical specificity.  I’m glad they included it, even if it’s just a bit Too High.


Brantley Gilbert, “Country Must Be Country Wide’

#1 | 2011

ZK: I don’t disagree with the sentiment, honestly; I just don’t need the Motley Crue backdrop to go with it. So Wrong (Doesn’t Belong)

KJC: Ah, the “from his wranglers to his boots” song that irritates me when just a five-second clip of it surfaces during a round of SongPop.  Flat out terrible. Words cannot fully capture my disdain for songs that fiercely cling to country as a “mine and not yours” identity without bothering to respect the roots of the music itself.   So Wrong (Doesn’t Belong)

JK: We ended up with Brantley Gilbert as a B-list country star, presumably, because VH-1 stopped producing shows like Tool Academy and Daisy of Love after a contestant on Megan Wants to Marry a Millionaire murdered his real-life girlfriend. There’s a subset of country fans who insist that Gilbert is secretly a brilliant songwriter, but just-awful hits like this have not inspired me to dig very deep into his catalogue to find out if that’s true, when he seems better-suited for a reboot of the Flavorverse. So Wrong (Doesn’t Belong)



Zac Brown Band, “Whatever It Is”

#2 | 2009

KJC:  I confused this with David Nail’s “Whatever She’s Got” and was poised to…still be baffled by its placement.  So Wrong (Doesn’t Belong)

JK: I have absolutely no recollection of this song, and this is from the era when I still liked Zac Brown Band. How on earth is this ranked so high? Or at all? So Wrong (Doesn’t Belong)

ZK: Pleasant filler for this band, but as far as its placement here, “whatever,” indeed. So Wrong (Doesn’t Belong)



Trace Adkins, “Every Light in the House”

#3 | 1996

JK: A well-written song that Adkins dials up to 11 like he’s trying to be the male version of Reba… And it kind of works? I still wish he had a better sense of pitch, but this is one of Adkins’ best. Still, in the grand scheme of things, this ranking is far Too High.

ZK: A bit oversold, as certain ’90s singles tended to be. But there’s a part of me that enjoys a healthy dose of earnest melodrama, too, and there’s a darker subtext here that’s always elevated its wistful lonesomeness. Really, Adkins could have made several modern classics if he’d just used his talent for good. Too High 

KJC:  A deserved breakthrough hit from his early days, when he still carried the air of a gentleman.  From his entire catalog, I’d only put “I’m Tryin’” this high.  Too High


Previous: #360-#351 | Next:  #340-#331



  1. It’s hard to believe, looking back on it, that Jake Owen was the guy who recorded “Startin’ With Me.” I suppose “Eight Second Ride” should’ve been a warning, but just the same he still started out so promising.

    I could say much the same for Dierks Bentley. I did actually make the observation some time ago that it was such a shame to see him start out so promising and then peak with his sophomore album. Long Trip Alone wasn’t terrible, but it wasn’t as good as the albums that preceded it, and hearing the first couple of singles from Feel That Fire got me off the Dierks train.

    The Trace Adkins selection here has always been one of my favorites from him; it was actually what got me to buy his debut album. I wish it’d been his first No. 1, but it did come close.

  2. “Silver Wings” was the flip side of “Working Man Blues” – I was living in England at the time this single was released but by this time I was buying every Haggard album as soon as it became available. The DJ on the BBC 1 radio show ‘Country Style’, Pat Campbell, had a copy of the US single and played both sides of the single several times over the next few months.

    I think the Bobby Bare selection is just a little too high. Otherwise I largely agree with the group’s comments on this group on this mostly undistinguished group of songs

  3. Re. “Whose Bed Have Your Boots Been Under?”: I know that Shania has a lot of fans, and I can totally understand their admiration for her, based on that song and her other hits. That being said, though, I am not one of those fans, because I don’t think she stood out as being in the vocal class of Trisha or Martina.

    Re. “Country Must Be Country Wide”: Fair enough. Doing it through loud, half-assed, death-warmed-over Southern rock, and name checking Johnny Cash, Hank Williams (Sr. and Jr.) and Waylon Jennings without a bit of context, however, isn’t the way (IMHO).

    Re. “Guitars, Cadillacs”: One can make the convincing case that it was this first big hit for Dwight that helped him become an ambassador for the country music world, especially among listeners who might not otherwise have even bothered. He was, and remains, the real deal (IMHO).

  4. Okay, I’ve settled down. Agreed with Erik per Shania’s limited singing ability. Disagree with the entire panel about Every Light. Top 100, probably 50, for me. But I could never deal with that extraneous “do” that ruins the meter.

  5. I always really enjoyed “Every Light In The House” and most all of Trace’s music from 1996-2002 before he started going overboard with the novelties. My personal favorites, though, are “The Rest Of Mine,” “Lonely Won’t Leave Me Alone,” “Don’t Lie,” and “I’m Gonna Love You Anyway.” Also agree with the mention of “I’m Tryin’.” I’m pretty much ok with the ranking of “Every Light.” Yet another artist who wasted his talent on too many songs that were either silly or godawful.

    “Silver Wings” is one of my all time favorites from the Hag, and I’m also surprised to learn that it was actually a B-side. It was still getting some recurrent airplay on one of our stations around early 1991, as I have it on one of my tapes I recorded then. What an insult it is to see this classic placed below Brantley Gilbert.

    Same goes for Dwight’s “Guitars, Cadillacs.” WAY too friggin’ low for such an iconic single. This song alone is proof that traditional country with downbeat lyrics can also be fun to listen to. Looking at what he have now on the radio, it’s hard to believe that there was a time when guys like Dwight and Randy Travis were two of the hottest people in mainstream country. I’m truly thankful that I got to be around during that era before it ended, even though I was still pretty young then.

    I’m in total agreement in swapping “Who’s Boots Have Your Boots Been Under” with “No One Needs To Know.” That’s my personal favorite of the The Woman In Me singles, and it’s the strongest one, imo.

    Unlike many of the other bros, Jake Owen actually had some tolerable and even some pretty good songs out before diving headfirst into the subgenre, imo. His first album was pretty decent for the most part, and even the Barefoot Blue Jean Night album has some good cuts that never made it to radio. I agree that if the title track had to show up here, I’d have it MUCH lower.

    I agree with most all of the comments here on Dierks Bentley. The Feel That Fire album is also when I started losing interest in him, and he’s become very hit or miss for me ever since. While I agree that some of his attempts at bro-country are not quite as bad as the efforts of many of his peers, I never got the appeal of “Sideways” specifically (always thought it was forgettable), and I’m simply baffled on how it made the list at all.

    And yeah, same goes for “Whatever It Is” by ZBB. I never was a huge fan of theirs to begin with and always found them to be “meh” at best.

  6. I’m usually late to comment (as I am with this post) and I find I quite often have very similar opinions as Jamie does, so I’ll highlight a couple of those here:

    “I’m in total agreement in swapping “Who’s Boots Have Your Boots Been Under” with “No One Needs To Know.” That’s my personal favorite of the The Woman In Me singles, and it’s the strongest one, imo.”
    – Agreed – “No One Needs to Know” is my favourite (and best) song on this album.

    “I always really enjoyed “Every Light In The House” and most all of Trace’s music from 1996-2002 before he started going overboard with the novelties. My personal favorites, though, are “The Rest Of Mine,” “Lonely Won’t Leave Me Alone,” “Don’t Lie,” and “I’m Gonna Love You Anyway.” Also agree with the mention of “I’m Tryin’.” I’m pretty much ok with the ranking of “Every Light.” Yet another artist who wasted his talent on too many songs that were either silly or godawful.”
    – I like this song a lot and his first few singles were great, but his quality went downhill soon after that.

    Also, “Silver Wings” and “Guitars, Cadillacs” are both much too low.

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