A Country Music Conversation: Sirius Top 1000 Country Songs of All Time, #380-#371

Clint Black, Willie Nelson, and Ernest Tubb are the blue skies here.


Willie Nelson, “Blue Skies”

#1 | 1978

JK: This list is psychologically abusive: For every ten just heinous choices, they’ll throw in an inspired, surprising pick and place it correctly. This one doesn’t get talked about much within the context of Nelson’s legendary career, but it’s a winner. About Right

ZK: In what seems to be the year of the cover project, it’s important to point back to classics like this for how it’s properly done. What Nelson has lacked in pure power, he’s always made up for in pure charisma and emotive subtlety, and this song – as well as Stardust as a whole – is a testament to that. A fine choice, placed About Right.

KJC: I love me some Stardust.  “Blue Skies” might as well be the thesis statement for the entire project.  As Jonathan says, an inspired, surprising, and well-placed pick.  About Right



Keith Urban, “You’ll Think of Me”

#1 | 2003

ZK: Keith Urban is just too nice to be bitter. I mean, “take your cat and leave my sweater, ’cause we have nothing left to weather,” that was seriously all he had? So Wrong (Doesn’t Belong)

KJC: I’ll respectfully disagree with my colleagues, here. I think this is one of Urban’s greatest moments because of the tension between who he is and how he feels. He’s a nice guy to his core, and he’s trying really, really hard to hold in the deserved bitterness and rage.  For nice guys, this is a signature kiss-off anthem that has them saying, “Well, I told her!”  You didn’t, really, but you tried just enough to preserve your dignity and your decency. About Right

JK: The line Zack quoted is one of the worst bits of songwriting to hit country radio in the last twenty years, and I’m fully aware of the implications of that statement. Easily the worst single from Urban’s best era. He’s over-represented on this list, so this is an obvious one to cut. So Wrong (Doesn’t Belong)



Clint Black, “Killin’ Time”

#1 | 1989

KJC:  Did a happy marriage derail his path to becoming one of the all-time greats? I mean, yeah. It did. Probably better to be happy in life than to be miserable and make brilliant country music out of it.  But he was a modern day Haggard on those first three albums.  This single is an all-time classic.  Too Low

JK: Few artists have been as immediately great as Black; that he only had about six years’ worth of good material remains a pity. About Right

ZK: Clint Black peaked early and fast, but when his contribution to the country music canon was this, that’s OK. About Right 



Faron Young, “Wine Me Up”

#2 | 1969

JK: I mean, it’s more clever than “Alcohol You Later” as far as country’s hit-or-miss history with booze puns go, but Young’s performance is what makes this record work to the extent that it does. Which is to say this ranking is Too High.

ZK: An energetic honky-tonk classic that, if I’m being honest, isn’t among the best of its kind, even if it does stand out for the era in which it stems. It’s still a lot of fun to revisit. Too High 

KJC: I don’t think the title is particularly clever, or the record’s general conceit.  But those fiddles! That twang! That wailing vocal!  I’m still down with it.  Too High



Jason Aldean, “My Kinda Party”

#2 | 2010

ZK: A decade after the fact, I can still smell the Axe Body Spray permeating from this record; the rest of it found its way to Brantley Gilbert’s catalog, I think. So Wrong (Doesn’t Belong)

KJC: These lyrics could’ve been made by a monkey using a bro country word generator.  Tragic. So Wrong (Doesn’t Belong)

JK: The idea of Aldean’s kind of party was repellent even before we knew it would, in today’s world, be called a Superspreader Event. So Wrong (Doesn’t Belong)



John Michael Montgomery, “Be My Baby Tonight”

#1 | 1994

KJC:  God, this sounds like Shakespeare after “My Kinda Party.”  Montgomery wasn’t even that great back in the day.  But the women in his songs had agency, at least.  There’s something almost quaint now about his lovesick “please go out with me” shtick.  So Wrong (Doesn’t Belong)

JK: Songs like this actually masked what a limited vocalist Montgomery was. A fun enough record for what it is, but slate this back in the 900s somewhere. Too High

ZK: I liked John Michael Montgomery’s rapid-fire flow on songs like this and “Sold” more than I liked his actual material. So Wrong (Doesn’t Belong)



Luke Bryan, “Do I”

#2 | 2009

JK: I just cannot get my head around the idea that anyone thought that, in the entire history of country music, there are only 373 songs better than this. So Wrong (Doesn’t Belong)

ZK: I never cared much for Luke Bryan’s “aw, shucks” demeanor even before he sucked. This is OK, if milquetoast and overblown, but super forgettable. So Wrong (Doesn’t Belong)

KJC:  He’d never try something this mature these days.  He’s like the Benjamin Button of country music.  (Still So Wrong (Doesn’t Belong), though.)



Ernest Tubb, “Walking the Floor Over You”

Pre-Chart | 1941

ZK: That is not a Rascal Flatts song I see *just* ahead of this.

Oh, God, it is. Bless this broken road, indeed. Too Low 

KJC: I feel like there are some songs that if you weren’t going to put them in the top 100, you were better off not including them at all. Somehow placing this at #373 is more egregious than leaving it out completely.  Too Low

JK: I 100% agree with Kevin: The ranking is an outright insult, whereas leaving it off would be easier to dismiss in the context of the wrong-headedness of the list overall. This is a t50 record at minimum. Too Fucking Low



Rascal Flatts, “Bless the Broken Road”

#1 | 2004

KJC:  This was one of those songs that was eventually going to be a hit, once an artist with a track record at radio put it out.  I think this is quite worthy of a place on this list, even if it pales in comparison to the Marcus Hummon recording.  Too High 

JK: That it’s the best-written and best-produced song in their catalogue says very, very little. It belongs on the list on commercial impact and for no other reason, but this is far Too High.

ZK: If you stare at a mirror and sing the hook three times, a Hallmark store pops up behind you. Works every time. So Wrong (Doesn’t Belong)



Restless Heart, “When She Cries”

#9 | 1992

JK: A far better adult contemporary single than a country one. I’m not mad that it was included, per se, but this ranking is just Too High.

ZK: I’ll give them credit for including one of the band’s last big singles. But of the Restless Heart singles included – for one, I’m sad not to see “Dancy’s Dream” here, but I also don’t think that I’d put any of them in the top half. Too High 

KJC: An excellent pop song that has aged well.  I’d have placed it in the 900’s.  Too High


Previous: #390-#381 | Next:  #370-#361



  1. My goodness. Ernest Tubb….this is the second worst rating of the entire list, behind “When I Call Your Name”. I agree it’d have been more palatable to not be listed than to be listed this low. It should be top 50 for sure. Clint Black is notttttt quite great, notttttt quite the best songwriter, notttttttt quite the most magnetic personality, notttttt quite an especially memorable/distinctive voice. I’m okay with the JMM entry, as it beats to death that sappy crap way too many people seem to fall for. I lovvvvvvvvvvvvvvvvvvvvvvve how you love me. Wow, hold the word “love” for 2 bars. What lyrical craftsmanship and emotional depth! Reminds me of Faith and Tim, rhyming “to me” and “through me”. Wow, what a command of the English language.

  2. Re. “Blue Skies”: This is one of many great examples of why Willie is a great ambassador, not only for country music but for American popular music in general. Maybe his way of doing it is not necessarily the way of a Frank Sinatra…but then there was only ever one Sinatra, and there is always going to be only one Willie Nelson.

    Re. “Walking The Floor Over You”: Yes, this one is way too low, given that it is one of at least 100 legitimate candidates for the perfect country-and-western song. After Ernest’s mega-classic version, it has been done hundreds of times by country and country-adjacent artists alike. Seeing it on the list should be enough, but to see it interspersed with Bromeisters like Bryan and Aldean is, to put it mildly, an embarrassment.

  3. Oh boy! “Walking the Floor Over You” should be top twenty or higher, but as one of the very oldest recordings (1941) on this list, I am glad they remembered it at all. In fact, most folks who recall the song at all tend to remember the stereo re-recordings featuring Billy Byrd or Leon Rhodes on electric guitar, rather than the much simpler (almost semi-acoustic) 1941 recording featuring Smitty Smith on lead guitar.

    I love “Stardust” and I think Willie did a nice job with the song BUT it is not a country song and I regard the Artie Shaw instrumental recording (1941) and the Bing Crosby and Frank Sinatra versions as superior to Willie’s recording (I suspect Willie would agree)

    “Wine Me Up” marked Faron’s return to a more hard core country sound. It reached #1 on Record World and kicked off the most successful five year chsrting period of Faron’s career.

    I think that “Killing Time” is much too low but I largely agree with the rest of the comments

  4. I’m with the consensus here that the ranking of the Ernest Tubb all time classic is yet another major embarrassment in this list. Seeing it sandwiched between Luke Bryan and the Flatts makes me sick to my stomach.

    Also totally with you guys on Clint Black, in general. While I would still no doubt take most of his more recent music over what mostly gets on the radio these days, he was pretty much unbeatable on those first three albums. Nearly every song he released as a single during that period is worthy of a spot on this list, imo. “Killin’ Time” is a classic and is probably his most popular song, but I also think “Nobody’s Home,” “Nothing’s News,” “Loving Blind,” “One More Payment,” “Where Are You Now,” “Burn One Down,” “When My Ship Comes In,” etc. deserve some love, too. One song I absolutely love from his second album, “A Heart Like Mine,” would’ve made an excellent single too, imo.

    I’m actually quite happy to see “When She Cries” on this list. It’s yet another song that instantly takes me back to my childhood when I hear it, and I would definitely not complain if most pop country sounded like this. Such an irresistible melody, love that guitar solo, and John Dittrich did a good job sounding similar to Larry Stewart on the lead vocals.

    “Be My Baby Tonight” is still a fun little tune, but definitely shouldn’t be this high. Also, when it comes to JMM’s uptempos, “Sold” is my favorite. From this album, “Rope The Moon” and “If You’ve Got Love” are my favorite singles.

    On “You’ll Think Of Me,” the “take your cat and leave my sweater” line is definitely cringe worthy, but I otherwise agree with Kevin that this is one of Urban’s better singles. I like his description of it being the nice guy’s kiss off anthem, and I’ll easily take it over just about anything he’s released to radio over the last decade.

    Glad to see Faron Young here, and I always did like “Wine Me Up.” I also like Gary Allan’s cover of it on his first album.

    Also love me some Stardust Willie, and I’m glad to see another selection from that album represented here.

    Even though “Do I” may be one of Luke’s better songs before he went full bro, I still find it pretty boring and forgettable, overall, and not worthy of this list.

    I always personally found “Bless The Broken Road” to be overrated (the Flatts version, at least), and it was definitely overplayed in my area. To make matters worse, just about everyone and their brother was singing it on all those TV talent shows, as well. Anyway, I’ve way past had my fill of seeing these guys on this list.

  5. Taken together, your commentary on Clint Black perfectly encapsulates his career. I agree with Kevin that this song is too low.

    As expected, this list continues to be baffling as “Walkin’ the Floor Over You” is way too low.

    I always enjoyed this JMM song (and most of his up-tempo) songs, but this is much too high for this list (if it even belongs at all).

    Not only were all the singles from Clint Black’s first three albums really good to great, but almost every album cut was really good as well.
    I also really enjoy Gary Allan’s cover of “Wine Me Up” – his first two albums were full of great songs and are still really enjoyable listens. (I should state that the Faron Young version is great as well, but the Gary Allan version is the first one I remember hearing).

  6. Frank The Tank – Gary’s version of “Wine Me Up” is actually the first one I heard, as well. Also, I’m totally with you on his first two albums! Love the straight up neo-traditional and honky tonk style he had then. I’ve especially always loved the It Would Be You album. He began to develop his own unique style starting with “Smoke Rings…” but was still very consistent with the high quality up until after his Greatest Hits album, imo.

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