A Country Music Conversation: Sirius Top 1000 Country Songs of All Time, #250-#241

So many classics in this section that the non-classics seem more out of place than usual.



Willie Nelson, “City of New Orleans”

#1 | 1984

JK: Another of Nelson’s bigger radio hits that doesn’t seem to figure into the overall conversation about his greatness to the extent that it should. Ranking-wise, this strikes me as just slightly Too High, but not by all that much.

ZK: That harmonica provides a meaty groove, and it’s just such a brightly enjoyable record to revisit. We’re at the point where it’s got to be all killer and no filler, but I’d make room for a wildcard pick like this about here. About Right

KJC: This is one of his very best hits, a slice of Americana from the days when Americana was a state of mind, and not its own genre.  About Right



Conway Twitty, “Slow Hand”

#1 | 1982

ZK: Yeah, sure, it probably belongs here. I just personally can’t with the cheesy early ’80s production that dates this like hell, and the overblown, more-ragged-and-rougher-than-it-should-be performance that doesn’t come close to Twitty’s other hokey-pokey jams. Too High

KJC: The gender swap turns “Slow Hand” into a sexy anthem of affirmative consent.  Still a bit Too High

JK: Each time one of Twitty’s sex jams turns up here, I’m reminded anew of how much better he was at this kind of thing than literally any man who’s gotten significant airplay in the last decade. This record is kind of perfect, and this ranking is a bit Too Low.



Hank Locklin, “Please Help Me, I’m Falling”

#1 | 1960

KJC:  Again, if you know enough to include the song, you should know enough to rank it higher. Too Low

JK: Another top 50 classic that they slighted in favor of Jason Aldean. I don’t know how much more of this my blood pressure can take. Too Low

ZK: Peek ahead to see what we end with for today, and then try not to get mad at this placement. Too Low



Brad Paisley, “She’s Everything”

#1 | 2006

JK: I’ve stuck my neck out for Paisley more than any of the rest of the Crew over the course of this list, but this is not one of his hits I’ll try to defend. I wouldn’t have it ranked at all, let alone this high. Gross. So Wrong (Doesn’t Belong)

ZK: I’m in the same boat as Jonathan regarding Paisley, and this hit in particular. His romantic ballads are among his weakest, most generic cuts. So Wrong (Doesn’t Belong)

KJC: This doesn’t have the cringeworthy condescension that mars many of his love songs, but it’s bursting at the seams with too many trivial details that distract from the larger message he’s trying to send.  So Wrong (Doesn’t Belong)



George Strait, “The Chair”

#1 | 1985

ZK: This is the Strait song referenced most in popular culture after “Amarillo By Morning,” and after feeling like there were so many entries where I had to say, “eh, this is fine,” I can finally say it. This is among Strait’s best, and the “drink you a buy” line is gold. Too Low

KJC: George Strait’s greatest gift as a singer has been the material provided to him by Dean Dillion, whose irregular and complex songwriting reveals Strait’s remarkable gifts as an interpretive vocalist. Easily one of his best records.  Too Low

JK: The only Strait single I’d have ranked ahead of “The Chair” is “Amarillo By Morning,” so this is obviously far Too Low.



Merle Haggard, “I Think I’ll Just Stay Here and Drink”

#1 | 1980

KJC:  One of those songs that seems so obvious it’s surprising that it took so long for Merle Haggard to write it.  Lyrically fantastic, brilliantly sung, and with a killer musical outro that makes any radio edit a travesty.  Too Low

JK: I swear to every last named and unnamed god. Too Fucking Low

ZK: Haggard entered the ’80s with a commercial and artistic upswing, and this is among “Big City” and “Pancho & Lefty” as the best showcase of that. Criminally Too Low



Dierks Bentley, “What Was I Thinkin’”

#1 | 2003

JK: Dierks Bentley is a solid dude who would nutpunch whoever ranked this song of his ahead of “I’ll Just Stay Here And Drink.” So Wrong (Doesn’t Belong)

ZK: I’d be mad at anything ahead of Haggard’s song, but it’s not like it’s Dierks Bentley’s fault. An argument to be made that this is his best single, and there’s a reason he started his career with a bang and unique presence that, while never enough to push him into A-list territory, has made him a reliable modern presence. Too High

KJC: I don’t have an issue with Dierks Bentley’s breakthrough hit being on the list, but it being this high suggests that the listmakers don’t understand his development as an artist.  Too High



Kris Kristofferson, “Why Me”

#1 | 1973

ZK: Vocalists like Kristofferson can be pretty hit-or-miss as far as who they’re going to appeal to, and it’s usually a case-by-case basis. He’s an objectively bad singer, but it’s never bothered me, if only because the haggard, weary resignation can work on tracks like “Sunday Morning Coming Down” or this song. With that said, I know they picked this solely because it’s the “big hit.” Not complaining, mind you, just noting predictability. Too High

KJC:  The one track where Kristofferson’s vocals are perfectly matched to the material, allowing the humility of the songwriting to really shine through.  Also worth checking out: Johnny Cash’s version from American Recordings, which draws a similar power from its withered vocal.  

JK: I’m not going to object to the inclusion of some of Kristofferson’s own recordings, but, real talk, none of those records belong ranked this highly. Plenty of the covers do, of course, but not this. Too High



Clint Black, “A Better Man”

#1 | 1989

KJC:  Nineties country starts here.  Black’s entire Killin’ Time album is essential, but his debut single in particular serves as a historical marker, as he seamlessly incorporates elements of seventies and eighties rock and pop into a production and vocal that present themselves as pure country.  The lyric could’ve been an outtake from Rumours, but Black’s modern day Haggard stylings made “A Better Man” turn the crossover mentality on its head: country music could, and would, mix traditional country elements with vintage rock and pop, and the crossover audience could cross right over to country, thank you very much.  Too Low

JK: Black’s historic opening run of singles should all be included and should all be ranked highly. He’d never match that run, but he set the bar perhaps unattainably high. This is an extraordinary song that Black performs with real warmth and introspection, and it’s a rightful classic. Too Low

ZK: When it came to declaring a valedictorian for the beloved “class of ’89,” many forget that it was Clint Black – not Garth Brooks – that had the biggest start out of the gate. And when you go back to that debut album, it’s easy to see why. Crisp neotraditional country performed with a raucous fire on, say, “Killin’ Time” and warm, understated poise here. Too Low



Brantley Gilbert, “Bottoms Up”

#1 | 2014

JK: The absolute hackery of this shit: This song and this list. So Wrong (Doesn’t Belong)

ZK: Look, you want to represent the bro-country era, you do it with the obvious contenders that, yes, are already featured here. You don’t include the hacks that tried it on for style and utterly failed with it. Heresy as it is to say, Brantley Gilbert is a good songwriter who has some gems as deep cuts. But his single choices thus far have ranged from “shit” to “not-quite-shit,” and the artistic persona of an inauthentic “bad boy” doesn’t help, either. This is his most atrocious offering, and the country music story is just fine without him. So Wrong (Doesn’t Belong)

KJC:  This is the obvious inclusion from Brantley Gilbert, and hey, it’s good to know that after selling ten million records but before redeeming his legacy with Lil Nas X, Billy Ray Cyrus was able to claim that he influenced somebody’s music.  Too High


Previous: #260-#251 | Next:  #240-#231


  1. I really don’t like The Chair. Just a little syrupy for my tastes. Please Help Me is far too low, likewise I’ll Sit Here and Drink. City of New Orleans is simply not as good as the original. Slow Hand is fine, I don’t care for it as much as most country fans. Clint Black is fine, this is a bit high for an artist who is consistently good but never seems to hit one out of the park.

    I recall someone mentioning a while back that there is no method to the list. I agree more and more as the list rolls out. But really, if you’re going to create a list of 1000 songs, there MUST be a methodology. Such things end up carrying a great deal of weight down the road.

  2. I forgot to mention that Why Me is a bit overwrought, which makes it about perfect as a country song. I’m not sure how that works, but it somehow does.

  3. Re. “City Of New Orleans”: I think this is one of only a handful of times when Willie was caught short in covering a song, since it got such a memorable rendition back in 1972 in the hands of Arlo Guthrie. Still, to say the least, it ain’t Brantley Gilbert!

    Re. “Slow Hand”: Is it inappropriate to point out that Conway’s “slow jam” here is a Pointer Sisters cover (from just two years before)? Not that his is bad at all. The irony here is that the Pointer Sisters themselves cracked the country music world’s racial glass ceiling with “Fairytale” a decade before.

    Re. “Why Me?”: Kind of like Dylan, or Johnny Cash, or Lucinda Williams, Kris Kristofferson’s voice is an acquired taste, very weathered and imperfect–something he’d likely readily admit. But still, this was the biggest hit he ever had, not only country but pop as well (#16). And during the year this single was a hit, he portrayed the notorious 1880’s outlaw William Bonney in what is arguably the greatest Western film of the 1970’s, director Sam Peckinpah’s PAT GARRETT AND BILLY THE KID (alongside James Coburn, who portrayed Garrett).

  4. Zack, that assessment of Brantley Gilbert was spot-on. The ranking of his song right ahead of that Clint Black classic was more than a little jarring, honestly, and not in a good way.

    In re: Clint Black, though, I’m gonna have to respectfully disagree with you there, Steve, because the entire Killin’ Time album was just one out-of-the-park slam after another. Now, if you want to say that he never really topped that album, I think there’s a case to be made for that, as good as individual songs may have been since.

    I think I have noted here before that I by and large prefer Merle Haggard’s Capitol Records output to his MCA/Epic periods, but “I Think I’ll Just Stay Here and Drink” has always been one of my absolute favorites from him. Too Low? Damn right.

    Aside from “Red Neckin’ Love Makin’ Night,” I agree with your assessment of Conway Twitty, Jonathan. And even with that song, it’s the arrangement that bugs me more than anything else. I think my favorite of his songs in that vein, though, was “I’d Love To Lay You Down.”

  5. Oh boy. Actually there are a lot of classics here but “Slow Hand” and “The Chair” are much too high, Brantley Gilbert doesn’t belong here at all, and “Why Me” is too low.

  6. By the way, “City of New Orleans” was first recorded by its composer Steve Goodman, who struggled against leukemia his entire adult life, finally losing his battle in 1984 at the age of 36. Although a folk singer, his 1972 recording shows a strong country feel and the arrangment (although not the tempo) presages Willie’s recording


  7. i only have the Haggard song by Suzy Bogguss on her Lucky cd. Never cared much for Haggard. I’m not against drinking songs. I made up a playlist of my 25 favorite country drinking songs about 10 years ago and if I had to revise it, i still wouldn’t include “I Think I’ll Just Stay Here and Drink”.

    i love “City of New Orleans” but I only have John Denver’s cover. After seeing Paul’s comment about Steve Goodman (sad story), i checked him on “second hand songs” which lists 118 covers for City of N.O. The first 4 recordings follow:

    Title Performer Release date Info
    City of New Orleans Steve Goodman 1970 First recording on March 23, 1970
    First release
    City of New Orleans John Denver November 1971
    City of New Orleans Pete Sayers 1972
    City of New Orleans Arlo Guthrie 1972 More famous than the original

  8. I hadn’t really thought of it before, but I have no idea how to even create a personal Top 50 or Top 100 list. Every time I see a classic song show up that should clearly be much, much higher and that should be in, say, the Top 50 (eg. Coat of Many Colours), there are more and more that show up that could also easily be Top 50.

    As Zack noted for #250, from now on “it’s got to be all killer and no filler.” Every song from now on should be easily identifiable as a great/classic/essential song (every if not every song will be a personal favourite). For example, I like “The Chair” just fine and and it belongs in the Top 250, but it’s far from one of my personal George Strait favourites.

    For this grouping, I mostly agree with the consensus. “What Was I Thinkin'” belongs on the list, but not this high. The Brad Paisley and Brantley Gilbert songs don’t belong at all.

    @ Steve – “if you’re going to create a list of 1000 songs, there MUST be a methodology.” – Agreed! It’s difficult to see what the methodology is (if there is one at all). They seem to be trying too much to appeal to everyone.

    @ Pistolero – I agree completely about the “Killin’ Time” album. No weak songs at all. I don’t believe he ever did top that album, but “No Time to Kill” is his other album that comes closest. I also agree with you re: “Slow Hand” and “I’d Love to Lay You Down” is one of my top Conway songs.

  9. Frank The Tank – In my opinion, Clint’s second album, Put Yourself In My Shoes, was just as good as his debut. I’d also include all of the singles from Killin’ Time on the list, plus most of the ones from that second album, as well, especially “Loving Blind.” His first two records simply represent some of the absolute best of the late 80’s/early 90’s neo-traditional period. As for “A Better Man,” it’s one of the very first country songs I remember really being a fan of, and one that I’d always get excited about hearing on the radio in the back of my parents car. For such a classic debut single that introduced one of the then most successful members of the Class of ’89, it’s definitely too low.

    “Please Help Me I’m Falling” is another great standard that’s shamefully ranked way too low. It’s always been one of my mom’s favorites, as well, and she remembers it being popular on the jukebox at the diner she worked in as a teen. To see this ranked seven spots behind that Brantley Gilbert song is not only an insult, but a big kick in the a** for any longtime country music fan and the genre’s history.

    Dean Dillon is one of my all time favorite songwriters in the genre, and I’ve always loved the melodies in a lot of his songs. The smooth, easygoing style of most of his material really fits George Strait like a glove, “The Chair” being a great example. Even after hearing it so many times and knowing how it all ends, it’s never lost it’s charm for me.

    I put Conway’s “Slow Hand” in the “must be in the mood for early 80’s Urban Cowboy sound to enjoy” category. For me, it belongs since it’s definitely an essential cut from that era, but not this high. Otherwise, I totally agree with Jonathan’s comment.

    Willie’s “City Of New Orleans” has always been such a fun listen for me, though I have to admit that I haven’t heard any of the other versions. I’d say this one is about right.

    I liked “What Was I Thinkin'” when it first came out because it sounded a lot more country compared to what else was new on the radio at the time, and I especially loved the dobro riffs, which reminded me more of early 90’s country. But I eventually got tired of it because well.. you already know…radio and ditties. Still better than a lot of Bentley’s more recent singles, but it’s definitely NOT better than “Please Help Me I’m Falling” and the countless other classics it’s ahead of.

    Paisley’s “She’s Everything” never did a thing for me, pretty much for the very reason Kevin states: it’s just too listy, especially for what’s supposed to be an emotional love song. Yet another one of his songs I just never got what the fuss was all about. “We Danced” is still one of his best songs in the romantic category, imo. Even the recent “My Miracle” I felt did a better job than this one.

    Believe it or not, I’ve listened to that Brantley Gilbert album, and there are actually some decent cuts on there. This was definitely NOT one of them.

  10. Brantley doesnt belong on this list at all…OMG 241?!

    Dierks is a little too High, and the Brad song is several hundred spots too high, but it probably does belong somewhere.

    Love me some Merle and Conway.

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