A Country Music Conversation: Sirius Top 1000 Country Songs of All Time, #170-#161

Two consecutive CMA Single of the Year winners from the nineties are among this set of ten.



Zac Brown Band, “Toes”

#1 | 2009

ZK: I generally enjoy their beach-inspired material – mostly because they offer more than just pure escapism, like here – but that they include at least one song like it on every album of theirs is telling of how much they’ve tried to recapture the magic of the original. I wouldn’t have it anywhere near here, though. Too High 

KJC: Their best beach-flavored song, and a highlight of this country music subgenre overall. But it’s still Too High

JK: I like “Toes” better on principle than literally any one of Kenny Chesney’s hundred thousand Buffett-country hits because Zac Brown can actually sing on key, but I wouldn’t have ranked this higher than #900. Too High



Johnny Horton, “North to Alaska”

#1 | 1960

KJC:  Ah, Johnny Horton.  My father spun his Greatest Hits in the car more times than I can count.  As great as “The Battle of New Orleans,” “Honky Tonk Man,” “Sink the Bismarck,” and “When it’s Springtime in Alaska” are, this is his very best single, and it’s ranked About Right

JK: As songs of this type go, it’s no “El Paso,” but what else is? The narrative is structured so well and Horton is such a terrific singer that I don’t even mind that it is perhaps so specific in its details, bound to a just awful John Wayne movie, that it lacks a real point of entry. About Right

ZK: The short-lived saga song trend is one of my favorites in country music history, mostly because the genre that prided itself on storytelling got super creative with its topics. Case in point. About Right 



Jo Dee Messina, “Heads Carolina, Tails California”

#2 | 1996

JK: Messina never bettered her opening salvo. The devil-may-care narrative is perfectly matched to the optimism of what would become central to her artistic persona, and the song itself allows her to deliver an exuberant performance that doesn’t exceed her technical limitations. There are other hits of this era wildly misranked in comparison– “Strawberry Wine” waves from way, way too far back– and, as great a single as this is, it’s still Too High.

ZK: Going to have to side with Jonathan here, even though I do agree with Kevin that she’s had other great ones. There’s a natural urgency to this escapism that worked for Messina’s delivery. But, you know, we’re in the 100s, y’all, so … Too High 

KJC: I love this record, too, but I will disagree with it being her best effort.  Her pair of Phil Vassar-penned hits (“Bye Bye” and “I’m Alright”) were a perfect match for her particular cadence; she has to stretch out the melody a bit too much in the verses here, and it doesn’t sound as natural as those other two hits.  Still a winner, though!  Too High



Kenny Rogers, “Lucille”

#1 | 1977

ZK: Inconsistent as his overall discography is, Kenny Rogers at his best is arguably country music at its best. I love, love, love this and I still would rank it just behind “Ruby … ” and The Gambler.” But for a good representation of his country side, this is a placement that feels Too Low.

KJC: I’d have this as his highest-ranked record, with no shade intended to the other big hits that outrank it.  Too Low

JK: “You picked a fine time to leave me, Lucille,” is one of the densest, most emotionally fraught lines in the genre’s history, delivered perfectly by Rogers, and what in the absolute fuck with this ranking. Shameful. It’s a top 20 record. Too Low



Chris Cagle, “What Kinda Gone”

#3 | 2007

KJC: “Laredo” at #919 was just fine as an acknowledgment of Cagle’s career.  In my version of this list, there would be a ton of B- and C-list country stars with one song only, and in the bottom 200.   This entry is gratuitous and unnecessary.  So Wrong (Doesn’t Belong)

JK: Can we just start responding to things with images and GIFs? I have a whole bunch of Effing Birds memes just ready to capture my feelings here. So Wrong (Doesn’t Belong)

ZK: I mean, it was a career comeback record, sure, but did we really need more than one Chris Cagle single here? And this high?!? So Wrong (Doesn’t Belong)



John Michael Montgomery, “I Swear”

#1 | 1993

JK: I mean, it has to be on here on commercial impact, but there’s just absolutely no way JMM should be anywhere in the top 200 of a list like this. Too High

ZK: “I swear” I say the same thing about Montgomery every time he pop ups, so as far as overblown, sappy wedding songs go … yeah, fine. Whatever. I don’t want to see any others after this, though. Too High 

KJC: This is the best of his romantic ballads, and its quality and historical impact make this ranking About Right.



Loretta Lynn, “Don’t Come Home a Drinkin’ (With Lovin’ On Your Mind)”

#1 | 1966

ZK: It’s right up there with “The Pill” as one of Lynn’s most important records, which means it’s far Too Low in the context of this list. What else is new, am I right? 

KJC: I agree with Jonathan that this should be higher; I’d swap it with the Twitty duet at #87 because the Twitty duet at #87 somehow isn’t “After the Fire is Gone.”  Too Low

JK: Impossible to overstate how radical a statement this was for a woman in the country music space– in any space– at the time. Or how radical a statement like this would be on country radio in 2021, given the way the genre still holds women in contempt. It’s one of my favorite of Loretta’s vocal performances, too. Far Too Low



Alan Jackson, “Chattahoochee”

#1 | 1993

KJC:  Remember when this was Alan Jackson’s signature hit?  Over time, other songs have stood the test of time better. But this was a Single and Song of the Year winner that had a massive impact and firmly established the playful persona that would be present in so many future hits.  About Right

JK: Look, it’s catchy AF, and what I love best about it is Jackson’s command of the natural meter of the language– the rhythm of the line, “So I settled for a burger and a grape snowcone / I dropped her off early, but I didn’t go home,” is just perfect. But there’s no way I’d have it ranked this highly overall or even in the context of Jackson’s hits. Too High

ZK: It’s not Jackson’s fault, but it feels wrong to see a summer song ahead of the last selection. But … this is catchy, surprisingly more mature and nuanced than it’s ever gotten credit for, and benefits from Jackson’s affable charm. Dang it, I’m doing it. About Right 



Willie Nelson, “If You’ve Got the Money I’ve Got the Time”

#1 | 1976

JK: I genuinely don’t remember if we’ve already covered the Lefty Frizzell version of this classic song. If so, WTF at Willie’s good but clearly lesser rendition being ranked higher. If not, we’d better see it eventually. Too High

ZK: If you, Sirius, have got the wack-ass methodology for the songs on this list, I’ve got the rankings. Too High

KJC:  We saw Lefty already at #436.  Swap them and call it a day.  Too High



Thompson Square, “Are You Gonna Kiss Me or Not”

#1 | 2010

ZK: Kevin already made a good point about starting off his own list with C and B-list acts, so considering that literally no one remembers Thompson Square a decade later, slot it in the 900s and call it a day. Too High 

KJC: Again, if I made this list, would I include it or not? I would.  But there is no way on God’s green earth that it would be anywhere near #161.  Too High

JK: A massive hit, sure, but an impactful or important one? Absolutely not. Slot this one in the first 100, but ranking it ahead of “Maybe It Was Memphis” is just heresy. Far Too High


Previous: #180-#171 | Next: #160-#151



  1. I will say I have always had a special place for “Are You Gonna Kiss Me Or Not” because it was such a cute song and I love how simple the song is. That and I have always wished Thompson Square connected more than they did as they deserved better imo.

    I will say I do think while maybe not Top 200, I think the song rightfully deserved to be at least Top 500 and I do think it has had an impact. This song was everywhere from 2011 onwards, and still to this day and I have heard it on the radio, stores, heck even school dances of mine played this song. Not to mention it’s a wedding staple.

  2. I pretty much agree with the consensus/majority comments on this set of songs. One thing noted previously is that Lefty barely shows up at all. If I recall correctly, a total of three songs, two of the in the mid-to-late 900s

  3. Re. “Toes”: I know that these “beach anthems” are a staple of country, and have been for a couple of decades now. But I think it’d be better to leave them to Mr. Buffett, or, in another context, to Brian Wilson.

    Re. “Lucille”: There is a certain irony in knowing that Kenny almost didn’t cut what would be his first big solo hit because it wasn’t upbeat enough, but Waylon Jennings (a.k.a. A Man Called Hoss) told him, “Take my advice, buddy, cut it.” Needless to say, this wasn’t the worst advice Mr. Rogers got; it got up to #5 on the Hot 100, not to mention #1 C&W, of course.

    Re. “North To Alaska”: Well it wasn’t exactly one of John Wayne’s best movies, this “North Western” (LOL), but as a song, thanks to J.H.’s delivery, it kind of hit the spot as one of the great story songs of that era (1960). Sadly, he passed away right as that song was becoming a bit C&W/pop crossover hit.

  4. JMM……..my eyes bleed. Pure saccharine. And you guys think Deeper than the Holler is too syrupy? Come on, man. Again, his ballads are everything wrong with country music.

    “995 Lefty Frizzell I Never Go Around Mirrors” Excuse me while I scream. Unbelievable. Maybe the 9 key stuck when they tried to make it top 100?

    I’m really not into Johnny Horton. I think most everything he does amounts to novelty songs. Nice voice, but hardly first rate.

    Zac Brown and Thompson Square…ZZZZZZZZZZZZZzzzzzzzzzz

  5. Erik North- I too would’ve preferred leaving the beach anthems to Jimmy Buffett instead of having Kenny Chesney, Zac Brown, Jake Owen, and others copying his style for the last two decades. I guess “Toes” is not a bad song in general, but these kind of songs have never been my thing personally, and I grew tired of it very quickly. I miss the 90’s when it was still seemingly more common to hear songs about cowboys than songs about the beach in country music. That said, I don’t mind Jimmy Buffett or the Beach Boys, and I’ve been known to enjoy their music from time to time.

    I really love “Heads Carolina, Tails California,” and I consider it to be one of the most perfect road trip/windows rolled down kind of songs. You just can’t help but be in a good mood and feel like going for a drive whenever you hear it. However, I have to side with Kevin here in that I would rank most of the I’m Alright singles higher than this one. Besides the two songs he mentioned, I also really love both “Stand Beside Me” and “Because You Love Me.”

    I have my step dad to thank for introducing me to Johnny Horton when he got me a greatest hits cd of his for Christmas in 1992. This and “The Battle Of New Orleans” have always been favorites, but on that cd, I also really enjoyed “Comanche The Brave Horse” and the beautiful “Whispering Pines.” The latter song showed that besides story songs, he could also do mournful ballads just as well.

    “Chattahoochie” probably deserves its high ranking based on its commercial success alone, and there’s no doubt it’s catchy and has way more charm and substance than most modern day summer anthems. Still, it’s never been one of my personal favorites of his, and it’s been a bit frustrating that many of his even better songs have been overlooked/forgotten while this one continued to get overplayed. That said, it would actually be refreshing to hear it on the radio these days.

    “I Swear” is not my top favorite of JMM’s love songs, but I still really like it, and this ranking is probably about right due to its monster success.

    “Lucille” definitely needs to be higher.

    Never got what the big deal was for either the Chris Cagle or Thompson Square songs. Easily two of the most overrated singles from the last 10-15 years, imo. If this list needed another song to represent Chris Cagle (I liked “Laredo”) I would’ve gone with “I Breathe In, I Breathe Out.”

  6. “Lucille” and “I swear” are noth too low, although the latter not by much.

    Many of these dont even belong in the list at all.

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