A Country Music Conversation: Sirius Top 1000 Country Songs of All Time, #340-#331

As we inch closer to the top, the ratio of legends to newer artists is slightly more narrow.  Six Hall of Fame inductees rub elbows here with established superstars, with only one relatively new act in the mix.



Kenny Rogers & The First Edition, “Ruby, Don’t Take Your Love to Town”

#39 | 1969

ZK: An all-time favorite of mine from Rogers. Kevin nails why with his own description, but it’s definitely a track I kept in mind last year, when Rogers passed away. Far Too Low

KJC: Mel Tillis penned this tense and foreboding tale of a Vietnam vet watching helplessly while his lady gets dolled up to go cheat on him.  It’s cinematic in scope and a career-defining performance from a future superstar.   Way Too Low

JK: One of the genre’s most perfect recordings. Rogers’ performance is a masterclass of emotional range, and the song itself is Tillis’ finest. A top 50 entry, to be sure. Too Low



Lonestar, “I’m Already There”

#1 |2001

KJC:  I’m sure that this song has brought a lot of comfort to families separated from each other.  This takes me back to the post-9/11 days and makes me wince far less than the jingoistic anthems of that day. Too High

JK: Dammit, Kevin, I was all set to call this cloying, maudlin pap, and now you’ve made me feel at least a tiny bit guilty about it… So Wrong (Doesn’t Belong)

ZK: Had honestly never considered the post-9/11 effects this could have had until Kevin mentioned it. It doesn’t necessarily make me love this, but yeah, I’d definitely include it now. Not sure we need any other Lonestar singles not named “No News,” though. Too High 



George Strait, “Give it Away”

#1 | 2006

JK: Weirdly enough, it has always been the production on this one that I like best about it– certainly more than the repetitive songwriting. Why it ended up being such an impactful single, I have no idea. Far Too High

ZK: I think I’ve always liked the, ahem, strait-laced delivery, in which this relationship is utterly dead and both parties couldn’t care less about it. A little sad, a little humorous, and all in good fun. I’d include it, I guess. Too High 

KJC: I am a huge George Strait fan, and I’ve never understood the appeal of this particular song.  But it won Single of the Year, so I guess it was significant? (Side note: “How ‘Bout Them Cowgirls” is an underrated gem from the same album.) Too High



Garth Brooks, “The Beaches of Cheyenne”

#1 | 1996

ZK: An obscure story song that I’ve always appreciated for its framing, even if the execution falters a bit. Brooks could emote well when the time called for it, and you couldn’t help but feel sorry for both parties here. Too High 

KJC: This was described as being “geographically challenged” in a contemporary review of Fresh Horses and that always stuck with me.  I just can’t figure out what she’s doing on the beaches of Cheyenne if she isn’t the one who died there.  So Wrong (Doesn’t Belong)

JK: Aims for profundity and mystery and misses, badly. It’s like listening to Garth try to emote his way through Keith Morrison’s narration on a particularly dull Dateline. An easy Garth entry to cut. So Wrong (Doesn’t Belong)



Don Williams, “Some Broken Hearts Never Mend”

#1 | 1977

KJC:  Williams was the master at the understated delivery of devastating material.  This is one of his finest moments, and I will not quibble with its ranking.  About Right

JK: I mean, yes, this one is correct in an absolute sense, but I still think Williams is represented poorly on this list. About Right

ZK: A big hit that feels relatively forgotten in conversations and debates of Williams’ best tunes, and I’m not sure this is quite on that level – it’s a bit too tonally chipper to sell itself well – but I’m not, like, mad about it being here. Too High



Cole Swindell, “Ain’t Worth the Whiskey”

#3 | 2014

JK: Dude literally just performed a maskless indoor concert because of course he did, and I cannot imagine the collective thought process among the people in attendance who just couldn’t pass up the opportunity to spread Covid just to hear Luke Bryan’s utterly talentless merch guy try to sing this shitty song without Autotune. So Wrong (Doesn’t Belong)

ZK: I just debated whether a really good Don Williams tune belonged in the upper half of this list. Spent a lot of good time with it, I did. I’m trying to really think to myself as I do this, “what would a proper list of this magnitude look like?” And then I move on to see this and I’m just like “oh fuuuuucccckkk you, Sirius.” So Wrong (Doesn’t Belong)

KJC:  Ain’t worth the placement, either.  So Wrong (Doesn’t Belong)



Alan Jackson, “Where I Come From”

#1 | 2001

ZK: Ah, yes, the song that mentions dropping a “load of salsa.” For a performer who excels at simplicity, this is just stupid. So Wrong (Doesn’t Belong)

KJC: This is annoying.  For the second time in as many of his entries on this list, I have to say that an Alan Jackson song has no business on this list, let alone being given a ranking so high. This is corny and dull.  So Wrong (Doesn’t Belong)

JK: Suzy Bogguss isn’t on this list at all, yet here we are with this. I suppose I should be glad it’s not “www.memory” or “I Still Like Bologna,” but whatever. So Wrong (Doesn’t Belong)



Tim McGraw, “Please Remember Me”

#1 | 1999

KJC:  With a riveting harmony by Patty Loveless to lift up the chorus, Tim McGraw delivered his finest single to date with this Rodney Crowell cover.  He’s never been a powerhouse vocalist, but he can emote, and knocks it out of the park when he’s given a great song to work with. I’d honestly bump this one up at least 150 spots. Too Low

JK: The song and production far outpace his technical ability, but McGraw does emote like his life depended on it. I’d keep it here somewhere based on impact, in the same way I’d keep, say, “My Heart Will Go On” on a comparable list of pop singles. Too High

ZK: I definitely think Tim McGraw is a strong emotive interpreter, but he’s at his best when the backdrop is a bit more subtle and/or builds the dramatic swell naturally (“Live Like You Were Dying,” for instance). This, to me, has always been just … loud for the sake of being loud. So Wrong (This Song)



Statler Brothers, “I’ll Go to My Grave Loving You”

#3 | 1975

JK: I am stunned they remembered this one. This makes two entries in this batch that are just egregiously Too Low.

ZK: They could be singing about dead puppies and I’d still enjoy the harmonies. About Right 

KJC: And then I’d bump this one up right after.  The goosebump-inducing harmonies and timeless sentiment make this an all-time classic.  Too Low



Sugarland, “Baby Girl”

#2 | 2004

ZK: Their debut album really is just stellar. And this is the sort of single choice that works best as its first. Self-aware enough to know success isn’t guaranteed, but optimistic enough to have fun with the ride. Truthfully, I could only see me putting “Stay” this high, but this should definitely be here. Too High 

KJC: It earned its placement on this list with the line, “Girl, you’ll remember what your knees are for.”  A reminder of how great Sugarland was out of the gate, back when they were a trio.  Still a little bit Too High, though. 

JK: I love Jennifer Nettles’ delivery on this breakthrough hit: There’s such empathy and joy in her performance, all the way through the over-the-top melisma at the end. It’s over-ranked here by a pretty big margin, but it’s a deserving entry. Too High

Previous: #350-#341 | Next:  #330-#321


  1. Re. “Ruby”: I think Mel Tillis wrote it about a paralyzed veteran of the Korean conflict; but because of the time it came out, it was assumed that the subject was a Vietnam veteran. Also, its low country chart placement (#39), doesn’t quite tell the whole story, as it got up to #6 on the Hot 100.

    Re. “Please Remember Me”: Tim McGraw’s isn’t a bad version, but (full disclosure of my bias here) I prefer Aaron Neville’s take on it, with Linda Ronstadt’s duet vocal.

    Re. “Ain’t Worth The Whiskey”: The epitome of the Bromeister genre, as I like to call it, with a gratuitously thrown-in shout-out to our troops “protectin’ our asses overseas”. Sick!

  2. I found the wildly varying opinions on “Please Remember Me” interesting – I’m in the ‘So Wrong (Doesn’t Belong)’ camp.

    Ruby’s #39 chart placing may have surprised some of the younger readers, but the song was already very familiar to country audiences – Johnny Darrell had a top ten country single in 1967, and it appears on a half dozen albums in my collection from around 1967, including the Statler Brothers, Bobby Bare, Waylon Jennings and Mel Tillis. Jennings was the first to record the song but I still prefer the Johnny Darrell version.

    “I’ll Go To My Grave Loving You” went to #1 in a lot of markets and both Cash Box and Record World had it reach #1. The original Statler Brothers with Lew Dewitt as the high tenor had a very distinctive sound that was impossible to imitate. Jimmy Fortune, who replaced DeWitt when Crohn’s Disease forced DeWitt to retire, was an excellent singer but still something was lost from the Statler sound

    The Alan Jackson entry is a dud. On the other hand, it is hard to come up with a Don Williams recording that I do not like. This one is positioned about right

  3. In an interview Alan Jackson admitted he was pitched “Chicken Fried” but turned it down because he had just recorded that “cornbread and chicken” song and thought it was too soon. It’s a dud like Paul said. I’ve always found “www.memory” to be amusing but the real winner from that album is the underrated title track.

    I’ve always loved Tim McGraw’s version of “Please Remember Me” probably because it’s the first version of that song I ever heard. Another great lyric from Rodney Crowell.

    “Baby Girl” is the perfect example of a distinctive and memorable debut record. As for Don Williams, I don’t think he ever misstepped once in his career. Just one great tastefully produced song after another.

  4. I do think Cole Swindell is at least marginally talented and gets more hate for his music than he deserves but “Ain’t Worth The Whiskey” is pretty boring

  5. I got through 24 seconds of Sugarland before having to stop it. Man, is it boring. I continue to not like anything by Tim McGraw. Ugh. A country version of the prototypical local lounge singer. Some Broken Hearts is not Don Williams’ best. I disagree with the panel and love Give It Away. And I’m far from the biggest George Strait fan in the world. I’ll Go to My Grave is an easy top 100, maybe 50, and is by miles the best of this group.

    A thought for the regular posters. When we get to say, #250, 100, I don’t know, sometime before your whole list is gone, sometime, tell the world what your top 10 is.

  6. I should at least give a mention to Ruby. I like it, although unlike the panel, I think this seems about right. A bit faux dramatic for my tastes.

  7. That any criticism of Brooks’ song as being “geographically challenged” still persists drives me nuts. I feel as crazy as the woman in the song having to deconstruct the lyrics, but I get the sense this is one of those songs that has been misheard too often for far too long. So here I go!

    For starters, the Beaches of Cheyenne is an imagined, parabolic place. You can get out your map books but they really won’t help find what we are looking for. It’s a song about regret and unrequited love.

    A grief-crazed phantom walks the California shoreline, forever separated from her lover in Cheyenne, Wyoming. She is haunted by her final words to her rodeo man. He dies in the Wyoming sand while she is left to walk the California sand alone with her remorse and anguish.

    The California beaches of her dreams are as close as she can get to the blood-stained rodeo sands of Cheyenne to a mind hysterical with heartbreak and despair. An ocean of regret keeps her from her cowboy.

    Unable to walk the same sand as her lover, to say she is sorry for the words she spoke in anger, she is lost to that ocean of regret. She kills herself. To this day, her desolate ghost still leaves footprints in that same California shoreline she wishes were somehow magically Cheyenne sand so should could be reunited with her man.

    The Beaches of Cheyenne” exist only in our imagination and what the metaphor suggests: an impossible to conceive, insurmountable distance. Death.

    Brooks’ song is smarter than it get’s credit for. Its more about the dreams of where their love once lived (California) than the geography of where their loved died (Cheyenne).

    I am embarrassed in advance if I just explained why 2+2=4.

  8. Agree completely with the comments on AJ’s “Where I Come From.” When it first came out, it was good for a chuckle or two, but it’s easily one of his most overrated and overplayed singles. As a big Alan Jackson fan, there have been quite a few selections of his on this list that have me scratching my head, while a good number of his much superior singles have seemingly been forgotten and overlooked. I’m with Jon all the way with the title track being the best single from that album. There are also many terrific album cuts that never made it to radio like “I Still Love You,” “The Thrill Is Back,” “Life Or Love,” and “Maybe I Should Stay Here”.

    Thank you. Thank you. Thank you! For the longest time, I thought I was the only one who just didn’t quite get the popularity with “Give It Away.” I’m pretty much with Jonathan in that I’ve always liked the instrumentation and production, but just couldn’t get on board with the repetitive lyrics, and the spoken parts got old pretty quick for me. Strait has loads of other singles much more deserving of a spot than this one, imo.

    Have to disagree with “The Beaches Of Cheyanne.” This has always been one of my favorite singles from Garth, and I absolutely love the fiddle and steel playing throughout. There’s no way a song with such a tragic story like this one could make it on the radio today. I also really miss hearing songs about rodeo cowboys on the radio, as well. I must admit that it took me years to completely figure out what was going on in the song (I was only ten when it came out, after all), and I think Peter Saros did a great job in explaining the lyrics.

    I’ve always really enjoyed “Some Broken Hearts Never Mend,” especially with that lovely steel solo in the end. I agree completely with Kevin’s comment, and his first sentence describes one of the reasons why I’ve always been a big fan of Don’s music. I remember this song still being a popular recurrent on one of our stations as recent as the late 90’s.

    When I first heard Tim McGraw’s “Please Remember Me” in the spring of 1999, I remember noticing how it was his most contemporary sounding single yet, and it was probably the most pop sounding song on the radio at the time besides Shania’s singles. It wouldn’t be too long, though, that I would grow to love the song’s beautiful melody and McGraw’s emotional performance, and now it’s one of my all time favorites of his. If only more mainstream contemporary country could still be this good.

    I was also never the biggest fan of “I’m Already There,” and while I do like it a little better now than I did then (perhaps only because it sounds better now compared to what we’ve been dealing with in mainstream country the last ten years), it’s still not one of my favorites by Lonestar. Kevin does bring up a good point on how many people it’s likely affected after 9/11, though, and for that reason I’m ok with this having a spot on the list, but much lower.

    The Statlers song is definitely a pleasant surprise to see here. I’ve been enjoying much their music lately, and I’ve discovered plenty of underrated/forgotten singles of theirs and been adding them to my playlists. Even their latter day albums from the early 90’s when they were no longer being played on the radio have some really good cuts on them. My all time favorite, though, is probably “More Than A Name On A Wall.” Can never listen to that one and not have dry eyes afterwards. RIP to bass singer, (and also a man with a great sense of humor, from what I’ve seen) Harold Reid.

  9. Favorite songs in this group:

    Kenny Rogers & First Edition’s “Ruby Don’t Take Your Love to Town”

    Lonestar’s “I’m Already There”

    Sugarland’s “Baby Girl”

    Don Williams’ “Some Broken Hearts Never Mend”

    McGraw’s “Please Remember Me”

    Statler Brothers “I’ll Go to My Grave Loving You”

  10. Garth is polarizing. I loved him when he first came out. Then I choked back throats full of vomit by the late 90s. Everything was an event. AN EVENT!!!!!!!

    “Beaches of Cheyenne” is better than I remembered. It’s a very good song. Garth’s performing often overwhelmed his very good songwriting.

  11. I like all these songs, except for Where I Come from. Most of them are well placed too. Although I wouldnt argue if Some Broken Hearts Never Mend” and “Ruby” were both 50-100 spots higher. And Please Remember Me is a top 200 song

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