A Country Music Conversation: Sirius Top 1000 Country Songs of All Time, #320-#311

A stretch of the list that has caused enough saltiness on my part to put Morton’s out of business. – KJC


Mark Chesnutt, “It’s a Little Too Late”

#1 | 1996

JK: So, I fully co-sign Kevin’s list below– and, of those, “Brother Jukebox” or “I’ll Think of Somethin’” would be my pick to replace this one– but I will say this is the only one of Chesnutt’s hits that I’ve heard get any recurrent play since about 2010. So Wrong (This Song)

ZK: Another fun ’90s cut that doesn’t belong anywhere near the top half, even though I’d have a few Chesnutt songs here. They really thought this was his best song and that “Too Cold at Home” only barely belonged here? Not All That Wrong, Really – Just (Doesn’t Belong)

KJC: The most notable thing about this single? That a pre-stardom Lee Ann Womack appears in the video.  This is their highest-ranking Chesnutt single, and only “Too Cold at Home,” their lowest-ranking, warranted inclusion.  Okay, fine. “Bubba Shot the Jukebox,” too.  Here’s an incomplete list of some of the Chesnutt songs that should’ve been on here instead: “Brother Jukebox,” “Old Flames Have New Names,” “I’ll Think of Something,” “It Sure is Monday,” “Almost Goodbye,” “I Just Wanted You to Know,”  “Trouble,” “It Wouldn’t Hurt to Have Wings,” “Wrong Place, Wrong Time,” “Thank God For Believers,” “It’s Not Over,” “The Lord Loves the Drinkin’ Man,” “Hard Secret to Keep,”…So Wrong (This Song)



Willie Nelson, “Georgia On My Mind”

#1 | 1978

ZK: I suppose it wouldn’t have technically counted – I say, not knowing what the hell the criteria was for this list – but I wouldn’t have minded seeing the Ray Charles version here. Hell, I would have preferred it. But I like how lonesome Nelson’s version is too, though. Fantastic song. Too Low

KJC: A beautiful rendition of a song best immortalized by Ray Charles, as Zack notes above.  Too High

JK: I’d have included both Nelson’s and Charles’ versions of this song on a list like this. I’d have Charles’ ranked hereabouts and Willie’s back just a bit. Too High



Jason Aldean, “Amarillo Sky”

#4 | 2006

KJC:  Back when this was released, it was an encouraging sign of promise that not only wasn’t realized, but was completely squandered.  I mean, artistically, at least.  Dude did end up Entertainer of the Decade.  Too High

JK: Probably his best single, and one I’d describe as competent rather than legitimately good, and I’d have it listed back in the first 100 entries or so on principle. Too High

ZK: Back when he wasn’t just the worst, and back when he actually emoted well instead of doing that weird, oddly moody thing he does now that’s not nearly as dark or convincing as he thinks it is. If we have to have a few of his cuts, this and “The Truth” belong. That’s good enough. Too High 



Shania Twain, “You’re Still the One”

#1 | 1998

JK: Her official crossover to the pop market, though one certainly doesn’t move the number of copies The Woman In Me had already sold before this hit without having already courted that demo. It has to be here on impact, but I’d have it ranked well below “Whose Bed Have Your Boots Been Under” and “No One Needs to Know,” both of which we’ve already covered. Too High

ZK: Well, it aged like milk. Still, it’s a rare moment in Twain’s discography that emphasized her underrated vocals. Put it several hundred spots lower and call it a day, I guess. Too High 

KJC:  For many years, No Fences was the top-selling country album of all time. All four of its singles are on this list, and three of them are higher than this, with one topping the list overall.

Come On Over not only supplanted No Fences as the top-selling country album of all time, but it is also the top-selling album ever by a female artist of any genre, both domestically and worldwide.

Twelve singles pulled from it in total.  Eleven sent to domestic country radio.  Eight of them top were top ten hits.  Three went to #1.

Yet the highest representation of this landmark album is “You’re Still the One.”  Let me first dispense with the idea that historical significance is the only reason I’d rank this higher. As an actual record, it is flawless, the ultimate proof of concept for “Mutt” Lange’s approach of making records with a pop structure and country instrumentation.  If this album had sold less than The Woman in Me, I’d still be clamoring for this particular record to be much higher.

But I can’t think of any example – not even “Jolene” – that better demonstrates this list’s dismissal of female artists than the biggest country album of all time being only represented with three tracks, with the highest being #317.  Two of the most impactful hits from the album – “Man! I Feel Like a Woman!” and “From This Moment On” – aren’t on the list at all, nor is “Love Gets Me Every Time,” which spent five weeks at #1.

The pop crossover argument doesn’t fly with me.  More than half of the top twenty on this list were crossover hits, and there’s a top five entry by another female crossover star that is only that high because of a massive pop cover cementing its legacy.  Notably, of course, most of those crossover hits toward the top are by male artists. 

This ranking is a flat-out insult, and representative of the casual dismissal of legendary female artists that Sirius has demonstrated along the way, with C-list bro country acts getting more entries than the most significant female artists of all time.  

So, yeah.  Too Low



Rodney Atkins, “Watching You”

#1 | 2006

ZK: Poor Rodney Atkins. He’s like the Nickelback of country music – his material isn’t as bad as you remember, but nightmares from radio overplay of yesterday say otherwise. It’s twee in a way where I wouldn’t probably have it on my own list, but cute enough to not get me that bothered about it. Still, we can probably stick with “If You’re Going Through Hell” and leave it at that. So Wrong (Doesn’t Belong)

KJC: The sheer earnestness of this song, combined with the chicken nuggets reference and the contrast between swearing and praying, has always endeared it to me.  I prefer it over the rest of the singles from that one big album that he had.  But I’d still say it’s way Too High. 

JK: I definitely appreciate the comparison, but I’d still argue Nickelback was that bad, though. But I fully agree that “If You’re Going Through Hell” is plenty for Atkins’ representation. So Wrong (Doesn’t Belong)



Keith Whitley, “Don’t Close Your Eyes”

#1 | 1988

KJC:   Whitley is under-represented on the list, and this should be a bit higher.  But the real travesty for me remains “I’m No Stranger to the Rain” being in the 700s.  But, yeah. Too Low

JK: Probably my favorite vocal performance from Whitley, ranked shamefully Too Low.

ZK: Three singles from a short-lived career and it still doesn’t feel like enough. Couldn’t they have gotten the placements right, at least? Too Low 



Waylon Jennings, “I’ve Always Been Crazy”

#1 | 1978

JK: It’s not necessarily his best single by any stretch, but it’s one of my favorite Jennings hits. That said, I’d drop it back a good 200 or 300 spots. Too High

ZK: Always loved that hook. Not an essential Jennings cut and a little by-the-numbers for the era, but I like it. I’d easily replace it with “Dreaming My Dreams with You,” though, and bump that one several slots higher. So Wrong (This Song)

KJC:  I love the Carlene Carter cover of this Jennings song that is mid-level Waylon.  Too High



Kenny Chesney, “Save it For a Rainy Day”

#4 | 2015

ZK: Even on a rainy day, I’m probably going with Gary Allan’s “Songs About Rain.” So Wrong (Doesn’t Belong)

KJC: This list’s rainy day fund has way too much Chesney in it.  So Wrong (Doesn’t Belong)

JK: Just completely forgettable, and he has like seventy more entries on this list than he should. I’m so tired of seeing his name pop up, especially since we already covered the only songs of his worth a damn ages ago. So Wrong (Doesn’t Belong)



Johnny Cash, “Don’t Take Your Guns to Town”

#1 | 1959

KJC:  An excellent story song that is worthy of inclusion, but a bit Too High

JK: One of his songs that, for whatever reason, rarely gets talked about as being among his best. I’ve always dug it, and its inclusion at all is a pleasant surprise. Still, I think this is a bit Too High.

ZK: Mama tried to raise him better, which leaves only Bill to blame for being a nincompoop. I love this seemingly underrated Cash tune. About Right 



Kenny Rogers and Sheena Easton, “We’ve Got Tonight”

#1 | 1983

JK: Look, I’ll go to bat for “Strut” and “Morning Train (9 to 5)” as much as any other 80s kid ought to, but Sheena Easton having an entry on this list when Suzy Bogguss and Lari White and so many others don’t? And ranked ahead of Rogers’ own “Ruby, Don’t Take Your Love To Town?” I cannot with you today, Sirius XM. Too High

ZK: Campy as hell, but earnest as hell, too. Overblown, sugary goodness of a cover from my least favorite time period in country music (next to the early ’60s) that I wouldn’t have ever thought to put here, but might now have in the lower tier if I was making my own list. How did they make this work?!? Too High

KJC: Hey, a Bob Seger cover with a British reality show winner that made better music with Prince than with Kenny Rogers.  So Wrong (Doesn’t Belong)


Previous: #330-#321 | Next:  #310-#301



  1. They should have done better on Mark Chesnutt – I like the song but it is not one of the 1000 best of all time. Ditto Waylon’ “I’ve Always Been Crazy” and Rodney Akins’ “Watching You”

    “Georgia On My Mind” is a song many have done well. My favorite version is by the writer Hoagie Carmichael with Bix Beiderbecke on trumpet, then the Ray Charles version. This is such a great song that some version of the song should be here, and I am okay with Willie Nelson’s being the one (I think it is placed about right)

    “Amarillo Sky” is the only Jason Aldean single I even halfway like, but I don’t think it belongs on this list. Ditto for Kenny Chesney (although there are songs of his that I do like).

    “Still The One” is probably my favorite Shania Twain song and I think it is placed correctly.

    There is nothing country about “We’ve Got Tonight”, at best a mediocre pop ballad. On the other hand, the list simply cannot have too much Keith Whitley – I can think of several more that should have made this list.

  2. Most frequently played Chesnutt song is “Too Cold at Home” (even though he mentions the Dodgers instead of my Yankees) followed by “When You Love Her Like Crazy”.
    I like Amarillo Sky
    When You Say Nothing at All
    Morning Train

    Never liked Shania:

    August 31, 2009 at 9:38 am

    In addition to being beautiful Shania could be a regular Mother Theresa for all I know. I just can’t listen to her. Her voice sounds so whiny to me. I may be the only country music fan who owns 7 Lisa Brokop cds and nary a Twain. Saw Lisa at the Bluebird Cafe in January accompanied only by her guitar and she was great. A Canadian like Twain, she has never had a top 40 hit in the U.S. but I love her music.

  3. I still enjoy the video for “It’s A Little Too Late.” Kind of along the lines of Blackhawk’s “Goodbye Says It All.”

    I had NO idea Lee Ann Womack is in the video! So cool. Has me thinking about other pre-stardom country singers who were in music videos:

    Keith Urban in Alan Jackson’s “Mercury Blues”
    Chris Young in Reba’s “I’ll Be”

    Just curious if anyone knows of any more?

  4. Agreed with the anti-Shania crowd. Despite the attitude and female empowerment and all, I get that, the voice is simply forgettable. Meanwhile, no Suzy Bogguss? And no “A Broken Wing”? One of my Top 10.

    “Brother Jukebox” is far better than It’s a Little Too Late”.

    For someone so into classic country, I remain lukewarm about Keith Whitley. I don’t get what the fuss is all about.

  5. Re. “You’re Still The One”: Although I’ve never really been a fan of Shania’s (not because her voice is bad [it really isn’t, IMHO], but because some of her material is lyrically downright silly), I think this is a good representation of her approach to late 1990’s pop/country. It’s not off-the-chart great like Trisha Yearwood (or her spiritual role model Linda Ronstadt), but then it’s never easy to get to that level.

    Re. “We’ve Got Tonight”: I always preferred Bob Seger’s original 1978 recording of this. And to be honest, I have never cared for Sheena Easton’s voice here, it’s rather (okay, shoot me for saying this) whiny.

    Re. “Don’t Take Your Guns To Town”: True, it’s not exactly one of The Man In Black’s better known songs or recordings. In the final analysis, however, it is still one of the reasons why he was one of the great ambassadors for country music, especially for those who, but for him, might not have been caught dead listening to it.

  6. I am fully on board with almost any of the Chesnutt songs Kevin mentioned being on this list in place of “It’s A Little Too Late.” If I had to pick one to replace it, it’d be “I’ll Think of Something,” with “I Just Wanted You to Know” running a real close second. Also, does anyone besides me remember his excellent cover of John Anderson’s “Down in Tennessee”? Shame that song only peaked at No. 23.

    …I actually think Willie Nelson did TBE best version of ” Georgia On My Mind.” I liked Ray Charles’ version as well, but Willie’s just did it for me in a way I can’t quite explain.

    “Amarillo Sky” and “The Truth” are the only Jason Aldean songs that belong here. Wasted potential indeed.

  7. My favorite Mark Chesnutt songs are also “I’ll Think of Something” followed by “I Just Wanted You to Know”, Pisolero. The former may even be a contender for my all-time favorite country song of the 90s. I echo your sentiments for “Lizzie and the Rainman” in the previous batch too.

  8. Funny to hear Lisa Brokop mentioned – I have two of her US CDs and three of her Canadian releases – I have no idea why her Canadian success did not translate to the US – she was a tremendous singer who should have had at least a couple of songs on this list

  9. I agree with everyone here concerning Mark Chesnutt. It’s a real shame that he’s another artist who’s seemingly become most remembered for his ditties and not much else. Except for “Too Cold At Home,” they definitely whiffed on the other selections (Okay, maybe “Bubba” is deserving). “I’ll Think Of Something” and “Ol’ Country” are ones I’d include for sure, but I also love “Brother Jukebox,” “Broken Promise Land,” “Old Flames,” “Your Love Is A Miracle,” “It Wouldn’t Hurt To Have Wings,” and “Thank God For Believers.” And also, thanks for mentioning “It’s Not Over.” I only heard that one a few times on the radio when it came out during the Winter in early ’98, but it always really stuck with me. Such a great, underrated song! And Pistolero, I do remember “Down In Tennessee.” Love both his and John Anderson’s versions.

    Also a shame that there’s only three Keith Whitley selections here, and “Don’t Close Your Eyes” is WAY too low. Seriously, Sirius XM, you actually think “Save It For A Rainy Day” is a better song? Will Chesney’s song still be listened to and covered thousands of times by both aspiring AND successful singers over 30 years from now like “Don’t Close Your Eyes” is today? I nearly forgot it even existed until seeing it on the list just now.

    Always really enjoyed Willie’s version of “Georgia,” especially the harmonica solo. It was also a favorite of my step dad’s, and I just rediscovered an old home video in which he is lip syncing the song in front of the camera while it was playing on the stereo, and I was just running around at five years old being silly and occasionally trying to sing along. So yeah, it now has more sentimental value to me than ever before. (Same goes for George Strait’s “Love Without End, Amen” which he also lip synced to.)

    While I’m also maybe not the biggest Shania fan, I do certainly enjoy her music a lot more now than I did during her late 90’s/early 00’s commercial peak, and I have to completely agree with Kevin’s rant. “You’re Still The One” is my favorite of the Come On Over singles, and its placement is definitely too low. Again, will most of these random bro tunes included still be remembered over 20 years from now? Also, what a shame to learn that “From This Moment on” was left off. Personally, I’ll gladly take Shania’s pop country over most bro-country any day. It has been quite disappointing (but not too surprising) how little 80’s and 90’s female artists have been represented on this list so far, overall (No Suzy Bogguss, barely any Kathy Mattea, too little Pam Tillis, Patty Loveless, Lorrie Morgan, MCC, etc.)

    Finally, we see an Aldean single that’s actually good, but still too high.

    Same with Rodney Atkins. I would have just included this one and “If You’re Going Through Hell,” put them somewhere in the bottom half of the list, and called it a day.

  10. Oh, and on the topic of pre-stardom country artists appearing in music videos, I found this little clip while going through different obscure early 90’s country videos on YouTube the other night: Rob Crosby – “She Wrote The Book” https://www.youtube.com/watch?v=Gm5S_FAxuwQ

    I had to do a double take on the young lady playing the school teacher, and sure enough, it’s a pre-stardom Faith Hill just a year before she made her debut with “Wild One.” So cool!!

  11. FWIW, I thought Mark’s first version of “It’s Not Over” (from Longnecks & Short Stories) was the better of the two. As I remember, they were more or less the same recording but with subtle differences in the mix.

    Reba also did a good version of the song on My Kind of Country.

  12. keith Whitley could have 4 or 5 songs in the top 200 for my money, including this one. Why didnt we get any Suzy or Lari White on this entire list?

    My Favorite Mark Chesnutt song is either “Bubba” or “Old Flames have New Names” depending on my mood, but he has several good ones

  13. I am glad to have popped into this conversation at a moment where my *very limited* scope of familiarity with country music — mid nineties and early aughts, largely by virtue of my parents’ own preference for country radio at that time — corresponds to the topics being discussed.

    One of the things your commentary has definitively established in my mind is that I simply don’t comprehend enough of the genre to second-guess most of the list myself, especially lacking the time to inch through recordings of the 690(!) songs already discussed. Having said that, I am in broad agreement with what you have said so far, *especially* on this page, regarding recency bias and the under-representation of women.

    The absence of Suzy Bogguss, best represented by her signature song, “Aces”, is particularly glaring. It peaked long (in radio years) before my time listening to country music, yet was still played often enough that when I dug it up from Suzy’s catalogue after seeing the video for “Nobody Love, Nobody Gets Hurt”, it was like meeting an old friend.

    Ms. Bogguss has a pleasant voice, but not a peerless one. I don’t think she could ever match the hard edge of Reba, or the bombast of Martina, the range of Trisha, or the shifts in vocal tone Sara Evans used to such great effect in (e.g.) “Born to Fly” or “No Place That Far”.

    Then again, I don’t think *any* of the above — not even Trisha — could have interpreted “Aces” as well as Ms. Bogguss did. It is an incredibly complex song in emotional intention. This isn’t “She’s in Love with the Boy”; this is “How did chasing the dream you gave me become an affront to you?”, couched in far more expressive language than I am capable of. :-p

    Now that I check up on it, of course, I find that the only song peaked at #9. Doesn’t matter; I stand by what I said. Probably wouldn’t have cracked the top 40 sung by any other artist. Throw out an unnecessary single (all but two) by Lady formerly-known-as-before-the-Civil-War, Kenny Chesney — one of the ones where he wears sandals in the video; doesn’t matter which — or Brad Paisley (def. “Ticks” or “Little Moments”).

    Better yet, throw out “Redneck Crazy”. I felt better about this world before I knew Tyler Farr existed. Discovering Laura Bell Bundy’s existence and “Giddy on Up” barely makes up for it.

    Mark Chesnutt seems among the most obvious casualties of country radio’s shift from traditionalism — new or otherwise — toward undifferentiated pop/rock, as the Hot 100 itself shifted from alt. rock toward rap and r&b. “Too Little Too Late” was pleasant enough, quite ubiquitous on the radio in its day, and probably the correct choice if we’re gauging his career only on what might still see some airplay today, but even it feels like a bit of a “compromise single”, albeit one not nearly so bad in that regard as “I Don’t Wanna Miss a Thing”.

    I like Mark Chesnutt better — and he’s clearly having more fun, if only musically — unmoored from commercial whims, in “Somebody Save the Honky-Tonks” and his very minor hit cover of “Rolling With the Flow”. My favorite song of his is “Thank God for Believers”, but I recognize that’s probably down to my nostalgia and limited experience of his full catalogue.

    Rodney Atkins deserves, *at most*, two songs on this list. “If You’re Going Through Hell…” deserves placement, and IMHO should have been placed higher than it was. The writing (not Atkins own, it must be noted) is witty when it has to be (“…use the needle of your compass…”) (“…a genie in a bottle…”), and when it is idiosyncratic (“…bad to worse you think they can’t get worse than that…”), it is idiosyncratic in a way that suits Atkins’ limited capacity as a vocalist.

    If there was a *second* song of Atkins that deserved placement on this list, it would doubtless be this one, but I’ve just decided that I’m going to judge every single song on this entire list by the absence of Vince Gill’s “Go Rest High…”. If I’d rather be listening to that song — not my favorite song of his by a long shot, mind you — your song doesn’t belong. By that measure, Rodney Atkins deserves no more than one.

    I could go on, but I’m already conscious of rambling. I apologize if my anyone stubs their toe on my soapbox.

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