A Country Music Conversation: Sirius Top 1000 Country Songs of All Time, #90-#81

Wasting away again in Siriusville.



Tim McGraw, “Something Like That”

#1 | 1999

KJC: This was a massive hit, but for me, it was a step down in quality from his Everywhere singles and “Please Remember Me.”  Too High

JK: It’s been a while since we covered the only two singles of his that I’d have anywhere near the top half of this list, let alone in the top 100… Too High

ZK: On personal preference, I’d only maybe have “Just to See You Smile” here. On impact, “Live Like You Were Dying.” We don’t just need the big hits anymore.  We need the enduring classics. This is a fun and easy to sing along to, but … Too High 



Roger Miller, “Dang Me”

#1 | 1964

JK: I actually like this one significantly less than “Chug-A-Lug,” which I know isn’t the correct opinion. Certainly an entry for the top 250 or so, but this strikes me as Too High.

ZK: That thing when a writer is known for his wit and humor yet actually pens songs with much sadder subtexts. It’s not Miller’s crowing moment – we’ll get to that – but I’m absolutely OK, with this being here. About Right 

KJC: I’ve been a bit critical of them ranking so many Roger Miller songs toward the top of the list, but this one definitely belongs here.  About Right



Ronnie Milsap, “Smoky Mountain Rain”

#1 | 1980

ZK: I agree with my colleagues below that Milsap should have one single here. I’m at the point where I’m nitpicky to slot this in the 90s, but it is a really love song that may be among Milsap’s best. Too High 

KJC: This is an interesting choice for top ranked Ronnie Milsap hit.  It’s certainly one of his best records, though truth be told, I’d rather see “It Was Almost Like a Song” up here.  Too High

JK: I’m surprised that this is the one they ranked highest for Milsap. I’m not mad about it; just surprised. It’s a lovely record that has held up better than many of his hits that are badly dated by their production. Milsap certainly deserves an entry in the top 100, so I’ll say this is probably About Right.



Loretta Lynn & Conway Twitty, “Louisiana Woman, Mississippi Man”

#1 | 1973

KJC: They spelled “After the Fire is Gone” wrong.  Too High

JK: A terrific duet, sure, but no way it belongs here. Too High

ZK: Think of an alternate timeline where we already discussed this somewhere in the 300s or so and we’re here to talk about “After the Fire is Gone” instead. Nice, isn’t it? Too High 



Dierks Bentley, “Drunk On a Plane”

#3 | 2014

JK: I went to bat for this single when we did our year-end wrap up in 2014, and even I would have this, at best, ranked somewhere in the 900s. This is the first ranking that strikes me as outright trolling. Too High

ZK: Clever for the bro era, I’ll give it that. And it’s ridiculously stupid to the point of being really good. But unless y’all are looking to Up On the Ridge for inspiration for one of Bentley’s highest-ranked songs, try again. Too High 

KJC:  The melody is a poor man’s version of the New Radicals’ “You Get What You Give” coda.  It’s still a charming song.  But #86?  Way Too High



Sammy Kershaw, “She Don’t Know She’s Beautiful”

#1 | 1993

ZK: Kershaw would get my vote as one of the more underrated artists of the ’90s, but I don’t even know if my favorite single from him – “Yard Sale” – is top 100 worthy. Too High 

KJC: Definitely the best of his big hit singles, but not one of the hundred best records of the last hundred years.  Too High

JK: I genuinely don’t know what I would tag as Kershaw’s best single– he was consistently good and never great– and this hit is reasonable to include on the list, but one of the top 10% in the genre’s history? Really? Too High



Jimmy Dean, “Big Bad John”

#1 | 1961

KJC: A fantastic inclusion that is very worthy of its ranking. Good catch, Sirius.  About Right

JK: It’s so strange to see something like this ranked About Right.

ZK: I love this strange little saga song in all of its intentionally overblown glory. Absolutely About Right.



Don Williams, “Tulsa Time”

#1 | 1978

JK: I’d have three Williams singles in my own top 100; this wouldn’t be one of the three, but I’d have it in the top half of the overall list. Heresy: I prefer Pistol Annies’ cover of this to Williams’ original. Too High

ZK: Heresy as it is to say, I’m not a huge Williams fan. But this song has a killer groove and real kick to it that I’ve always adored to his softer material. Not the correct opinion, I know, but it’s only Too High by a little bit. Also, TIL there’s a Pistol Annies version. 

KJC:  It’s an ACM Single of the Year, but I’ve never fully understood its notoriety. I’d swap it with “I Believe in You.”  Too High



Luke Bryan, “Drink a Beer”

#1 | 2013

ZK: “Get it? ‘Cause it’s a Luke Bryan song and, like, not actually about beer?” 

This isn’t a clever bait-and-switch; it’s cementing your A-list status as a walking, ass-shaking stereotype that can’t understand actual depth. So Wrong (Doesn’t Belong)

KJC: For me, this is Luke Bryan’s finest moment on record, and it’s an early indication that its co-writer, Chris Stapleton, could capture desperate sadness like lightning in a bottle. I’ll get the knives back out for his other top 100 entry, but this one is only a little Too High.

JK: I generally find it pathetic when the Bros attempt to feign depth: Things like Florida Georgia Line’s “Dirt” or Chase Rice’s “Three Chords and the Truth” prove that these acts truly are the shallow, emotionally stunted man-children that their party anthems suggest. This song is no exception. It’s impossible to praise without a for Luke Bryan qualifier, and I tapped out my praise for him on “Country Girl (Shake It For Me),” which is at least honest about his capabilities and is catchy. This? Pass. So Wrong (Doesn’t Belong)



Jimmy Buffett, “Margaritaville”

#13 | 1977

KJC: Why not just add Bonnie Tyler’s “It’s a Heartache” and Debby Boone’s “You Light Up My Life,” too?  This is a waste of valuable space.  So Wrong (Doesn’t Belong)

JK: I would 100% include that Bonnie Tyler song in the top half of my own list. I would not for a nanosecond consider including “Margaritaville,” no matter how many Chesney’s and Zac Brown Band hits it directly inspired. So Wrong (Doesn’t Belong)

ZK: No, I actually like the idea of including this, and not just because it could easily replace whatever Kenny Chesney entries are left here. Buffett understood that sometimes the island life had a somber emptiness to it, and this is brutal enough to compete with the best in country. Too High 

Previous: #100-#91 | Next: #80-#71



  1. “Dang Me” and ” Big Bad John’ are the only real classics in this group. Everything else is either too high or doesn’t belong

  2. I unabashedly love “A Place in the Sun” as one of my all-time favorite albums, but yeah, “Something Like That” should be a couple hundred spots lower.

  3. I love “Dang Me.”

    It might not be popular to say, but “Smokey Mountain Rain”, “Pure Love” and “What A Difference You Made in My Life” are my favorite Milsap songs by far. For some reason, I would have guessed that “Smokey Mountain Rain” would be their highest ranking song.

    I like the Dierks Bently song a lot, but I would never place it this high or even put it on a list of the best country songs of all time.

    I just don’t think any Luke Bryan song should be in the top 100 of a top 1000 list! I think I genuinely only like 3 Luke Bryan songs.

  4. Re. “Dang Me”: Well, clearly this one is a novelty, a kind of early form of “country rap”. But it was the one that gave Roger Miller his first big crossover smash; it hit #7 on the Hot 100 in August 1964, which was something of a rarity given that the Beatles were dominating virtually everything else.

    Re. “Margaritaville”: Unquestionably, this song’s themes are the most overexploited in country music, especially from people like Kenny Chesney. I would guess Chesney and a lot of other guys (including the Bromeisters) thought that exploiting JB’s 1977 beach anthem was a Sure Thing for success, ignoring what film director Stanley Kubrick said: “Nothing is as dangerous as a Sure Thing”. In the end, there’s only one “Margaritaville”, and only one mayor of that mythical place.

    Re. “Big Bad John”: If you’re going to be known for two big things (the other being the king of Pork Sausages), it might as well be this massive narrative song hit, in which you can imagine what it means to see how “a crashing blow from a huge right hand/sent a Louisiana fellow to the Promised Land.”

  5. There’s also a version of “Tulsa Time” out there by Reba. She recorded it for her 20th Anniversary covers project in 95 but didn’t release it until a few years later on some random CD I remember picking up… I think it was a tie-in with a book.

  6. …”tulsa time”? can’t recount how often i heard that one as an encore covered by somebody at a live show anywhere. great international classic and therefore a worthy top 100 entry in my book.

    “margaritaville” – a song that sounds like a million insta holiday pics of today. that’s what i call standing the test of time. occasionally you guys have a slight tendency to miss the forrest for the trees. i perhaps would have been on your side of the ball park when it comes to “cheeseburger in paradise”, but not on this one.

  7. Dang Me can be top 500, I guess, but top 100? This should be essential country music, and I don’t think is close to that. Smokey Mountain Rain is an obvious ripoff of Kentucky Rain, and much too high. Nice song, but hardly essential. Big Bad John is a bit high. Tulsa Time is incredibly catchy, but that doesn’t rate “Essential” in my book. Maybe I Believe in You would be a better choice. Margaritaville? Well, okay, but if that’s country, where in the world is John Denver? BJ Thomas has gotten short shrift too.

    Someone previously mentioned how random the list is. A thought has been rolling around in my head for a few months over that, and I think I’ve got a hold of it. I’ve come to realize that the list is so random because post Y2K country is……random. Who exactly decided the bros were…..you know, good? ANY of their songs is a randomly good/bad/decent song, so if you include ANY of them, this list is ipso facto, random.

  8. Top 100, hey, I might as well mention all of the entries. She Don’t Know is fine, but top 100? Ditto Louisiana Woman. Come on, man. Drink a Beer is too high, but I sort of see how someone might rate it top 100. Then there’s I Got Drunk on a Plane. Top 100……how does ANYONE think that? The King’s English fails me.

  9. I’m with Kevin all the way on “Somethin’ Like That.” It’s still a pretty fun summer song that I like to crank up every now and then (much better than most of today’s summer anthems), but it’s definitely not better than the Everywhere singles or “Please Remember Me.”

    I’ve always enjoyed Roger Miller’s humorous ditties, and while I agree that some of his numbers were ranked a bit too high on the list, I really do like “Dang Me,” and think it’s about right.

    I actually think they got it right in putting “Smokey Mountain Rain” as Milsap’s highest ranking song, though a case could definitely be made for “It Was Almost like A Song.” I honestly never get tired of “Smokey Mountain Rain,” and I absolutely love the beautiful melody and strings in the background. This one stayed a steady recurrent for us on the radio into the early 00’s.

    I completely agree with the panel concerning the Conway and Loretta duets. “After The Fire Is Gone” should definitely be in this spot. I’ve honestly gotten tired of hearing “Louisiana Woman…” so many times whenever I turn to a classic country channel or classic country tribute. “After The Fire Is Gone,” on the other hand, holds up much better, imo.

    While “She Don’t Know She’s Beautiful” may be Sammy’s biggest hit, and I do like the song, it wouldn’t really my top pick for him. I personally like “Cadillac Style,” “Yard Sale,” “Meant To Be,” “Love Of My Life” and “Matches” even more.

    I agree that “Big Bad John” is right. It’s another true classic that my parents and I always enjoyed together.

    While I’m a huge Don Williams fan, and I do think “Tulsa Time” is a pretty fun listen, I never quite got what made it so much more popular than many of his even better (imo) songs. I’m with Kevin in putting “I Believe In You” here instead.

    While I’m not sure I’d include “Margaritaville” at all, I’d much rather see it on here than any of the countless knockoffs that Kenny, Zac Brown, and company have produced in the last two decades. Either way, it’s way too high. “Come Monday” on the other hand, it one I actually wouldn’t have minded seeing on the list at all.

    “Drunk On A Plane” is indeed one of the more tolerable hits from the Bro era, and it’s at least self aware in how goofy it is. Like Leeann, I don’t think I’d actually put it on the list, though.

    Sorry Kevin, but I’m more with Jonathan and Zack on “Drink A Beer.”

  10. “Spmething like that” and any Roger Miller is way too High.
    “Smoky Mountain Rain” is a little too high, but its not a big error.
    “Drink a beer” belongs in the list but not in the damn top 100!

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