A Country Music Conversation: Sirius Top 1000 Country Songs of All Time, #920-#911

A lot of first (and only) entries in this part of the list.


Oak Ridge Boys, “Trying to Love Two Women”

#1 | 1980

JK: I’d love for contemporary country to have a corollary to the Oaks, but there are so few men in the genre these days who can actually sing. I’m surprised that this is one of the singles selected to represent them for this list, but I’m not mad that it’s here. Too High

KJC: I’m surprised that this is one of the three songs from this band, and that they left off their breakthrough hit, “Y’all Come Back Saloon,” and their late career smash, “Gonna Take a Lot of River.”  So Wrong (This Song)


Chris Cagle, “Laredo”

#8 | 2001

KJC: “John Michael Montgomery – no, wait – Michael Peterson – no, wait – Chris Cagle is the new Garth Brooks!”  So Wrong (Doesn’t Belong)

JK: There’s nothing wrong with this single, per se, but there’s very little about it that’s distinctive enough to warrant inclusion here, especially not at a ranking higher than something like “I Never Go Around Mirrors” or the one Connie Smith single they chose and now I’m mad about that again… So Wrong (Doesn’t Belong)


Merle Haggard, “If We’re Not Back in Love By Monday”

#2 | 1977

JK: I already mentioned some of the obvious misses for The Hag when it comes to this list; as with the Oak Ridge Boys’ single a few notches below, I don’t object to the inclusion of this particular song on the list so much as I don’t see any rationale for its selection at the expense of others. Too High

KJC:  The storytelling is so strong here that it can be overlooked just how much this borrows from the melody and structure of “If We Make it Through December.” Not sure how they left off that one, though.   About Right


Jason Aldean, “Tonight Looks Good On You”

#6 | 2015

KJC:  This guy has maybe two songs worth listening to, yet seventeen of his singles are on this list. So I’m going to say it for the first of many times: This isn’t good enough.  So Wrong (Doesn’t Belong)

JK: Aldean apologists insist that he has really great album tracks that justify his A-list stature on C-list talent. I’ve never heard one of those tracks that convinced me, and this single certainly never changed my mind that he’s country music’s single-most overpraised act. So Wrong (Doesn’t Belong)


George Strait, “Baby’s Gotten Good at Goodbye”

#1 | 1989

JK:  One of Strait’s very best singles, which is really saying something. Too Low

KJC:  Probably my favorite George Strait track of all time.  So glad it’s on this list. I’d rank it quite a bit higher.  Too Low


Moe Bandy, “Bandy the Rodeo Clown”

#7 | 1975

KJC:   This is the kind of entry I was hoping would be more common on this list: a token representation of a reasonably successful artist that didn’t leave a huge impact.  This allows him a footprint. Cute song, too.  About Right

JK: I agree about the breadth of representation as one possibility for a list like this, and I wish that had been the case more often. I honestly didn’t know this single by Bandy before checking it out for this feature, but I’m not at all mad that it’s here, if maybe higher than some better songs. Too High.


Brooks & Dunn with Reba McEntire, “Cowgirls Don’t Cry”

#2 | 2008

JK: I still hold out hope that Reba and Brooks & Dunn will team up for a truly great duet that plays to their respective strengths instead of duets that are merely fine-to-good. So Wrong (Doesn’t Belong)

KJC:  Three Reba duets on the list, and one of them isn’t “The Heart Won’t Lie.”  But I’ll take this over “If You See Him/If You See Her,” so at least they picked the right Reba/B&D collaboration. Brooks & Dunn were never great at writing female characters, but this cowgirl transforms from an archetype to the real deal as soon as Reba takes control of her voice.  About Right


Earl Thomas Conley, “Holding Her and Loving You”

#1 | 1983


KJC:  Before streaming shenanigans kept Florida Georgia Line at #1 for a year, Earl Thomas Conley was the ultimate example of chart history diverging from meaningful impact.  He scored sixteen consecutive #1 hits, but he’s only on this list once. I think they kinda got that right, though I would’ve squeezed in his Keith Whitley duet, too. About Right

JK: A very good vocalist forever in need of better songs than he actually recorded. It seems like he ought to be listed more often here, but, reviewing his full singles discography, I can’t pick even one of his solo hits that truly feels like a sin of omission. Like Kevin, I’d have included “Brotherly Love” and also would’ve made room for his duet with Emmylou Harris, “We Believe in Happy Endings.” About Right.


Kenny Chesney, “Everybody Wants to Go to Heaven”

# 1 | 2008

KJC:  In heaven, George Strait is the one singing this song. So Wrong (Doesn’t Belong)

JK: Yes, that. Here on earth, I’d settle for a vocalist who isn’t completely tone deaf. So Wrong (Doesn’t Belong)


George Jones, “The Window Up Above”

#2 | 1960

JK: I’m honestly surprised that this wonderful single made the list: It’s rarely cited among Jones’ litany of obvious classics, but it should be. He has bigger hits, sure, but this is one of The Possum’s very best. Too Low

KJC:  He’s underrepresented on this list, despite having seventeen songs on it! “A Good Year For the Roses” is a shocking exclusion.  But this is one of his best, and I’d say it should be higher. Too Low

Previous: #930-#921  | Next: #910-#901


  1. Considering that “Holding Her and Loving You” is one of my all-time favorite country songs, I’d rate it considerably higher than #913. Yes, ETC needed better material in his career, but that song hits everything just right.

  2. I haven’t bothered to play catch-up after part 1, but I just came here to point out that it says “Baby’s Gotten Good at Goodbye” is listed as being from 2011, not 1989.

  3. I really enjoyed listening to “The Window Up Above”, which I was not familiar with. That’s the maddening thing about this list…you get something like that, almost like a hidden gem, and then see “Laredo” and “Tonight Looks Good on You” right before it. This list is such a bizarre collection of hodgepodge material.

    As far as Earl Thomas Conley solo material goes, I will put a plug in for “What I’d Say”, which I think is the best thing he ever did. I think that song is a really nice depiction of the conflicted feelings someone has after a break-up, especially when they’re still clearly “not over it”. I always thought of Earl Thomas Conley as a “good” artist that definitely tried to do some intelligent material, but a lot of the production caused his songs to blend into the background. There are other songs I like from him (“Holding Her”, “That was a Close One”, “Brotherly Love”), but…I’ll concede a lot of his material is forgettable, considering the amount of hits he had. Still, given some of the choices on this list…I’d be happy to throw another entry or two his way.

    Finally, as someone that’s not a diehard fan of these guys, even I’m confused by the Oak Ridge Boys entries. “Leaving Lousiana in the Broad Daylight”, and both of the songs that Kevin mentioned would have been better choices than what was included on this list.

  4. Please tell us you’re joking. Did Jason Aldean really place seventeen songs on this list? Seventeen?? And the terrific Moe Bandy could only muster one? I’d certainly put Bandy’s “It’s a Cheating Situation” (with Janie Fricke), “Bandy The Rodeo Clown”, and novelty hit “Just Good Ol’ Boys” (w/Joe Stampley) ahead of most anything that Aldean has cranked out, though I know he’s had a handful of songs worthy of inclusion.

    Now you’ve got me wondering if we are unlikely to see Bandy’s singing partner, Joe Stampley, appear in the countdown. I’d sure like to see “Roll On Big Mama” make the cut.

  5. “Baby’s Gotten Good at Goodbye” is George Strait at the top of his game. its mythird favorite George song (I just Want to Dance with You” and the incomparable “Meanwhile”), and is Much Too Low

    Moe Bandy should gotten “Americana” on here, as well as “Till I’m Too Old to Die Young”

  6. I only have 4 Chris Cagle songs in my i-tunes library, one of which is “What Kinda Gone”:
    November 2, 2010
    Gone Country Songs

    There are quite a few country songs with the word “Gone” in the title. If you want to know what kind of gone, ask Chris Cagle. If you want to know how long gone, ask Brooks & Dunn. You may find out from Randy Travis that he or she is too gone too long. If Natalie doesn’t come back, the Dixie Chicks may soon be a long time gone. Diamond Rio is already gone from the charts but they had 3 gone songs; one was a single. If you want someone to stay gone, ask Jimmy Wayne. If you don’t believe someone’s really gone, ask Tim McGraw. If you don’t think all the good ones are gone, tell Pam Tillis. Or tell the Every Brothers that you’re gone, gone, gone, cause you done me wrong. Sounds like a country song.

    And since Michael Peterson was mentioned w Cagle, I’ll mention some of my favorite MP songs: “For a Song”, “From Here to Eternity”, “Two of the Lucky Ones” w Bekka Bramlett (my wife’s ringtone) and “I Finally Passed the Bar” w Travis Tritt. Saw MP twice at Bluebird bird – very personable and a very good singer.

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