A Country Music Conversation: Sirius Top 1000 Country Songs of All Time, #680-#671

Two veterans of the Mercury Records Triple Play gambit kick off this batch of entries.


Toby Keith, “How Do You Like Me Now?”

#1 | 1999

JK: A deeply misogynist record that, honestly, deserves to draw a lot more ire than “Courtesy of the Red, White, and Blue.” But it was a massive single that launched the second half of Keith’s career, and the song’s construction and the production choices are both kind of perfect. About Right

KJC: Given its pivotal role in launching Toby Keith, this placement is fair. God, it’s a mean spirited record, though.  Also, if a guy writes your number and says “Call for a good time” after you’ve rejected his advances, you made the right decision turning him down in the first place.  About Right




Shania Twain, “Honey, I’m Home”

#1 | 1998

KJC: A retread of “Any Man of Mine” that isn’t as memorable as the other Come On Over hits. Swap this one out for “Man! I Feel Like a Woman” or throw in a hit from Up!, as that album was left off of this list completely.  So Wrong (This Song)

JK: If people want to attack Shania Twain’s artistry, this is the single to do it with. The rhymes here are vapid and childish. She has countless other singles that showcase her unique POV and genuinely clever songwriting. So Wrong (This Song)



Cole Swindell, “Hope You Get Lonely Tonight”

#7 | 2014

JK: Absolutely not. So Wrong (Doesn’t Belong)

KJC:  A good traditional vocalist being drowned out by flaccid rock production. So Wrong (Doesn’t Belong)



Merle Haggard, “Are the Good Times Really Over (I Wish a Buck was Still Silver)”

#2 | 1982

KJC:  A relentlessly pessimistic white man’s lament, which Haggard did better than anybody else.  About Right

JK: I’m a believer that things are only ever as bad as they’ve always been, and what Haggard does so well is give voice to of-the-moment struggles without developing a persecution complex. About Right



Zac Brown Band, “Sweet Annie”

#6 | 2013

JK: Zac Brown Band were one of the most consistent bright spots at country radio over the last decade thanks to hits like this one. It isn’t my favorite single of theirs, but it’s worth including on this list. Too High

KJC:  When they get it right, they get it right.  What a gorgeous lament. About Right


Terri Clark, “Poor, Poor Pitiful Me”

#5 | 1996

KJC:  It doesn’t happen often, but it happened here. Terri Clark covered a Linda Ronstadt hit, and made it better.  Her delivery of “sort of like a Waring blender” is the best three seconds of her entire recording career. About Right

JK: I’m not going to incur the wrath of our friend Erik North by claiming Clark’s version of this Warren Zevon song is better than Ronstadt’s, but I do think this is one of Clark’s very best singles. She’s underrepresented on this list, just as she’s underrated across-the-board. About Right




Jason Aldean, “Why”

#1 | 2005

JK: I’ve never heard what it is that’s supposed to be so great about Aldean. So Wrong (Doesn’t Belong)

KJC: His early stuff was pretty good, but it still wasn’t great.  So Wrong (Doesn’t Belong)



Conway Twitty, “This Time I’ve Hurt Her More Than She Loves Me”

#1 | 1975

KJC:  Another stone cold country classic. “Lord, she’s already stood more than I was ever good for.”  God, that’s good. Too Low

JK: When Twitty gets talked about at all today, it’s for his bumpkin-lothario material. Which was often great, yes, and which stands as a useful counterpoint to the sleazy men currently dominating country radio. But that also reduces the breadth of Twitty’s talents: This is a brilliantly written song, perfectly delivered. Too Low



Tracy Byrd, “Watermelon Crawl”

#4 | 1994

JK: Byrd was like if Mark Chesnutt couldn’t sing on pitch or pick decent songs. So Wrong (Doesn’t Belong)

KJC:  That they tried to spin this mind-boggingly dumb line dance number as an anti-drunk driving message song during its chart run was nearly as insulting as the record itself. So Wrong (Doesn’t Belong)



Luke Bryan, “Roller Coaster”

#5 | 2014

KJC: He’s a big star and his best hits should be included.  I guess this one qualifies? Too High

JK: I mean, at least “Country Girl (Shake It For Me)” is catchy. So Wrong (Doesn’t Belong)


Previous: #690-#681 | Next: #670-#661


  1. Re. Terri Clark’s version of “Poor, Poor, Pitiful Me”: In all good honesty, I am secure enough as a fan of Linda’s to be less harsh on Terri’s version than I was when it came out in 1996. I’m also much more inclined to think Terri recorded hers as a nod to Linda’s influence on her rather than to show her up…because trying to show up Linda is a fool’s errand to start with (IMHO).

  2. While I liked both Terri’s and Linda’s recordings of “Poor,Poor,Pitiful Me”, the song itself is a piece of fluff and both artists recorded much better material during their careers, so I would rate the song as Too High

    Cole Swindell’s career I would regard (thus far) as wasted potential.

    “This Time I’ve Hurt Her More Than She Loves Me” is but one of many great Conway Twitty songs that could belong in this countdown (I suspect that there aren’t many on the actual list). He was consistently good

  3. I went thru the sirius list and didn’t find any other Terri Clark songs. (I certainly could have missed 1 or 2 others.) PPPM is far from my favorite TC song. I rather listen to Girls Lie Too – my most frequently played TC song according to my i-tunes library – You’re Easy on the Eyes, Better Things to Do, No Fear, Getting Even with the Blues, etc.

  4. At the risk of seeming a touch defensive, I don’t know that I would call “Poor, Poor, Pitiful Me”, which was written by the late, great Warren Zevon, a piece of fluff, considering that it’s a blackly comic song that’s more or less about (implied) rape and sadomasochism; and Linda herself certainly knew this when she recorded it in 1977. If it really were a piece of fluff, then it would be a first by any stretch of the imagination, to put it mildly.

    Funny, by the way, how many Bromeisters there are on these lists, including three (Cole Swindell; Luke Bryan; Jason Aldean), and four if you count Toby Keith’s “How Do You Like Me Now?” as a precursor of things to come.

  5. I strongly prefer Toby keith’s older stuff. Give me “Dream Walkin'” “Me Too” or “Blue moon” over anything he did post 9-11 or in response to it.

    PPPM isn’t bad, but not even close to Terri Clark’s best. Ditto the Aldean song, and the one from ZBB.

  6. Agree for the most part w Scott re TK’s older stuff. He got off to a great start w Should’ve Been a Cowboy. My List is about the last song I liked. Couldn’t stand get drunk and be somebody, get my drink on, etc.

  7. I actually like “Hope You Get Lonely Tonight”. Agreed, the production could have been better, but compared to other examples of the bro country subgenre and even on its own, this record is pretty good.
    I also like “How Do You Like Me Now?”, mostly for its fantastic hook. I wish we could keep it and ditch the rest.
    Also, re both Keith and Swindell: what bob said made me realize that in bro country, we have cheap knock-offs of what made classic country great. Later Keith is a cheap copy of classic drinking songs, Swindell is a cheap copy of Conway Twitty.
    Hard no on Bryant and Aldean.

  8. Kind of a weak group ,overall. The Conway and Haggard tunes are pretty much head and shoulders above everything else here.

    I thought it was pretty cool to learn that Earl Thomas Conley wrote “This Time I Hurt Her More Than She Loves Me.” It’s a lot more country than most of what ETC put out himself which was more on the contemporary side (which I also like). I also enjoy Neal McCoy’s cover that he released from his debut album.

    I’m with those who say that Toby’s older stuff is much superior. But even though the title track is not one of my favorites, the How Do You Like Me Now album is actually one of my favorites of his. It has quite a few strong album cuts, imo. Same goes for the follow up to that album, Pull My Chain. After “Courtesy” is when I feel that he started going overboard with the patriotic and drinking songs.

    Sighh..It figures that by the time I saw Tracy Byrd on this list, it would be one of his silly novelties which were arguably the weakest singles of his career, “Watermelon Crawl” being a prime example, as fun as it might be. The man actually has a pretty good voice, and it’s best showcased on his ballads like “Put Your Hand In Mine,” “I Wanna Feel That Way Again,” “Heaven In My Woman’s Eyes,” and “Keeper Of The Stars” (the radio version). Unfortunately, the No Ordinary Man album (his weakest, imo) pretty much established him as mostly a singer of novelties, and from that point on, that’s what the record label and a lot of the fans wanted from him.

    “Poor Poor Pitiful Me” is also not one of my favorites by Terri, but I still like it. How sad if this really is her only entry. I was also hoping to see “If I Were You,” “Better Things To Do,” “Emotional Girl,” “Now That I Found You,” or “No Fear”. Definitely one of the more underappreciated artists when it comes to 90’s/early 00’s country.

    Cole Swindell is also one of the more tolerable bros for me. Still, to include any of his songs, but none by Suzy Bogguss or only one from Terri Clark is just wrong.

    I actually consider “Roller Coaster” to be one of Luke’s more decent singles and will take it over “Country Girl” any day.

  9. I really liked “Poor Poor Pitiful Me,” and Terri Clark in general. I remember her saying the second single from her first album, “When Boy Meets Girl,” was inspired by that song, and I could definitely hear the similarities.

    The Conway song has always been a favorite. He had his more pop/rock moments, but he could nail a country song with the best of ’em, and the entry here was a prime example of that.

    No argument from me on “Watermelon Crawl,” but I completely agree with Jamie re: Tracy Byrd and his voice. It’s a shame that he really only broke out with his second album, because much like Tom McGraw’s, his first album was very good the whole way through and tremendously underrated.

  10. Pistolero, totally agree with you on Tim McGraw’s debut album. It’s a solid album full of enjoyable early 90’s neo-traditional country. It’s too bad that it flopped so badly. Also agree with Tracy Byrd’s debut. That’s one of his best albums, imo, and I wish he broke out with that one instead of No Ordinary Man. Love his cover of “Someone To Give My Love To.”

  11. “That’s The Thing About A Memory” was actually the first single from Byrd’s debut, and it was what grabbed me. I also liked “Why,” “Edge of a Memory,” and his version of “Talk To Me Texas” (which was previously recorded by Keith Whitley.)

  12. Tracy Byrd’s debut album was solid. It sold really well before it finally had its one radio hit. I remember thinking that his early singles were a bit too thoughtful and sophisticated for radio. He certainly adjusted that approach with future material.

  13. He certainly adjusted that approach with future material.

    Sigh. Yeah, he sure did. One of the best voices from that era and it was wasted on so much novelty crap. I am still a bit sore about that, 25 years later.

  14. Ha! You and me both. Even though I was only in grade school during the early-mid 90’s, it still kinda irks me when I look back and notice how certain artists had huge success with lightweight songs that weren’t really worthy of their talents (imo) but were not as successful with much superior material (again, imo). I find Joe Diffie’s career to be a similar case to Tracy’s, though I’ll admit I still enjoy some of Diffie’s novelties unlike most of Byrd’s. Btw, Pistolero, I love all of those songs you mentioned from Tracy’s debut! I also love “Back In The Swing Of Things,” “Hat Trick,” and “Why Don’t That Telephone Ring.” Like you guys said, it was a solid record.

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