A Country Music Conversation: Sirius Top 1000 Country Songs of All Time, #750-#741

Sugarland refuses to settle for less, while some outright country classics are forced to during this section of the list.


Sugarland, “Settlin’”

#1 | 2007

JK: Where Sugarland struggled was in distinguishing between having a niche and simply repeating yourself. I’d replace this one with “Already Gone” or the fantastic cover of “Life in a Northern Town” they did with Little Big Town and Jake Owen. So Wrong (This Song)

KJC: Jennifer Nettles sounds great, but this song is a less infectious retread of “Something More.”  So Wrong (Doesn’t Belong)


Porter Wagoner, “The Carroll County Accident”

#2 | 1968

KJC:  An absolute classic story song.  This is what Wagoner did best. About Right

JK: Agreed. But that also means this ranking is Too Low.


Ronnie Milsap, “Stranger in My House”

#5 | 1983

JK: One of the slick country-pop hits of its era that holds up today, and a worthy addition to the list. Too High

KJC:  A catchy pop hit that has a cool, almost creepy vibe.  About Right


Dustin Lynch, “Where it’s At”

#4 | 2014

KJC:  I’ve been playing SongPop again, and in the country categories, I always kill it…unless I get a playlist of songs from the past decade. ALL OF THESE DUDES’ SONGS SOUND THE SAME. So Wrong (Doesn’t Belong)

JK: I swear to God. Imagine believing this is better than “Lovesick Blues.” So Wrong (Doesn’t Belong)


Jo Dee Messina, “Lesson in Leavin’”

#2 | 1999

JK: Messina’s cover doesn’t reinvent Dottie West’s original, but it absolutely plays to her own strengths and falls into her fairly limited wheelhouse. I don’t mind its inclusion on the list. Too High

KJC:  This is a great cover of the Dottie West hit, but the cover should be lower and the original should’ve made the list. Too High


Brad Paisley, “Letter to Me”

#1 | 2007

KJC:  The best of his self-written hits. About Right

JK: When Paisley’s sentimental streak really hits, he comes up with songs like “Letter to Me,” and he did them better than any of his contemporaries. Too Low


Roger Miller, “Do-Wacka-Do”

#15 | 1964

JK: Another choice that falls into the, “If they remembered this one, how is the rest of the list so bad?” category. About Right

KJC:  One of the silliest of his silly hits, and its charm still holds up today.  About Right


Brooks & Dunn, “Play Something Country”

#1 | 2005

KJC: The hook is directly lifted from Mary Chapin Carpenter’s “Shut Up and Kiss Me,” which had memorable lyrics to go with that hook, something that the B&D rewrite doesn’t.  So Wrong (Doesn’t Belong)

JK: By 2005, though, Carpenter’s footprint at radio had been reduced to rare recurrent plays of “Down At the Twist and Shout” and maybe “I Feel Lucky,” so I doubt the hook on this even registered as the blatant rip-off it was. The rest of it was just strident pandering for ongoing radio approval. Hard pass. So Wrong (Doesn’t Belong)


The Judds, “Why Not Me”

#1 | 1984

JK: There’s just enough blues in the arrangement for Wynonna really to sink her teeth into it, elevating what was already a well-written variation on a familiar theme. About Right

KJC: You can totally understand how America fell in love with the Judds just by listening to the warmth and earnestness of “Why Not Me.”  A golden classic. About Right


Toby Keith, “Whiskey Girl”

#1 | 2004

KJC:  A downside of Toby Keith’s breaking the multi-platinum barrier in the 2000s was his ambition dropped, as if he knew he was big enough to phone it in on a few songs. This isn’t the first of his hits to be clumsily written, but it’s the first one that was so lazily written.  I remember my Dad, a big Keith fan at the time, seeing this video for the first time, remaining quiet for a few moments, and then saying to me, “He’s not really trying here, is he?”  So Wrong (Doesn’t Belong)

JK: Country radio had made it clear that it had taken his side in the Dixie Chicks fallout by this point, and his singles were too often half-assed and pandering afterward, leaving him a shadow of the credible artist he’d been prior. So Wrong (Doesn’t Belong)

Previous: #760-#751 | Next: #740-#731


  1. Love a lot of Ronnie Milsap’s pop country hits from the 80’s and late 70’s, and “Stranger In My House” is one of them.

    While I’ve always liked Jo Dee Messina’s version of Lesson In Leavin’ (It’s the first one I heard), I’ve come to really enjoy Dottie West’s original version, too, and actually like it a bit more than Messina’s. I agree that the original should’ve made the list.

    Again, how on earth are so many of these bro-country songs making the list? I actually don’t mind songs like “Where It’s At” too much if I’m at some party or if the occasion is right for it. Some of these songs can be a fun listen. But for a “greatest country songs of all time” list? I don’t think so.

    The Brooks & Dunn song is an example of why I began to lose interest in them after 2003. “Play Something Country” is one of the many “I’m Country” pandering songs that gave me a reason to start tuning out of country radio around this time.

    Ditto to Toby Keith’s “Whiskey Girl.” He redeemed himself some with the Honky Tonk University album, but it was downhill again after that, imo. What a shame that radio chose songs like this over the Dixie Chicks, and other songs and artists that have something more to say.

    “Why Not Me” is one of my all time favorite songs from the Judds, along with “Love Is Alive.” Most of their music is like a soundtrack to my early childhood. :)

  2. Re. “Stranger In My House”: It’s important to remember that many of Ronnie Milsap’s biggest hits, especially when they crossed over onto the Hot 100 as this one did, had a noticeable R&B influence. Very early on, like say 1969, he was part of the studio crew at Chips Moman’s American Studios in Memphis when they had a local client recording there by the name of Elvis Presley. And in some ways, “Stranger In My House” has parallels with Elvis’ classic “Suspicious Minds” in its story of love and paranoia.

  3. Favorite here is “Stranger in My House”. If a free download of TK’s “Whiskey Girl” and B&D’s “Play Something Country” were offered I’d pass.

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