This batch of ten is about as good as this list will ever get.
Hank Williams, “Your Cheatin’ Heart”
#1 | 1953
JK: I’d have it as his second or third highest entry, but I’m not chuffed that it’s his highest here. How-the-fuck-ever: That his highest entry is at #20 is, as so many things about this list have been, an affront to most of the things I value about country music. About Right in an absolute sense.
ZK: “Your cheatin’ heart will tell on you” … hot damn, the top 20 is off to an excellent start! Still feels a little Too Low, though, especially as his highest-ranked song.
KJC: It’s about right in its ranking on a normal list, but Too Low to be the highest-ranked single from Hank WIlliams.
Tim McGraw, “Live Like You Were Dying”
#1 | 2004
ZK: Considering we just talked about “Don’t Take the Girl” not that long ago, it’s worth noting how much McGraw grew as an emotive interpreter just a decade later. He sells this tale of mortality with grace and sincerity, and far from being overwrought, it’s anthemic. I wouldn’t say it’s a top 20 all-timer, but it definitely belongs in the top 100 or so. Too High
KJC: Songs like this feel over the top until life itself goes over the top. I didn’t fully grasp the power of this song until I watched my father react to the video after he was diagnosed with pancreatic cancer. My dad never went skydiving or Rocky Mountain climbing, but I do believe that he loved deeper, spoke sweeter, and gave forgiveness he’d been denying. I’m eternally grateful for a song that was able to help him process what we aren’t designed to process. About Right
JK: I’ll play the contrarian on this one: This is well-intentioned and a fine enough sentiment for a country song, undone by hackneyed writing. The chorus is a mess from a compositional standpoint, and putting it ahead of something as pure and flawless in its construction as “Your Cheatin’ Heart” lays bare the sloppiness of the songwriting. McGraw emotes the hell out of it, as is his wont, which overcomes some of its limitations, but nowhere near enough to have it ranked here. I wouldn’t even have it in my personal top 200 for its decade, but I’d slot this somewhere in the 800s on impact and intent. Far Too High
Johnny Cash, “Ring of Fire”
#1 | 1963
KJC: I’m going to say this again, and I’ve said it already: Cash’s top one hundred entries are all correct. They’re just in the wrong order. That being said, if you bump “Sunday Morning Coming Down” to the top ten, I can sign off on this being About Right
JK: Remember like five years ago when genre purists lost their collective shit about Sturgill Simpson’s use of a brass section? That was neat. Not my favorite Cash, but this is as close to fine as they’ve come with ranking just work. About Right
ZK: I’m out of unique things to say about Johnny Cash … uh, Mariachi horns! Wooh! About Right
Alan Jackson, “Livin’ On Love”
#1 | 1994
JK: A lovely hit that I enjoyed in 1994 and still enjoy now and would put as maybe Jackson’s own 17th-best single and do not mean as a slight in this song or Jackson but absolutely mean as a slight against this baffling list. Too High
ZK: A bizarre choice for Alan Jackson’s highest-ranked song. I mean, I’m not mad about seeing a Jackson tune here, but it’s not “Remember When” or “Midnight in Montgomery.” Still a very nice song, though. Too High
KJC: My parents loved this song. “Hold Me” by K.T. Oslin was their “marriage is hard” song, while “Livin’ On Love” was their “all we need is each other” song. I’m not quite sure this is the right top twenty song for Alan Jackson – I’d probably go with “Remember When” or “Drive (For Daddy Gene)” – but even if it’s Too High, I’m still glad that it’s here.
Tammy Wynette, “Stand By Your Man”
#1 | 1968
ZK: Absolutely not. It’s iconic, I concede, but horribly dated in a way that’s always made it one of the few classics I just hate. Too High
KJC: Without question, one of the biggest and most important records of its day. It even topped the U.K. pop charts seven years after its stateside run. Tammy once said that she spent fifteen minutes writing the song and the rest of her life defending it, to the point where she even had to explain to a Chipmunk that “You only stand by your man if he stands by you.” I wouldn’t argue with its placement if it was even higher than this. About Right
JK: On impact and status as an iconic single? Fine. It’s About Right. But Candi Staton’s version blows Wynette’s out of the water and always has.
Kenny Chesney, “How Forever Feels”
#1 | 1998
KJC: It does Kenny Chesney as much a disservice as the rest of us to pretend that this Tim McGraw castaway is one of the top fifteen records of all time, when it clearly is So Wrong (Doesn’t Belong)
JK: With just 14 entries remaining above this one, you might think this would be the last time I’d give myself a migraine from clenching my jaw over the utter dumbfuckery of this list. Sadly, you’d be wrong. As wrong as including this nothing of a song on this list at all. So Wrong (Doesn’t Belong)
ZK: With all of the wack-ass entries we’ve gone through, we certainly do know how forever feels, Mr. Chesney. So Wrong (Doesn’t Belong)
Alabama, “Mountain Music”
#1 | 1982
JK: Whatever. Makes sense as their peak entry. Would still have their peak entry outside the top 100 on this list, barely in the top 500 on my personal version. Delighted not to have to consider them again. Too High
ZK: I co-sign what Kevin says below. This is my favorite song by country music’s biggest band, and I can’t quibble much with the placements between No. 50 and here, but this just feels a little Too High.
KJC: Totally appropriate for this to be the highest ranked song from Alabama. Completely inappropriate for it to be within spitting distance of the top ten. Too High
Willie Nelson, “On the Road Again”
#1 | 1980
ZK: It’s likely his most referenced and iconic single in modern popular culture, but if we’re going by what captures his aura best as an artist, it’s got to be “Always On My Mind” here, or “Blue Eyes Crying in the Rain.” Too High
KJC: This is a great record that captures the spirit of Willie Nelson as well as anything that he’s ever done. But again, it comes down to an appropriate ranking of the canon, which places “Always On My Mind” and “Blue Eyes Crying in the Rain” well above “On the Road Again.” Too High
JK: My fellow hostages to this list said what needed to be said. Too High
Garth Brooks, “The Dance”
KJC: I don’t think there should be two songs in the top ten from the same artist, and this has to be slotted below “Friends in Low Places,” so I suppose this is About Right
JK: Certainly. A gorgeously written and produced song that Brooks delivers with the kind of real pathos and restraint he’d quickly abandon. A deserved classic (that I want Kelly Clarkson to record a proper studio rendition of…). About Right
ZK: Given that – spoiler alert – we’ll be seeing Brooks top this list very soon, I’m not mad about this placement in context. A phenomenal song elevated by Brooks’ best-ever delivery. About Right
Patsy Cline, “I Fall to Pieces”
#1 | 1961
JK: My choice for Cline’s best is forever in flux, with “whatever I listened to last” usually pulling rank. I agree with what Kevin says below about how “Crazy” highlights Cline’s real interpretive gifts. But this is an exquisite record that’s certainly ranked About Right.
ZK: Second spoiler alert: Patsy Cline’s “Crazy” is one of the few records within the top 10 that feels correctly ranked, and like with the Garth Brooks selection above, I can’t argue with this placement when factoring context into consideration. Another iconic song by an iconic artist. About Right
KJC: You could swap this with “Crazy” and I’d be just as happy with where both records landed. I do think that “Crazy” is just a hair better because of what Patsy does vocally with Willie’s melody. But they both belong in the top eleven, for sure. About Right