As we enter the top 500 of this list, here’s a refresh on the five rankings. Also, beginning with this entry, a YouTube playlist of the available entries can now be found at the end of each post.
- TOO HIGH: A worthy entry to the list, but is ranked too high in relation to its worth
- ABOUT RIGHT: A worthy entry to the list, and is ranked about right in relation to its worth
- TOO LOW: A worthy entry to the list, but is ranked too low in relation to its worth
- SO WRONG (THIS SONG): An entry that has no place on this list but could be replaced by a worthy song from the same artist
- SO WRONG (DOESN’T BELONG): An entry that has no place on this list and cannot be replaced by a better entry from the same artist
#500
Neal McCoy, “Wink”
#1 | 1994
JK: A fun single that has held up well, but let’s be real: “Put This In The Top 500, My Ass (I Won’t Put This In The Top 500).” Too High
ZK: His signature hit, so yeah, why not. Though I’d hesitate tocall it more than decent filler that I wouldn’t have minded seeing in the earliest editions of this series. Too High
KJC: A massive hit that represents McCoy’s musical personality well. Why on earth is it in the top 500? Too High
#499
Waylon Jennings & Willie Nelson, “The Year That Clayton Delaney Died”
LP Cut | 1982
KJC: Why on earth is this on the list at all? So Wrong (Doesn’t Belong)
JK: Well, this sure as shit isn’t anything I ever expected to see on here… I mean, it’s a great song and recording, but also what. So Wrong (Doesn’t Belong)
ZK: Love the song. Love the singers. Am confused by the choice. So Wrong (Doesn’t Belong)
#498
Sugarland, “Something More”
#2 | 2005
JK: One of Sugarland’s best singles, and Nettles sings the fire out of it. Still, this placement is far Too High.
ZK: A passionate ode to “making it” elevated by Nettles’ strong performance, but a top 500 country song? Nah. Too High
KJC: One of the best uptempo records of the century. Totally belongs here. About Right
#497
Carrie Underwood, “Undo It”
#1 | 2010
ZK: That hook – especially the way she stretches it out – always makes me cringe. A rocker without any real firepower. So Wrong (This Song)
KJC: This is easily my favorite single from Play On, but none of those four singles are even essential Carrie Underwood records, let alone among the best country singles in history. So Wrong (Doesn’t Belong)
JK: The chorus of this is but a dumbed-down knock-off of Lucinda Williams’ “Joy,” and I’d include that killer track here, instead. So Wrong (This Song)
#496
Restless Heart, “Bluest Eyes in Texas”
#1 | 1988
KJC: Excellent harmonies here. Why is it in the top 500? Too High
JK: They remain an underrated act, but wow does this placement overcompensate for that. Too High
ZK: A cool selection, for sure. But we’re at the point where this list needs to start meeting expectations rather than surprising us, even if this isn’t as weird as the above Willie & Waylon selection. Too High
#495
Ray Charles and His Orchestra, “Busted”
#4 (Pop) | 1963
JK: I think the only version of this standard I prefer to Charles’ is Patty Loveless’. An essential recording, correctly placed. Wild that it charted so high on pop radio, too. About Right
ZK: It can’t be overstated how important Ray Charles was for country music. Literally anything from him would suffice in this top half. About Right
KJC: So many great versions of this song, and this one might be the best. About Right
#494
Billy Currington, “Hey Girl”
#5 | 2013
ZK: Bye, boy. So Wrong (Doesn’t Belong)
KJC: Terrible. Just terrible. So Wrong (Doesn’t Belong)
JK: Per his Wikipedia discography page, he’s released 20 singles to country radio, and I swear to God it feels like his name has cropped up on this list at least 60 times so far. So Wrong (Doesn’t Belong)
#493
Travis Tritt, “T-R-O-U-B-L-E”
#13 | 1992
KJC: I’m sending my therapy bill to Sirius for reminding me of Travis Tritt wiggling around in red leather chaps. So Wrong (Doesn’t Belong)
JK: I dig this cover, but this placement is just as absurd as those red chaps… Too High
ZK: I’ll take Tritt over Presley any day, but as a cover of a novelty cut and nothing more, I wanted to see this a few hundred entries ago. Too High
#492
Conway Twitty, “You’ve Never Been This Far Before”
#1 | 1973
JK: Seeing this ranked so low is making me worried that we’re going to get “Happy Birthday, Darlin’” as his top-ranked song, and then I’ll just be screaming forever. Too Low
ZK: If only country dudes of the modern era could be this sultry without being creepy. Too Low
KJC: Twitty’s greatest hit, as far as I’m concerned. Too Low
#491
Zac Brown Band, “Highway 20 Ride”
#1 | 2009
ZK: This, to me, proved this band had more to offer to country music than just “Chicken Fried.” To echo Kevin’s sentiment, something certainly did go wrong in the 2010s, especially for this band. About Right
KJC: It’s hard to believe that such a gorgeous country ballad about a divorced father pining for his son was able to top the radio charts just a decade ago. Something went wrong in the 2010s. About Right
JK: Such a shame that they derailed to such a spectacular extent. Considering some classics we’ve already seen, I’d still say this is Too High, but I’m not super mad at it.
Previous: #510-#501 | Next: #490-#481
Re. “The Year That Clayton Delaney Died”: That song should be on this list, but in the original version that The Storyteller, Tom T. Hall, wrote and reocrded in 1971. Waylon and Willie have clearly done superior stuff as a pairing.
Re. “You’ve Never Been This Far Before”: Interestingly, this was also C.T.’s first Top 40 pop entry since 1961, and his final one.
Re. “T-R-O-U-B-L-E”: I have to say it, I found Travis Tritt’s version of this, in my humble opinion, unfairly obscure 1975 Elvis hit loud, brash, and, dare I say it, a tad obnoxious after just a few listens–something that I can’t say about Elvis’. But to each his own.
Re. “Busted”: Well, it’s Brother Ray, and another sterling recording from the man. He took a great Harlan Howard song and made it stick with a fine R&B/big band arrangement.
I completely agree with Erik North’s comments above
Restless Heart’s “Bluest Eyes in Texas” strikes me as about right, but otherwise I’m in line with the consensus
I’d have to be crazy, plum out of my mind, to accept that Waylon and Willie’s cover of “The Year That Clayton Delaney Died” merits a higher ranking than Willie’s superlative “Angel Flying Too Close to the Ground,” or, for that matter, belongs anywhere on this list. I do, though, lament that Tom T. Hall’s original version of the classic song apparently did not make the cut. Sigh.
Restless Hwaert is a little too low, and so is Conway.
Favorites in this group:
Sugarland – Nettles (have her solo albums too. love her duet with Josh Groban, “99 years”)
Ray Charles – Busted – didn’t know it was solely written by Harlan Howard
Zac Brown Band – Highway Twenty Ride – great song (too bad Zac went off the track beginning with the Grohl Sessions and Jekyll & Hyde
Tom T’s version of Clayton Delaney is much better. Wink is really a novelty song, so a bit high. Conway is way too low.