Signature songs from Kitty Wells and Lee Ann Womack appear way too early in this countdown.
Kitty Wells, “It Wasn’t God Who Made Honky Tonk Angels”
#1 | 1952
JK: The placement of this landmark single is perhaps the most egregious example of historical genre ignorance on this entire list. My God. Too Low
KJC: Top 100 classic. Maybe top 50. Too Low
Mark Chesnutt, “I Don’t Want to Miss a Thing”
#1 | 1998
KJC: Mark Chesnutt was among the finest traditionalists of the nineties, and there were many of them. This was his last big hit, and it wasn’t very good. Jonathan’s pick below is my favorite Chesnutt single, and I’d also have made room for “Almost Goodbye” and “Thank God For Believers,” just for starters. So Wrong (This Song)
JK: Where even to begin. One of the best male artists of his era barely figures on this list at all, but they made room for a cover of a just awful pop power ballad that he’s on record as hating. “I’ll Think Of Something” isn’t on here. Let’s go with that one as just one hit of many that should replace this. So Wrong (This Song)
Rascal Flatts, “Prayin’ For Daylight”
#3 | 2000
JK: I couldn’t stand them from the shrill, nasal opening notes of their debut hit. The first cut is the deepest, indeed. So Wrong (Doesn’t Belong)
KJC: The correct answer for early Rascal Flatts is “I’m Movin’ On,” which I would rank well above #618. It’s not on the list at all. So Wrong (This Song)
Lee Ann Womack featuring Sons of the Desert, “I Hope You Dance”
#1 | 2000
KJC: This is a modern country music standard that belongs in the upper quarter of the list. Too Low.
JK: One of the few songs of this type that avoids being overly maudlin. Its success hinges on the sweetness and sincerity of Womack’s delivery and the soulful backing vocals by (the underrated) Sons of the Desert. Not Womack’s best single, but it’s a classic that earns its place here, and I’d even say it’s a bit Too Low.
Clint Black and Lisa Hartman Black, “When I Said I Do”
#1 | 1999
JK: Whereas “I Hope You Dance” avoids mawkish sentimentality, “When I Said I Do” drowns in it. The hook at the time was the surprise that Lisa Hartman Black was a competent singer. There’s little to latch onto two decades later, especially when Black has songs like “No Time to Kill” and “We Tell Ourselves” that didn’t make the cut. So Wrong (This Song)
KJC: Clint Black made his best music before he got married and went all Doug Stone on us. He was the biggest artist in the genre during his debut album cycle. I’d replace this entry with “Nobody’s Home,” his longest running #1 hit. So Wrong (This Song)
Dierks Bentley, “5-1-5-0”
#1 | 2012
KJC: A novelty record that wore out its novelty before it finished its run on radio. So Wrong (Doesn’t Belong)
JK: I think Bentley is represented by the correct quantity of singles on this list, but not the correct quality. Swap this for “Say You Do,” “Up on the Ridge,” or “Bourbon in Kentucky.” So Wrong (This Song)
Waylon Jennings, “This Time”
#1 | 1974
JK: Six entries into this batch, and I’ll give my first About Right.
KJC: It’s hard to go wrong with Waylon Jennings, and this is one of his underrated hits. About Right
Jason Aldean, “The Truth”
#1 | 2009
KJC: The embodiment of mediocrity. Aldean’s hits aren’t as awful as the hat acts that followed him, but they don’t hold a candle to the ones who came before him. So Wrong (Doesn’t Belong)
JK: The chasm between Aldean’s talent and his commercial success remains an unknowable void. So Wrong (This Song)
Mark Wills, “I Do (Cherish You)”
#2 | 1998
JK: Ah, yes, that late 90s run when pretty well every woman with a major label deal was knocking it out of the park on song after song, and the B-list men were doing tepid covers of R&B ballads. So Wrong (Doesn’t Belong)
KJC: At least they didn’t include his Brandy cover. So Wrong (Doesn’t Belong)
Miranda Lambert, “Gunpowder & Lead”
#7 | 2008
KJC: Lambert’s much deserved breakthrough single, and still one of the best things she’s ever recorded. Too Low
JK: God, how I miss when she would use slant rhyme to emphasize a point in her songwriting. A triumph of detail, performance, and production, and one of the best country singles of the aughts. Too Low.