The thing that I realized as I was listening through to the first batch of country #1 hits from 1998 is that in terms of genre charts, the country chart has a certain base level consistency that I don't see elsewhere. Now when I say 'consistency,' I mean it in a mildly pejorative sense. While the consistent nature of the chart has some positive bearing on its overall quality - my first pass at rating the initial batch yielded a plethora of s with very few deviants, which I'll bet the rock charts would kill for when their time comes - it also makes for a very, VERY samey group of songs in the end. There's so much standard issue Nashville paraphernalia on each of the year's biggest hits that makes them hard to tell apart on a cursory level, which essentially means that if I like one song I wind up liking them all.
That's where I'm glad I have a bit of an outside standardizing force to judge things against. Knowing that Ty Herndon's "It Must Be Love" was a solid  in terms of the less insular confines of the one hit wonders section meant that, in the early goings, I found myself mostly thinking about each song matched up to that. As skewed as that methodology is, it means that in the end I'm at least placing the songs in a more generalized context in a round about way. Even then, though, there was a certain base level quality at least in terms of the craftsmanship that goes into the songs. Yes, I'm saying that the mass-produced sound of the Nashville machine is a good thing in the end, because even songs that are objectively lesser still sound fantastic on an aesthetic level.
The deciding factor, then, comes in the form of the performance of the artist in question. Like I said way back in my top 150 singles of the 00s series, when it comes to country music, performance is absolutely key. The more factory-issue the genre, the more it depends on the artist to imbue the songs with any semblance of personality. The ones that do this best are by default the ones that I gravitate towards. Serviceable may result in a higher rating here than it does in other fields, but that also makes those outliers particularly noteworthy.
So, without further ado...
QUARTER ONE (Week of January 3rd - Week of March 28th)
Note: I'd generally provide YouTube links for these, but since only about half of them seem to have even lyric videos up at this point - and those that have videos up are often in very low quality - that's not gonna be an option 100% of the time.
Garth Brooks "Longneck Bottle" (#1 US & CAN Country)
Speaking of serviceable...well, Garth might as well be the poster boy for that particular term as we'll apply it here. If we're using "It Must Be Love" as the standardizing agent for this stuff in the larger picture of 1998's pop music, we might as well call Garth the internal standard - putting that Chem degree to use here guys - since, with a few exceptions, when he does a song of a particular style, it'll fall prety much dead center of my estimations of that particular form. Thus, when I rate this you'll know that my opinion of the upbeat drinkin' song is slightly higher than my opinion of certian other styles we'll get to as we go on. 
Martina McBride "A Broken Wing" (#1 US Country, #17 CAN Country, #61 US Pop)
Overwrought ballads are the norm for country music. I accept that while not being necessarily thrilled by it...but there are limits to what I'll grit my teeth and sit through. Normally I love Martina McBride - hell, if I were to go back and do this for '94 I wouldn't be surprised if "Independence Day" would get a solid  out of me - but while this does give her ample opportunity to show off her pipes. outside of that it's just a plain, underwhelming overwrought ballad. Then they feel the need to add in a fucking gospel choir. Because the song wasn't over the top enough. 
Shania Twain "Don't Be Stupid" (#6 US Country, #1 CAN Country, #40 US Pop)
I'll give Shania her fair share of shit for the overwrought ballad thing later on, so I might as well give her a measure of praise here while she's kind of earning it. Well, she's not earning it by herself I guess, since most of my goodwill towards this number comess from the nimble fiddling choir that props it up. Shania's doing her usual thing, which is to say making calculated attempts at imbuing the track with this whole "personality" thing that she used to possess at one point but can't quite form anymore - seriously, 'Relax...Max!'? That's the sound of someone trying so hard that comes around to sounding like she's not even trying.
Oh, and I'd be remiss to not mention the godawful remix that this got. It's so bad that it makes me like the original that much more by sheer virtue of it not deserving that kind of treatment. 
Tim McGraw "Just to See You Smile" (#1 US & CAN Country)
This is a gimme of a song. It could have been given to pretty much any contemporary of McGraw's and they'd have hit it out of the park. Hell, even when Will Oldham covered it a a piss-take on his More Revelry EP it shone through as a great piece of songwriting. So why do I feel that McGraw sells it a bit short? I could commend him for sitting back and letting the song shine through, but it winds up feeling a bit lacking because he doesn't do more with it. There's that moment in the second verse where he allows a bit of a laugh into his voice as he delivers the 'and given the chance I'd lie again' punchline, but other than that he seems to be on autopilot, which is rarely becoming of him. It also doesn't help that the arrangement here goes a bit overboard with showing just how many instruments can be added to a country song. I mean, that's probably the case on a lot of these songs but it stands out here for some reason. 
Chris Cummings "The Kind of Heart That Breaks" (#50 US Country, #1 CAN Country)
So pervasive is that textbook Nashville sound that even the Canadian detours I'll be taking at various points here feel like they were cranked out of the same machine as any other song in this project. I mean, look at this song in the abstract; pleasant, unobtrusive vocals, heavy steel guitar and dobro overlay, lots of production, lyrical twist that thinks its more clever than it actually is...it's all textbook Nashville 1998 despite it's much more northern pedigree. So it's only fitting that it's most notable feature is Cummings' delivery, which stands out as uniquely Canadian in a way. I think I mostly like that aspect because it underplays the aforementioned twist rather than underlining it the way I'd expect most others of this time to. Plus the odd hitch in his voice on the 'easy does it for goodness' sake' parts is the sort of personality-driven touch that I appreciate so much in this type of song. 
Brooks and Dunn "He's Got You" (#2 US Country, #3 CAN Country)
Consider this an overwrought ballad done right. All the pieces are there for me to absolutely hate this song, yet in practice it doens't come across as over the top or irritating. Credit the relatively light touch in the production, and - say it with me - the vocal performance which may be a lot less subtle than the ideal, but certainly doesn't go to the lengths that so many others would to make it artificially sad. Really this is right in B&D's wheelhouse, Dunn can sell the shit out of a broken-hearted screed and Brooks knows how to properly deploy a good harmony in these situations. They don't hit it out of the park, but given where it could have gone they pull it off admirably. 
Bruce Guthro "Walk This Road" (#1 CAN Country)
There's really no excuse for this to sound as faceless as it does. Given that right around this time Guthro was also part of long-running Celtic rockers Runrig it doesn't seem like much of a stretch to expect some sort of cross-contamination between that project and his solo work, but aside from a nice touch of accordion during the chorus there's nothing that sets this apart from the rest of the country landscape of this time. It's one of those songs that I'd label as being aggressively mediocre, seemingly making every effort to void itself of individuality so as to better meld in, and while it did get Guthro a hit up here it feels a bit unearned. 
Lila McCann "I Wanna Fall in Love" (#3 US Country, #1 CAN Country)
There's something about the way that the vocals on this one are mixed, especially during the chorus where the background vox seem to be mixed higher up than the ostensible lead vocals. Or it could be the fact that McCann is a bit of a cipher so the character that those backing vocals contains easily overpowers her. Yeah, once again we're in total faceless territory. It's easy to see why this was a hit in general, but there's never anything that indicates why it was a hit for McCann in particular. 
Anita Cochran and Steve Wariner "What If I Said" (#1 US & CAN Country, #59 US Pop)
OK, the vocal interplay on the chorus is the deciding factor here. Outside of that it's a standard issue duet, perfect for a Valentine's Day bump in the charts. That chorus though...that's the sort of touch I look for in this type of song, something that may be overly obvious to some extent but stands out by virtue of not sounding like anyhting else in this sphere at the time. 
George Strait "Round About Way" (#1 US & CAN Country)
Consistency is the watchword for Strait the same way that that serviceable is for Garth Brooks. Similarly, you know exactly what you're getting with every new Strait single, so you know exactly what this sounds like when I tell you that it's an upbeat ode to heartbreak. You know this even before I tell you that it quotes his own "Unwound" lyrically. And you know how good it is, because really he doesn't know how to be either better or worse at this point. 
Garth Brooks "She's Gonna Make It" (#2 US Country, #1 CAN Country)
Like I said, my ratings for Garth Brooks singles will, by and large, show you the hierarchy of the various types of songs that become hits on country radio. You now know how I feel about ballads. 
Clint Black "Nothin' But the Taillights" (#1 US & CAN Country)
The downside of the whole consistency thing I'm noticing here is that as I get deeper into the writeups, I find that I'm running out of things to say about the most average of the ranks here. And thus, we get to this particular song, which the only thing I can think to say about it is that it's perfectly serviceable, moderately clever - actually clever, not more clever than it thinks it is like 90% of songs of this ilk - upbeat country shit. Really outside of the chorus there's very little that stands out here, but that's OK since the chorus is all that really matters. 
Collin Raye "Little Red Rodeo" (#3 US Country, #1 CAN Country)
And then came the advent of Phil Vassar. Given how much emphasis I wind up placing on the performers it may seem odd that i'm all of a sudden turning my focus on to the songwriter at work here, but as much as Raye's performance works in the song's favour it's Vassar's songwriting that gives this a lot of its charm. He's also one of the few people in the Nashville songwriting game that has anything resembling his own personal touch to his material, so it's easier to give him praise than anyone else in this game. It's also no coincidence that three of the best songs I'm gonna be talking about here are all Vassar-penned. While this might be the lesser of those three, it's certianly the highlight of the hit parade so far. Or maybe it's just that the writing and delivery of the third verse's 'I'm a man, I'm in love and I'm desperate' that cinches my love for it.