The Best Hit Songs Of 2000

‘Best Hit Songs’ is a recurring (and lighthearted) feature where I take a look back at the “best” hit songs of a particular year. It’s the only feature I operate where Wikipedia is a handy source, and to qualify, songs have to have a top 20 placement or higher. This time around, we’re taking a trip back to 2000. To see what years I’ve already written about, click here or scroll to the bottom of this page.

I wanted to post something fun and harmless for “Super Bowl Monday,” but this may prove to be more controversial than I initially thought.

2000 was a transitional year for country music, in more ways than one; a literal turn of the decade, and and an offering of what was to come. Garth Brooks and Shania Twain would never be forgotten in country music history, but their respective reigns had lost steam by this point; and country music wouldn’t see another boom period like that again anyway, at least not as of this writing. As such, it’s not surprising that, when looking back specifically at 2000, country music felt “safe” – a melting pot of easy-listening ballads, smoother production and story songs that blatantly aimed to tug at the heartstrings, often in the most cloying ways possible.

And as the sound of my childhood, maybe I’m biased in saying it sometimes worked; but it’s not unfair to say the genre lacked a clear sense of direction during this time, defined more by individual artists than by trends (think the Dixie Chicks or Taylor Swift). At any rate, we’re not here to approach that subject; we’re here to discuss the best hit songs of 2000. Filling out the top 10 was harder than it’s been in other years, but there’s still room for a few honorable mentions:

  • Dixie Chicks – “Cowboy Take Me Away” (It’s not the group’s most stunning lyric, but it’s hard not to love that instrumental bedrock.)
  • Montgomery Gentry – “Daddy Won’t Sell The Farm” (I just discussed with a friend yesterday how Montgomery Gentry could sing about well-worn topics without resorting to clichés. There’s a bit of dark humor imbued here, and the duo damn well owns the sentiment shown.)
  • Reba McEntire – “What Do You Say” (This is, more or less, the quintessential type of mawkish song that ruled the turn of the decade, as I said before. I think this song works better than other examples by offering a more cutting message, but it’s still a bit too disconnected to work as a whole.)

On with the list!

No. 10 – Phil Vassar, “Carlene”

I won’t say the bulk of Phil Vassar’s material sticks out much in the mind, but his best material showed a strong sense of melody and true songwriting chops. His debut single “Carlene” set him on the right track: the interplay of the fiddle and piano creates an undeniably jubilant mood with a fun, memorable chorus; and there’s a more interesting story here than what initially meets the eye. Both characters left their town to see the world only to chase their own paths, likely disappointing anyone who thought they were destined for more. It’s a lighthearted story of two wayward souls coming together where the characters have a surprising amount of personality.

No. 9 – Tim McGraw, “My Next Thirty Years”

I guess we’re not done talking about Phil Vassar. Anyway, “My Next Thirty Years” has always felt perfectly suited for Tim McGraw. He was already an established act on country radio by the 2000s, and was enjoying that success while also starting a family with fellow superstar Faith Hill. “My Next Thirty Years,” therefore, is a perfect dividing point, where McGraw looks back at a younger version of himself he can appreciate, but can no longer relate to; meanwhile looking at the future with confidence. Again, it’s lighthearted optimism that was the theme of the year, but McGraw’s easy-going demeanor manages to keep it grounded. We’ll just forget his next thirty years included “Truck Yeah,” “Looking For That Girl” and “Way Down.”

No. 8 – Brad Paisley, “Me Neither”

“Me Neither” was sort of perfect for this point in Brad Paisley’s career; he was the shy, quirky newcomer who subtly imbued humor into his material that helped him stand out. He’d abuse that power at times later on this decade, but “Me Neither” is a quiet standout in his discography – a twangy, shuffling tune that finds an awkwardly shy Paisley trip over himself trying to impress a woman to hilarious degrees, all of which Paisley slyly underplays. And that fake ending is, quite simply, brilliant, and a fantastic instrumental showcase. Do you think there’s anything wrong with it? Yeah, me neither.

No. 7 – Lee Ann Womack, “I Hope You Dance (feat. Sons Of The Desert)”

This is either a perfectly fine choice or one you’ll roll your eyes at, and I understand either reaction. I’ll admit it sticks out like a sore thumb in Womack’s discography, and, commercial accolades aside, probably caused more harm than good to Womack’s traditional artistic brand early on. But as I said in the introduction, this brand of feel-good inspirational material can sometimes work. Despite the predictable sentiment, it’s a well-written song, and Womack never sells this with anything less than serious, grounded conviction – which does matter. Sure, it’s a song basically birthed from a sign of the times, but it’s earned its place in Womack’s extensive catalog of great songs.

No. 6 – Clay Walker, “The Chain Of Love”

OK, so it’s another example of a song possibly going overboard with its sentimentality – what can I say? “The Chain Of Love” may carry one heck of a coincidence with its story, but it’s still a nice twist anyway; and the fact that it’s grounded more in simplistic storytelling than easy clichés fits more in line with the genre, too. The production is surprisingly restrained and lets the story take hold, and Clay Walker is a capable personality to carry this track. Simple, kind of corny, yet endearing nonetheless.

No. 5 – Travis Tritt, “Best Of Intentions”

Aside from aforementioned cheesy sentimentalities, 2000 was also a heavy year for piano leads in country music, all of which were meant to beat listeners over the head with said sentimentalities. “Best Of Intentions” is a fake-out, in that sense. It’s a tale of devotion, but one that never actually materializes, putting a twist on it that separates it from similar songs of the era opting for that fairy tale ending. For Tritt, too, it was his huge comeback single, and while his upbeat material is strong, it’s his tender ballads that showcase his vocal abilities best.

No. 4 – Eric Heatherly, “Flowers On The Wall”

Yes, it’s a cover of the Statler Brothers song, but one that’s vastly different from the original. Oddly enough, too, it was Eric Heatherly’s debut single, and only hit. Unlike the folk styling of the original, Heatherly’s version plays to much darker territory, with that lingering drum beat and moodier bassline giving the song a more ominous, meatier presence. It plays to the pure paranoia of it all so well, and even if Heatherly couldn’t duplicate the harmonies of the original, he makes it up for it by leaning into the character’s role. A very odd choice for a debut single, cover or not, but one that Heatherly managed to sell with his own spin.

No. 3 – John Michael Montgomery, “The Little Girl (feat. Alison Krauss & Dan Tyminski)”

“I Hope You Dance” was one pick I knew would be slightly divisive; this is the other one. Not to say this isn’t aiming for a specific emotion like other songs of the year, but it goes through a lot of obstacles to get there, including domestic, substance, and alcohol abuse. I will say the religious overtones do feel forced and slightly pandering, especially in the last verse; but John Michael Montgomery surprisingly underplays the emotion of the track to an effective degree. And when you have a great voice like his matched against Alison Krauss and Dan Tyminski, especially when it’s backed by tender instrumentation, “The Little Girl” hits hard even without even having to try.

No. 2 – Dixie Chicks, “Goodbye Earl”

I’ve never really known what to make of “Goodbye Earl.” It’s a murder ballad, but it’s not aiming for the same raw, visceral undertones of country music’s most notable examples. And I don’t really want to call it a lighthearted tale of dark humor when domestic abuse is nothing to laugh at; but I don’t know, maybe it’s best to just not think of it as anything more than songwriter Dennis Linde finally killing off his infamous “Earl” character. Regardless, it’s hard not to appreciate the Thelma & Louise absurdity of this song, especially when it features cowbell of all things.

No. 1 – Gary Allan, “Smoke Rings In The Dark”

Country music changed in 2000, and so did Gary Allan, albeit in much different respects. Allan’s late ‘90s material was always enjoyable, but he could never rise above being another indistinguishable hat act; that is, until “Smoke Rings In The Dark” came along. There isn’t much not to love about this song: the sweeping, dreary atmosphere; the liquid strums of guitar or pedal steel lingering faintly to great degree; or Allan’s tired resignation that things are over between him and his significant other, with the relationship simply running its natural course. It’s a dark wonder of a track, and one where Allan unearthed his potential to craft songs painting him as the wandering loner – not an aimless drifter, but rather someone who needs to follow his own path. “Smoke Rings To The Dark” is one of Allan’s best showcases of that, to this day.