I still feel bad about how I played country on my top lists for the 90s. I breathed it between 1993-1997. I had CMT on all day for much of my youth. But I outgrew it and I’ll be blunt, I haven’t had the nostalgia rush you’d think to go back. I think a lot of it doesn’t hold up.
That’s because country music is to a great degree music for people without problems except love. And look, nobody is more about a good romance than me. But a lot of country is thin compared to even the good love songs in pop. Adulthood didn’t reach Nashville. Country is also weirdly unoriginal, either trend chasing or cover heavy. In fact, I wanted to do a no covers rule but too many songs I like are. So country is a mess.
I do want to be honest. I was going to do a top 30. Then 20. Then 15. Then back to 20 because I hit a cluster of songs I really love. It shrank because I was sickened by so much I saw. Even if I liked it I didn’t love it now. I considered cutting this. But there are songs on this list I had to cut for the main that bother me. I need to celebrate them if I can.
I also want to dissect my disdain for 90s country by what isn’t here. The big names made my main list often so I’m not adverse to Billy Ray or Garth. But you’ll see some pivotal names not here and a few of them will get excoriated.
But there was good. And I want to celebrate some interesting voices. I also want to pick apart some fascinating trends and problems.
I’m keeping to standard rules. One entry per artist. I’m only saying what I think. The following songs are ineligible due to already making earlier lists: Garth Brooks: Friends in Low Places. Billy Ray Cyrus: Achy Breaky Heart/In The Heart of a Woman. John Anderson: Bend It Until It Breaks. Clint Black: A Good Run of Bad Luck. Mary Chapin Carpenter: He Thinks He’ll Keep Her/Shut Up and Kiss Me. Pam Tillis: It’s Lonely Out There. Vince Gill: Worlds Apart. Sawyer Brown: This Night Won’t Last Forever. George Strait: Blue Clear Sky. Mavericks: Missing You.
We start with someone I think deserves the love he got. Alan Jackson was someone who was angry at what country was becoming. If you think I’m kidding, look at the songs he chose to do. Murder on Music Row is explicitly about this. Don’t Rock the Jukebox is a cry for listening to classic country. His songs often sounded just as vintage as country got. He did a number of great covers. And then there’s this.
20 Alan Jackson- Gone Country. Jackson says the song is a fun celebration of how country is accessible to anyone. Bullshit. The song is a sarcastic, bitter middle finger that got popular because nobody listens to the lyrics except the chorus. This is an attack on how people sell out and turn to country music when their careers crash. And Jackson just crushes it with his charming delivery. It’s not a joke he misunderstands. It’s honestly funnier for how light it is. Perfect start.
One thing I love about going through this list: I’ll be bringing up a lot of film credits I love. A lot of country singers crush acting. Believe me, there’s a big one coming. And let’s get an obvious name in. A cast member from Tremors. Star of her own beloved sitcom. And an important figure.
19 Reba McEntire- The Heart is a Lonely Hunter. If I was ranking this on canons of the 90s, Reba would be top 10. It’s by song. Her whole is better than her parts so I tried to nail it down to a perfect symbol. Reba McEntire wasn’t the face of country in the 90s. She was older. She sounded older. She looked older. She was 39 when this hit for example. And that’s why she was great. She sang about having lived a bit and you felt it. This song is about loneliness and desperation and someone 15 years her junior couldn’t have crushed it. Just a fine, adult song.
Country music was extremely manipulative in the 90s. Can I call that out? I hate Don’t Take The Girl. I hate basically every song where someone dies. I just find so much of country music pathetically exploiting easy subjects. If you’re going to hurt me, earn it. And that brings me to a song named after and referencing my current location.
18 Collin Raye- Little Rock. This one is good. The thing is the song deals with a real issue. Alcoholism is a genuinely sad topic and the song is honest about how painful it is. The lyrics depict someone struggling with the issue. They want to relapse due to loneliness. Hell they might. But they’re trying. Raye is probably the worst artist on this list honestly but he interprets the song well. It’s not a fun song but of the 90s weepies in the genre, the best.
I hate Lonestar. I’m Already There is wretched tearjerking crap. Amazed is a theft of Bryan Adams’ Please Forgive Me. To me they’re a symbol of what country became. Accented pop. And they didn’t start this way. I like Tequila Talking. I love this song.
17 Lonestar- No News. A simple premise. A man’s lover disappears. He wonders where she is. It’s a good joke. The lyrics crush it. The performance is in on the joke. Again, country can be funny. It’s funny that the band crossed over with glurge because this feels perfect next to Everything Falls Apart. It’s fast too. Just a long series of guesses that get incredibly weird. Good enough.
I do these lists by picking the songs one day then ranking as I write later. And I’m realizing how good this list is when I’m hitting this song at 16. Classic country has a sound. It’s George Strait.
16 George Strait- Carrying Your Love With Me. Again, older counts. George Strait had well over a decade as a hitmaker before this song. And he would exit the decade an elder statesman. This song is proof of my. Again, a simple idea of a man who must travel telling the woman he loves that she never leaves his mind. From a boy like Clay Walker or Tim McGraw, it means nothing. Strait sounds tired but he means it. It’s just sweet.
From age to the youngest artist on this list. But not a novelty. LeAnn Rimes was written off as a freak at first. Time killed that. She has a one of a kind instrument she’s taken care of. She’s an old school country singer and she sounds like it. I could pick so many songs. I mean she made my nemesis Diane Warren sound good! But I’m going to the start.
15 LeAnn Rimes- Blue. Here’s the thing, this is an old person’s country song. If you didn’t know she was young, you might not even crack it. She sounds mature. And she crushes the delivery. That deep, sad, mournful delivery. The song itself is old school Patsy Cline music. Kind of exactly for me. It’s from 1996 but it belongs to 1966. Retro did very poorly in this decade. But this is choice.
14 and 13 are kind of the same song. They exemplify why country did actually matter. It was a place to deal with real emotions like heartbreak. And these two songs both express the same idea. That you’ll be better off when you’re over the situation. First up, Randy Travis, a man who was an early country heartthrob and a phenomenal voice. His life is a tragic one filled with alcoholism, violence, rumors that definitely didn’t help his career, and illness that eventually robbed him of his gift. Gifted singer though.
14 Randy Travis- Out of My Bones. I want it noted we’re up to 14 and not one singer has a credit for writing. This is a great example of why I’m not bothered. This is just a good song about wanting to get over heartbreak that was finely written and performed. Travis was a great interpreter. His complicated life seeps into this song by accident almost by fate. He sounds grizzled. The result is a beautiful little song about what we do to move on. Just nice.
Country is all about heartbreak. So it really is rare to find a song that truly sounds triumphant after a breakup. Me being me, there’s at least one more after this one on the list. That song looks at a relationship that ended much more poorly. This one? Well let me jump in.
13 Tracy Lawrence- Better Man, Better Off. How many songs about a breakup are this warm about the relationship? Seriously, half the song is about how good it was. But I think that’s why this song is great. Tracy Lawrence never did catch on. He was talented. Had a few good years. He’s forgotten now. But he was as good as it got. Here he’s strong but not too strong. He’s honest. He delivers the lyrics so well. And the lyrics are great. It feels like it was written the day after a breakup rant and you’re realizing she’s not the devil. Just a fine song.
Finally, at #12, a song actually written by the singer. There were many studio manufactured groups in the 90s. Guys who couldn’t cut it on their own but worked well together. None better than Brooks & Dunn. Kix Brooks was a sublime guitarist. Ronnie Dunn a fine vocalist and a longtime Nashville songwriter who finally broke in. They had a great canon. Some great ballads. But no, I like the fun.
12 Brooks And Dunn- Little Miss Honky Tonk. Brooks & Dunn probably had the highest ratio of chart success to works they penned themselves. This isn’t their big one but it showcases their gift. The song is a goofy joke song about a guy just in awe of how hot his girlfriend is. But isn’t that kind of a great sentiment? It’s a lot of fun and sweetly sexy in a way country doesn’t get. The production is immaculate too. I love these dudes. My Maria almost made the list and only missed it because I wanted to shout out Ronnie Dunn’s writing skills.
I end this half of the list on a group that shouldn’t have done well in the 1990s and were done after 1997. But they did great while they were successful. Sawyer Brown is true country. So much so I’ll put a ballad on. Because this is a good one.
11 Sawyer Brown- Treat Her Right. Compared to the list to come, this is such a low key song. It’s a simple advice song and country has many of them. This is a good one. I think again, it comes down to age. Mark Millar sounds like a grown man speaking, not a boy like so many of his peers. He knows what he’s saying. The song is also so simple. Piano driven country is far from rare but I love it here. Not a big song but I prefer it to many hits.
John Berry feels like the last plane out on a very specific type of country singer. He wasn’t attractive. He wasn’t a great vocalist. He was just fine. But he broke through anyway. I think that’s on his songs. Because damn did he have the songs.
10 John Berry- Standing On The Edge Of Goodbye. Berry cowrote this, the only song he cowrote on the album, and it’s a beast. A song about the edge of a relationship ending. We’ve all been there. It’s a very specific hell. Berry nails it. His delivery was always a bit strong where it didn’t fit but here he just goes for it and the production meets him. Will this relationship survive? It doesn’t feel likely. But they’ll try. The chorus kills too. This is a painful cry.
I want to be clear. I’m not mad at country for how pretty it got. That’s what happens when you get popular. You get sexier. I’m at peace with that. I’m not mad at the pretty voices either. I get pushing Tanya Tucker aside for Faith Hill. One of those made the pop charts three times. But I like my rasp. I like my age. Like here.
9 Kathy Mattea- Walking Away A Winner. Cowriter Bob DiPiero made the list multiple times in 1996 and he scores another notch here. This is the triumphant cry song. It’s good to have songs like this one. It sounds bold and proud. Kathy Mattea had a killer voice. She sounded a bit rough hewn but also had a lovely texture. Admittedly the gambling metaphor is a bit tired. But this song makes it work because you get the feeling she has played this game before. It’s very effective.
My latest song comes from 1999. And it’s a damn fine one. Traditional quality country was still around. Still is. Here’s an example from a guy who went on to cover Vertical Horizon. And honestly improved the song in the cover.
8 Gary Allan- Smoke Rings in the Dark. A song about unrequited love. Great topic. Not enough of those. And this is a good one. Allan wasn’t a writer but he interprets this song great. What I love is how honest it is about the topic. You can try to make someone love you but you won’t. It’s not going to happen. I like how this is honest and accepting. It’s not an incel song. Allan sounds so good. What a great grizzled voice.
Time to touch on one of my favorite artists. Pam Tillis had a nice run. I could’ve put a number of songs here. I think her skill was she had just a nice voice. She was a good interpreter. She had a gift for sad songs. She was a comforting artist to listen to when life was painful. So here’s a nice song.
7 Pam Tillis- In Between Dances. Consider this a sentimental pick. Other songs were bigger to me. But this one mattered. I get why. It’s about grief and the terror of opening up. It’s beautiful. The metaphor of being between dances, is it even a metaphor? I mean that’s basically literally what the song is about: being between partners. Dance, romance, all the same. And Tillis never sounded better. She did a lot of heartache songs. I get the feeling she knew it. Only one unhappy marriage listed on Wikipedia.
There was a weird moment in the 1990s where country songs were sold as R&B songs as well. And I mean moment. The same group All-4-One covered two songs recorded by the same artist John Michael Montgomery. I like the pop versions. I don’t like the country versions. But Montgomery has one very important song to me. On the list.
6 John Michael Montgomery- Long As I Live. Sometimes it’s all in the execution. This is a dark, sad song. Except it isn’t. It’s a sweet love song. But it sounds so mournful and pained. There’s a real sense you’re not listening to a successful relationship so much as one that barely survived. The strings here gut you. The whole instrumentation actually just sounds dark and wrong. I can’t explain why. This song just drips with grief. Love it.
One last time, I’m looking at a woman whose career died when the Shania Effect hit and country women got a lot prettier. At least that’s the easy way to explain the end of the career of Patty Loveless. In truth, the big thing that happened was country got a lot less songwriter driven and a lot more image driven. Industry fronts like Loveless, and make no mistake her push was all industry, couldn’t compete because they didn’t fit this era. She was perfectly fine looking but not exactly modern and her voice didn’t stand out. But she had one perfect song.
5 Patty Loveless- Blame it on Your Heart. There is not a time in country music this would’ve been a flop. Even now I think it could still work. It’s got a perfect hook. That list of adjectives is just so perfectly crafted. Each one is worse than the other. It builds. It’s a perfect chorus to sing along to. The craft is perfect. And the verses are a bullet. Loveless does a great job with it too, to be fair. It’s just such an angry song. The production sparkles too. For sheer perfect songwriting, listen to this. Oh, and look up The Mavericks covering it. They kill it with a very Latin flair.
Top 4. And we come to our highest singer/songwriter. Which is funny because if anyone makes sense to be an image driven front, it’s the best actor on the list. Dwight Yoakum is an incredible actor in films like Panic Room, Sling Blade, and Logan Lucky. He’s in the opening of Wedding Crashers and scores a few laughs. So I’m happy to have him on the lust. I’m also happy to admire another perfectly written song.
4 Dwight Yoakum- Fast As You. A song about a guy mad his girlfriend is abusive and controlling is actually kind of shocking. Like this is not typical subject matter and even less typical that it’s played light. But it’s so well done. Yoakum gets all the credit here both as a writer and as a performer because he’s a star at both. The lyrics are phenomenal and piercing. His vocals are seductive and intense. The man is a titan at performing and he really does bring the same energy he would later bring to his acting here. And can I stress the guitar work here is incredible if you’re a fan.
I don’t plan this but one man has two spots in the top 3. Back to back at that. I’ll cover the writer on this spot. Dennis Linde is probably the most influential country songwriter ever that you don’t know the name of. John Deere Green. Goodbye Earl. It Sure Is Monday. Bubba Shot the Jukebox. Burning Love! The number of songs he wrote that were huge hits in the genre can’t be counted here. Well here’s one.
3 Sammy Kershaw- Queen of My Double Wide Trailer. This so narrowly missed the 1993 list I’m amazed it did. It’s a perfect country joke song. It runs through so many cliches to where the video even mocks the song for being that cliched, making it the perfect symbol of country in 1993. But they’re great cliches so I let it go. This is also heavily on Kershaw, whose Louisiana vocals are one of a kind. It’s a funny song that basically gives up the game. Country music was changing. Kershaw would actually ride it out a good distance despite not fitting. The perfect bridge song in country.
Oh Garth, how do I address you. I have complicated feelings about Garth Brooks. I was a huge fan growing up but I’m not one now that I’m better versed in music. He’s a fine singer but in the technical sense. He’s deeply uninteresting actually as a performer. He doesn’t write. He doesn’t play an instrument. And yet he became big because he had the songs and I guess had the presence. It doesn’t matter why he broke. He had the songs. And he scores the runner up spot.
2 Garth Brooks- Callin’ Baton Rouge. On a songwriting level, this song is bizarre and I think that’s why it speaks to me. It’s basically one verse, a chorus, a bridge, and a chorus. Obviously it’s short. But it’s perfect. I think the key is Brooks loves the hell out of the song. It’s a cover of a New Grass Revival song and he got them to play on it. Brooks has rarely sounded as alive as he does here. The use of Sam Bush’s fiddle and Bela Fleck on banjo makes it sound unlike anything in Brooks’ fairly anodyne catalog. This is as alive as country gets. It still fires me up. I’m glad it goes to number 2.
Number one is the biggest omission in my entire history of writing on music. I look at my 1994 list and not only do I not know how this missed the list. Maybe topped it would’ve been more accurate. It’s just a perfect song. And it comes from one of the best groups to do it. No further ado.
1 Mavericks- What a Crying Shame. I love songs that have a subtext of “the singer is the asshole” and this is as good as they get. The lyrics are one long whine basically and they’re so sarcastic the song pops for it. Raul Malo has one of the greatest natural voices in country and he uses every note. He sounds so smooth and cool even while being a giant jerk. The song also has immaculate production. The Mavericks have several guitarists and that gives them a unique sound. The guitar here is seriously 10/10. I just can’t praise this song enough. The best song I’ve missed.
A Flickering Life 