’90s Country Songs That Got Us Through 2020

by Clayton Edwards

It’s been a long year. Some people would say that its’s the worst one they’ve had. 2020 has left us longing for a potentially brighter future or a fondly-remembered past. One of the best ways to look back at the past is by listening to the music that colored the moments. For many of us, that music is ’90s country. The decade was arguably a high point for the genre. There are so many memorable songs from some of country music’s biggest and brightest stars.

In this list, we’re going to look at some of the ’90s country songs that helped us get through the year. The songs will be divided by category. Just like 2020, this list has some happy, some sad, and plenty of booze. Without further adieu, let’s dig into the list.

’90s Country Tear Jerkers

Let’s get the sad songs out of the way so we can get into drinking, laughing, and feeling hopeful, shall we?

This year has been an emotional one for millions of people. Instead of ignoring the sadness or trying to turn it around, sometimes you just have to get down in it and live there. Sometimes you have to feel the depth of your lows to get to the other side of them. Sad songs are made for the moments where all you need in the world is a good, long, soul-cleansing cry. 90s country is full of those.

“High Lonesome Sound” (1996) Vince Gill, Allison Krauss, and Union Station

Let’s start off with something a little lighter. “High Lonesome Sound” is a pretty standard sad country song. It’s all about pining for a lover who isn’t there. That’s something many can relate to this year. Whether due to quarantine restrictions, breakups, or worse, there’s a lot of longing for someone going on in the world.

Not only is it a lighter song but also it’s a great way to encapsulate this part of the list. In the song, Gill sings, “When I’m lost in this ocean of darkness/ Not knowing which way I should turn/ And my eyes are filled with sadness/ Of knowing you’ll never return/ I want to hear that high lonesome sound.” We feel that.

“Go Rest High on That Mountain” (1994) Vince Gill

Can you have a list of sad songs without “Go Rest High on That Mountain” on it? Maybe, but you can’t include Vince Gill in a list of sad ’90s country songs and not add this song. It’s such a big, beautiful, majestic, and profoundly sad song.

The reason it’s so effective is that the lyrics aren’t just a poetic ode to some fictional person. Gill started writing the song after the death of Keith Whitley and finished it shortly after his brother died. The mourning in these lyrics is real.

“The Dance” (1990) Garth Brooks

This song is one of Garth Brooks’ biggest hits. It might also be one of the saddest songs he’s ever performed. It’s a real tear-jerker. It’s looking back at the pain of loss. He knows if he could go back and change things he could live a life without the heartbreak. However, he would have to give up the good times that defined that life before the pain. It’s a gorgeous song and Garth truly shines on the recording. but it’s tough to get through.

“Time Marches On” (1996) Tracy Lawrence

Let’s lighten it up a bit before moving on with the list. After “Go Rest High on That Mountain” and “The Dance” this one may not seem as sad. The song tells the story of a family in brief snapshots. The kids grow up and have their own lives. The parents get old and the dad dies while the mom slips into dementia. It’s not a great life but it’s a full one. The lyrics leave plenty of room for interpretation and introspection. It’s not a grand eulogy or mournful reminiscence, it’s just life. Sometimes, that’s all it takes.

’90s Country Drinking Songs

If there’s one lesson you can learn from country music in general it is that alcohol can be the cure for and cause of just about any problem. You can drink yourself single then drink until you forget your woes. Sometimes you just want to have a good time and the alcohol helps. Either way, ’90s country is full of great drinking songs.

Getting back to the structure of the list, sometimes when you’re deep down in that pool of sadness, the only flotation device you can find looks a whole lot like a whiskey glass. Other times it might look like a bottle, More specifically, it might look like a…

“Longneck Bottle” (1997) Garth Brooks

This is just a fun song. It’s one of those that really showcases the 90s country sound. The steel guitar and fiddle really bring this barroom song to life and the lyrics are great. It’s an upbeat song about a rounder who can’t seem to get that damned old longneck bottle to let go of his hand. You can’t go wrong with 90s Garth Brooks.

“Straight Tequila Night” (1992) John Anderson

“Straight Tequila Night” isn’t as fun as “Longneck Bottle” but, man, it’s a good one. It’s basically just about a woman who drinks at this bar all the time. Sometimes she’s there to have some fun but when she’s drinking straight tequila, she’s trying to forget her ex. It’s a good drinking song even if it’s not a raucous party tune.

“Watermelon Crawl” (1994) Tracy Byrd

Yeah, this song is goofy as hell. On the other hand, it checks a lot of boxes for great country songs in general. It also has that ’90s country sound. Firstly, it’s a story song. It’s all about coming upon this little middle of nowhere town that happens to be having a watermelon festival. The stars of the show are the Watermelon Queen and 100 gallons of sweet watermelon wine. It’s a good time and one hell of a tune to crank up while you’re putting a few drinks away.

“Bubba Shot the Jukebox” (1992) Mark Chesnutt

This song doesn’t specifically mention alcohol but it’s about being out at a bar with friends. So, we’ll call it a drinking song for this list. The song is about a guy named Bubba who hears a sad song on the jukebox. The song makes him cry right there at his table. So, he goes out to his truck, gets his old .45, and plugs the jukebox. It’s another great story song and after “The Dance” and “Go Rest High on That Mountain,” it’s relatable.

’90s Country Songs That Are Just Plain Fun

This is the next logical step. We’ve been sad, we got drunk, now it’s time to have a little fun. This is one of those years when all of the little bright moments seem that much bigger and brighter. It’s always important to have a good time, especially when everything is going to hell in a handbasket.

“Chattahoochee” (1992) Alan Jackson

This song is kind of like this section of the list. It’s all about looking back at the good old days and remembering some of the best times. Who isn’t doing that at least a couple of times a week this year? Jackson is singing about his old stomping grounds, how much he learned from them, and just generally having fond memories of his roots. While it has that distinct ’90s country sound, there are some little flourishes of bluegrass and Cajun-style music tossed in there as well. It’s a great nostalgic time all the way around.

“Should’ve Been a Cowboy” (1993) Toby Keith

There’s something so fun about listening to Toby Keith fantasizing about being a cowboy. The first verse talks about Matt Dillon and Miss Kitty from “Gunsmoke.” and their simmering love affair. He wraps the verse up with, “They never tied the knot, his heart wasn’t in it/He just stole a kiss and rode away/ He never hung is hat up at Kitty’s place.” then moves into the chorus which starts out, “I should’ve been a cowboy.”

It’s just a fun song about not settling down. It’s all about wanting to live a life of adventure just like an old western hero. As an added bonus, the music video to this track is pure ’90s gold.

“Achy Breaky Heart” (1992) Billy Ray Cyrus

Songs like this are the reason for the phrase “guilty pleasure.” It’s one of those songs that you don’t even want to admit to liking. It was, however, an inescapable part of ’90s country. It’s dumb and ridiculous but you can’t say it isn’t fun.

“Heads Carolina, Tails California” (1996) Jo Dee Messina

This song is just so good. It could have fit in several sections of this list. It’s a love song, it’s full of hope for the feature, but most importantly, it’s a great time. This is one of those that you can’t sit still while you’re listening to it. It’s an ode to spontaneity and being happy wherever you find yourself.

“Man! I Feel Like a Woman” (1997) Shania Twain

It doesn’t matter how big or burly you are or how impressive your beard is. When this comes on, everybody has a good time. Admit it, fellas, if no one is around and this song comes on, you sing along. ’90s country was full of amazingly talented women and Shania is near the top of that list. This song is a highlight of what made her popular at the time and why her career has lasted so long.

This is another one that has an awesome video. I really dig the backup band/dancers in this video. It’s a smart satire of all the scantily clad women in music videos that look like they were made from the same mold.

“Cash on the Barrelhead” (1999) Dolly Parton

At the end of the decade, Dolly Parton dropped an album called “The Grass Is Blue.” If the name didn’t give it away, it’s a bluegrass album. Dolly grew up in Appalachia and bluegrass was part of her life. Her doing a bluegrass album seems natural. This is her cover of an old Louvin Brothers tune. It’s hard to beat hearing Dolly do one of these old bluegrass outlaw songs. Between her energy and the band, this song is such a good time.

“Too Much Fun” (1995) Daryle Singletary

“No matter what they say I’ve done/ I ain’t never had too much fun.” The last line of the chorus sums this one up pretty well. It’s just a party song about getting drunk and raising hell. It’s got cops, bar fights, and all manners of good ol’ boy shenanigans. “Too Much Fun” could be a 90s country Friday afternoon anthem. Or Tuesday. Just whenever you want to tie one on and get a little wild.

Sure, this could have been in the drinking songs category but it’s really more about the wild times than the booze.

It’s Alright to Be Angry

This whole year has been stressful. Even little things like going to the grocery store have become a big deal. No one would fault you for looking at the world and being pissed off about it for one reason or another. Before we get into all the love and hope, let’s take a moment to be angry. Here’s a couple of ’90s country songs that go perfectly with a side of anger.

“I’d Love to Knock the Hell Out of You” (1999) Hank Williams Jr.

This is such a great song to play when you’re good and mad. It’s also the only one on the list with NSFW lyrics. That seems fitting, though, sometimes it’s hard to keep a clean mouth when you’re ready to let your hands do the talking.

In the song, Hank Jr. sings about just wanting to be left alone. He goes on to explain that he’s a peaceful man but it doesn’t take much to get him to the point of throwing hands. He closes the song out with some sound reasoning. “Now ladies and gentlemen. I know that David Allen Coe thought he had the Perfect Country and Western song. But you don’t have to talk about drinking, or prison, or dying, or divorce. All you have to talk about is the basic deep down human emotion we all feel inside. That’s why this is the perfect Country and Western Song.” Sounds fair.

“Friends in Low Places” (1990) Garth Brooks

There may be a law against compiling a list of ’90s country songs and not including this one. At least, there should be. It isn’t just an amazing sing-along song; it’s one of the most beautifully crafted middle fingers in musical history. It’s a song about petty revenge fueled by spite and probably a little jealousy. Where the Hank Jr. song is brash and violent, this one is more laid back. He knows who his real friends are and he’s fine with that. Thank you very much.

’90s Country Love Songs

Two things are constant in all eras of country music: sad songs and love songs. ’90s country has a wealth of great love songs.

Hard times can make love stronger. So, this year these love songs hit a little harder than usual.

“Dust on the Bottle” (1994) David Lee Murphy

Dust on the Bottle” is an amazing love song. Like the bottle of wine in the story, this song has just gotten better with age. The story follows a couple’s relationship from their first date into their old age. It’s beautiful.

“Tennessee Stud” (1994) Jonny Cash

Now, this isn’t your typical ’90s country song. It’s not even the typical love song. It is, however, a great tune and Johnny Cash does a stellar cover.

The song was originally recorded in 1959 by Jimmy Driftwood. It was bluegrass legend Doc Watson that made the song famous, though. He recorded several versions of the song. It’s about a young man who leaves Tennessee fleeing from his girlfriend’s dad and brother. His horse, the Tennessee Stud, is a sun-colored, green-eyed stallion. The horse is fast and strong. The song ends with the narrator reuniting with his lover. It’s a story about what a young man was willing to go through for the love of his lady.

“Check Yes or No” (1995)  George Strait

’90s country wouldn’t have been the same without the King, George Strait. This is one of his most iconic tracks and might be one of the sweetest love songs released during the decade. This one really speaks for itself.

“Strawberry Wine” (1996) Deana Carter

“Strawberry Wine” is a sweet and sultry ode to young love. It tells the story of a young woman’s first lover and their powerful connection. It was so poignant that she keeps coming back to the place where they spent time together just to look back on the fond memories. She questions in the song if it was “Him or the loss of my innocence” that made it so powerful. Either way, it’s a beautiful song.

Inspirational 90s Country Songs

I want to close this list out the way I hope you’re closing out 2020. With hope. It might feel like hope has been in short supply over the last ten months or so, but tomorrow is always a new day. We’ve got a new year coming at us like a speeding train. Let’s try to hop on it and ride it somewhere nice.

This is really a mixed bag of songs. They all either deal with hoping for a better future, being thankful for what you have or overcoming hardships. Either way, most of them hit a little different after the year we’ve had.

“Fancy” (1990) Reba McEntire

Reba McEntire is an absolute legend. This might be a cover but she made it her’ own from start to finish. “Fancy” is the ultimate story of overcoming adversity and playing the hand you’re dealt like a champion.

“Unanswered Prayers” (1990) Garth Brooks

The lesson in this song is that sometimes you don’t get what you want now because it’s not what you need. Some of the best gifts you can receive are unanswered prayers. It’s about being thankful. At the same time, it’s a way to look for the good in life that could be right around the corner. Even if that seems out of reach right now.

“Standing Outside the Fire” (1997) Garth Brooks

Back to back Garth Brooks songs? Yes. The word “anthem” gets thrown around pretty often. This song deserves it. It’s an ode to taking chances and going and getting what you want in life. “Life is not tried, it’s merely survived if you’re standing outside the fire.” That’s something we can get behind.

 “It Is What It Is” (1995) The Highwaymen

The Highwaymen is a group made up of country legends. Willie, Waylon, Kris, and Johnny are outlaw country royalty. They lived lives that will be talked about for decades after they’re all dead and gone. It’s safe to say that they can impart a little wisdom about life and living. This song is all about realizing who you are, who you want to be, and making changes. The lyric, “Oh, you can go on forever and make the same mistakes/ or you can stand up on your hind legs and change your fate/ Go on and do until you finally see/ What it is that it was that you don’t wanna be,” sums it up pretty well.

’90s Country Got Us Through 2020

It feels like this year should have been over eight months ago. ’90s country music really helped us tough it out. Whether we needed to be sad, drunk, or angry, we could count on this decade to provide the soundtrack. We can learn a lot about life, love, and hope from these songs. Some of them hit a little differently this year, but they’re all just as good as they were when they came out. Some of them are even better now.

Here’s to a new year full of hope, happiness, love, and just enough booze.