Only A True Cowboy Can Match These Country Songs To The Singer

Cards out on the table here, I really have never been the biggest fan of country music through most of my life. I can recall morning after morning when I would wake to the sound of that ridiculous twang thanks to the country station my parents had on the radio day after day for year after year while I was living at home. It really put me off of country music for a long time.

Of course, then I started playing bars as a musician and it seems that no matter where one travels, people always want to hear some sort of country music. I went out of my way to find country songs that I enjoyed listening to and that I enjoyed playing. I did also learn some I wasn't too fond of, but the people want what they want, I guess.

Now, the list of 50 country songs below has fewer of the songs that I play but for someone who likes to think of themselves as a true fan of country; a true cowboy or cowgirl, these 50 songs are a great test of character. Who here really thinks that they have what it takes to match all of these country songs to their rightful singer? Only a true cowboy can!

Question 1

Rhinestone Cowboy

"Like a rhinestone cowboy / Riding out on a horse in a star-spangled rodeo / Like a rhinestone cowboy / Getting cards and letters from people I don't even know / And offers comin' over the phone." I really did not need to add the lyrics here for people to know who did this song. Or at least I should not have needed to. That being said...this guy was so star-spangled awesome with his country writing that there is just no way that I could resist putting a few lines in here. There was a great documentary about this guy on Netflix a few years back.

Question 2

I Walk The Line

"Because you're mine / I walk the line." I really do not think that this song needs much more of a clue or hint for anyone here to know who it is that wrote and/or sang it. I mean...it is pretty straight forward. If nothing else, this is pretty much a giveaway for those people who are finding this quiz too hard and need a confidence booster so they can feel like a real cowboy or cowgirl. I mean, there really should not be any excuse here. I'll admit I'm not a cowboy, but I definitely know this tune, for sure.

Question 3

Dear John

"Dear John, I see it all now that you're gone / Don't you think I was too young to be messed with? / The girl in the dress, cried the whole way home / Dear John, I see it all, now it was wrong / Don't you think nineteen is too young / To be played by your dark twisted games, when I loved you so? / I should've known." This singer has simply made a whole business out of writing albums dedicated to relationships that she's been through. I mean, that's how she made it big in the first place. She pretty well just writes break up albums

Question 4

Chicken Fried

"Well I was raised underneath the shade of a Georgia pine / And that's home you know / Sweet tea pecan pie and homemade wine / Where the peaches grow / And my house it's not much to talk about / But it's filled with love that's grown in southern ground / And a little bit of chicken fried." Well, if nothing else, this is a really fun song. And I don't think that it's meant for much more than that. I mean, there is pretty well every reason why it is nice to relax with an actual fun country song. They're usually sad.

Question 5

Any Man Of Mine

Who here remembers some pretty repetitive country music from the 90s? If so, then this song should be a pretty easy one to guess. I mean, this song is still played all the time on country stations all over. And while this singer might be from further up in the great white north than I am, that doesn't mean that she isn't still pretty popular down in the south. She has certainly made a huge name for herself and she is known and loved the world over. And that is saying a lot when one's country music can reach past this continent.

Question 6

Friends in Low Places

Here is a song that I spend every single bar gig of mine trying to avoid. Of course, I live at what is called the "gateway to the north", and there is a whole ton of country music fans here who love nothing more than a good 'ol sing-song with "classics" that everyone knows, even if not everyone like them. This is definitely one of those most popular of bar songs that everyone can sing to, even if they really would rather not. This song was written by one of the most prolific country music writers out there too, so this should be easy.

Question 7

Say Something

This is probably one of the newest songs on this list and it would be a very interesting one to think about as well because it may or may not feature a singer who is very VERY far from country music. However, a new album of said singer was supposed to be something about getting back to the woods and there was an interesting pop country song that followed and featured one of the greatest country musicians out there today. And that is a musician I actually have no qualms speaking well of. I probably play more of his songs than any other country singer's.

Question 8

The Dance

Only a country singer could take a song about a beautiful dance that they shared with a lover and use it to tell the story of how their relationship just didn't work out and ended in some tragic way. It's only a few steps removed from singing about the truck having a flat or using car seats as a couch. Either way though, this particular country singer just so happens to be one of the wealthiest of all the down-home musicians. I'm actually pretty sure this one is the most successful, in terms of money, over any other country musician out there.

Question 9

Carrying Your Love With Me

"Baby all I've got is this beat-up leather bag. And everything I own don't fill up half. But don't you worry 'bout the way I pack. All I care about is getting back real soon. A goodbye kiss is all I need from you. 'Cause I'm carrying your love with me." It is never a dull moment when it comes to relatively sweet songs about missing a lover. At least this one seems to have a sort of happy vibe to it in that this singer will eventually make it home to their loved one and it is that very love that keeps them going.

Question 10

Achy Breaky Heart

This song. This song better get stuck in everyone else's head as well because this song just hurts my brain in ways that I think people will never quite understand. See, growing up in a very small town with farmland and forest and trails all around sort of led to a lot of country fans. My parents used to hold dances time and again to raise funds for the Children's Wish Foundation...and I promise every quiz-taker here that this incredibly annoying song played at every single one of those dances. The only saving grace? I at least got to show off my dance skills to the Grease Megamix before the end of the night.

Question 11

Simple

"The way your fingers fit in mine It's five plus five, not rocket science. This day in time, that's hard to find It's true. The road we're on ain't a traffic jam. It's a Sunday drive on a piece of land. It's paradise as long as I'm with you." Well, I can't really fault the singer of this country song given that the title of the song is "Simple". And so to are all the lyrics, it would seem. It comes across as a pretty simple song and that is sort of the life of country music. There aren't too many complicated tunes out there.

Question 12

Cry Pretty

"You can pretty lie and say it's okay. You can pretty smile and just walk away. Pretty much fake your way through anything. But you can't cry pretty" There is something about this song that is pretty well wholly saddening. I mean, it is nothing more than the singer talking about how they can fake their way through life however they need to in order to keep up a sham of a relationship but they just can't make crying appealing. And hey, at least they're not wrong. I mean...I'm sure people here have seen other people cry. It really isn't pretty.

Question 13

I Cross My Heart

"I cross my heart and promise to give all I've got to give. To make all your dreams come true. In all the world you'll never find a love as true as mine." Some of these songs have some pretty interesting lyrics and an even more interesting idea of what a rhyme scheme is but that is all beside the point. The point here is to name the singer who performs this song. I think the title might be a little cliched, but what is country music if not an incredible amount of cliches one on top of the other?

Question 14

The Thunder Rolls

I am not even going to grace this question with even a sliver of the lyrics. Why? Because anyone who knows even the tiniest bit about country music should very easily be able to determine just who it is who sings this tune. My parents went to go see this very musician only about two years ago. They brought me back a bunch of guitar picks from the swag tables. I still have them too, but haven't used them. At any rate, this guy is one of the biggest names in country and there should be no mistaking this if the quiz-taker is truly a cowboy.

Question 15

Drowns The Whiskey

"All the folks down in Lynchburg, Tennessee / Been working hard for good ol' boys like me / I don't wanna be the one to tell 'em / That stuff that they've been selling / Ain't working like it should / But I damn sure wish it would". This is actually a song that I just started learning the other night...and finished learning the other night. The great thing about learning country songs for gigs is that there really are not all that many difficult tunes out there to pick up. Not unless digging into bluegrass or something of the like.

Question 16

Don't Take The Girl

"Johnny's daddy was taking him fishin' / When he was eight years old / Little girl came through the front gate / Holdin' a fishin' pole / His dad looked down and smiled / He said, "We can't leave her behind" / "Son, I know you don't want her to go / But someday you'll change your mind"." Well, here is a very sad song, indeed. It's all about how this guy holds on to this girl for years and years. But it ends with him praying when the girl is giving birth to their kid because the doctor says "she's fading fast". No idea how it ends though...

Question 17

Should've Been A Cowboy

"I bet you've never heard ol' Marshal Dillon say / Miss Kitty, have you ever thought of runnin' away? / Settlin' down, would you marry me / If I asked you twice and begged you, pretty please? / She'd have said, "Yes", in a New York minute." This guy sings about Marshal Dillon and all I can think about is Bob Dylan and then I don't really bother to think much more of the song. That being said, let's think about who might bring up Marshal Dillon in a song of their own. Any guesses just who this country singer could be?

Question 18

Mercy

"Mercy / Why you gotta show up lookin' so good just to hurt me? / Why you wanna stop this whole damn world from turning? / Mercy / Why you hanging on so tight if this ain't working? / Why you wanna stop this flame if it's still burning? / Cause it's still burning" This song is all about a man who is pretty well just waiting for a girl to make up her mind about whether or not she even really loves and/or wants to be with him. There is almost always a sad angle to pretty well every country song.

Question 19

Chattahoochee

"Yeah way down yonder on the Chattahoochee / Never knew how much that muddy water meant to me / But I learned how to swim and I learned who I was / A lot about livin' and a little 'bout love." This song was a huge hit in the 90s. I know because I heard it almost every other morning on that very same radio station my parents would never turn the dial away from. I also know because this song is still played all the time and I still manage to remember how it goes when the title is brought up.

Question 20

Boot Scootin' Boogie

"Yeah heel toe do si do / Come on baby let's go boot scootin' / Oh cadillac blackjack baby meet me out back / We're gonna boogie / Oh, get down, turn around, go to town / Boot scootin' boogie." This song gets stuck in my head way more than I would like it to. Anyone who brings this song up is ultimately responsible for hours of my brain being hammered with these lyrics. And since I just brought it up to everyone here, I can only blame myself for the ensuing madness. Either way though, this is a country boy hit for all those cowboys out there.

Question 21

Desperate Man

"I've seen the Joshua Tree / Got down on my knees" This is definitely an interesting song with shades of cultural insensitivity all throughout the lyrics, but that is not wholly unusual in country music, I've discovered. Either way though, this clearly tells the story of a man who has nothing left and is essentially living on a prayer of some sort or another. This country singer is actually fairly new to the game compared to some of the artists on this list.

Question 22

Life Changes

"Ain't it funny how life changes / You wake up, ain't nothing the same and life changes / You can't stop it, just hop on the train and / You never know what's gonna happen / You make your plans and you hear god laughing." Well, there is no surprise here that there is a bit of religious reference in this tune. It's one of the biggest plot drivers in all of country music, it seems. This particular country singer was responsible for the first dance at my cousin's wedding this past summer. That's not to say the musician was there. But the mp3 of the song was pretty good.

Question 23

Sunrise, Sunburn, Sunset

"Sunrise, sunburn, sunset, repeat / Moonlight, all night, crashing into me / Nothing will ever be easy as you and me / Tangled up with nowhere to be / Just sunrise, sunburn, sunset, repeat." I know that most stories are love stories in one way or another but country music has a way of making love stories completely obvious and pretty simple. But that is good, in a way. The majority of people who listen to country music will not have to bother thinking too hard about it. They just know the meaning right away because it is right there for them.

Question 24

Unanswered Prayers

"Just the other night, at a hometown football game / My wife and I ran into my old high school flame / And as I introduced them, the past came back to me / And I couldn't help but think of the way things used to be." Well, this song is all about a former lover coming back into a guy's life while he is with his wife and he can't help but wonder how things could have been. Of course, and thankfully for the wife, after chatting a bit with that old flame, he discovered he made the right choice after all.

Question 25

Here's A Quarter (Call Somone Who Cares)

"You say you were wrong to ever leave me alone / Now you're sorry, you're lonesome and scared / And you say you'd be happy if I you could just come back home / Well, here's a quarter, call someone who cares." This tune is actually pretty harsh, in a way. But understandably so. It's all about a guy who's former lover seems to be trying to pick him up again but he is just having nothing to do with her because of all the hurt that she has caused him. He's moved on and she needs to do what the title suggests...

Question 26

Don't Rock the Jukebox

"Don't rock the jukebox / I want to hear some Jones / 'Cause my heart ain't ready / For the Rolling Stones / I don't feel like rockin' / Since my baby's gone / So don't rock the jukebox / Play me a country song." Another country song that sticks in my head. Ugh. This will be on my mind all day now. This is an interesting song that pretty well just gives away the whole notion that country music is for sad people. This guy isn't ready to listen to rock because his love left him, so he wants to hear country...

Question 27

Fancy

"Standin' back from the lookin' glass / There stood a woman where a half gown kid had stood / She said here's your one chance Fancy don't let me down / Here's your one chance Fancy don't let me down." The country music experience can often be very different for guys and girls. I mean...take this song. It's all about a mother spending the last of her money on her daughter to get her dolled up to make sure that she finds a man somewhere out there. I think that is pretty old school, sad, and maybe a bit too hopeful.

Question 28

Strawberry Wine

"Like strawberry wine and seventeen / The hot July moon saw everything / My first taste of love oh bittersweet / Green on the vine / Like strawberry wine." Now, I have to give credit here where credit is due. The comparison of new love to strawberry wine is a level of sophistication I really did not expect to hear in a country music song. Typically, it's all about beer or whisky. That's pretty well all people get. But this was a bit of a turning point. And it really didn't bother this singer, I'm sure, that this song was a hit!

Question 29

Meet In The Middle

"We'd gain a lot of ground / 'Cause we'd both give a little / And their ain't no road too long / When you meet in the middle." Alright, to be fair here, this song is a pretty cute country song. But I cannot help but point out that 700 fenceposts is really not all that far a walk, and this song is all about growing up next to each on farm land and the effort this young and loving couple took to "meet in the middle". Come on...it's not that much effort. Daily exercise is a good thing, I think.

Question 30

Ain't Goin' Down ('Til the Sun Comes Up)

"Ain't goin' down 'til the sun comes up / Ain't givin' in 'til they get enough / Goin' 'round the world in a pickup truck / Ain't goin' down 'til the sun comes up." Alright, to be totally fair here, this song describes a lot of what my youth was like. Staying up until the sunrise with friends and lovers. That was pretty much my high school life...and some of my college life too...and some of my post-college life. I didn't do any of it with a pickup truck, for the most part, but this song does at least ring true beyond the country life.

Question 31

Never Comin’ Down

"We're so high, we could paint the sky / Tear the top right off the ceiling / And I swear we're never, ever coming down / Never coming down." Well, it is pretty clear that the person who sings this song is a lot more interested in partying than in getting their life together. Of course, given the fame this singer has, I don't think that will be much of a problem. They already have their life together. However, it is a little irresponsible to sing all about getting paid...and then just spending all that money on nothing but a party.

Question 32

Head Over Boots

Here is a song that I learned a few years ago now. I will put my cards right out on the table and admit that I only learned it for a girl who used to work at a bar I played at. I was smitten with her from day one and I always thought there was something there. So, I learned the song, but ended up moving before I could play it for her. Two years later, I came back to town and she came to a gig of mine and I played her the song. I think there's a country song there!

Question 33

Tennessee Whiskey

Whether or not this song is an original of this singer's, it hardly matters because this is the one singer that everyone knows best when this song is mentioned and I am sorry to all quiz-takers here but if this question cannot be answered correctly, then there is just no honest way anyone here can call themselves a a cowboy or a cowgirl. This is a song I learned for a few girls at the current bar I play at most often. I think I play this song there at least once every week. And it seems to do the trick.

Question 34

How Do You Like Me Now?!

"How do you like me now / Now that I'm on my way / Do you still think I'm crazy standing here today / I couldn't make you love me / But I always dreamed about living in your radio / How do you like me now?!." This song has a special place in my heart for no other reason than my mom having a bit of a dyslexic moment while trying to sing this at home once. Instead of "do you still think I'm crazy", she said "do you thill stink I'm azy". It is a constant source of laughter in my family now.

Question 35

Thank God I'm A Country Boy

Here is a song that needs no lyrics and shouldn't even need a hint of any sort when it comes to just who could've written and sang this song. I mean this is one of the most iconic country theme songs out there. And no, I don't mean that this is a theme song to a specific country show or something. It might very well be, but I mean to say that this is sort of like the poster song for all things country. And it has stood the test of time. It is still played out there often. Great song.

Question 36

Needle And The Damage Done

This should be one of those iconic songs that some people might consider more folk than country but is still written and sung by a musician who has definitely dabbled in country on more than one occasion and should be recognized for that, for sure. This guy happens to hail from north of the border but he has snuck down south several times to record, even when it was illegal for him to do so. That is dedication to the craft, that's for sure. At any rate, who can match this song title with its true singer? Is there anyone here?

Question 37

Wagon Wheel (Cover)

This is a classic tune that has been covered and covered and performed and performed to a tiring degree, and it will probably go on until the end of time itself. And don't worry, I am more than aware that this song will pop up more than once in this quiz, but I bet there were some true cowboys out there who thought that they might give a different answer than the other time this one is brought up. And since I think that both famous versions of this song are well-known enough, I may pay credit to both.

Question 38

Amazed

"I don't know how you do what you do / I'm so in love with you / It just keeps getting better / I want to spend the rest of my life with you by my side / Forever and ever / Every little thing that you do / Baby, I'm amazed by you." This song is probably one of the most iconic country ballads of all time but it definitely was the most popular country ballad of the 90s. Hands down. And that is actually saying quite a lot considering that this song actually didn't come out until 1999.

Question 39

This Kiss

"It's the way you love me / It's a feeling like this / It's centrifugal motion / It's perpetual bliss / It's that pivotal moment / It's impossible / This kiss, this kiss." I really do not want to make it seem like I am insulting all country music here but I am very impressed that there is a country singer who managed to actually get "centrifugal motion" into a song without anyone really ever questioning what it is that she's on about. I mean...even 80s pop music would just run with "you spin me right round baby, right round".

Question 40

Folsom Prison Blues

This is a song that I actually did not know much of the history to until very recently. Which is interesting because I probably play this at least once a week when I'm out at gigs. It is one of those iconic songs that people can sort of sing to if they really think about it. Or if the beer is talking. At any rate, Folsom is the second oldest facility in the U.S., I've discovered and they used to treat people there very poorly. And this singer actually performed this very song in that facility 12 years after he first penned a song of this title.

Question 41

Long Time Gone

"My brother found work in Indiana, / Sister's a nurse at the old folks home. / Mama's still cooking too much for supper, / And me, I've been a long time gone. / Been a long time gone, / No, I ain't hoed a row since I don't know when. / Long time gone, and it ain't coming back again." I remember thinking stuff like this when I was readying myself to leave home. I always thought that I just could not wait to get out of there and be in a place where the people were different. Little did I know that the people back home are the best.

Question 42

Mud On The Tires

"There's a place I know about where the dirt road runs out / And we can try out the four-wheel drive / Come on now what do you say / Girl, I can hardly wait to get a little mud on the tires." Well, here it is. One of the most iconic subjects for a country song to have. The big old TRUCK! Everyone knows that country music is about the dog, the wife who left, the drink, and the truck. That is pretty well all there needs to be in a song to make it a complete country tune.

Question 43

In Spite Of Ourselves

This is probably one of my favorite comedy songs when it comes to country music. This musician has made a hit with this, and I have definitely done this tune with a number of lovely ladies at bar gigs. It is a priceless story of two lovers going over each other's flaws and then saying that "in spite of [themselves]" there will pretty well be nothing but love. "There'll be nothing but big old hearts dancin' in our eyes", is the way that this singer puts it. I think that this song should get more praise than what it does.

Question 44

Not Ready To Make Nice

Here is a song that I don't think requires much in the way of lyrical aid. I mean, this song really did make a huge stir for these singers. They happen to be from Texas, they happened to not like the person who ended up in charge of the country (who was also from Texas)...so they wrote a song, after telling him off, about how they are just not ready to "make nice" with the guy. And this caused a bit of an issue with a lot of people in the country music community. All sorts of fans gave up on this band. Of course, there were a lot of people who didn't like country who took up their cause.

Question 45

Wagon Wheel (Original)

The number of times I'm asked to play this song out at a bar almost rivals the number of times people shout out "Free Bird" while I'm playing. It is pretty ridiculous. That being said, everyone in the bar will sing along with this one when it's played so at least it keeps the crowd going. That's got to count for something, right? But which artist recorded this song first? Those who really know their stuff should be able to give a different answer this time about just who it is that has performed this incredibly iconic and overplayed tune.

Question 46

Whiskey Lullaby

This song is probably one of the saddest of all the country songs I've ever listened to and it is definitely the saddest of all the country songs that I happen to play at gigs. I actually haven't played this one in a few months now because sometimes the crowds are just not up for getting their hearts hurt in this way. But, every so often, I will get someone who wants to come up and sing the sing along with me. It is a duet, but I only put down one musician here when it comes to who is the main singer.

Question 47

Need You Now

"It's a quarter after one, I'm all alone and I need you now / Said I wouldn't call but I lost all control and I need you now / And I don't know how I can do without, I just need you now." This is one of those songs that has permeated through the decades now to become a true hit. I mean, this is definitely a 00s song through and through but I think it will continue to carry on because there is just something so haunting and beautiful about it. And that is really not something I say about a lot of country music.

Question 48

Broken Halos

"Seen my share of broken halos." And that is all that people will get here in terms of a lyrical hint. I mean, the singer of this song is such a big name in country music right now that there is pretty well no excuse for people to not know the answer here. This guy has done music with all manner of people. He's even sung with Justin Timberlake for cryin' out loud. He is well known, for sure. This happens to be one of the songs that I play every week or so out at the bars. People seem to like it.

Question 49

Walkin' After Midnight

"I go out walkin' after midnight / Out in the moonlight / Just like we used to do, I'm always walkin' / After midnight, searchin' for you (wa-wa-walking, wa-wa-walking)." Alright now, I have to say that this singer is probably one of the most famous country singers of all time. And that is saying a lot. I also have to say that she is actually very good in my opinion too, and I don't even really crush hard on much country music. Let me stress the "SHE" part of that point again. She is definitely one of the world's greatest female country stars.

Question 50

Okie From Muskogee

"I'm proud to be an Okie from Muskogee, / A place where even squares can have a ball / We still wave Old Glory down at the courthouse, / And white lightnin's still the biggest thrill of all." All of the old timers taking this quiz (if there are any) will know this song right away with no issue at all. They will only need to look at the title. Now, anyone here who is truly a cowboy or cowgirl should also know this right off the bat. It is perhaps one of the most famous of country songs out there.

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