400 Best Contemporary Country Singles: #25-#1

The 400 Best Contemporary Country Singles
Part 16:
#25-#1

#25
“Dancin’ Circles ‘Round The Sun (Epictetus Speaks)”
Rodney Crowell
2005
Peak: did not chart

I don’t want to begin quoting lyrics from this song, since every one of the lines is memorable. What can I say about Crowell drawing inspiration from an ancient Greek philosopher from the Stoic era? This song jump-started me out of my mid-summer lull, provoking me to find a fresh approach to the world around me. “Disregard what don’t concern you, don’t let disappointment turn you, avoid adopting other people’s view.” “In between the masks you wear, wash your face and comb your hair.” “Your reputation doesn’t matter, let idle gossip chirp and chatter, no one else can tell you how you feel.” “Bend the rules until it breaks, stand your ground until it shakes.” It’s everything I needed to hear to rediscover my inner fearlessness. The change has been duly noted by all of those around me, and greater happiness has followed.

#24
“The Fear Of Being Alone”
Reba McEntire
1996
Peak: #2

I am something of an anomaly in that I am remarkably self-reliant. I enjoy companionship but don’t yearn for it; the need for it doesn’t cloud my judgement. So I hear a lot of my inner voice in this song that warns against believing something is love when it’s really just your fear of being alone that’s making you think you’re in love. Here, McEntire’s head is clearly in charge of her heart, which is almost never the case in her songs. The result is her finest single of this era.

#23
“Shake The Sugar Tree”
Pam Tillis
1992
Peak: #3

The mandolin and fiddle create a warm, back-porch sound that complements Tillis’ playful vocal. You could listen to this song for years and simply enjoy it as a fun, nagging little tune that asks for a little more attention from a lover with a sing-along chorus and a catchy melody. I certainly did.
But listen a bit closer and you realize there’s a lot more going on here, as Tillis is calling for more than just a hug and kiss, and she’s going to do a lot more than just ask for the attention she wants. The blues-borrowed sexual message here is so subtle that even a close listener could miss it, so let me just say that unlike the woman in Lorrie Morgan’s “Something In Red”, Tillis isn’t going to use a designer dress to get the fire back in her marriage. More like Gretchen Wilson’s “Redneck Woman”, she doesn’t need that designer tag to make her man want her. She’s going to use everything God gave her to get her man begging for more; her vocal indicates that one shake of her hips and a come-hither stare is all she’s going to need to raise that commotion that will make him show her some real emotion. She’s the only woman in the genre’s history who could pull off this double-entendre so deftly; everybody else would’ve missed the subtext completely or made it so obvious that radio wouldn’t dare touch it.

#22
“Callin’ Baton Rouge”
Garth Brooks
1994
Peak: #2

I never fully understood the Garth Brooks phenomenon until I saw him live. The burning intensity in his eyes and ferocious energy of his performance was mind-blowing. I have still never been part of a concert crowd that was so completely committed to the artist in front of them. That intensity is almost impossible to capture in the recording studio, but the closest he came to doing so was with this fiery cover of the New Grass Revival hit “Callin’ Baton Rouge”, which opens with an explosion of Cajun fiddle and never lets up. I cannot sit still when this record is on; even typing this while listening to it, my head is involuntarily bopping along.

#21
“I Don’t Paint Myself Into Corners”
Trisha Yearwood
2002
Peak: #47

The ultimate statement of personal accountability. In her most traditional performance, Yearwood looks back on a bad relationship with the clarity-assisted understanding that yes, even though this person was unfair to her, she was responsible for allowing herself to be emotionally manipulated – “in the light of truth, it wasn’t you, it was me.” She has gotten to the point of not even recognizing herself, and while drowning in her misery, she suddenly realizes she’s not even trying to pull herself up. Taking back control, she celebrates that she won’t paint herself into corners anymore; as her convictions grow stronger while the song progresses, so does her vocal. Her first declaration is a near-whisper; by the end, it’s a heart-stopping wail that can only be produced by the most powerful vocalist in the history of country music.

#20
“You Don’t Seem To Miss Me”
Patty Loveless with George Jones
1997
Peak: #14

I’m drawn to songs that deal with emotions that are not commonly expressed in song. Love and loss songs are everywhere, but a song about people beginning to grow apart is harder to find. I still can’t believe Jim Lauderdale was observant enough to capture that feeling that a person who is always on your mind doesn’t seem to miss you as much as you miss them. There’s no anger or resentment here; just confused desperation. The chorus is also the closest thing I’ve ever heard to head-banging country music.

#19
“Monday Morning Church”
Alan Jackson
2004
Peak: #5

Faith is a funny thing; you’re expected to believe in what you cannot see. If you aren’t a faithful person by nature, it helps to have somebody who is to emulate. I was a lapsed Catholic for many years; I didn’t really believe in anything from about fifth grade on, despite receiving Confirmation during that time. It took seeing a college professor of mine living her faith for me to want to explore my own again; the strength she derived from it was very real to me, and something I could get a handle on. I would not be active in my faith if I had not had her example to follow.
My aunt had the strongest faith of anybody I ever knew, but by the time I was curious enough to ask her about it, she had passed away. I can’t help but think of her when I hear this song about a man who loses his faith when his wife dies: “You left your Bible on the dresser, so I put it in the drawer, cause I can’t seem to talk to God without yelling anymore.” What happens to your connection to God when the very model of your faith is no longer there as a living, breathing example of the power faith can have? I fear I’m watching my uncle slip into the same emptiness as the man in this song: “I still believe in heaven, and I’m sure you made it there. But as for me, without your love, I don’t have a prayer.”

#18
“Aces”
Suzy Bogguss
1992
Peak: #9

There’s a mystery to this Cheryl Wheeler song. I can never quite be sure who is to blame for the breaking point that has been reached in this relationship. I think that’s why the song has resonated with me so deeply. I’ve related to the person here who is being walked away from, and doesn’t understand exactly what has happened, pleading “Talk to me, can’t you see I would never want to do what it seems I’ve done?” And I relate to the stubborn person who is threatening to walk away, the one who seems to have unrealistic expectations and is never fully satisfied with the effort being given: “The things you think I should do, I’ve never understood that part of you. You know I’ve tried to be a friend, but you feel undermined and hurt again.” There’s usually not a good person and bad person when things go south; it’s almost always more complicated than that. This Bogguss hit captures that dynamic perfectly.

#17
“Suspicious Minds”
Dwight Yoakam
1992
Peak: #35

Dwight Yoakam succeeded in creating a musical sound that is completely unique and all his own. It’s so distinctive that when he covers another artist’s material, he takes complete ownership of it. A Yoakam fan not versed in the history of rock music would not even suspect this was an Elvis Presley classic, not a Yoakam original. In the Presley rendition, you never fully believe that the man has been faithful; Presley gives credibility to his woman’s suspicions with his shaky vocal. With Yoakam singing this and Pete Anderson’s aggressive production, you fully believe that the man is being unfairly accused; you want to shake this woman back into reality and get her to appreciate the love she has. A monumental reworking, and ultimately an improvement, of a durable classic.

#16
“House of Cards”
Mary Chapin Carpenter
1995
Peak: #21

There is a darkness lying underneath the perfect surface of American suburbia. In the ten years since this hit was released, thanks to everything from school shootings to Desperate Housewives, this is now common wisdom. But when Carpenter was singing it, she was among the first to begin poking holes in our idealistic notions of community and family life, and she did so by having the courage to pull back the curtain and expose the naked truth: the perfect image we try to portray to our neighbors is a facade; what’s going on behind closed doors is as dysfunctional and damaging as anything you’d find in the big city. The pain of trying to keep up appearances instead of tending to emotional needs – “God forbid if word got out about your house of cards” – silently destroys families that would be better off if they put their skeletons on the lawn and just took care of each other, caring less about what the person across the street is saying about them.

#15
“Please Remember Me”
Tim McGraw
1999
Peak: #1

If you truly love someone, but you know that you’re not good for them, how do you find the strength to let them go? On this classic Rodney Crowell-penned hit, McGraw struggles with this very question, and comes to the understanding that she’ll be better off “when I can’t hurt you anymore.” He doesn’t spell out exactly what he’s done to hurt her, but judging from the soaring chorus claiming she’ll find “better love, strong as it ever was” and all he’s hoping for is that she will, once in a while, think back and remember him, you can imagine that this was quite the one-sided relationship. In ending it, he finally is the man that she needed him to be.

#14
“The River & The Highway”
Pam Tillis
1996
Peak: #8

The woman in this song goes with the flow. She has no direction in her life and changes with the wind. She’s a river. The man is controlled by structure and rules. He does everything as he’s expected to and has nothing resembling a restless spirit. He’s a highway. Two people like this can never travel together, as their approaches to life are fundamentally incompatible. But they can meet at a crossroads, and give each other the comfort they need: “Every now and then he offers her a shoulder, and every now and then she overflows. And every now and then a bridge crosses over, and it’s a moment that every lover knows.” Love is a funny thing; sometimes the person who is all you ever wanted can give you the greatest moments of your life, but love can’t make two people that different follow the same path together.

#13
“Where Are You Now”
Trisha Yearwood
2000
Peak: #45

“I’m good one of a kind, but I would rather be two. And I still speak my mind, but I miss talking with you.” My mouth dropped open when I heard that line for the first time. The raw vulnerability of this Mary Chapin Carpenter/Kim Richey song takes no prisoners. Those women are great writers, but it takes Yearwood’s vocal to reveal all of the anger, disappointment and yearning that this woman is feeling towards the man who is nowhere to be found. There’s not only a love that’s died here; innocence has been lost, too : “Who would’ve ever thought that you and me would let forever come to used to be?” It took a week for me to get past track one of the Real Live Woman album this song opened; when that last guitar fades out, you can’t help but press repeat and experience this powerful song again.

#12
“Love Travels”
Kathy Mattea
1997
Peak: #39

This is the sound of a creativity that had simmered under the surface of a standard country career suddenly rising up and taking control. This ambitious and spiritually empowering anthem for those tender hearts that Heaven makes the strongest celebrates how true love will find you wherever you are. How do you let somebody you love be so far away? Only if you can say that “the dream that saves me is that you’re happy and that you’re free.” This is such an overwhelmingly positive expression of true love that you’ll have a knowing smile listening to it if you have given or recieived such selfless love.

#11
“After All This Time”
Rodney Crowell
1989
Peak: #1
Crowell’s plaintive and honest sonnet to his long-time love is a pure declaration completely lacking any unnecessary sap or sentiment. “There were ways I should have thrilled you, there were days I could have killed you, you’re the only love my heart has ever known.” This isn’t a romanticized or idealized version of love; this is a man speaking from his heart about a love that has had its ups and downs, and its share of mistakes on both sides. But it has survived. There has never been a better country song that could also double as an anniversary song.

#10
“Hurt”
Johnny Cash
2003
Peak: #56
The greatest contribution of Johnny Cash to country music, in my opinion, was his uncanny ability to take the most reprehensible members of society – murderers, adulterers, and common criminals – and give them a voice, becoming a sympathetic advocate for their regret and sorrow, if not for the actions that they have taken. When he covered this Trent Reznor song about the depths of drug addiction, many misintepreted it as him trying to apologize for a life full of regrets, using Reznor’s imagery as metaphor. This is a frustrating misreading of his performance, aided by a brilliant video that too many interpreted as documentary rather than the fiction it was.
Johnny Cash did not shoot a man in Reno just to watch him die, as he sang in “Folsom Prison Blues”, and he did not hurt everyone he loves, as he sings in this song. This was the final major example of Cash being able to get into the head of a tragic figure and give him a sympathetic voice on record. This is not biography; it is performance art at its finest.

#9
“Independence Day”
Martina McBride
1994
Peak: #12

A fearless, landmark record about an abused wife finally standing up for herself, this permanently expanded the realm of what was acceptable to talk about in a mainstream country song. It was so shocking on first release that the opening line – “She seemed alright by dawn’s early light, though she looked a little worried and weak. She tried to pretend he wasn’t drinking again, but Daddy had left the proof on her cheek” – was an electric jolt. McBride’s powerful voice has never found another song so worthy of her volume – the fact that we never heard her this intense until this single suggested she hadn’t found anything worth screaming about until “Independence Day.” This is a historically significant and important record, giving voice to countless women and children who were suffering in silence.

#8
“I May Hate Myself In The Morning”
Lee Ann Womack
2004
Peak: #10

Never has the steel guitar sounded so passionate. Never has a fiddle sounded so romantic. Never has a record sounded so intimate and honest as this flawless single from last year. This is the perfect example of how country instrumentation and production can capture the cold, honest truth in under five minutes. The sentiment is so instantly familiar that I wondered upon first listen how nobody had ever written this before – “I may hate myself in the morning, but I’m gonna love you tonight.”

As she gives into temptation by the bridge, wailing “I know it’s wrong, but it ain’t easy moving on”, you’re sinking along with her. Then those fiddles, that steel guitar, the soft string section pushing everything along. Even when her singing is done, the band keeps going for another minute, producing the best instrumental fade-out I have ever heard in a country song. Check out the steel guitar solo at 3:38, and try to name another instrument or another genre that could produce that same gut feeling when you hear it, so perfectly reinforcing the lyrics that have preceded it. This is a hillbilly masterpiece.

#7
“Travelin’ Soldier”
Dixie Chicks
2003
Peak: #1

How perfect was the album Home? Any one of the songs on it would’ve made the list if they had been released as a single. If “Truth No. 2” or “Top of the World” had been sent to radio, they would’ve ranked even higher than “Travelin’ Soldier”, a powerful story written and originally recorded by Bruce Robison. Here, a young man meets a young woman at a cafe before he heads off to war. She’s too young for him, but she falls anyway, and he sends her letters from an army camp, and then Vietnam.

You know pretty early on that he won’t be making it home, but what elevates this tale is the cold indifference to his death: “One Friday night at a football game, the Lord’s prayer said and the anthem played, a man said ‘Folks, would you bow your heads for a list of local Vietnam dead. Crying all alone under the stairs was the piccolo player in the marching band, one name read, and nobody really cared, but a pretty little girl with a bow in her hair.”

When you can’t match a name with a face, the death doesn’t really affect you. There has been a turning in support for the current war, and I think it has a lot less to do with the incompetence it’s been conducted and the dishonest foundations for it, and a lot more to do with more and more people knowing somebody who has died (nearly 2, 100) or been seriously wounded (over 16,000) in combat. There’s a lesson here about death by violence: we seem to be able to care so much more about people dying if we either know them or can imagine ourselves in the same situation. Nearly 3,000 civilian deaths in terrorist attacks on New York and Washington four years ago completely shook us to the core; at least 26,000 civilian deaths in Iraq since we invaded doesn’t bother us quite as much. I fear that we are, as a nation, a lot more like the football crowd wanting the game to start than the piccolo player under the stairs. Perhaps I’m hearing more in this song than is actually there, but these are the thoughts that go through my mind when I listen to “Travelin’ Soldier”, and why it has impacted me enough to rank so highly on this list.

#6
“In Between Dances”
Pam Tillis
1995
Peak: #3

A gorgeous waltz that captures the difficulty of starting another relationship when the last one has let you down so badly, this is the best single of a remarkably illustrious career of great singles. There’s no bitterness here, not even much regret. Just a quiet wariness of putting yourself out there again, knowing that you could be hurt again: “I could sure use your company now, but don’t be mistaking my smile. I’m only in between dances, sitting it out for a while.” Tillis perfectly captures the tentativeness of a woman that is too unsure to enter the dance again, but still longs for companionship. By the bridge, she is looking for a reason to dance again: “Have you been in my shoes? I search your eyes for signs. Will you remain, remember my name, after it’s closing time?” A classic performance by one of the genre’s strongest talents in history.

#5
“Cafe On The Corner”
Sawyer Brown
2002
Peak: #5

There are some jobs you can have that are more than just what you do; they become an essential part of who you are, your identity nearly synonymous with your line of work. After a few years, I’ve learned that teaching is one of those jobs. To a much stronger degree, being a farmer is one of those jobs. Your work and your family and your home are all in one place, tied together and supported by the job you do in the fields. When family farms began to close down on a large scale, shut down by banks and repurchased by large companies, many farmers had the unfortunate experience of finding their identity in crisis, with the job that had defined them no longer being a viable option for them to perform.

This Sawyer Brown classic tells the story of a man who is forced to take a job as a waiter at a small-town cafe because the bank has repossessed his family farm: “The coffee is cold, and he’s fifty years old, and he’s got to learn to live some other way.” A sharp use of biblical imagery drives the tragedy of the situation home: “And the meek shall inherit the earth, and the bank shall repossess it. This job don’t pay half what it’s worth, but it’s a thankful man that gets it.”

Using the backdrop of the cafe, the story is quietly expanded to include the other lost souls of the early-nineties recession, which was the worst to hit the country since the Great Depression: “All these soldiers without wars, and hometown boys without a home. Farmers without fields, dealers without deals, and they sit here drinking coffee all alone.” They all know they need to make a change, but they can’t begin to figure out how, as they don’t know another way. One of the primary reasons country music must exist is to give voice to everyday trials like this, which captures an ongoing undercurrent in American society better than any documentary ever could.

#4
“Here I Am”
Patty Loveless
1994
Peak: #4

Tony Arata is justly lauded for writing “The Dance”, but this Patty Loveless ballad is his masterpiece, a brilliantly written declaration of ongoing love that slowly reveals itself over the course of three minutes. It begins as a bitter taunt, reminding the man who left her behind that he’s still in love with her – “You said you didn’t want to see me, but you’ve been looking for me everywhere.” She teases him almost snidely for trying to get over her through drinking his problems away, reminding him that “honey I’m right there waiting on you at the bottom of your glass.”

The first hint that she’s not quite over him surfaces in the second verse, as she continues to mock him for not being able to make it work with the women he has been with since leaving her: “It ain’t workin’ darlin’, hard as you may try, you keep hearing the words you told me in everyone’s goodbye, and you know that you’re just one step from another one being gone.” She then begins to show her cards ever so slightly: “I know I’ve seen them all unravel, I’ve been watching it all along.”

As she builds to the bridge, the lies she has told to herself and to him about just how well she’s doing without him begin to be exposed, but she’s struggling to maintain a surface indifference to the whole situation, telling him: “Honey I got over you passing me over a long time ago,” then letting slip that “My pride was stronger when I was younger, now I’d rather have you to know…”

And then, with the twist in the final verse, comes her secret confession: “Here I am, here I am, I still carry a flame for you burning me like a brand, here I am.” Loveless’ vocal perfectly captures the shifting emotions as she goes from cold indifference to desperate vulnerability. It’s a flawless performance of a perfect country song.

#3
“You’re Gone”
Diamond Rio
1998
Peak: #4

This isn’t how it’s supposed to work. When you find the woman who makes you a better person just by being with her, and she changes your life in the process, you’re supposed to either (a) marry her and live happily ever after, or (b) drown in misery when she leaves you. This fantastic Jon Vezner-penned Diamond Rio hit suggests a third way: be grateful that you were touched by her presence and that she made you a better person, even though she’s gone: “I bless the day I met you, and I thank God that he let you stand beside me for a moment that lives on; and the good news is I’m better for the time we spent together, and the bad news is you’re gone.”

The man in this song is remarkably candid about his own failings, and how lucky he was to find someone willing to call him on it: “I said, ‘Hello I think I’m broken’, and though I was only joking, it took me by surprise when you agreed. I was trying to be clever, for the life of me I never would have guessed how far the simple truth would lead. You knew all my lines, you knew all my tricks, you knew how to heal that pain no medicine can fix.”

I suppose there is a mystery to this song, in that it’s not necessarily clear that she’s gone because she left him, or because she has died. I’ve always preferred the first reading, because I think it makes the song more poignant: “Looking back it’s still surprising, I was sinking, you were rising, and with a look you caught me in mid-air.” I think there’s a beauty in the fact that our relationships have a beginning and an end; no matter how close you are with a lover, or a friend, there will come a time when that relationship ends, but the impact they had on you will remain. I think the man of this song wasn’t able to make it work with the woman and she left, but I also think he’s going to be a better man in his next romance because of how she transformed him.

#2
“The Song Remembers When”
Trisha Yearwood
1993
Peak: #2

This classic Hugh Prestwood-penned hit is the ultimate song about songs, and the memories that go along with them. Yearwood “was standing at the counter, I was waiting for the change, when I heard that old familiar music start. It was like a lighted match had been tossed into my soul, it was like a dam had broken in my heart.” Suddenly, all those memories of a forgotten love come flooding back as she hears the song they sang along with in the car.
Prestwood wrote more than a song here; it can only be described as poetry: “We were rolling through the Rockies, we were up above the clouds, when a station out of Jackson played that song. And it seemed to fit the moment, and the moment seemed to freeze, when we turned the music up and sang along. And there was a God in Heaven, and the world made perfect sense. We were young and were in love, and we were easy to convince. We were headed straight for Eden, it was just around the bend, and though I had forgotten all about it, the song remembers when.”
Yearwood is the perfect vocalist for such a celebration of the power of a great song. She has always had the good taste to let the song tell the story, never showing off her vocal powers at the expense of the material. Her nuanced performance captures all of the melancholy-tinged regret that results from the flood of memories the song triggers. In a genre that often claims it’s all about the song, Yearwood makes a stunningly effective case for that claim.

#1
“Where’ve You Been”
Kathy Mattea
1990
Peak: #10

Everybody loved the song, but nobody wanted to cut it. A slow and simple tale of an aging couple that ends with them both in a hospital, as the wife is succumbing to Alzheimer’s? Not exactly the formula for a smash hit. Co-writers Jon Vezner and Don Henry pitched the song all around Nashville, and it was finally Vezner’s wife, Kathy Mattea, who committed to recording the song that was piercing her heart with every listen.

The tale of Claire & Edwin starts unassumingly enough, with Claire wondering “where’ve you been” when they fall in love, and she finds the man she always dreamed of. She asks the same question when a storm delays his coming home from work – “Her frightened tears fell to the floor, until his key turned in the door.”

The gentle instrumentation – Mattea is accompanied only by acoustic guitar through much of the song – gives the tale and unassuming nature. There’s no foreshadowing of the turn the lyrics will take, and country fans certainly hadn’t been conditioned to three-act story songs that end like this, even though there would be countless numbers of them during the boom years. But the turn comes, as the bridge pulls the rug out from under the listener with disarming humor: “They never spent a night apart, for sixty years she heard him snore; now they’re in a hospital, in separate beds on different floors.”

The final verse, where Edwin and Claire have their last conversation, captures the very best of what country music can be, revealing deep truths about the human experience through careful observation of word and deed: “Then one day they wheeled him in. He held her hand and stroked her head, and in a fragile voice she said, ‘Where’ve you been? I’ve looked for you forever and a day.'”

There is no bombast, no cheap appeals for sentiment or manipulative vocals. Mattea lets the song shine, and only slightly increases the intensity of the last “where’ve you been”. The quiet grace of this single, which would go on to win the CMA, ACM & Grammy Award for Song of the Year, is the perfect illustration of what country music can be, without any of the annoyances that often bring the genre down. Great song, fantastic vocalist, tasteful arrangement and the honest truth – these are the things that keep country fans wading through a sea of mediocrity to find treasures like this.