400 Best Contemporary Country Singles: #225-#201

The 400 Best Contemporary Country Singles
Part 8:
#225-#201

#225
“Heads Carolina, Tails California”
Jo Dee Messina
1996
Peak: #2

Messina’s debut single established her edgy sound right out of the gate. Here, she’s convincing her lover to bail the small town that’s holding them down; just flip a coin, and we’ll head in that direction.

#224
“For My Broken Heart”
Reba McEntire
1991
Peak: #1

Reba McEntire’s For My Broken Heart album was recorded in the wake of the plane crash that killed most of her band members and her road manager. There’s a sense of gloom and melancholy that pervades that entire project, which is easily the best album she ever recorded. On the title track, she copes with life going on despite her suffering: “Lord the sun is blinding me, as it wakes me from the dark/I guess the world didn’t stop for my broken heart.”

#223
“Brand New Man”
Brooks & Dunn
1991
Peak: #1

The retiring of Naomi Judd from the music business produced a brilliant solo artist in Wynonna, and left a gaping void on the country duo landscape. Just when those also-rans like Sweethearts of the Rodeo and The Bellamy Brothers thought they had a shot at that Vocal Duo trophy the Judd girls had monopolized, out of nowhere came Brooks & Dunn, with this brassy, confident honky-tonk hit that launched them to the top of the charts. Using born-again imagery to praise the love of the woman that “saved him” from a life of one-night stands, lead vocalist Ronnie Dunn’s powerful vocals announced there was a new duo in town; they would go on to win more Vocal Duo awards than any twosome in history.

#222
“On a Bus to St. Cloud”
Trisha Yearwood
1995
Peak: #59

A sweeping orchestral intro melts into a quiet piano-laden ballad about being haunted by an ex-lover who seemed to leave too fast. Yearwood holds her cards close to her chest in the verses, but lets out a powerful ache on the bridge when she pleads, “You chase me like a shadow/and you haunt me like a ghost/And I hate you some, and I love you some, but I miss you most.”

#221
“Mississippi Girl”
Faith Hill
2005
Peak: #1

Okay, I confess. When I first heard this (and reviewed it here), I said this was self-indulgent. And I still think it is. But it’s damn catchy self-indulgence. Perhaps it’s no coincidence that John Rich co-wrote this and “Redneck Woman.” He has a way of making specific declarations feel universal. One of the finest lines heard on country radio this year was “Some people seem to think that I’ve changed, that I’m different than I was back then/But in my soul, I know that I’m the same way that I’ve really always been.” That one cut pretty deep with me; there’s more going on here than just Mississippi pride.

#220
“I Would Cry”
Amy Dalley
2005
Peak: #29

Can Curb put out this damn album already? How can you release five great singles, some of which hit the top 30, and not give consumers a chance to bring them home? Dalley has one of the freshest songwriting styles I’ve heard in a long time. On this, the best single she’s released so far, she matter-of-factly deals with her cheating man: “If I could pull you back from where you’ve been I would, but you’ve left me no reason left to fight.” If her tears had any power to undo the damage he’s done, she would cry. But they can’t, so she won’t.

#219
“The Long Goodbye”
Brooks & Dunn
2001
Peak: #1

Usually in music, break-ups are clean and neat. There’s some confrontation, and it’s over. Here, Brooks & Dunn capture a more realistic death of a relationship; it’s just slowly dying over time, and nobody wants to admit it because it used to be so good. This is the best ballad of their career.

#218
“Girls Lie Too”
Terri Clark
2004
Peak: #1

How funny is this? Clark lets the guys in on a secret – girls tell just as many lies as they do. Sorry, buddy: she doesn’t like that spare tire, she wishes you made more money, and quite frankly, she’s not always thinking about you when you’re together. Clark has just the kind of good-natured banter needed to pull this off without offending half the species.

#217
“Seminole Wind”
John Anderson
1992
Peak: #2

John Anderson tacked this on the end of what became his comeback album. When it was released as a single, it sold more records for him than he ever dreamed of. His passionate plea for preserving the Florida swamps where the Seminole tribe resides is one of his finest moments.

#216
“Outbound Plane”
Suzy Bogguss
1992
Peak: #9

It’s hard to imagine an artist as quirky as Nanci Griffith recording for a major Nashville label, but it happened. She didn’t have much success on the singles charts as an artist, but as a writer she launched two artists into the top ten for the first time. In 1986, her composition “Love at the Five & Dime” became Kathy Mattea’s breakthrough hit. Six years later, Suzy Bogguss did a rollicking rendition of “Outbound Plane”, finding her voice and first success in the process. On the strength of this and its follow-up single, Bogguss was the surprise Horizon Award winner at the 1992 CMA’s.

#215
“Grandpa Told Me So”
Kenny Chesney
1996
Peak: #23

Until very recently, this country-boy ode to the down-home wisdom of grandpa was my favorite record Chesney ever did. This was way before his girl thought his tractor was sexy; he is still very green and even more sincere. The chorus is a solid list of life lessons all rolled into one: “He said, ‘Life is made for you to live, the best love is the love that you give/There’ll be times when you wanna hold on but you gotta let go,’ and I live by those words, ’cause Grandpa told me so.”

#214
“To Have You Back Again”
Patty Loveless
1998
Peak: #12

“Time is a river, flowing forever, away from the sound of your heart.” If you’re wondering why Loveless keeps popping up on this list, it’s because of lyrics like that, coupled with a mountain voice that is unparalleled in modern country music. With husband Emory Gordy Jr. at the producer’s helm, she made the most artistically significant traditional country music of the last 20 years. Am I exaggerating? Go download “To Have You Back Again” and give it a listen, then tell me who’s done better music in the traditional vein.

#213
“If You Ever Stop Loving Me”
Montgomery Gentry
2004
Peak: #1

I’ve always found Montgomery Gentry a little too eager; the little guy reminds me of one of those irritating dogs that jumps up and humps your leg, and the guy in the hat? I keep hoping he’ll knock himself out while he twirls the microphone stand for the millionth time. But I’ll give credit where it’s due: this infectious hit from last summer had me singing along each time the video came on.

#212
“Restless”
Alison Krauss & Union Station
2004
Peak: #36

About as far away as you can get from Montgomery Gentry and still be in the realm of country music, this reflective and melancholy bluegrass ballad (do they ever record anything but?) is so understated that it took a few listens to fully grab me. The way she whispers, “I just can’t stand being alone. I’m gonna have to change that someday” leaves just enough indifference to make you think she doesn’t mind being alone all that much.

#211
“Everyday Angel”
Radney Foster
2002
Peak: #43

Foster finds everyday angels in his son’s sunday school teacher, who marched with Martin Luther King, Jr.; in his own father, who let a woman at work who was being abused by her husband stay with them during his childhood; and finally, a firefighter on 9/11 who gave his life trying to save others. His impassioned call at the end to “go be an everyday angel” is a bold challenge worth following.

#210
“Lonely Too Long”
Patty Loveless
1996
Peak: #1

No post-coital regret here. A conversation the morning after a potential one-night stand reveals the honest truth as she tells the man beside her, we’ve just been lonely too long. We haven’t done anything wrong by giving in to loneliness, at least if we make this the first step towards something bigger.

#209
“Give Me Some Wheels”
Suzy Bogguss
1996
Peak: #60

These women are just all over the road, aren’t they? Bogguss is tired of being put up on a pedestal by the man who idolizes her; she just wants to be loved for who she is, an imperfect woman. So she tells him, “I’ll never be the angel you see in your dreams. Give me some wheels if I can’t have wings.” A rocking declaration of freedom.

#208
“Goodbye Earl”
Dixie Chicks
2000
Peak: #13

Somewhere around my junior year of college at Belmont University in Nashville, all of these bumper stickers started popping up on the cars of female students: “EARL’S IN THE TRUNK.” This southern gothic tale of a man who never met a restraining order that could hold him back and the two high school friends who feed him his last meal offended some people with its snide tone, as lead Chick Natalie Maines is clearly reveling in his demise. But this tale of revenge is one of the best story songs in the history of the genre. Anyway, where were those protesters when Garth Brooks put out that song about running a cheating woman over with an 18-wheeler?

#207
“Blue”
LeAnn Rimes
1996
Peak: #10

For about two and a half minutes, 1996 became 1963. Rimes came out of nowhere with this torch ballad that actually had people thinking she was the reincarnate of Patsy Cline. Rimes never made another record like this again, but she deserves credit for lovingly turning back the clock to the golden era of the Nashville Sound.

#206
“Delia’s Gone”
Johnny Cash
1994
Peak: did not chart

Earl could’ve taken some tips from Johnny Cash. The Man in Black never sounded so dark as he did on his landmark acoustic album American Recordings, the first of his celebrated collaborations with producer Rick Rubin. Here he ties his cheating lover to the chair, and, well… “First time I shot her, I shot her in the side; Hard to watch her suffer, but with a second shot she died. Delia’s gone, one more round, Delia’s gone.” Even MTV wouldn’t play the video for this one.

#205
“Check Please”
Paul Jefferson
1996
Peak: #50

What a dirty little record. Jefferson is getting good and horny at the restaurant with a sexy-talking lady friend, but she keeps killing the mood by saying she wants to get married and have kids. When he finally relents on the third date and says he’ll wait, it turns her on so much she tells him to get the check so they can do the nasty as soon as they get out of there. I’m amazed this got as high as it did on the charts.

#204
“Who You’d Be Today”
Kenny Chesney
2005
Peak: #2

The best thing Chesney has ever recorded. This ode to a person who went before their time is heartbreaking: “It ain’t fair, you died too young/Like a story that had just begun/But death ripped the pages all away.” Beware of the video; you’ll be crying long after it’s over.

#203
“Remember When”
Alan Jackson
2004
Peak: #1

He had already written a classic anniversary song with “I’d Love You All Over Again”, but this blew that one out of the water. This tender recollection of memories, including when the marriage almost fell apart, is clearly a reflection on his own life. It was a gift for listeners that he chose to share something so personal.

#202
“You Can Feel Bad”
Patty Loveless
1996
Peak: #3

Listen, go ahead and dump me. But don’t pretend you’re all despondent because I’m handling it so well. It’s just a pat to your ego for you to picture me suffering, but hey – “You can feel bad if it makes you feel better.” A classic example of the brilliant writing talent of Matraca Berg.

#201
“Earthbound”
Rodney Crowell
2003
Peak: #60
Rodney wants to go to heaven, but not anytime soon. He’s enjoying life too much to be heaven bound; he’s earthbound. A joyous celebration of life, and how all of our sins are forgiven with time.