The Best Singles of 2010, Part 2: #30-#21

#30

Roll With It
Easton Corbin

It’s easy to overlook Corbin’s second single as just another breezy summer tune, but it stands above the rest, thanks to its near-perfect execution. From the spirited delivery to the skillful handling of otherwise trite phrases –like the title phrase and “it won’t be no thang”— “Roll With It” makes a fresh, invigorating case for shedding everyday troubles and, well, rolling with it. – Tara Seetharam

#29

I Put My Ring Back On
Mary Chapin Carpenter

“I Put My Ring Back On” is a throwback to the sounds of Mary Chapin Carpenter’s glory days on the charts. It’s catchy with a message of relational perseverance. As a result, it’s one of the two most memorable songs on her latest album. – Leeann Ward

#28

Who Are You When I’m Not Looking
Blake Shelton

Blake Shelton has a strong voice, but it’s most expressive when he dials it back enough to allow the sensitivity to cut through. Exhibit A: “Who Are You When I’m Not Looking.” As one of the beautifully understated productions of the year, he loves everything that he knows about his woman, therefore, he can’t help but imagine and wonder about what he’s not seeing. – LW

#27

Put You in a Song
Keith Urban

Creating hooky pieces of ear candy is one of Urban’s defining talents, and the lead single from his November release is further proof. Blessedly, it’s devoid of the distracting electronic instrumentation that has lately plagued his recordings, which makes for one of Urban’s cleanest releases in recent years. – LW

#26

American Honey
Lady Antebellum

Look, I still don’t know what American honey is, and I’m guessing you don’t either. What I do know is this: Hillary Scott’s performance is layered, vulnerable and desperate – a perfect encapsulation of the wave of nostalgia that finds you in your early 20s. Coupled with the wistful melody, it’s enough to override the wacky metaphor and lift the song to one of the most poignant of the year. – TS

#25

A Father’s Love (The Only Way He Knew How)
Bucky Covington

This is probably Covington’s best performance to date. The song manages to be sweet without crossing the line to sickeningly cloying. It depicts a father who shows his love through action rather than verbal affirmation, which is something that the son ultimately accepts as just as good. – LW

#24

Playing the Part
Jamey Johnson

Something that Jamey Johnson isn’t afraid to do in this radio era of watered down, trite messages is expose himself as less than a perfect human being. Instead, he will sing about drug addiction (“High Cost of Living”) and depression, as we hear in this tale of disappointment that is a result of the crushing disappointment of unattained success. – LW

#23

Fearless
Taylor Swift

As a single release, it was little more than an afterthought, the album of the same name having already flexed most of its world-conquering muscles. As a sort of mission-statement album track, though, “Fearless” still rocks, adeptly capturing the jitters and giddiness of young romance and sort of arguing for embracing such sensations while you can. That Swift tells herself at a certain point to “capture it, remember it” suggests she knows there’s more loneliness and disappointment on the flip-side of this one elated moment. – Dan Milliken

#22

She Won’t Be Lonely Long
Clay Walker

Ringing with effortless charisma and playful sincerity, the lead single off Walker’s latest album was a welcomed reintroduction to his most beloved qualities. Interestingly, though the song serves as a tribute to his classic 90s sound, it fit snugly –and refreshingly– on country radio. – TS

#21

Only Prettier
Miranda Lambert

Lambert exposes the sneaky bitchery lurking behind so much Southern sweetness. Country radio is all like, “Whaaat?” – DM

Check out the rest of the list:

• The Best Singles of 2010, Part 1: #40-#31
• The Best Singles of 2010, Part 3: #20-#11
• The Best Singles of 2010, Part 4: #10-#1

Only she doesn’t. Her performance misses the mark on all accounts: she blasts her notes with so much splashy aggression that they can barely find their pitch, and her phrasing is painfully affected (what’s with the varying pronunciations of the word “you”?). Gone is her soulful conviction and unshakeable control; in its place is a voice that begs for a recharge. And then there’s Naomi Judd’s harmony vocals, which manage to be both barely there and glaringly off-key.

The vocals are so off-putting that they almost completely mask the semi-cool arrangement, which weaves in a tinge of Celtic flavoring – a little Mary Chapin Carpenter, a little Keith Urban. Some vocal fine-tuning might have allowed this driving production to make a more powerful impact.

Given that this is The Judds’ first single in over a decade –charity single or not– it’s a shame you have to wonder how many times the ladies went through this in the studio. What’s your guess? I know mine.

Written by Steven Lee Olsen, Robert Ellis Orrall & Angelo Petraglia

Grade: D+

Listen: I Will Stand By You

Buy:

I don’t know what’s going on with Mary Chapin Carptenter.  She made my favorite album of all-time, Stones in the Road, and it wasn’t particularly upbeat.  But the songs were amazingly good. I’m still learning new things from that album a full sixteen years after its release.

With a singer-songwriter cut from the folk cloth, there’s not much left to work with if the song itself isn’t that great.  “The Way I Feel” isn’t that great, much like most of what Carpenter’s recorded for her last few albums.

So ultimately, what’s most disappointing about this song  is that its  mediocrity doesn’t disappoint me. I fully expected it.

Written by Mary Chapin Carpenter

Grade:  C

Listen: The Way I Feel

400 Greatest Singles of the Nineties: #25-#1

#25
Smoke Rings in the Dark
Gary Allan
1999 | Peak: #12

Listen

A dark, atmospheric wonder, as Allan delivers the final eulogy for a love that couldn’t help burning out. – Dan Milliken

#24
Just to See You Smile
Tim McGraw
1997 | Peak: #1

Listen

Being deeply enamored of someone can make it easy – even appealing – to forfeit your own well-being. This single’s sunny tone reflects the persistent affection running through its protagonist, but its story demonstrates the heartbreak to which such unmeasured selflessness leads. – DM

#23
Small Town Saturday Night
Hal Ketchum
1991 | Peak: #2

Listen

Country music is rife with songs that elaborate on small town life, but none are as catchy or even as clever as Ketchum’s take on it: “Bobby told Lucy, ‘The world ain’t round/Drops off sharp at the edge of town/Lucy, you know the world must be flat/’Cause when people leave town, they never come back.’” Sounds like the fate of the small town that I grew up in. – Leeann Ward

#22
Choices
George Jones
1999 | Peak: #30

Listen

The hard-living George Jones did not write this reflective song about the consequences of various life choices, but you’d never know it, because it sounds as if he feels every word and emotion of it. With regret he he acknowledges, “I guess I’m payin’/For the things that I have done/If I could go back/Oh, Lord knows I’d run/But I’m still losin’/This game of life I play/Living and dying/With the choices I’ve made.” – LW

#21
For My Broken Heart
Reba McEntire
1991 | Peak: #1

Listen

In a state of shock, very little about everyday life seems significant. The body and mind become transfixed on the impossible new information they’re supposed to process, and suddenly everything else feels shallow, unnecessary, intrusive. In classic country tradition, McEntire’s shock here is from a love walking away, but the sensation the song beautifully captures can haunt any manner of broken heart. – DM

#20
Fast as You
Dwight Yoakam
1993 | Peak: #2

Listen

Hearing the opening hard driving riff of this Yoakam classic is all that any country music listener needs to hear to know just what song it is. There’s probably not a more recognizable introduction of the nineties. While the song is sonically bold, the character within isn’t so confident. He’s being emotionally run over by his lover, but hopes that the roles will reverse someday: “Maybe I’ll be fast as you/Maybe I’ll break hearts too/But I think you’ll slow down/When your turn to hurt comes around/Maybe I’ll break hearts and be as fast as you.” – LW

#19
Neon Moon
Brooks & Dunn
1992 | Peak: #1

Listen

Night after night, a heartbroken man drinks his sorrows away at a rundown bar. An average scenario for country music, no doubt, but Dunn spins it into a classic with his spot-on performance, dripping with wistfulness. – Tara Seetharam

#18
You’re Gone
Diamond Rio
1998 | Peak: #4

Listen

The lyric’s clarity and gratitude in the face of a great loss suggest that he’s reached the acceptance stage of grief.  The mournful vocal suggests that the grief will never go away. – Kevin Coyne

#17
Callin’ Baton Rouge
Garth Brooks
1994 | Peak: #2

Listen

This is country music on a stadium scale.  Never before or since has Garth Brooks so perfectly captured the fiery exuberance of his legendary live performances. – KC

#16
Café on the Corner
Sawyer Brown
1992 | Peak: #5

Listen

We’re truly defined by only two things in our life: our work, and our relationships.  The man in this song has lost his farm, and has to work bussing tables to support his family.  The crippling loss of dignity our protagonist feels is restored by the narrator’s sympathetic portrait and the empathy of the listener.  – KC

#15
The Dance
Garth Brooks
1990 | Peak: #1

Listen

A gorgeous moment of resolve, as love’s joys are deemed well worth its ultimate sadness. Brooks’ rich, warm performance stands among the most affecting of the era. – DM

#14
I Still Believe in You
Vince Gill
1992 | Peak: #1

Listen

Some singles are beloved because they feel technically perfect. This isn’t necessarily one of them. The keyboard production sounds dated, and the lyrics, while serviceable, are somewhat colorless. At first, it sounds dangerously close to an easy-listening snoozer. But then that chorus hits, and the melody – and Gill – launch this weathered re-declaration of commitment into the high heavens. And there’s no coming back down. – DM

#13
Hard Rock Bottom of Your Heart
Randy Travis
1990 | Peak: #1

Listen

This song is so brilliantly constructed that it accomplishes what should be an impossible feat: it makes us sympathize with the one who broke the marriage vows, instead of the woman who he has disgracefully betrayed. – KC

#12
He Thinks He’ll Keep Her
Mary Chapin Carpenter
1993 | Peak: #2

Listen

A sharp, melodic feminist anthem with a marked nineties sound but a timeless sentiment about the true value of capable, giving women. – DM

#11
Brand New Man
Brooks & Dunn
1991 | Peak: #1

Listen

Brooks and Dunn begin their long, successful run with the memorable strains of Ronnie Dunn’s incredible vocal pipes. As he begins, “I saw the light, I’ve been baptized”, we know that we’re hearing something special. Instead of the expected cerebral declaration of salvation, however, we’re treated to a rousing declaration of love and how it can save a person. – LW

#10
Strawberry Wine
Deana Carter
1996 | Peak: #1

Listen

Memories of lost innocence and a sweet, sighing vocal from Carter combine to create one of the crown jewels of nineties country, with an emotional core so resonant that even the specifics of the story feel like each listener’s own. – DM

#9
When I Call Your Name
Vince Gill
1990 | Peak: #2

Listen

About a man who’s drowning in loneliness, this ballad is elevated to masterpiece standards by its haunting chorus. No one can convey searing pain like Gill; pair his voice with one as sorrowful as Loveless’, and the result is nothing short of exquisite. – TS

#8
Shake the Sugar Tree
Pam Tillis
1992 | Peak: #3

Listen

If the bouncy “Shake the Sugar Tree” sounds organic, it’s because it is. Since the Homeward Looking Angel project was out of money to spend by the time Tillis found the song, Tillis and her producer took the demo recording and added her voice to it, because she had a strong feeling that the song was a hit. While it feels organic, it also sounds bright and undated, which is a testament to simplicity in recording tactics. The instructive lyrics cleverly advise on the importance of constantly tending to relationships in order to keep them alive. – LW

#7
Angry All the Time
Bruce Robison
1998 | Peak: Did Not Chart

Listen

As their marriage crumbles around him, he looks around for one last appraisal, a foot out the door and still not sure why things ever went and changed.  – DM

#6
Meet in the Middle
Diamond Rio
1991 | Peak: #1

Listen

A humble, plucky little record about the beauty of compromise in relationships. It’s so blissfully unassuming that it’s easy to take for granted the song’s sweeping truth: “Ain’t no road too long when we meet in the middle” is one of country music’s greatest slogans for humanity, intentional or not. – TS

#5
Friends in Low Places
Garth Brooks
1990 | Peak: #1

Listen

“Friends in Low Places” is the party anthem of party anthems. While the lyrics don’t exactly paint the setting of a rousing party, the vibe of the song does in a big way. While it is Garth Brooks’ signature song, it is also an iconic song in general. With its sing-along chorus, the song went beyond small country music listening circles; its popularity expanded far and wide beyond that smaller community, to the general music listening world at large. Even those who may not have heard a country song before could at least sing a line from “Friends in Low Places.” What made the song so larger than life? We will probably never really know. But we do know that it remains a memorable part of pop culture, which is really a rare accomplishment for a little ol’ lightweight country ditty. – LW

#4
The Greatest Man I Never Knew
Reba McEntire
1992 | Peak: #3

Listen

It’s often said that actions speak louder than words.  That isn’t always true, especially in the eyes of a child. Everything her father did said “I love you”, but never having heard him say the words, she didn’t know how he really felt.

Now, almost a year after his death, she finally knows. The real tragedy isn’t that her father never said “I love you” when he was alive, but rather that she’ll never have the earthly opportunity to respond, “I know. I love you, too.”  – KC

#3
The Song Remembers When
Trisha Yearwood
1993 | Peak: #2

Listen

A masterpiece that reduces the soul-shaking power of music to its very essence.  Not only can a great song heighten the intensity of the moment you’re living in. It can also take you back to that moment in a heartbeat, when you least expect and aren’t quite ready for it.

For an artist like Trisha Yearwood, who collected more excellent songs than just about anyone in the past twenty years, it’s only right that one of her signature songs is itself a poignant tribute to songcraft.  “The Song Remembers When”  both makes the case for the power of music, and validates it with its flawless execution. – KC

#2
Independence Day
Martina McBride
1994 | Peak: #12

Listen

“Let freedom ring.” It’s not just a hook used to characterize a suffering mother’s actions; it’s a war cry that represents everything “Independence Day” stands for. Because in a country founded on ideals of life and liberty, a woman felt there was no way to protect her or her child except to destroy. Because even in a small town where everyone knew everyone’s business, nobody stepped out of line to salvage their neighbors’ existence. Because freedom is still compromised everyday, everywhere, and the only chance of saving it sometimes is to shout.

“Independence Day” is certainly such a shout, combining a bold, stinging Gretchen Peters lyric with a thunderstorm vocal by McBride. The record is fearless in conveying the dark truth of domestic violence, and wise enough not to cast any more judgment on the scenario than necessary, knowing that the situation speaks for itself.

Ultimately, the record has done much to shed light on its subject matter, as well as expand the boundaries of what can be discussed in a mainstream country song. Today’s acts may not often choose to use those expanded boundaries, because even in fields of artistic expression, it’s often easier to take the safe route and look the other way when confronted with humanity’s more troubling truths. But “Independence Day” stands as an example to all brave enough to follow in its path: a shout of truth, well-considered and well-timed, can ring on. – DM

#1
Maybe it Was Memphis
Pam Tillis
1991 | Peak: #3

Listen

It’s only fitting that this nostalgic list should end with a song about longing for the past.  Those of us who discovered country music in the nineties embraced it with an evangelical zeal, imploring their family and friends to listen to this amazing song, to that incredible artist. But what felt like the beginning of something that would keep getting better turned out to be a magical moment in time.

“Maybe it Was Memphis” is the perfect embodiment of that moment.  The song is poetry set to music, effortlessly evoking Faulkner and Tennessee Williams in its romanticism of the south.  The arrangement is stunning, with hallmarks of rock in steadfast service of its country core. The Tillis vocal is raw and emotional without being overwrought.  All of the disparate elements are brought together in perfect harmony. With relentless energy, it demands to be heard.

It’s a record that could’ve only existed in the nineties, when country music was broad enough to allow outside influences, but self-confident enough to incorporate them without sacrificing its own identity and integrity.  “Maybe it Was Memphis” defines an era of country music that approached meritocracy, an era where genuine talent paired with a worthy song was regularly rewarded.  An era where an a young artist’s debut single could become a classic as easily as the latest from a veteran superstar.

That era is over.  Long over.  But we still hold out hope that the magic will return, so we hang around.  We cling to a “Stay” here, a “House That Built Me” there, but the glimmers of hope are few, and they always seem to fade away.  Just like that Memphis summer night,  the magic has come and gone.  But we’ll keep looking back, ’cause it sure felt right.    – KC

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Jump Around

#400 – #376
#375 – #351
#350 – #326
#325 – #301
#300 – #276
#275 – #251
#250 – #226
#225 – #201
#200 – #176
#175 – #151
#150 – #126
#125 – #101
#100 – #76
#75 – #51
#50 – #26
#25 – #1

400 Greatest Singles of the Nineties: #50-#26

#50
Here’s a Quarter (Call Someone Who Cares)
Travis Tritt
1991 | Peak: #2

Listen

From the first forceful guitar strum on, this kiss-off number somehow manages to seem unusually cool and collected in its own aggression. You get the impression that Tritt’s character has been anticipating this moment, and has already made up his mind that he’s going to relish every second of it. – Dan Milliken

#49
I’ve Come to Expect it From You
George Strait
1990 | Peak: #1

Listen

This is about as dark and bitter as George Strait gets. It’s a coat that he wears well. – Kevin Coyne

#48
House of Cards
Mary Chapin Carpenter
1995 | Peak: #21

Listen

No neighborhood or family is without its secrets, and the more time we spend trying to hide them, the worse they become. “House of Cards” is a plea: forget appearances. Just take care of each other. – DM

#47
Love Without End, Amen
George Strait
1990 | Peak: #1

Listen

A song about a father’s eternal love for his children, powered by a fundamental Christian truth. Once again, a grand message is told through relatable anecdotes, by one of the best storytellers in country music. – Tara Seetharam

#46
State of Mind
Clint Black
1993 | Peak: #2

Listen

A tribute to the power of a melody, done so tastefully that you could almost miss the depth of its hook: “Ain’t it funny how a melody can…completely change your state of mind?” I rarely go a day without wondering the same thing. – TS

#45
Burn One Down
Clint Black
1992 | Peak: #4

Listen

Black bids his final farewell to an unworthy lover. Steeped in traditionalism, this record could stand as a classic on its sound alone, but its lyrics are masterfully bitter. – TS

#44
Seminole Wind
John Anderson
1992 | Peak: #2

Listen

Couched in a beautiful, though sing-able melody, “Seminole Wind” is a gorgeous song that pays tribute to the hardships of Native Americans. While the sound is unique, with its mix of strong piano and fiddle, it’s an example of the diversity that nineties country music enjoyed. Likewise, it’s one of the finer instances of intelligence that was often displayed in that era. – LW

#43
Sticks and Stones
Tracy Lawrence
1991 | Peak: #1

Listen

This is the more subdued version of this decade’s “Give It Away.” Lawrence hands over all of the material possessions that they had acquired together, because “sticks and stones” are worthless without the love that they lost in the acquisition of them. – LW

#42
Whose Bed Have Your Boots Been Under?
Shania Twain
1995 | Peak: #11

Listen

To simply label this as one of Twain’s “countriest” records is to miss the massive slab of personality she throws into it. The snappy performance, the ridiculous, rhyming names and the terrifically cheesy bridge (“So next time you’re lonely/Don’t call on me/Try the operator/Maybe she’ll be free)? All signature Twain. – TS

#41
The Walk
Sawyer Brown
1991 | Peak: #2

Listen

While one of Sawyer Brown’s signature songs is quite possibly the most inspiring father-son song of country music, there is a strength of love that is ever-present in it. In its quiet way, it powerfully depicts a relationship of a family history of support and understanding. – LW

#40
Little Rock
Collin Raye
1994 | Peak: #2

Listen

A recovering alcoholic makes a candid phone call to the one he had to leave at home. Getting sober was only the beginning; now he has to pick up the pieces of the life he let fall to shambles. A lesser song would have resolved the situation tidily; “Little Rock” wisely abstains, leaving a realistic sense of ambiguity about whether the man is truly fit to rekindle the relationship. – DM

#39
Any Man of Mine
Shania Twain
1995 | Peak: #1

Listen

A landmark moment, both for Twain and country music. The combination of arena-stomping verses and honky-tonking choruses was a musical revelation, while the thematic demand that men continually work to deserve their women’s affections helped contribute to a major shift in the female point-of-view presented in mainstream country. – DM

#38
Suspicious Minds
Dwight Yoakam
1992 | Peak: #35

Listen

Ah, to cover an Elvis Presley song is a pretty daunting task. So, it’s no small feat to be one of the few to record a version to rival a Presley recording. – LW

#37
Straight Tequila Night
John Anderson
1991 | Peak: #1

Listen

About a bar regular who’s infamous for nursing her broken heart with hard stuff and subsequently taking out her frustrations on interested suitors. Where did these songs go? – DM

#36
This Kiss
Faith Hill
1998 | Peak: #1

Listen

A big heap of stars-in-your-eyes-head-in-the-clouds-Taylor-Swift-on-Ecstasy drivel. In other words: the perfect soundtrack to new love. – DM

#35
Nobody Wins
Radney Foster
1993 | Peak: #2

Listen

The hard truth: sometimes you’ve got to give up winning the argument in order to avoid losing the love. – DM

#34
Come Some Rainy Day
Wynonna
1997 | Peak: #14

Listen

The current of time flows forcefully in one direction, yet it’s only the most vulnerable of memories that are strong enough to swim against it.- KC

#33
Anymore
Travis Tritt
1991 | Peak: #1

Listen

Tritt tackles this confession of a song with rousing, ferocious conviction so intense that you can almost feel the narrator’s tipping point as he comes to terms with his emotions. One hell of a power ballad. – TS

#32
Love, Me
Collin Raye
1991 | Peak: #1

Listen

“Love, Me”  is like one of those tearjerker movies that gets you every time, no matter how many times you see it.  For you, it might be Titanic or Terms of Endearment. For me, it’s Toy Story 3.  This one is a sucker punch to the gut, as only the very saddest movies and the very saddest country songs can be. – KC

#31
Please Remember Me
Tim McGraw
1999 | Peak: #1

Listen

The original recording by Rodney Crowell was great in its own right. But McGraw took it to new heights, thanks in no small part to Patty Loveless lifting him up with her harmony vocal. This is a selfish man making a supreme act of selflessness. – KC

#30
Things I Wish I’d Said
Rodney Crowell
1991 | Peak: #72

Listen

It’s not a secret that Rodney Crowell endured a tumultuous relationship with his father.  As one of Crowell’s forgotten gems, “Things I Wish I’d Said”, is a  cathartic autobiographical reflection of healing between parent and child. – LW

#29
Fancy
Reba McEntire
1991 | Peak: #8

Listen

A mother pushes her daughter into prostitution, seeing it as the only way for her daughter to have any hope of escaping poverty. The daughter does, and speaks out confidently against those who judge her and her mothers’ decisions. It was a great song when Bobbie Gentry did it; when flamboyant Reba happened upon it, it became its own kind of anthem. – DM

#28
A Night to Remember
Joe Diffie
1999 | Peak: #6

Listen

He’s reeling from a tough week, ready to let loose and have “a night to remember.” But all is not as it seems. No spoilers here – you’ve got to enjoy a good country music twist where you can find one – but Diffie has never met better material. It’s enough to make you annoyed with “Pickup Man” all over again. – DM

#27
Song For the Life
Alan Jackson
1995 | Peak: #6

Listen

Alan Jackson is a masterful interpreter just as Rodney Crowell’s composition is masterfully written. It’s certainly not unheard of, but it’s rare that a single without a catchy chorus is a hit. The quiet and reflective “Song for the Life”, however, is effectively poignant with no bells and whistles to overshadow the intimacy of the performance and lyrics. – LW

#26
In Between Dances
Pam Tillis
1995 | Peak: #3

Listen

Pam Tillis was one of the women who helped bridge the gap between the victim queens that came before her and the Rah! Rah! Girl Power! ladies who came after, and she did it with songs like this.  Here, her heart is on the mend, and a potential suitor is circling. Is he a knight in shining armor, or a vulture who senses weakness? Doesn’t really matter. She’s taking a breather for now, and will proceed cautiously from here.  The hurt is palpable, but so is the strength that lies underneath it. – KC

400 Greatest Singles of the Nineties: #125-#101

#125
Breathe
Faith Hill
1999 | Peak: #1

Listen

Sure, the melody of the chorus sounds just like “It Matters to Me.” But “Breathe” took the country power ballad to new heights, becoming Hill’s signature hit in the process. – Kevin Coyne

#124
Life’s a Dance
John Michael Montgomery
1992 | Peak: #4

Listen

It’s the catchy fiddle riff that’s  so memorable about John Michael Montgomery’s debut, number one, single. He is known for being a balladeer, but this one is an up-tempo motivational song. – Leeann Ward

#123
All the Good Ones are Gone
Pam Tillis
1997 | Peak: #4

Listen

A far more nuanced take on single women than “She’d Give Anything,” this tender ballad finds Tillis battling regret and loneliness, resignation and frustration. The most heart-wrenching part for me is the exchange between mother and daughter, as there are few things in this world more painful than feeling like you’re failing to live out the dreams your mother has for you. – Tara Seetharam

#122
We Just Disagree
Billy Dean
1993 | Peak: #9

Listen

An interesting, refreshing record in its maturity and perspective. If only every conflict in the world was treated with this kind of respect. – TS

#121
Spilled Perfume
Pam Tillis
1994 | Peak: #5

Listen

The regrettable one-night stand is a significant part of country music lore, but this song approaches it from a unique angle: that of the consoling friend looking in on the wreckage the morning after. Tillis is both sweet and frank in that role, passing on wisdom she herself had to come by the hard way. – Dan Milliken

#120
Whole Lotta Love On the Line
Aaron Tippin
1994 | Peak: #30

Listen

The relentless hook here is the guitar loop that powers the entire track. Tippin matches it with one of his very best heartbroke vocals. – KC

#119
Man! I Feel Like a Woman!
Shania Twain
1999 | Peak: #4

Listen

The definitive girl power anthem of ever. (Apologies to Madonna, Spice Girls, etc.) And although the vast majority of this record is pure pop, due credit to the very country wordplay in the title. – DM

#118
Feed Jake
Pirates of the Mississippi
1991 | Peak: #15

Listen

A quirky country-folk nugget which somehow fuses that cliche about sad dog-related country songs with sympathetic social commentary on the poor and gays. And it was a top 20 hit. Only in the nineties! – DM

#117
Next to You, Next To Me
Shenandoah
1990 | Peak: #1

Listen

A wonderfully catchy title translates to an equally catchy song. The joyous celebration of active love is ever present here. – LW

#116
I Feel Lucky
Mary Chapin Carpenter
1992 | Peak: #4

Listen

One of the coolest name-dropping songs of the nineties: “Dwight Yoakam’s in the corner, trying to catch my eye / Lyle Lovett’s right beside me with his hand upon my thigh /…Hey Dwight, hey Lyle, boys, you don’t have to fight / Hot dog, I feel lucky tonight.” – LW

#115
Wrong Side of Memphis
Trisha Yearwood
1992 | Peak: #5

Listen

Never mind that she had four top ten hits from her first album. This is where Trisha Yearwood, the artist, truly begins. – KC

#114
Is it Over Yet
Wynonna
1993 | Peak: #6

Listen

Such a simple melody with hardly a chorus; such a simple production with little more than a piano. It’s Wynonna’s fabulously emotive voice that takes this song from something potentially lifeless to a whole other stratosphere of emotion. – LW

#113
Down at the Twist and Shout
Mary Chapin Carpenter
1991 | Peak: #2

Listen

It’s an unshakably catchy Cajun dance tune that finds Carpenter as loose as she’s ever been. – LW

#112
Safe in the Arms of Love
Martina McBride
1995 | Peak: #4

Listen

Another installment, another reminder of how good Martina McBride can be given the right material. She’s asking to be cradled and supported here, but interestingly, there’s nothing submissive or needy-sounding about her performance. These are things she knows she deserves, and she’s confident enough to proclaim her desire for them loudly and proudly. – DM

#111
Almost Home
Mary Chapin Carpenter
1999 | Peak: #22

Listen

A revitalizing revelation from a woman who’s discovered that inner-peace is the key to moving forward in life. She speaks specifically to her own situation, but the song is both anthemic and spiritual, and, as a result, wonderfully accessible. – TS

#110
It Works
Alabama
1996 | Peak: #19

Listen

The sweeping social changes that have led to greater autonomy and independence for women came too late for some generations. But that doesn’t mean that no women felt completely fulfilled without the opportunities of their daughters and granddaughters. Not by a long shot. Remember that when your grandchildren wonder how you ever lived happily in such primitive times. – KC

#109
Delia’s Gone
Johnny Cash
1994 | Peak: Did Not Chart

Listen

From the first of the American  Recordings series, Cash’s second version of the murder ballad, “Delia’s Gone”, is as sparse as technically possible. There’s only a single acoustic guitar recorded in mono rather than stereo, but Cash’s voice resonates so much that it’s hardly noticeable. – LW

#108
There Goes My Baby
Trisha Yearwood
1998 | Peak: #2

Listen

Belting isn’t always necessary. It’s rarely necessary. But when you know the right moments to do it, and you have the chops to pull it off, you get magic like this. – KC

#107
Stand Beside Me
Jo Dee Messina
1998 | Peak: #1

Listen

Songs about female empowerment were abundant in the nineties, but there’s something raw about Messina’s approach, perhaps because she doesn’t display blind optimism. She knows the struggles associated with sticking to her standards, and she faces them with a realistic mix of strength and vulnerability. Per usual, Messina nails this sentiment in her performance. – TS

#106
What a Crying Shame
The Mavericks
1994 | Peak: #25

Listen

The Raul Malo-penned single was The Maverick’s breakthrough hit. It showcased a band with a fresh sound that even the nineties needed at certain points in the decade. – LW

#105
Has Anybody Seen Amy
John & Audrey Wiggins
1994 | Peak: #22

Listen

A song about getting older and feeling out of place, masquerading as a song about a long lost love. “You can always go home but you can never go back.” – KC

#104
No One Else on Earth
Wynonna
1992 | Peak: #1

Listen

Trod to death now that it’s basically Wynonna’s only recurrent, but this celebration of an exceptional love remains groovy karaoke bait with some very groovy growls from Ms. Judd. If you haven’t tried to mimic the “HOW DID YOU GET TO ME” part before, your country music fandom may not yet be valid. – DM

#103
You Win Again
Mary Chapin Carpenter
1990 | Peak: #16

Listen

Desperate. Despondent. Ferociously Bitter. – KC

#102
Meanwhile
George Strait
1999 | Peak: #4

Listen

He’s settling for paradise, since what he really wants is lost forever to the past. – KC

#101
The Heart Won’t Lie
Reba McEntire & Vince Gill
1993 | Peak: #1

Listen

Two of the most distinct voices in country music tear their way through a throbbing sentiment on this power ballad. It’s one of those records that just soars. – TS

400 Greatest Singles of the Nineties: #225-#201

#225
Passionate Kisses
Mary Chapin Carpenter
1992 | Peak: #4

Listen

A lightweight wish list/love ditty that somehow seems to tap into a deep well of truth. Credit Carpenter’s soulful vocal, which digs in and finds the cohesive character written between the song’s separate cute lines. – Dan Milliken

#224
Black Coffee
Lacy J. Dalton
1990 | Peak: #15

Listen

The electric guitar line sounds cribbed from The Police’s “Every Breath You Take”, but the sentiment couldn’t be much more different. Dalton is tense all over, as bad omens seem to stack on top of each other while she waits in anticipation of one big let-down. – DM

#223
Everytime I Cry
Terri Clark
1999 | Peak: #12

Listen

The downward spiral of abuse may be more dramatic when it climaxes with a burning house. It certainly makes for a heck of a song. But choosing to walk away, overcoming the weakness inside in the process, makes for a heck of a song, too. – Kevin Coyne

#222
The Tips of My Fingers
Steve Wariner
1992 | Peak: #3

Listen

These days Bill Anderson is most known for co-writing Brad Paisley’s “Whiskey Lullaby” and George Strait’s “Give It Away”, but Steve Wariner’s “Tips of My Fingers” is yet another lonesome Anderson composition from the early nineties. The  soaring blend of Wariner’s lead and Vince Gill’s background vocals is the perfect combination to sell this song of self-inflicted heartache. – Leeann Ward

#221
Don’t Rock the Jukebox
Alan Jackson
1991 | Peak: #1

Listen

Only Jackson could turn one “heartbroke” hillbilly’s simple request to hear some Jones into an endearing tagline for country music. – Tara Seetharam

#220
Soon
Tanya Tucker
1993 | Peak: #2

Listen

They say that “someday never comes.” Such is the case with “Soon”, as Tucker’s character learns the hard way. – LW

#219
Rumor Has It
Clay Walker
1997 | Peak: #1

Listen

The roses, the wine and his unexplainable smile are giving away Walker’s secret, but the only thing he cares about is whether or not his special someone shares the same secret. I find myself wanting to use the word “charming” every time I write about Walker, but that’s just what this is: a charming little record that he sings with sincerity. – TS

#218
Sold (The Grundy County Auction Incident)
John Michael Montgomery
1995 | Peak: #1

Listen

I’m not sure how this scenario would play out in real life, but it makes for a part ridiculous, part ingenious toe-tapper. – TS

#217
Angels Working Overtime
Deana Carter
1999 | Peak: #35

Listen

Is the driving force here God’s plan for the girl or the girl’s faith that God will provide? Does it matter, given the glorious result? – KC

#216
I’ll Try
Alan Jackson
1995 | Peak: #1

Listen

On the surface, it seems like a halfhearted declaration of commitment, since we’re used to saying, “I promise to love only you.” However, anyone who’s in a committed relationship, even the strongest of relationships, learns that “I’ll try” is really the most honest promise one can make. – LW

#215
If I Didn’t Have You
Randy Travis
1992 | Peak: #1

Listen

Randy Travis is really good at the up-tempo love songs. “If I Didn’t Have You” isn’t necessarily lyrically original, but the jaunty production and Travis’ vocal exuberance elevates the song from sappy to delightful. – LW

#214
Whenever You Come Around
Vince Gill
1994 | Peak: #2

Listen

I stand by my belief that the best-written lyrics can’t touch the best-written melodies or the most expressive vocal performances. Case in point: “Whenever You Come Around,” in which Gill conveys through his vocal performance alone the intoxicating, paralyzing infatuation he has with a woman. He pays such careful attention to the synergistic rise and fall of the sentiment and melody that I’m convinced no combination of words could have told this story better. – TS

#213
If I Know Me
George Strait
1991 | Peak: #1

Listen

It’s a simple song of commitment. He knows that no matter the argument, they’ll be back in each other’s arms when all is said and done. – LW

#212
Tender When I Want to Be
Mary Chapin Carpenter
1994 | Peak: #6

Listen

Carpenter acknowledges that strength is an admirable quality, but a budding relationship shows her that a little tenderness isn’t a sign of weakness. – LW

#211
Norma Jean Riley
Diamond Rio
1992 | Peak: #2

Listen

Diamond Rio shows off their tight harmonies and instrumental prowess in this goofy song  that celebrates the steps of sheer infatuation. – LW

#210
Don’t Tell Me What to Do
Pam Tillis
1990 | Peak: #5

Listen

Tillis stands up for her right as an independent woman…to stay hopelessly in love with you. The drums drive it, the steel guitar defines it. A brilliant fusion of old and new in both theme and sound. This lady knew what she was doing. – DM

#209
Blue Clear Sky
George Strait
1996 | Peak: #1

Listen

There he goes again, turning one of life’s simplest truths – that love, like the best things in life, comes when you least expect it – into a solid hit, made all the more charming by its Forrest Gump-inspired turn-of-phrase. – TS

#208
Nowhere Bound
Diamond Rio
1992 | Peak: #7

Listen

How influential was sixties rock on nineties country? Diamond Rio did a country derivative on the Beatles classic “Nowhere Man” without compromising its integrity as a country record or cheapening the classic original. – KC

#207
Hey Cinderella
Suzy Bogguss
1993 | Peak: #5

Listen

Bogguss understands the wiser, more mature version of the fairy tale; the one where the mundane details of life take center stage. – LW

#206
Dust On the Bottle
David Lee Murphy
1995 | Peak: #1

Listen

My guess is that this spunky little record from the mid-90s is still in rotation today not just because it’s infectious ear candy, but because, like the best country songs, it uses a bite-size story to tell a timeless, life-size truth. – TS

#205
I’m Alright
Kim Richey
1997 | Peak: Did Not Chart

Listen

“After all was said and done…there was nothing left to do.” The weary smile embedded in that opening line lingers through the song, which doesn’t make a big show out of getting over someone and persevering through the occasional pain. This is what real people sound like when they decide to overcome stuff, I think. (I am also assuming that real people have sunny banjo parts playing somewhere during such decisions.) – DM

#204
Lead On
George Strait
1995 | Peak: #7

Listen

Two weary lovers who were burned in their youth find new hope in each other. Well, not so much hope as a willingness to believe that their potential future together might be better than being alone with the memories of love from days gone by. – KC

#203
Lord Have Mercy On a Country Boy
Don Williams
1991 | Peak: #7

Listen

Williams wistfully longs for the country  life that he once enjoyed, but his beloved country surroundings has slowly transformed into a city, which is difficult for him to endure. Unlike many “I’m from the country songs”, this one lacks the bravado and, instead, conveys humble befuddlement. – LW

#202
One of These Days
Tim McGraw
1998 | Peak: #2

Listen

Lays on enough sap to rival “Don’t Take the Girl”, but if you can sift through that, there’s a strikingly frank self-reflection here by a man with whom we might not normally think to sympathize. – DM

#201
Tempted
Marty Stuart
1991 | Peak: #5

Listen

Marty Stuart is respected for championing traditional country music today, but he wasn’t afraid to stray from the format at times back in the day. Listen to this song, and you hear some cool  old-time rock influences. – LW

400 Greatest Singles of the Nineties: #275-#251

#275
Somewhere Other Than the Night
Garth Brooks
1992 | Peak: #1

Listen

About a woman who only feels truly appreciated by her husband when they’re having sex. Practically literature, that. – Dan Milliken

#274
Looking Out For Number One
Travis Tritt
1993 | Peak: #11

Listen

From his rocking side, Tritt is tired of trying to please everyone around him, including his demanding lover. As a result, he brashly declares that he’s going to make some changes, which will include looking out for himself. Get out of the way, because his ferocious performance makes him seem quite serious about his epiphany. – Leeann Ward

#273
Let That Pony Run
Pam Tillis
1992 | Peak: #4

Listen

Gretchen Peters wrote the gorgeous song and Pam Tillis, in turn, beautifully sings it. The song is about Mary, a woman who is forced to start a new life after her husband confesses his infidelities with no apologies. The story is sad, it’s resilient, and it’s hopeful. – LW

#272
I Just Want to Dance With You
George Strait
1998 | Peak: #1

Listen

Any monotony in the verses is overcome by the song’s completely enticing rhythm and flavor. How can you not get lost in this? – Tara Seetharam

#271
Come Next Monday
K.T. Oslin
1990 | Peak: #1

Listen

The cheap-sounding keyboard production is actually a perfect fit for this plucky song about forgetting an old love…next week. Also a perfect fit for the song: the hilarious, similarly cheap video. – DM

#270
Keep it Between the Lines
Ricky Van Shelton
1991| Peak: #1

Listen

The rich voiced, traditionally minded Van Shelton seems almost forgotten today. In turn, “Keep It Between the Lines” is one of his nearly forgotten hits, which is a shame, as it’s a heartbreaking, yet tender, father song that’s rarely recognized on the annual Father’s Day lists. – LW

#269
I Can’t Do That Anymore
Faith Hill
1996 | Peak: #8

Listen

The sinking housewife is Faith Hill’s specialty role. If this Alan Jackson-penned confessional doesn’t have the striking vision of “Stealing Kisses”, it’s nonetheless powerful in its directness. – DM

#268
Holes in the Floor of Heaven
Steve Wariner
1998 | Peak: #2

Listen

Over-the-top sad but wonderfully written, Wariner’s classic serves as both a touching homage to lost loved ones and a comfort to those they’ve left behind. – TS

#267
Wish I Didn’t Know
Toby Keith
1994 | Peak: #2

Listen

Is ignorance bliss when it comes to cheating lovers? Keith wrestles with his conflicting feelings in this cleverly written song, proving once again that his gruff bravado is most effective when he’s expressing a multi-faceted sentiment. – TS

#266
Why Didn’t I Think of That
Doug Stone
1993 | Peak: #1

Listen

Call it the mature version of Mark Chesnutt’s “It’s a Little Too Late” – same concept, but more introspective and wistful. – TS

#265
Quittin’ Time
Mary Chapin Carpenter
1990 | Peak: #7

Listen

One of her earliest hits benefits from an aggressive vocal and escalating production that goes crazy with the drums in the final verse. – Kevin Coyne

#264
Wrong Again
Martina McBride
1998 | Peak: #1

Listen

Nobody likes to be wrong, but poor Martina seems to have a knack for it. Just when she’s sure that she’s finally found “the one”, she discovers that she’s, once again, wrong. It’s one of Martina’s best songs, which, just about marks the end of her time of  best songs. – LW

#263
One Way Ticket (Because I Can)
LeAnn Rimes
1996 | Peak: #1

Listen

There’s a distinct moment after every break-up when the pain subsides, the clouds part and there it is – a world of opportunities in front of you that you feel like you’re seeing for the first time. Rimes captures this experience perfectly in “One Way Ticket,” with a performance that exudes spirit and conviction. – TS

#262
Down to My Last Teardrop
Tanya Tucker
1991 | Peak: #2

Listen

A snappy, energetic performance brimming with self-assurance. – TS

#261
Sawmill Road
Diamond Rio
1993 | Peak: #21

Listen

In contrast to their very successful first few singles, this was  the first single of Diamond Rio’s to receive lukewarm radio reception. It is, however, a gem from their sophomore album that portrays a tight knit sibling group with ideal childhoods who all grew up to take vastly different paths as adults. – LW

#260
You’re Easy on the Eyes
Terri Clark
1998 | Peak: #1

Listen

Good-looking men and women who are otherwise terrible people are among the key recurring characters in country music lore. This song about one such man has become so well-known that it’s easy to take for granted how well it actually upholds the tradition. – DM

#259
Cheap Whiskey
Martina McBride
1992 | Peak: #44

Listen

Written by Emory Gordy, Jr. (Patty Loveless’ husband), “Cheap Whiskey” is a straight up country song that McBride mournfully tackles with complete success. The man chooses cheap whiskey over good love and he lives to regret it as a lonely, broken person. And who’s that guy singing in the background? Well, none other than Garth Brooks. – LW

#258
The Day That She Left Tulsa (In a Chevy)
Wade Hayes
1997 | Peak: #5

Listen

A great modern heartbreak story narrated by one of our great modern heartbreak singers. You just can’t go wrong. – DM

#257
Baby Likes to Rock It
The Tractors
1994 | Peak: #11

Listen

A bizarre, awesome, unique boogie-woogie record that somehow got to be a #11 country hit. My personal favorite part is how the lead singer’s riffs near the beginning of the song actually sound like a tractor revving. – DM

#256
Out of My Bones
Randy Travis
1998 | Peak: #2

Listen

How do you know that Travis will get this woman out of his bones? Because his searing voice and the fiery fiddle combine to cut right down to them. – KC

#255
Don’t Let Our Love Start Slippin’ Away
Vince Gill
1992 | Peak: #1

Listen

This song is essentially a plea to save a relationship, but I find it uplifting more than anything else, perhaps because the focus is kept on the couple’s underlying love. There’s a hopefulness to the song that’s woven into both Gill’s performance and the warm melody. – TS

#254
When I Said I Do
Clint Black and Lisa Hartman Black
1999 | Peak: #1

Listen

Don’t look at me like that. Not all schmaltz is inherently evil, and when it’s as well-crafted and exceptionally well-sung as it is here, who’s going to complain about a little extra sentimentality dripping off?  – DM

#253
Whatcha Gonna Do With a Cowboy
Chris LeDoux with Garth Brooks
1992 | Peak: #7

Listen

Garth Brooks gets to sing with one of his performing heroes and you can hear the joy in the recording as a result. The  comical, fiddle-laden song asks the unthinkable: “Whatchya gonna do with a cowboy when he don’t saddle up and ride away?” – LW

#252
Thinkin’ Problem
David Ball
1994 | Peak: #2

Listen

Again, all you have know is the title to know why country fans like us love songs like this. – DM

#251
Mama Knows the Highway
Hal Ketchum
1993 | Peak: #8

Listen

Country music chronicles a lot of trucking fathers, but the trucker in this song isn’t your typical truck driver character, but instead, a mama who knows the highway by heart, including its conditions at various points. – LW

400 Greatest Singles of the Nineties: #300-#276

#300
Does He Love You
Reba McEntire with Linda Davis
1993  |  Peak: #1

Listen

This two-female duet was a gamble at the time of its release, but it offers such a brilliant fusion of perspectives that it’s hard to imagine why. The song fleshes out the range of emotions that the two women are experiencing –from pain to longing to self-doubt– and culminates in one shared question that they’ll never know the answer to: “does he love you like he’s been loving me?” – Tara Seetharam

#299
The Hard Way
Mary Chapin Carpenter
1993  |  Peak: #11

Listen

The chorus is catchy, something that would work as a good audience participation song at a concert, so it’s possible to miss the message. “Show a little inspiration; show a little spark,” she implores. It might be work, even hard work, but a good relationship won’t last without it. – Leeann Ward

#298
He Ain’t Worth Missing
Toby Keith
1993  |  Peak: #5

Listen

Toby acknowledges the woman’s feelings in this song, but offers her a little straight talk, along the way. Not only does he assure her that her ex isn’t worth missing, he lets her know that he’s more than willing to be the replacement. – LW

#297
That Don’t Impress Me Much
Shania Twain
1998  |  Peak: #8

Listen

One of the campiest, sing-and-talk-a-longiest singles ever. Long after you’ve forgotten most of this year’s great serious songs, you’ll still remember the exact timing and inflection of, “OK, so you’re Brad Pitt.” – Dan Milliken

#296
Friends
John Michael Montgomery
1996  |  Peak: #2

Listen

A record that hinges on two sad truths. First, a love affair has ended. Second, all friendships come to an end. – Kevin Coyne

#295
Phones are Ringin’ All Over Town
Martina McBride
1996  |  Peak: #28

Listen

With the build up of the song, the frenzy that the repeat cheater is feeling is palpable. Even though he knows exactly why she’s left, he desperately tries to find her, which is why “phones are ringin’ all over town.” – LW

#294
Chains
Patty Loveless
1990  |  Peak: #1

Listen

One of Loveless’ earliest hits, “Chains” revolves around a hook that’s as simple as they come, but therein lies its charm. – TS

#293
Even the Man in the Moon is Crying
Mark Collie
1992  |  Peak: #5

Listen

Mark Collie is one of the casualties of the Ninetiescountry boom. Despite talent, he just couldn’t keep up with the big hit makers of the decade. “Even the Man on the Moon Is Crying” is one of his most memorable songs, however. From the moment he drops her off at the airport, he knows it’s over, despite putting on a brave front. It’s all so sad and final that even the man on the moon is crying. – LW

#292
Right On the Money
Alan Jackson
1998  |  Peak: #1

Listen

If only Phil Vassar, one of the song’s writers, would record a song this cool. The best line?: “She’s the best cook that’s ever melted cheese.” – LW

#291
Walkin’ Away
Clint Black
1990  |  Peak: #1

Listen

“Walking away, I saw a side of you that I knew was there all along.” Oh, how I long for the days when his word craft described love gone wrong instead of right. – KC

#290
Something Like That
Tim McGraw
1999  |  Peak: #1

Listen

On the surface, “Something Like That” is a fairly basic story of two teenagers’ first kiss. But the true value of this classic is spelled out in its bridge: “Like an old photograph, time can make a feeling fade/But the memory of the first love never fades away.” I’ve always viewed this song as a validation of puppy love: that no matter how trivial the details or circumstances –be it barbecue stains, miniskirts or skippin’ rocks on the river – the experience of your first love matters. – TS

#289
On a Bus to St. Cloud
Trisha Yearwood
1995  |  Peak: #59

Listen

Haunted by the ghost of a love that she sees everywhere that she goes, she loves him some, hates him some, but misses him most. – KC

#288
Easy Come, Easy Go
George Strait
1993  |  Peak: #1

Listen

Even though they’re saying goodbye, this song is as relaxed as the title suggests. If only the dissolution of all relationships were this calm. – LW

#287
Tall, Tall Trees
Alan Jackson
1995  |  Peak: #1

Listen

George Jones and Roger Miller both recorded versions of this quirky number they co-wrote, but it was latter-day traditionalist Jackson who made it a hit. The ridiculous lyrics – about a lovestruck man who pledges to buy his girl trees, limousines, and all the planet’s ocean waters – are equal parts spoof and celebration of the blissful irrationality of new love. – DM

#286
Clown in Your Rodeo
Kathy Mattea
1995  |  Peak: #20

Listen

In the contemporary Christian music world, Wayne Kirkpatrick wrote most of the lyrics to Michael W. Smith’s melodies. In country circles,  he is most known for his involvement in Garth Brook’s Chris Gaines project and, most recently, his contributions to Little Big Town’s career. Back in the mid-nineties, however, he was the writer of “Clown in Your rodeo”, a fun, sassy number from one of Kathy Mattea’s most popular albums. – LW

#285
It’s Lonely Out There
Pam Tillis
1996  |  Peak: #14

Listen

One of her strongest vocal performances, as the casual indifference to a man threatening to leave quickly escalates into genuine fear. By the end, she’s begging him to stay, realizing  it’ll be just as lonely in here if he’s gone. – KC

#284
You Lie
Reba McEntire
1990  |  Peak: #1

Listen

The modern heartbreak queen takes the weepy country ballad to spine-tingling heights that Kitty Wells and Tammy Wynette never dreamed of. – KC

#283
Why Walk When You Can Fly
Mary Chapin Carpenter
1995  |  Peak: #45

Listen

Nowadays, a song with this title would probably be all about one person trying to work up the self-confidence to achieve some kind of worldly success – an elementary-school “believe in your dreams” thing. But in the nineties, it was a warm, understated challenge to us all to break free of our cyclical demons – selfishness, fear, pointless finger-pointing – for the good of humankind as a whole. We walk or we fly together. – DM

#282
Nothin’ But the Taillights
Clint Black
1997 |  Peak: #1

Listen

Left on the side of the road by his lover, Black reflects on his sticky situation in this inescapably catchy number. – TS

#281
Unbreakable Heart
Carlene Carter
1993  |  Peak: #51

Listen

Radio loved her when she was rowdy, but she’s just as good when she’s nakedly vulnerable.- KC

#280
Burnin’ the Roadhouse Down
Steve Wariner with Garth Brooks
1998  |  Peak: #26

Listen

You’ve got to give them credit. Steve Wariner and his buddy, Garth Brooks, try to take an old fashioned sounding, western swing flavored song to mainstream country radio. Within the warm production, check out the cool guitar picking from Wariner, not to mention steel guitar aplenty. – LW

#279
Who Needs Pictures
Brad Paisley
1999 |  Peak: #12

Listen

A man thinks about going to develop a roll of pictures (remember those?) featuring his ex, but figures it would be redundant: “who needs pictures with a memory like mine?”. Still one of Paisley’s best moments.  – DM

#278
Whatever You Say
Martina McBride
1999  |  Peak: #2

Listen

New-millenium fans may not realize that there was a time when McBride’s whisper-then-BELT style actually seemed fresh. This ultimatum to a cold lover feels like a natural progression of the songs heartbroken women had always sung in country music, but the skyscraping vocal was McBride’s own twist on the model, and it was a truly cool innovation – until, of course, it became the insufferable norm. – DM

#277
You’ve Got a Way
Shania Twain
1998  |  Peak: #13

Listen

Twain was often criticized for being a subpar vocalist, but the difference between Twain and, say, Taylor Swift is the former’s ability to use her instrument to express shades of emotion, working with instead of against her vocal imperfections. “You’ve Got a Way” is a perfect example, with Twain soulfully and stirringly filling every crevice of the acoustic arrangement. – TS

#276
Two Sparrows in a Hurricane
Tanya Tucker
1992  |  Peak: #2

Listen

This is a straightforward, paint-by-numbers love story song, but one that manages to seem sweet and simple all the same. – LW

400 Greatest Singles of the Nineties: #350-#326

#350
How Do I Live
Trisha Yearwood
1997  |  Peak: #2

Listen

When Yearwood and LeAnn Rimes released dueling versions of this song in 1997, it was apparently a wake up call to country listeners: “Hey, wait a minute. Trisha Yearwood is an amazing singer!”  She elevates “How Do I Live” beyond its movie theme nature by adding layers of subtlety and nuance to the typical Diane Warren template. – Kevin Coyne

#349
Boot Scootin’ Boogie
Brooks & Dunn
1992  |  Peak: #1

Listen

I don’t claim to have any real knowledge of what it’s like to spend a night at the liveliest of honky-tonks, but I’ll be darned if this song doesn’t make me feel like I do. Because “Boot Scootin’ Boogie” isn’t really about a specific place where people go, and it isn’t even about the boogie itself; it’s about the universal thrill of busting out of the work week, kicking back and dancing your troubles away. From start to finish, Brooks & Dunn’s performance is a twangy blast of exhilaration, and that’s a feeling we can all relate to – outlaws, in-laws, crooks and straights alike. - Tara Seetharam

#348
Don’t Take Her She’s All I Got
Tracy Byrd
1997  |  Peak: #4

Listen

Just a damn catchy trad country sing-a-long. It was good fun when Johnny Paycheck had the original hit with it, and lost none of its steam when Tracy Byrd resurrected it for a new audience twenty-six years later. – Dan Milliken

#347
Walkaway Joe
Trisha Yearwood with Don Henley
1992  |  Peak: #2

Listen

Yearwood’s sad appraisal of a youthful infatuation feels almost like a parable in its scope and execution. You know the story’s ending from the very beginning, but you wait to hear it unfold anyway, possibly just so you can reflect on similar mistakes you wish you had seen coming. That might be why none of the characters in this song – Momma, Girl, Walkaway Joe – are given real names; as in any parable, they’re archetypes for us to see through as we try to rectify our own pasts and futures. – DM

#346
Ain’t Got Nothin’ On Us
John Michael Montgomery
1996  |  Peak: #15

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Montgomery is mostly known for his sappy, country-pop love songs. This is a love song, but the bluesy little number is more understated than his typical fare. - Leeann Ward

#345
I’ll Go On Loving You
Alan Jackson
1998  |  Peak: #3

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Jackson’s rarely more impressive than when he ventures out of his comfort zone. His bold choice to bring the recitation back to country radio made for one of his strongest singles from the latter half of the decade. – KC

#344
The Night the Lights Went Out in Georgia
Reba McEntire
1992  |  Peak: #12

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Reba sings the heck out of this epic tale of murder. The performance and accompanying production are both spooky and fun. - LW

#343
What About the Love We Made
Shelby Lynne
1995  |  Peak: #45

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Guilt trips on divorcing parents aren’t laid much thicker than this, at least without Tammy Wynette at the mic. Needless to say, Lynne sings the fire out of it.- KC

#342
It’s Only Love
Randy Scruggs with Mary Chapin Carpenter
1998  |  Peak: #67

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Carpenter’s got it right; When it comes to love, “there’s no choice but to surrender.” The lyrics are just this side of saccharine, but the jaunty production is irresistible. - LW

#341
Gone as a Girl Can Get
George Strait
1992  |  Peak: #5

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Due to an awesomely relaxed production that allows guitars and fiddles to shine without overwhelming the track, this is about the coolest  Strait hit there is. She’s not just kind of gone, “she’s about as gone as a girl can get.” - LW

#340
Daddy Never Was the Cadillac Kind
Confederate Railroad
1994  |  Peak: #9

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Our generation needed its own spin on “Coat of Many Colors”, and this gem from Confederate Railroad delivered the goods. – KC

#339
Tryin’ to Get Over You
Vince Gill
1994  |  Peak: #1

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It’s possible to attribute a morbid message to this song if you take the lyrics literally, but I think the focus was meant to be on the effects of an undying love rather than on a man who wants to die. Gill colors his performance with layers of aching, relentless pain so tangible that the emotion practically jumps off the track. - TS

#338
A Man Ain’t Made of Stone
Randy Travis
1999  |  Peak: #16

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Men get a lot of flack for having it better than women, but one disadvantage that they have is that they’re expected to control their emotions, especially any signs of weakness. The catch is that they’re also expected to be sensitive at the right moments, which is a difficult balance for anyone to try to strike. It takes his woman leaving him for this man to lose his emotional resolve, which, incidentally, is  what it seems the woman needed from him all along. - LW

#337
The Beaches of Cheyenne
Garth Brooks
1996  |  Peak: #1

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Another Garth Brooks epic, this time delving into the realm of ghosts with loaded regrets. Musically, a great example of Brooks’ arena-country style done right. – DM

#336
Take it Easy
Travis Tritt
1994  |  Peak: #21

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As a part of country music’s tribute to The Eagles, Tritt delivers a solid cover of “Take It Easy”, which turns out to have more body than the original. - LW

#335
Tell Me About It
Tanya Tucker and Delbert McClinton
1993  |  Peak: #4

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There’s no twang here, but the rocking guitar groove is addictive. Moreover, Tucker’s and McClinton’s rough-edged voices  have a familial-like sound. - LW

#334
Unanswered Prayers
Garth Brooks
1990  |  Peak: #1

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Through a snapshot of a run-in with an old flame, Brooks illustrates that God’s blessings aren’t always what we expect them to be, and his approach is near perfect – relatable, thoughtful and authentic. - TS

#333
She Can’t Save Him
Lisa Brokop
1995  |  Peak: #55

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A frank portrait of a woman wrestling with the fact that she can’t help her substance-abusing husband until he helps himself. The gorgeous bridge brings the song to life, using imagery to depict the couple’s relationship. - TS

#332
I’ve Got That Old Feeling
Alison Krauss
1991  |  Peak: Did Not Chart

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Even as a young bluegrass prodigy, Krauss did most of her best work while fixated on painful goodbyes. In this case, the goodbye hasn’t even happened yet, but it’s all the more painful because she has the experience to sense it coming. – DM

#331
High On a Mountain Top
Marty Stuart
1992  |  Peak: #24

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Stuart spends his life climbing his way to the top, leaving behind the ones who helped get him there along the way.  With a little help from a wailing Pam Tillis on harmony, he realizes it’s lonesome up there all by himself. – KC

#330
You Can Depend On Me
Restless Heart
1991  |  Peak: #3

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Restless Heart had some likable soft jams in their 80′s hey-day, but were never better than when they got their bluegrass-pop on with this awesome campfire anthem. – DM

#329
If You Came Back From Heaven
Lorrie Morgan
1994  |  Peak: #51

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Morgan writes and performs a fascinating composition in which she wonders how the reality would play out if her fantasy came true, and her late husband returned to her arms.  Among the questions she’d ask him: “Did you feel my body when I held your pillow tight?” – KC

#328
That Summer
Garth Brooks
1993  |  Peak: #1

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Brooks manages to make a tawdry love affair sound steamy without seeming dirty. - LW

#327
XXX’s and OOO’s (An American Girl)
Trisha Yearwood
1994  |  Peak: #1

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An all American girl grows up to become a woman who’s trying to “make it in her daddy’s world.” No more frivolous dressing up; it’s real life now. - LW

#326
Getcha Some
Toby Keith
1998  |  Peak: #18

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In the 2000s, Toby Keith has carefully crafted his image as a patriotic chest-thumper. In the nineties, however, his music seems more relaxed, as is the case with this delightful chronicle of a developing relationship. - LW