As we reach the halfway point of the countdown, seventies stars like Tanya Tucker and Don Williams prove just as relevant to the decade as newbies like Terri Clark and and Clay Walker. But it’s eighties original George Strait that dominates this section with three additional entries.
400 Greatest Singles of the Nineties: #225-#201
#225
Passionate Kisses Mary Chapin Carpenter
1992 | Peak: #4
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
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 (more…)
At least the third song on this list about a guy mulling over romantic gestures he wishes he’d made to his former love, and the most traditional among those songs. You could easily imagine this one being a minor classic by a 60′s or 70′s legend, so close is its replication of that style. – Dan Milliken
#249
I’m So Happy I Can’t Stop Crying Toby Keith with Sting
1997 | Peak: #2
My hard-and-fast rule for Toby Keith: The sadder he is, the happier the listening experience tends to be. He’s all kinds of sad in this snapshot of post-divorce melancholia, reflecting on everything from unfair custody protocol to the greater motions of the universe. Even a gratuitous Sting cameo can’t detract from the single’s gloomy grandeur. – DM
#248
You Ain’t Much Fun Toby Keith
1995 | Peak: #2
Toby Keith is also funny, though. What’s a man to do? Sobering up ain’t all that it’s cracked up to be from is perspective. Ever since he’s done so, his wife has been taking advantage of his increased functionality by giving him honey-do lists that he wasn’t ably tackling pre-sobriety. It’s enough to drive a man to drink. – Leeann Ward
#247
Tender Moment Lee Roy Parnell
1993 | Peak: #2
Every once and awhile an artist delivers a song so powerful that it seems to shatter all divides in its genre. A tribute to both the late Keith Whitley and Gill’s late brother, “Go Rest High On That Mountain” pairs deeply spiritual lyrics with a tender, emotion-soaked performance. The combination is magic. – TS
Living up to its title, the Yoakam’s barren heart and soul are replicated in the arrangement of the song. If emptiness has a sound, this is it. – Kevin Coyne
#244
(Who Says) You Can’t Have it All Alan Jackson
1994 | Peak: #4
A good power ballad shot to greatness by its artists’ striking chemistry – palpable, fiery and so very genuine. More than just a hit single, “It’s Your Love” represents the moment in country music history at which we were introduced to one of its definitive couples. – TS
#242
Grandpa Told Me So Kenny Chesney
1995 | Peak: #23
Amidst a collection of country life lessons passed down from two generations back is one to live by: “There’ll be times that you want to hold on but you’ve got to let go.” – KC
#241
Thank God For You Sawyer Brown
1993 | Peak: #1
An earnest, soulful confession of love. It’s hard to ignore the fact that it leans more in the adult-contemporary direction than that of anything else, but when a song is this moving, it’s also hard to care. – TS
#239
What She’s Doing Now Garth Brooks
1992 | Peak: #1
In an unusual tact for Mr. Brooks, he forgoes melodrama in order to allow the natural drama of pining for a lost love to speak for itself. The dialed down performance works in the service of the song, as the sadness appropriately penetrates through. – LW
#238
Find My Way Back to My Heart Alison Krauss & Union Station
1997 | Peak: #73
Some of the best songs from AKUS play on the home life that’s sacrificed by following the musical dream. Krauss remembers how she used to laugh at songs about the lonely traveling life, but she’s not laughing now. – KC
A man makes a soaring yet understated plea for his lover to let go of her past love. The song is made sadder by the touch of resignation in Wariner’s performance, which suggests the man knows he’s making his plea in vain. – TS
Roba Stanley once sang about the joys of the single life and its simplicities. Richey is about to leave it behind, and wonders just how lucky that makes her. – KC
A whole song about deciding whether or not to go all the way with one’s movie date. McCready gives a fantastically entertaining performance, speak-singing her lines with a a bold campiness that most other gals wouldn’t dare. – DM
#233
Chasin’ That Neon Rainbow Alan Jackson
1990 | Peak: #2
Stories of would-be stars trying to make it big in Nashville are nothing too novel, but Jackson’s plucky earnestness gives this one an accessibility many of the others lack. – DM
#232
Now That’s All Right With Me Mandy Barnett
1996 | Peak: #43
The other great Barnett single of the era, fusing Patsy Cline-style vocal class, Pam Tillis-style production and Gloriana-style youthful exuberance. – DM
Ten years before “You Belong With Me” made its splash, McCann set her sights on the same demographic with a song just as relatable, vibrant and passionate. That the song lacks Taylor Swift’s sharp perspective is perhaps what makes it such a great record: there’s something so pure about McCann’s fully unapologetic, headfirst fall into love. – TS
Chesnutt makes a phone call to an old love that could be construed as creepy, pathetic or terribly sad – take your pick. I’m going with a mixture of all three, with a pinch of selfishness thrown in. Either way, “I Just Wanted You to Know” is a memorable slice of the-one-that-got-away reality.- TS
In the twenty years that passed since the release of this song, the path to success in the music industry has morphed into something that looks very different than it used to. Unlike that of Bobby in the song, these days an artist’s journey can come in all shapes and forms, sometimes abrupt and sometimes completely unprecedented.
Think what you want about this paradigm shift, but here’s what I believe: regardless of how you shoot to the top, the only way you’ll achieve longevity and, most importantly, respect in country music is if you share the fire in Bobby’s eyes. This soul-stirring hunger and unshakable passion is the heart of “I’m Gonna Be Somebody” and the reason it remains a timeless classic. Here’s to hoping – and I’m optimistic – our modern artists are made of the same stuff. – TS
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 (more…)
The list continues with appearances from artists who first surfaced in the eighties and continued to thrive into the nineties, like Reba McEntire and Patty Loveless, along with new stars from the nineties who would find greater success in the next decade, like Toby Keith and Brad Paisley.
400 Greatest Singles of the Nineties: #300-#276
#300 Does He Love You Reba McEntire with Linda Davis
1993 | Peak: #1
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 (more…)
Sometimes the choices that you make linger forever. Here, a woman in her thirties drives past a high school football game, and her mind wanders to the painful void left in her heart from the son she gave up for adoption. – Kevin Coyne
Faith Hill’s sophomore album is a surprisingly deep set, filled with candid insights into different womens’ lives. The title track represents that approach well, with Hill’s protagonist speaking to the differences in her approach to love and her partner’s. Seems simple, but then again, people spend thousands in couples counseling trying to find a way to voice feelings this directly. – Dan Milliken
#323
She’d Give Anything Boy Howdy
1993 | Peak: #4
A not-so-subtle depiction of how elusive true love can be for some women – even those who desperately seek it – that resonates not despite of but because of its blatancy. There’s a beautiful honesty to the song’s precise articulation of the mixture of frustration and strength that builds up within these women. – Tara Seetharam
#322
The Trouble With the Truth Patty Loveless
1997 | Peak: #15
The trouble with the truth is that is just so demanding. We think we want it, but it often requires some sort of action from us once we have it. Loveless struggles with this quandary: “The trouble with the truth is it always begs for more. That’s the trouble with the truth.” – Leeann Ward
#321
Still Gonna Die Old Dogs
1999 | Peak: Did Not Chart
Waylon Jennings, Mel Tillis, Bobby Bare, and Jerry Reed united for an amazing live album dominated by Shel Silverstein songs. For anyone who read his brilliant poetry books for children, “Still Gonna Die” is the golden years equivalent: clever, frightening, and darkly hilarious. KC
An apology via a wanted ad could be disastrous in the hands of many male country artists, but it’s simply lovely in Jacksons’, ringing with sincerity and regret. – TS
#319
Finish What We Started Diamond Rio
1995 | Peak: #19
From the first strains of the song, we know this is going to be a dark one. While he hasn’t physically cheated yet, the thoughts of at least wishing to do so are spilling over, which begs the analogy of “It’s like trying to hide a fire in the dark.” – LW
#317
She is Gone Willie Nelson
1996 | Peak: Did Not Chart
As in his classic recording of “Blue Eyes Crying in the Rain”, Nelson’s sad remembrance of a lost love glows with unspoken warmth, as the beauty of his good memories shines through the outer layer of melancholy. – DM
As deft a take down of a departing lover there’s ever been. Not since “You’re So Vain” has a jilted lover struck back so powerfully by simply holding up a mirror. – KC
#314
Till I Found You Marty Stuart
1991 | Peak: #12
Presenting the perfect Country & Western song! This is a great David Allan Coe cover with some alterations, including the exclusion of a stanza (which does water down the song a bit), changes to the spoken part, and additions of some special guests. – LW
#311
Wine Into Water T. Graham Brown
1998 | Peak: #44
A kneeling drunkard’s plea for the modern age. A broken man struggling with his alcoholism asks Jesus to perform His first miracle in reverse. Brown’s rough and tumble voice is the best possible fit for this fine composition.- KC
#310
High Powered Love Emmylou Harris
1993 | Peak: #63
The added punch to the production shows that Harris could do nineties country as well as anybody on the radio back then, which is quite the compliment, given who was getting airplay in 1993. A perfect lament for a lover who won’t settle for skin deep treasures, she wonders, “Is there anyone left with teeth just a little uneven? Who won’t spend more time with a mirror than he does with me?” – KC
#309
You Won’t Ever Be Lonely Andy Griggs
1998 | Peak: #2
Griggs creates a touching ballad out of one of the sweetest, simplest promises that comes with making a commitment to someone – that no matter the storm outside, you’ll never have to face it alone. – TS
Instead of serving as a means to shut the other person out, the door that Tippin is suggesting is for the purpose of letting the other person in. “a door ain’t nothin’ but a way to get through a wall”, he sings. If they work together to create it, then they might be able to walk through it to meet each other halfway. – LW
Suzy Bogguss takes this Ian Tyson cowboy folk song and makes it her own. She successfully breathes emotion into this wistful song that, once again, pits woman against rodeo. – LW
Built on a poignantly written metaphor, “The River” gracefully weaves together elements of faith, inspiration and motivation. It’s a masterful single, from its poetic lyrics to its beautifully simplistic arrangement, but the heart and soul is Brooks’ gripping conviction – quiet yet fierce. On a personal note, this song contains one of my all-time favorite lyrics that I often revisit: “So don’t you sit upon the shoreline and say you’re satisfied/Choose to chance the rapids and dare to dance the tide.” – TS
Blessings are fleeting, and they’re best appreciated in the moment. It’s far more satisfying to celebrate them without the bittersweet tinge of regret. – KC
#304
You Can’t Stop Love Marty Stuart
1996 | Peak: #26
McGraw’s character leaves behind a lifelong love interest and a little home town to explore the world. But instead of getting good closure, the poor guy starts seeing the girl he left in every place he visits, even long after she has married and had children. That these visions could feasibly represent both unresolved romantic feelings and the inescapable imprint of one’s roots is just country-delicious. – DM
#302
You’re Beginning to Get to Me Clay Walker
1998 | Peak: #2
Walker’s falling head first for a girl, but he isn’t ready to take the plunge with the L-word just yet. In his catalogue of fabulous 90s hits, this understated “love” song gets overshadowed by some of the more distinct ones, but it’s nonetheless memorable. – TS
Travis Tritt is one of few country artists who is as known for his rocking side as he is for being a strong balladeer. “Help Me Hold on” is a plea to his lover to help him salvage what’s left of their relationship, which doesn’t seem to be much, since she’s already packing a suitcase. – LW
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
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
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 (more…)
The second segment of our countdown includes the first appearances by Garth Brooks and Reba McEntire, two of the biggest-selling stars of the decade.
#375 How Do I Get There Deana Carter
1997 | Peak: #1
It’s always a gamble when friends decide to take their relationship to the next level. “How Do I Get There” explores the struggle of following one’s heart, even though it’s taking a big emotional risk to do so. – Leeann Ward
#374
If I Could Make a Living Clay Walker
1994 | Peak: #1
This song is either ridiculously cheesy or irresistibly cheesy depending on your taste, but there’s no denying Walker sells the heck out of it with charm and enthusiasm. – Tara Seetharam
#373
It Sure is Monday Mark Chesnutt
1993 | Peak: #1
Mark Chesnutt is one of the best male vocalists of the nineties, but there were many times when he did not always rise to the challenge of conveying the energy to elevate a decent song to a good one. Case in point: “Friends in Low Places”, which was eventually properly energized by Garth Brooks. “It Sure Is Monday”, however, is a positive example of Chesnutt actually making a song his own by demonstrating the ability to breathe life into a decent song and make it really good. – LW (more…)
It’s hard to believe that twenty years have passed since the nineties first began. Perhaps that’s because so many of the artists who broke through during that decade remain relevant on the music scene today, whether they’re still getting major spins at radio or not.
For many of us, it was the nineties when we discovered and fell in love with country music, and it’s the music and artists from that decade that represent the pinnacle of the genre. It may be debatable whether the nineties were the most artistically significant decade in the history of country music, but there’s no debating that country music never had more commercial success or cultural impact than it did in that decade.
It was a time that when the C-list artists could sell gold or platinum on the strength of one or two hits, and that 24-hour video outlets could give wide exposure to songs and artists that radio playlists could not. When the four writers of this feature got together and combined our favorite singles from the decade, it was clear that this retrospective had to run far deeper than the one we recently completed for the first decade of the 21st century. There were simply far more good singles to choose from.
That being said, this list is a reflection of our personal tastes. While they often overlapped with what was commercially popular, with nineteen top ten hits and eleven #1 hits among the first 25 entries alone, we didn’t consider radio or retail success in our picks. So while you’ll see all of the big nineties stars represented on this list, it won’t always be with their biggest hits. There’s more than a few stars that never quite came to be as well, saved from the dustbins of history and easier to find now than they were back then, thanks to the twin marvels of YouTube and Amazon.
As always, share your thoughts in the comments!
400 Greatest Singles of the Nineties: #400-#376
#400 Little Good-Byes SHeDaisy
1999 | Peak: #3
Passive aggression finally got its due representation in modern country with SHeDAISY’s debut single, in which a mistreated protagonist exacts revenge on her ex by ever-so-slightly screwing up his house. Sort of like “Before He Cheats” for sane women. On the other hand – taking all the Beatles records and leaving only Billy Joel? Pretty cold, Osborn sisters. – Dan Milliken
#399
It Wouldn’t Hurt to Have Wings Mark Chesnutt
1995 | Peak: #7
Chesnutt is getting over you – promise – but he sure wouldn’t mind being lifted above the memories of your “mind-wrecking” love in this delightfully charming sing-along. – Tara Seetharam
#398
Fool, I’m a Woman Sara Evans
1999 | Peak: #32
The age-old stereotype that women can’t make up their minds is cleverly subverted into a threat toward an unkind man. A good combo of Loretta Lynn sass and Diana Ross sha-la-las. – DM
#397
One More Last Chance Vince Gill
1993 | Peak: #1
“One More Last Chance” may seem like a song about a man who is begging for just one more last chance to get things right. But under the surface, it’s about a man who is hopelessly addicted to alcohol and partying. Even when his wife takes away his obvious means of transportation by hiding the keys to the car, he resorts to riding his John Deere tractor to the bar instead. It’s a fun song, but one that is inspired by an incident associated with George Jones, who, incidentally, is infamous for his destructive alcohol addiction. – Leeann Ward
#396
The Cheap Seats Alabama
1994 | Peak: #13
“The Cheap Seats” aptly captures the spirit of America’s favorite pastime. – LW
#395
Lonely Too Long Patty Loveless
1996 | Peak: #1
A tender plea for the morning after to be the beginning of something more, with Loveless delivering both angst and cautious optimism through her vocal. – Kevin Coyne
#394
(If You’re Not in it For Love) I’m Outta Here! Shania Twain
1995 | Peak: #1
Look, guys, some of you are so transparent, it’s laughable. And to you I offer Twain’s deliciously audacious, merciless warning: if you’re not in it for love, we’re outta here. – TS
#393
Jenny Come Back Helen Darling
1995 | Peak: #69
Darling recalls watching a high school friend sacrifice her intelligence and ambition to please the boy she loves, who outgrows her in the end because she has nothing of her own to offer him. She ends up a high school dropout working at a movie theater. In short, how those fantasy Taylor Swift videos would end in the real world. – KC
#392
Dreaming With My Eyes Open Clay Walker
1994 | Peak: #1
Walker puts a clever twist on a fact of life that’s all too hard to grasp – the only thing we can control is the present. His infectious pledge to live in the moment is as effective as country’s finest inspirational ballads because it’s firmly grounded in reality: “I learned that one step forward will take you further on than a thousand back or a million that ain’t your own.” – TS
#391
There Ain’t Nothin’ Wrong With the Radio Aaron Tippin
1992 | Peak: #1
With an addicting guitar riff, Tippin celebrates the radio. It doesn’t matter that the car is falling apart, but at least there’s nothing wrong with the most important part of the vehicle, the souped up radio. – LW
#390
Write This Down George Strait
1999 | Peak: #1
One of the dittiest of all George Strait ditties? Sure. But there’s a subtle, maybe accidental wisdom to it, too. So much art is created in moments of unusual passion, when sensations like pain or love feel intense and everlasting. But most life isn’t lived in such moments, and any feeling is subject to fade away without some regular renewal. “Tell yourself ‘I love you and I don’t want you to go’” sounds light and cutesy on the surface, but it’s those little notes – and not grandiose gestures of unusual passion – that keep a relationship chugging along for the long haul. – DM
#389
Still in Love With You Travis Tritt
1997 | Peak: #23
With conspicuous steel guitar work, this minor hit for Tritt is a straight up country romper by today’s standards. – LW
#388
Walking Shoes Tanya Tucker
1990 | Peak: #3
She seems a little sad about it, but she’s had enough of being taken for granted and is gearing up to walk right on out of her underappreciating lover’s life. – LW
#387
Big Deal LeAnn Rimes
1999 | Peak: #6
A sassy little number that finds a regretful Rimes lashing out at the girl who nabbed her old boyfriend. Brash, spunky and so much fun. – TS
#386
That’s My Story Collin Raye
1993 | Peak: #6
What do you think – the grooviest song about a guy trying to craft an alibi out of a backyard hammock ever? – DM
#385
I Like It, I Love It Tim McGraw
1995 | Peak: #1
A melody destined for inclusion in Applebee’s commercials. A lyric about a horny guy and his teddy bear-loving girlfriend. I thought about trying to mount a good argument for it, but whatever. I know you sang along the first eight times you heard it. – DM
#384
You Can’t Make a Heart Love Somebody George Strait
1994 | Peak: #1
A simply sung, heartbreaking story of a woman who desperately wishes the heart could take orders – and a man who bears the brunt of the reality that it can’t. – TS
#383
Count Me In Deana Carter
1997 | Peak: #5
Easily the most understated of the five hit singles from her debut album, “Count Me In” is beautiful because of its innocent vulnerability. – KC
#382
Where Do I Fit in the Picture Clay Walker
1994 | Peak: #11
Sure, Walker milks this forlorn ballad for all it’s worth, but his ability to dramatically emote is the success of his trademark tear-soaked voice. – LW
#381
Some Girls Do Sawyer Brown
1992 | Peak: #1
Set to a hooky melody: Boy meets girl. Girl acts unimpressed. Boy knows better. Girl hooks up with boy. The end. – LW
#380
I Want to Be Your Girlfriend Mary Chapin Carpenter
1997 | Peak: #35
Even in the nineties, Carpenter was mostly known for her introspective lyrics. That’s the best part of her songwriting, but hearing the lighter side of MCC from time to time is fun, too. – LW
#379
Little Bitty Alan Jackson
1996 | Peak: #1
Alan Jackson has a knack for dressing up inriguing social themes as fluffy radio bait. Here, he counters the societal fixation on the “big” draws of money and prestige, expressing a peaceful acceptance of the rather small role most of us will ultimately play in the universe. We can’t all be famous or widely influential, but if we can love well and carry our chosen mantles with pride, things aren’t so bad. – DM
#378
Not a Moment Too Soon Tim McGraw
1994 | Peak: #1
Some people find the whole “you saved my life” concept melodramatic, but I think if there’s anything in life that calls for melodrama, it’s love. McGraw’s testimony is sweet and believable, and the weighty lyrics are cushioned by a simple yet moving arrangement. – TS
#377
Here in the Real World Alan Jackson
1990 | Peak: #3
Jackson’s breakthrough hit lamented that what we see in the movies – cowboy heroes, good winning out in the end, the boy getting the girl – doesn’t always work out that way in the real world. How fitting that he’d end up a real world cowboy hero, one of the good guys making great music for twenty years and counting. – KC
Most of your friends probably found you kind of boring when you were paired off and content. Now you’ve been dumped, and everyone’s got an opinion about what the relationship meant and what you should do next. Trisha is having none of it – just chocolate, a good mag and some much-needed alone time for her. – DM
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