And so we come to the end. The top of our list includes a wide range of artists singing a wide range of country music styles. Thematically, these entries are diverse, but what they all have in common is what has always made for great country music. They are all perfectly-written songs delivered with sincerity by the artists who brought them to life.
400 Greatest Singles of the Nineties: #25-#1
#25
Smoke Rings in the Dark Gary Allan
1999 | Peak: #12
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 (more…)
The themes of love and loss have permeated country music for as long as it’s been in existence. This second-to-last batch of great nineties hits contains songs that are direct descendants of well-known classics like “Can the Circle Be Unbroken” and “I’m So Lonesome I Could Cry”, along with a Shania Twain hit that would have made Roba Stanley smile.
400 Greatest Singles of the Nineties: #50-#26
#50
Here’s a Quarter (Call Someone Who Cares) Travis Tritt
1991 | Peak: #2
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
Johnny Cash may have been too dark for country radio back in 1994, but his morbid single lives on alongside debut singles, seventies covers, and a whole lot of Mary Chapin Carpenter.
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
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 (more…)
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…)
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…)
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…)
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
New fans of country music in the nineties were hit over the head with the assertion that country music was one big family. Nothing demonstrated this mythos better than the all star jams that cropped up during the boom years.
There were some variants of this approach. A popular one found a veteran star teaming up with one or more of the boom artists to increase their chances of radio airplay. George Jones was big on this approach, with the most high profile attempt being “I Don’t Need Your Rockin’ Chair.” Seventeen years later, it’s amazing to see how young everyone looks -- even Jones himself!
Jones shared the CMA Vocal Event of the Year trophy for that collaboration with Clint Black, Garth Brooks, T. Graham Brown, Mark Chesnutt, Joe Diffie, Vince Gill, Alan Jackson, Patty Loveless, Pam Tillis, and Travis Tritt. He’d continue with this approach by teaming up with his vocal chameleon Sammy Kershaw on “Never Bit a Bullet Like This”, and he recorded an entire album of his own songs as duets with mostly younger stars. The Bradley Barn Sessions was represented at radio with “A Good Year For the Roses”, which found him singing one of his best hits with Alan Jackson:
Among the legends, the only other one to be successful with this approach was Dolly Parton, who used collaborations with young stars to score consecutive platinum albums for the first and only time in her career. Her 1991 set Eagle When She Flies was powered by the #1 single “Rockin’ Years”, co-written by her brother and sung with Ricky Van Shelton:
That album also included a duet with Lorrie Morgan on “Best Woman Wins.” She upped the bandwagon ante on Slow Dancing With the Moon, bringing a whole caravan of young stars on board with her line dance cash-in “Romeo.”
That’s Mary Chapin Carpenter, Billy Ray Cyrus, Kathy Mattea, and Tanya Tucker in the video. Pam Tillis isn’t in the clip, but she sings on the record with them. Parton also duets with Billy Dean on that album on “(You Got Me Over a) Heartache Tonight.”
Her next collaboration was with fellow legends Loretta Lynn and Tammy Wynette, but they couldn’t resist the temptation to squeeze in several younger stars in the video for “Silver Threads and Golden Needles.” Alongside veterans like Chet Atkins, Bill Anderson, and Little Jimmy Dickens, you’ll catch cameos from Mark Collie, Confederate Railroad, Rodney Crowell, Diamond Rio, Sammy Kershaw, Doug Stone, and Marty Stuart.
Parton scored a CMA award when she resurrected “I Will Always Love You” as a duet with Vince Gill:
And while it didn’t burn up the charts, her version of “Just When I Needed You Most” with Alison Krauss and Dan Tyminski:
Tammy Wynette made an attempt to connect with the new country audience with her own album of duets, Without Walls. Her pairing with Wynonna on “Girl Thang” earned some unsolicited airplay:
Perhaps the most endearing project in this vein came from Roy Rogers. How cool is it to hear him singing with Clint Black?
The new stars liked pairing up with each other, too. A popular trend was to have other stars pop up in music videos. There’s the classic “Women of Country” version of “He Thinks He’ll Keep Her”, for starters. Mary Chapin Carpenter sounds pretty darn good with Suzy Bogguss, Emmylou Harris, Patty Loveless, Kathy Mattea, Pam Tillis, and Trisha Yearwood on backup:
That’s a live collaboration, so at least you hear the voices of the other stars. But Vince Gill put together an all-star band for his “Don’t Let Our Love Start Slippin’ Away” video without getting them to actually play. That’s Little Jimmy Dickens, Kentucky Headhunters, Patty Loveless, Lee Roy Parnell, Carl Perkins, Pam Tillis, and Kelly Willis behind him, with Reba McEntire reprising her waitress role from her own “Is There Life Out There” clip.
My personal favorite was Tracy Lawrence’s slightly less A-list spin on the above, with “My Second Home” featuring the future superstars Toby Keith, Tim McGraw, and Shania Twain, along with John Anderson, Holly Dunn, Hank Flamingo, Johnny Rodriguez, Tanya Tucker, Clay Walker, and a few people that I just can’t identify.
For pure star wattage, it took the bright lights of Hollywood to get a truly amazing group together. The Maverick Choir assembled to cover “Amazing Grace”, and it doesn’t get much better than country gospel delivered in a barn by John Anderson, Clint Black, Suzy Bogguss, Billy Dean, Radney Foster, Amy Grant, Faith Hill, Waylon Jennings, Tracy Lawrence, Kathy Mattea, Reba McEntire, John Michael Montgomery, Restless Heart, Ricky Van Shelton, Joy Lynn White, and Tammy Wynette.
What’s your favorite of the bunch? Any good ones I missed?
I’ve been wanting to write about Bobbie Cryner for a long time. Thanks to some kind folks uploading her music on to YouTube, I can finally do so. (For whatever reason, her two fantastic albums -- Bobbie Cryner and Girl o f Your Dreams -- have yet to see digital release.)
This woman was good. Real good. Possibly the best unheralded singer-songwriter of her time, with a sultry voice formed at the crossroads of Bobbie Gentry and Dottie West. She first surfaced on Sony, releasing her self-titled debut in 1993. It was previewed by the autobiographical “Daddy Laid the Blues on Me.”
It could’ve been the start of a legendary career, but the single stalled at #63. Next up was the haunting “He Feels Guilty”, which went to #68. It has an amazing guitar intro. That video can be viewed here. Her debut album produced a third single, the #72 “You Could Steal Me.” This one’s heartbreakingly gorgeous, but I can’t find an online way of sharing it with you.
The rest of that first album includes a duet with Dwight Yoakam on “I Don’t Care”, the Buck Owens classic. Another stellar cover is “The One I Love the Most”, which could’ve been a George Jones classic back in the early seventies.
But the best material comes from her own pen. Check out “I Think It’s Over Now”, which features the lyric, “You don’t have to say you love me if you think there’s any doubt. But if you have to think it over, well, I think it’s over now.”
Also worth seeking out is the closing track from that album, “This Heart Speaks For Itself,” which has every part of her body fooling others that she’s over the man who let her down.
In one of those glorious second chances that the music business rarely doles out, Cryner resurfaced on MCA three years later, sporting a more cosmopolitan sound and look. On Girl of Your Dreams, Cryner penned all five of the strongest tracks, while also credibly covering Dusty Springfield and Dottie West. The lead single was “I Just Can’t Stand to Be Unhappy”, a kiss-off anthem that was too smart for country radio, stopping at #63:
What followed was an absolute masterpiece, one that still only reached #56 (and only #66 when Lorrie Morgan revived it two years later.) “You’d Think He’d Know Me Better” is shockingly good, managing to tell the story of a selfish and cold woman by having her talk about how inconsiderate her man is. She’s the only one left in the dark at the end, as the listeners all realize who’s really to blame for this broken home:
Her final MCA single was “I Didn’t Know My Own Strength”, which chronicled Cryner’s battle with alcoholism. It didn’t chart.
Again, the album had gems beyond what went to radio. “Vision of Loneliness” is amazing, a song that gained new resonance with me when my mother related to it so well during her bereavement:
The title track should’ve been a single, though it’s hard to imagine radio playing it after passing on her earlier work. I’d argue that “The Girl of Your Dreams” isn’t just Cryner’s finest piece of writing, but that it rivals the very best of Matraca Berg, Mary Chapin Carpenter, and Rosanne Cash. It begs for Trisha Yearwood to cover it:
So what happened after that second album faded into obscurity? How could a songwriting talent like this get lost in the shuffle? Well, it didn’t happen right away. After Morgan covered “You’d Think He’d Know Me Better”, Cryner surfaced as a writer on albums by top-tier female artists.
The most high profile of these three came after Cryner left a demo in Yearwood’s mailbox that simply had the title, “Real Live Woman.” Yearwood later commented that she prayed before listening to it that it would live up to that title. It did, and ended up being Cryner’s biggest hit when Yearwood took it into the top twenty:
Suzy Bogguss took the compelling story song “Nobody Love, Nobody Gets Hurt” to #63 in 1998, titling her album after it as Yearwood did with “Real Live Woman” in 2000.
Finally, Lee Ann Womack included “Stronger Than I Am” on her smash album I Hope You Dance. It finds a woman in awe of her young daughter who seems so much stronger than she is.
After that, I have no idea what happened to this woman. Do you? In an era when country music isn’t made for adults, or even by adults, this woman’s contributions are desperately needed.
on 
on 
on 
on 
on 
on