400 Greatest Singles of the Nineties: #400-#376

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 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 are 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:



Little Good-Byes
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


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


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


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


The Cheap Seats
1994  |  Peak: #13

“The Cheap Seats” aptly captures the spirit of America’s favorite pastime. – LW


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


(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


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


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


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


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


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


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


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


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


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


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


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


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


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


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


Little Bitty
Alan Jackson
1996  |  Peak: #1

Alan Jackson has a knack for dressing up intriguing 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


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


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


Everybody Knows
Trisha Yearwood
1996  |  Peak: #3

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


400 Greatest Singles of the Nineties (2010 Edition)

#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


  1. From the perspective of musical cohesiveness, the 1990s actually ran from 1the 1986 emergence of Randy Travis, Dwight Yoakam and (to a lesser extent) Steve Earl to about 1998. While I wouldn’t regard it as a “golden era”, it was the last flowering of anything resembling traditional country music. By traditional country music I mean music influenced by Hank Sr, Lefty, the Hag, Loretta & Tammy rather than that influenced by faux-country musicians such as the Eagles, Lynyrd Skynyrd and Linda Ronstadt

    Although the last dozen years have produced some good songs and a few good singers, I would regard the last dozen years as largely an artistic wasteland, especiailly as regards to the pablum played on country radio.

    I look forward to this series. You’re off to a good start with the first twenty-five selections, although I kind of think selection #400 is emblematic of what went wrong with country music in the 00s

  2. Of the above-mentioned songs, I would count Trisha’s “Everybody Knows” as a personal favorite when it comes to country music for the Nineties. For me, it was her choice of songs and her notion, one she learned from Linda Ronstadt, that the songs should fit her own emotional nexus and not be done in a way where you appear to be second-guessing your audience. She has kept to that modus operandi ever since (IMHO).

  3. Yearwood deftly combines Ronstadt’s way with a song with Emmylou’s taste in picking them. Not that Ronstadt didn’t record a lot of great songs, but her country albums were dominated by covers. Same for Harris early on, but she quickly moved to primarily new material.

    Perhaps Matraca Berg is Yearwood’s Rodney Crowell, just like Garth Fundis is her Peter Asher!

    Hearing those seventies Emmylou and Linda albums for the first time was like discovering the reason why I liked contemporary country music so much. I’d grown up on the Wynette, Cash, Conlee, and Twitty that my parents loved, but it was harder to connect that type of country music to those Yearwood, Tillis, and Loveless albums that never left my CD changer.

  4. I grew up on rock ‘n’ roll beginning in the late 50’s but by the late 70’s I was becoming dissatisfied with post Eagles rock. Artists like Ronstadt, Anne Murray, John Denver, Ronnie Milsap, Gene Watson, Larry Gatlin and Alabama got me interested in country and the music of the 90’s completed the process. Loved those starter kits and 6 packs you were doing last year and articles like this one. I’m really looking forward to the rest of this series.

  5. Missed Paul’s first comment:

    I agree with you that a 1986-1998 list would be more musically cohesive, particularly in tracking the big wave of commercially successful artists who were largely traditionalists. You’d miss a few big ones before 1986 (John Anderson, The Judds, Reba, and Ricky Skaggs) but very few after 1998 (Brad Paisley, Dixie Chicks, and…?). Randy Travis is simply the perfect starting point because he was the first artist to go significantly multi-platinum with purely traditional music.

    I don’t know that it would be a 1986-1998 list would be a good fit for Country Universe, though, as our writers (especially me) don’t necessarily elevate traditional country music over its other forms. I think that we’ll do a better job covering the nineties in all of its varieties than we’d do capturing a golden era of traditionalism.

  6. …rumour has it that the world wide web was only invented to get cu lists out to country music fans all over the planet.

  7. I agree with Kevin’s way of doing these lists by complete decade; it works a lot better that way.

    Insofar as the 1990s goes, I definitely agree that country music enjoyed its greatest commercial success, and also that its artistic significance is a point of debate. The reason I say this is because, perhaps following Garth Brooks’ way of doing things, a lot of artists and bands have sought to up the spectacle level of their stage shows, so that they resemble 1980s arena-rock extravaganzas, with twang and drawl. In doing so, in my opinion, the essence and substance of the songs seemed to have gotten lost. That trend, unfortunately, seems only to have accelerated.

  8. On the other hand, I think that the commercial boom allowed for the industry to sustain more successful acts than at any other time. Could The Mavericks, Lee Roy Parnell, or Suzy Bogguss have been money-makers for their label in another time period? Even David Ball and The Tractors went platinum on the strength of one or two hits.

    I think a lot of acts that wouldn’t have gotten a chance in weaker commercial times were able to get some great music out there. Even the ones who didn’t break through were often given two or three albums to try. Heck, if Shania Twain hadn’t been making mega-millions for Mercury, there’s no way that label would’ve bankrolled four Kim Richey albums.

  9. I loved this post. The 90s were definitely my favorite decade in country music. I was converted to the genre thanks to the 90s hits of Garth Brooks, Lorrie Morgan, and LeAnn Rimes. In my opinion, 90s country music struck just the right balance between traditional and modern influences. The songs sounded great, and they had great lyrics as well. You don’t hear as much of that in modern-day country music. There were definitely far more good singles to choose from in the 90s than from the previous decade.

    By the way, I was pleased to see my favorite singer, Sara Evans, included in this list, even though the majority of her success came after the turn of the millenium.

    Great post! I saw some of my favorites on this list, and some that I hadn’t heard before but that I will have to check out. I can hardly wait to read the rest of this series!

  10. By the way, when I said “previous” decade, I meant 2000-2009 – the decade previous to the current decade. It probably looks like I meant the 80s, but I didn’t. I just realized that that probably wasn’t very clear.

  11. Nice to see Helen Darling there and Deana Carter’s best single is on the list as well off to a great start, now just make sure Matraca Berg and Bobbie Cryner make an appearance and all is well

  12. I’ve been waiting for this list since y’all mentioned you were doing it last month. Awesome start! Thank you for reminding me of some of these. The Patty Loveless song didn’t sound immediately familiar, but when I YouTubed the awesomely 1990s video, it came back to me– that’s a good song!

    Side note: isn’t the Mark Chesnutt song “It Wouldn’t Hurt to Have Wings”? That’s how I remember hearing it.

  13. “Here in the Real World” is far too low.

    And Mary Chapin . . . well I’m interested to see how much of her introspective stuff makes the list – because most of it just really sucked. I listened to “I Am A Town” the other day and it reeked, man – high school poetry club pretension (which, of course, is a little better than college poetry class pretension, i.e., “Stones in the Road”).

  14. I’m super excited for this list! Like you said in the post, I fell in love with country music during the 1990’s. Sure I was raised with the old school country my parents listened to, but my obsession came about when I discovered artists like Leann Rimes, Patty Loveless, Pam Tillis, Alan Jackson, Lee Ann Womack, and many many more that emerged in the 90’s. Great list so far and can’t wait to see more!

  15. Wow, there’s a lot of really good stuff here. For me, Patty Loveless’s “Lonely Too Long” is one of the best things that she ever did. “Here in the Real World” is a classic, and I always thought “You Can’t Make a Heart Love Somebody” was an underrated Strait song. Between Aaron Tippen, Alabama, Vince Gill, Deana Carter, Shania Twain, Mark Chesnutt, and Collin Raye…there’s a lot of quality here.

  16. I loved the concept of 5 disc CD players, Trisha Yearwood, Pam Tillis, The Judds, Lorrie Morgan, Patty Loveless and lived in mine in the early 90s!

    Great part about the 90s was you didnt have to have a huge #1 smash for everyone to hear your music, radio had so much more variety, and I lived infront of TNN

  17. Always a fan of the lists, and the banter they can elicit. Surprised to see “You Can’t Make a Heart Love Somebody” so low on the list, but I suppose the top 100 can’t be all Strait. Glad to see “Cheap Seats” and some hits from Clay Walker that radio has forgotten about. No real beef with any of the picks with the exception of “There Ain’t Nothin’ Wrong With the Radio”, which I would have in my bottom 10 of singles from the ’90s.

  18. there was a song in the 90’s talking about michael angelo painted the Sistine chapel, wright brothers flew a plane and several other well know things and had to do with something about because they didn’t have a woman. I can’t recall the artist or the actual words to the song but I would love to know who the artist was and the name of the song

    any help is greatly appreciated.

  19. @David – I believe the song is “Just What I Do” by Trick Pony. It mentions Jesses James, the Wright Brothers and Picasso. The lyrics are available on line.

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