400 Greatest Singles of the Nineties: #100-#76

Many a star was launched in the nineties, a few of them right out of the gate. This section includes the debut singles from Toby Keith, Jo Dee Messina, LeAnn Rimes, and Doug Stone, along with Grammy-winning hits by Alison Krauss and Dwight Yoakam.

400 Greatest Singles of the Nineties:


The Battle Hymn of Love
Kathy Mattea & Tim O’Brien
1990 | Peak: #9

Wedding songs are typically made of the same fiber, but this one is a little different: it’s energized by burning conviction and fierce pledges. – Tara Seetharam

LeAnn Rimes
1996 | Peak: #10

Sure, the novelty of thirteen year-old Rimes’ prodigious Patsy imitation helped things along. But that unshakable yodeled hook would have made “Blue” a classic in any era of country music. – Dan Milliken

The River and the Highway
Pam Tillis
1996 | Peak: #8

Just an unbelievably haunting and gorgeous song. – Leeann Ward

Standing Knee Deep in a River (Dying of Thirst)
Kathy Mattea
1993 | Peak: #19

A moving reflection on our tendency to miss the true blessings and enriching opportunities around us. It would be a great song if it just stuck to lost friendship and love; that it twists in the third verse to consider our relationship to the less fortunate puts it on a completely different level. The way things are, we’re all left “parched and empty” in some sense – the poor who struggle in a culture of incredible wealth, and the financially secure who march on in self-absorbed, self-contained existences, wondering why they never feel quite whole. – DM

Yard Sale
Sammy Kershaw
1992 | Peak: #17

As if the dissolution of his marriage wasn’t bad enough, now he gets to sit around acting friendly for a bunch of strangers “sortin’ through what’s left of you and me” and paying him chump change for it. A Jones-worthy lament. – DM

Where Are You Now
Clint Black
1991 | Peak: #1

What happens when you take for granted the person you always assume will be there for you, then realize that this time, they’ve finally stopped waiting around for you? You ask the question that Clint Black is asking here. – Kevin Coyne

Back When We Were Beautiful
Matraca Berg
1997 | Peak: Did Not Chart

So beautifully raw that it makes almost every other depiction of the elderly in modern country music feel like a hollow, oversimplified contrivance. – DM

I Guess You Had to Be There
Lorrie Morgan
1993 | Peak: #14

Imagine loving someone so much that you’re willing to accept their tryst with sad resignation, realizing that there’s no happiness left for them at home.  Love hurts. – KC

Deep Down
Pam Tillis
1995 | Peak: #6

Excellent lyric aside, what makes this record truly unique is the way that Tillis has a conversation with the band. She sings a line in the first verse, the guitar responds to it. In the second verse, she’s answered by the fiddle. By the time the song builds to a crescendo, they’re singing in harmony. It’s cool. – KC

Heads Carolina, Tails California
Jo Dee Messina
1996 | Peak: #2

Right out of the gate, Messina demands positive proactivity, charms world. – DM

Baby, Now That I’ve Found You
Alison Krauss
1995 | Peak: #49

Krauss turns forgettable Motown fodder into a sad, hushed plea to a lover who already has a foot out the door and probably isn’t coming back. – DM

Ships That Don’t Come In
Joe Diffie
1992 | Peak: #5

This single presents Joe Diffie at his very finest. Humanity permeates each and every note. – LW

Something in Red
Lorrie Morgan
1992 | Peak: #14

An ingeniously poetic story song, told through parallel-structured stanzas that chronicle a woman’s life by her clothing choices at given points. You could write a good paper on the themes presented here, so richly drawn is the woman’s character. – DM

Should’ve Been a Cowboy
Toby Keith
1993 | Peak: #1

This is the song that started it all for Toby Keith. It’s the voice of a more youthful, less egotistical man with a fine song on his hands to kick start his national career. – LW

I’ll Think of Something
Mark Chesnutt
1992 | Peak: #1

In this cover of an old Hank Jr. single, Chesnutt is fully submerged in post-breakup despair. You’re not sure he actually even wants to think of something to help him along. – DM

Come On Back
Carlene Carter
1990 | Peak: #3

There’s such a sprightly, inviting sound going on here that you might not even notice that Carter’s actually proposing something pretty serious: that her man stops running around on her in random dive bars. However deep your understanding of the single, though, it’s a definite toe-tapper. – DM

Ain’t That Lonely Yet
Dwight Yoakam
1993 | Peak: #3

Bitterness and melancholy aren’t supposed to go down this smoothly. – KC

You’re Gonna Miss Me When I’m Gone
Brooks & Dunn
1995 | Peak: #1

Kix Brooks takes the lead here, and turns in a better single than the vast majority of Dunn-led hits. – KC


The Fear of Being Alone
Reba McEntire
1996 | Peak: #2

For all of her theatrics and melodramatic flair, the best Reba McEntire singles are the ones that are deeply grounded in the realities of everyday people. Here, she gets in touch with her inner Oslin, with a candid conversation between two older adults resisting the urge to mistake loneliness for love. – KC


You Don’t Even Know Who I Am
Patty Loveless
1995 | Peak: #5

As is typically the case when relationships dissolve, there are two sides to the story, two perspectives. Often times, neither side is completely wrong. The Gretchen Peters penned, “You Don’t Even Know Who I Am”, vividly explores both sides of the story. She feels emotionally abandoned; he feels unappreciated. The one thing they can agree on is that it’s over. The punch of “What do I care if you go” is the brilliant conclusion that none of us see coming. – LW

I Saw the Light
1992 | Peak: #1

Wynonna’s inspired performance elevates what could have been a familiar done-me-wrong song to a smart, unforgettable hit. – TS

No Place That Far
Sara Evans
1998 | Peak: #1

Rarely has Evans sounded as good as she does on this treasure of a love song, fueled by the raw emotion in her performance. As always, Vince Gill’s back-up vocals add another layer of soul to the stirring ballad. – TS

A Little Past Little Rock
Lee Ann Womack
1998 | Peak: #2

It’s lonely out there on the road after finally leaving for good, nothing but a little self-mocking wordplay to comfort you. – DM

Who’s That Man
Toby Keith
1994 | Peak: #1

Country music reaches some of its highest highs and lowest lows when its conceits are at their most potentially ridiculous. “Who’s That Man” is a serious song inspired by that exaggerative joke about what happens when you play a country song backwards – getting your house back, your woman back, your dog back – so you might expect it to be one of those “lowest lows.” In Keith’s hands, though, the losses feel relevant and real. Go figure. – DM


I’d Be Better Off (In a Pine Box)
Doug Stone
1990 | Peak: #4

Stone would rather lay out in a coffin, do time in jail, or go to Hell and confront the devil than see his lady happy with someone else. Rumor has it that Rascal Flatts, Taylor Swift and Lady Antebellum are planning a collaborative cover of this one soon. – 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. Standing Knee Deep in a River, Back When We Were Beautiful, You Don’t Even Know Who I Am, and Ships That Don’t Come In are some of my favorite ugly-crying, on the verge of despair songs. Remind me not to read these synopses at 2am again…
    But Heads Carolina, Tails California is a damn catchy song. Can’t wait to see the rest of the list!

  2. It was an absolute travesty that “Blue” made it only to #10. Many country stations refused to play the song because it was “too country”. Others falsely claimed that their listeners wouldn’t be interested in the song, an interesting commentary since the CD-single sold many millions of copies. The song reached #26 on the pop stations

    This song should rate much higher among the top 400 – probably in the top ten. It is arguably the most successful cover version in the last thirty year, being a cover of Kenny Roberts’ 1967 recording

  3. I remember “Blue” raced up the country airplay chart before stopping rather suddenly at #10. It was pretty much treated as a novelty record, in spite of the big album sales, and radio ignored the follow-up single, too. It wasn’t until sustained album sales that Rimes got another shot, with “One Way Ticket” ending up her only #1 single to date.

    “Blue” didn’t get any airplay on the pop stations. It reached #26 on the Hot 100 on sales alone. This was still a couple of years before the Hot 100 included country airplay, so it was limited in how high it could go. The single didn’t get any higher than #11 on the Singles Sales chart, but it did sell over 1/2 a million copies, becoming one of only a handful of country singles in the mid-nineties to earn gold certification.

    “Blue” is one of those songs that makes a powerful case for including sales on the country singles chart again. It would more accurately reflect the popularity of a song if sales and airplay were included. There have been some very big hits that radio didn’t warm up to as much as listeners did. With digital availability now the norm, there wouldn’t be an issue of some songs being held back because there wasn’t a commercial single.

  4. Love “Should’ve Been a Cowboy”. Maybe it’s because I grew up watching all those cowboy/western tv shows in the 50’s & 60’s. When I hear this song it reminds me of “Whatever Happened to Randolph Scott” by the Statler Brothers.

    Great songs here by Mattea, Messina & Morgan. Yard Sale is a good one I hadn’t heard before.

  5. Lots of good stuff on this list.
    Totally agree about the Kix Brooks vocals… this had to be the ONE time it worked.

    Love Mattea’s “Lonesome Standard Time”… probably my favorite of her collection.

    And let’s hear it for Toby and Joe’s mullets! :-O

  6. “Deep Down” is one of my all time favorite Pam Tillis songs, only behind “Maybe It Was Memphis”, which I pray is in the top ten!

    Love the Reba song too, that song came out when I really started getting into country music. I remember getting the “What If It’s You” album on casset for christmas when I was in the 7th grade. I played it to death!!!!!

    Also love “Standing Knee Deep”, the line “friends I can count on I can count on one hand with a left over finger or two” is so true! The whole “lonesome standard time” album is a masterpiece!!

    “Come on Back” is my favorite Carle Carter song off all time. Never has a cheating song sounded so rocking. !!!

    Patty Loveless”You Don’t Even Know Who I Am” kills me every time, as does most of her sad stuff. Nobody, and I mean NOBODY, does heartach like Patty!!!!!!

    This list has been my favorite so far! Love all the songs but the ones by th eladies are the best

  7. Really looking forward to the last few installments in this trip down memory lane. “The River and the Highway” and “I’ll Think of Something” would surely be in my personal Top 20, maybe even Top 10. I’m so curious to see the reveal of the Top 75! Many of the songs in this batch (and the previous) weren’t huge favorites of mine, but I’d probably take any one of them over anything released in the last five years that I really like. Ah, nostalgia…

  8. Re. “Baby Now That I’ve Found You”–A slight little error here, it’s not a song from the Motown catalogue; it was originally a hit in late 1967 for the Foundations, who were from England. But anyway, it was a benchmark in Alison’s career in which she would surpass the Queen of Soul, Aretha Franklin, for most Grammys won by a female artist in history.

    Re. “Blue”–I remember a lot of talk about LeAnn’s performance here being compared to Patsy Cline (and I think this record was supposed to be recorded by Patsy before her death in 1963), which is an extremely heavy burden to carry for someone who was only thirteen at the time.

  9. Some great Pam Tillis songs here. “River and Highway” is a beautiful story-song rich in symbolism and outstandingly poetic lyrics. “Deep Down” is actually my personal favorite in her catalogue. Lyrics and vocals are great, but I must admit that it was the hooky fiddles that really sold me on it. I like the point you made about her having a conversation with the instruments. I never thought of that before, but it’s so true.

    It’s so cool how this countdown not only reminds us of great old songs, but it also causes us to see them in new ways, and appreciate qualities that we might not have noticed before.

    Also have to say how much I love “No Place That Far” and “The Fear of Being Alone.” “Something in Red” has been one of my mom’s all-time favorite songs ever since I was little kid, and I can see why.

  10. The LeAnn Rimes, Sammy Kershaw, and Clint Black entries are among my favorite songs from each artist. Similarly, the Lorrie Morgan tracks are two of her best ever. But I am also very fond of ‘I’ll Think of Something’, ‘Aint’ That Lonely Yet’, ‘The River and The Highway’, ‘You Don’t Even Know Who I Am’ …

    I’ll also add that this is the first installment in this countdown where I really love every song – past editions have included at least one song I was indifferent to. Like Ben, I’ve found new reasons to appreciate these songs by reading your summaries too. That’s one of my favorite things about discussing music with other fans: you get to hear a completely different perspective that your own ears have missed, and continue to miss, with repeated listenings.

    Looking forward to the rest of this and I expect to be reminded of a lot more excellent songs as you all approach the end.

  11. Re: Alison Krauss – Grammy wins. Alison didn’t surpass Aretha Franklin until the 2003 Grammy Awards. Alison Krauss won 3 awards that evening taking her career total to 17, Aretha won 1 award taking her total to 16.

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