400 Greatest Singles of the Nineties: #150-#126

Signature hits, breakthrough hits, and why-weren’t-they-hits abound in this entry.

400 Greatest Singles of the Nineties:


Gone Country
Alan Jackson
1994 | Peak: #1

A perfect time capsule of the boom times, as Jackson wryly notes all of those genre-hoppers who saw dollar signs in the growing country music scene. Funny how they didn’t arrive on radio until a decade later. – Kevin Coyne

I Want to Be Loved Like That
1993 | Peak: #3

Sometimes the deepest understanding of love comes from what you see around you. The narrator in this song won’t settle for anything less than the unwavering love he’s witnessed in his life, and his examples are stunning in the way they slice straight to the core of love, to the bond that can’t be broken by the physical world. This is one of the purest tributes to love I’ve ever heard. – Tara Seetharam

Trail of Tears
Billy Ray Cyrus
1996 | Peak: #69

The sensitive portrayal of the plight of Native Americans is far removed from the bombastic “Achy, Breaky Heart” for which Billy Ray Cyrus is most associated. With its acoustic-bluegrass production, it may have been a little too quiet for even the nineties, but it’s his most elegant piece of art to date. – Leeann Ward

This Woman and This Man
Clay Walker
1995 | Peak: #1

Country music is rich with stories of broken relationships, but I’ve always found this one to be particularly tragic. Against a pleading melody, Walker sings of a man who’s trying desperately to make his other half understand that there’s still a chance to save their relationship. That he feels the only way he can communicate this is by stripping the situation down to an anonymous woman and man is heartbreaking. – TS

Ball and Chain
Paul Overstreet
1991 | Peak: #5

Part of a string of “family man”-themed singles, Overstreet turns out the best of them with a joyous ode to settling down. – LW

I’ve Been Everywhere
Johnny Cash
1996 | Peak: Did Not Chart

It works because he has. Some songs just sound better when sung by an older man. – KC

Lord Have Mercy On the Working Man
Travis Tritt
1992 | Peak: #5

The best working man anthem of the nineties is among the best working man anthems in general. – LW

Look Heart, No Hands
Randy Travis
1992 | Peak: #1

Likening his confidence in love to a reckless, carefree youth, Travis delivers one of his many simple, but poetic, love songs. – LW

When it Comes to You
John Anderson
1992 | Peak: #3

I’ve never heard Anderson’s signature vocal style so well complemented by the music. All the truth, with room for it to breathe. – KC

Cold Day in July
Joy White
1993 | Peak: #71

A swell of pain and shock, as White tries to make sense of a goodbye she didn’t even get to see coming. The Dixie Chicks made the song a moderate hit years later, but seek this original version out; the quivering vocal sells it with unmatchable pathos. – Dan Milliken

Outbound Plane
Suzy Bogguss
1992 | Peak: #9

Is Bogguss’ perspective on love a pessimistic one, or a realistic one based on the idea that you create your own happiness? I’m not sure, to be honest, but the terrific arrangement and vocal performance steal the spotlight on this record, anyway. – TS

How Do You Like Me Now?!
Toby Keith
1999 | Peak: #1

Keith skillfully slaps his swag on one of the most spirited revenge anthems of the decade. I give him bonus points for working the teasing “na-na na-na boo boo” into the melody. Brilliant. – TS

Learning to Live Again
Garth Brooks
1993 | Peak: #2

Another dose of melodrama that’s completely justified. Brooks uses his first experience back on the dating scene to flesh out the depth of his scars from a painful break-up. It’s a tasteful and understated record, highlighted by a fully-invested performance from Brooks. – TS

Alan Jackson
1993 | Peak: #1

Simple, catchy nostalgia, destined to play in Nashville bars for all eternity. In a good way. – DM

I’m in a Hurry (and Don’t Know Why)
1992 | Peak: #1

As a fun lament to always being in a hurry, “I’m in A Hurry” showcases one of Alabama’s finest harmonies of their career. – LW

Don’t Worry Baby
The Beach Boys featuring Lorrie Morgan
1996 | Peak: #73

Sometimes a woman covers a song originally sung by the man, and changes the lyrics around a bit to make it make sense. Sometimes the song makes more sense in its new incarnation. Oh, and she sings the fire out of it. – KC

She’s in Love With the Boy
Trisha Yearwood
1991 | Peak: #1

One of country music’s most all-around lovable singles, like Romeo and Juliet with a happier ending and a Tastee-Freez shout-out. – DM

You Know Me Better Than That
George Strait
1991 | Peak: #1

Not only does the character in this song know that his ex-lover knows the real him that his new lover hasn’t yet seen, he’s self-aware enough to acknowledge his faults as well. Lest you think this song is serious, however, it’s one of Strait’s more amusing singles. – LW

Wild Angels
Martina McBride
1995 | Peak: #1

It’s nice – and humbling – looking back and realizing how many things you’ve survived that could have wrecked you. McBride is counting her lucky stars for the unlikely endurance of her relationship, and  her soaring performance rings with infectious joy. It makes me think I’d probably still like her glory-note stylings if the songs had just happened to remain this good. – DM

No One Needs to Know
Shania Twain
1996 | Peak: #1

Reveling in a love that’s only hers to know, Twain is playful, charming and romantic all at once on what remains one of her finest singles. – TS

Look at Us
Vince Gill
1991 | Peak: #4

A love that is standing the test of time, leaving Gill awestruck and deeply appreciative. – KC

I Don’t Call Him Daddy
Doug Supernaw
1993 | Peak: #1

The biggest casualty of divorce is the innocent children who are forced to adjust to new situations that they didn’t ask for. Part of such adjustments include new parental figures that they are expected to accept with grace. The most heartbreaking part of this song is the little boy who obviously knows that his loyalty is divided, as he assures his long distance father that his stepfather is reliable, but still isn’t considered “Daddy.” – LW

I Walk the Line Revisited
Rodney Crowell with Johnny Cash
1998 | Peak: #61

Crowell audaciously reworks the melody of Johnny Cash’s classic “I Walk the Line” to tell the story of how that classic impacted him growing up. Somewhat blasphemic, but mostly just cool. – DM

Live Until I Die
Clay Walker
1993 | Peak: #1

Unlike similar songs of today, this is one of the few instances when the theme of celebrating a carefree life is set to a pretty melody and restrained production. – LW

How Can I Help You Say Goodbye
Patty Loveless
1994 | Peak: #3

One of the most solid examples of selfless love from a mother to her daughter. – LW

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. Lots of good stuff again – for me the songs here by Overstreet, Vince, Martina, TK, Shenandoah, Alabama, Lorrie Morgan, Travis and Tritt.

    Gone Country is one of my favorite AJ songs and not just because it’s one of the few country songs that mentions Long Island where I lived for 60 years.

    There’s a different “Trail of Tears”, written by Randy Handley and sung by Hal Ketchum on his “Sure Love” cd in 1992. John Denver also recorded the Handley song.

    For “Cold Day in July”, I prefer the Suzy Bogguss version on her 1992 album “Voices in the Wind”

  2. Re. “Trail Of Tears”–it seems like this was the Nineties equivalent of Johnny Cash’s 1964 classic “The Ballad Of Ira Hayes” in how sympathetic it is to the Native American. If only there were a greater understanding of those brave people from the country music community, and not a blinkered version borne out of John Wayne movies…

    Re. “I’ve Been Everywhere”–yes, the Man In Black definitely knows whereof he speaks. And to roll off the names of the places he’s been to would tie anyone else’s tongue up (IMHO). A great cover of a song that I believe was originally done in the early 1950s by the equally legendary Hank Snow.

    Re. “She’s In Love With The Boy”–It’s ironic to say this, but on the basis of this debut song of Trisha’s, if anyone had asked me whether I could have ever gotten around to liking her back in 1991, I probably would have said “No”, and I really can’t explain why that is. By the time THE SONG REMEMBERS WHEN was released two and a half years later, I had changed my mind. These days, however, “She’s In Love With The Boy” is almost the only song of Trisha’s that country radio plays anymore, and I think this really obscures what Trisha has done in the nearly twenty years since.

  3. Loved the Billy Ray Cyrus song. That’s a side of him that you don’t really see from Achy Breaky Heart.

    You’re right – “She’s in Love with the Boy” really is one of the most lovable singles ever, and “Wild Angels” was one of Martina’s best. If only Martina would return to singing great songs like that instead of so many less-memorable girl power anthems. She’s not as much of a risk taker now as what she used to be.

  4. A very good list. I especially like “Learning to Live Again”, “Look Heart, No Hands”, and “This Woman and This Man”. I’ve never gotten into “She’s in Love with the Boy” (probably because, like an earlier poster noted, it gets played way too often on radio), which also sort of lowers “Chattahoochee” and “I’m in a Hurry” in my mind.

    Side note: While I do like the Shenandoah song, that has to be one of the worst album covers I’ve ever seen. Marty Raybon’s expression, in particular, is just priceless: “Um, duh? We’re under kudzu! It’s literal, see!”

  5. OMG I canr believe How Can I help You Say Goodbye isn’t at least in the top 50!!!!!!!!!!!!!! IMO the best country song ever written sung by the queen of heartbreak. I feel so attached to this song as I lost my dad a few years ago and my grandmother last sept. It has helped me deal with th epain more than any other song!

  6. “I Walk The Line Revised” is the real gem among these songs. I marvel that Cash was able to sing the words so accurately since the song uses a chorus melody line just slightly altered from the original. It would drive me nuts trying to stick to that new melody line since it is so similar to, yet different from, the original melody line

  7. I would have to agree that “No One Needs to Know” is one of Shania’s finest singles. Shania took a lot of flak for her incorporating pop elements into her music, but it’s fun to hear her traditional side as well. She just had a very diverse style. I can’t imagine a song like that doing well on the charts today, especially not if it were recorded by a female artist.

  8. With ‘No One Needs to Know’ being too traditional for country radio today got me thinking. At the end of this decade are we going to be looking back at 2000-2009’s as fondly as we are with the 90’s as a golden age, longing for a time when country was traditional with songs like ‘Undo It’ and ‘She’s Country’ With ‘Stuck Like Glue’ and ‘Mine’ taking the country elements right out now it’s a scary thought. We didn’t know how good we had it in the 90’s until we look back.

  9. Pretty sure there’s no situation that could cause me to have fond feelings about “She’s Country” :) That said, I have to say I’ve been much more impressed with new mainstream albums/singles this year than I was last year. Maybe this decade will turn around.

  10. I think The Woman in Me is a fair bit countrier than Come On Over or Up! from a compositional standpoint, too, though the pop elements are still very much there.

  11. They definitely pushed it more on COO and Up!, though I think that the Green/Red/Blue strategy of Up! allowed them to find a happy medium between TWIM and COO.

    I always gave them props for opening COO with “Man! I Feel Like a Woman!”, which was the least country thing on there, after sending probably the most country song to radio as the lead single. It was startling to hear that album for the first time.

  12. @Stephen H.:

    Mind you, I’m not saying they overplay “She’s In Love With The Boy” on country radio, just that they might be giving the wrong impression to more recent country music converts about Trisha, that she was only a one-hit wonder.

    Re. “Wild Angels”–this is the kind of edgier material that I kind of hope Martina gets back to, as well as understanding that dialing down the volume can be even more effective than hitting high notes. She managed to do this more recently on “Wrong Baby Wrong” (IMHO).

  13. Damn, you’re still criticizing her! Why are you portraying Martina as a washed-up has-been? It’s so insulting to see a great vocalist torn up like this.

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