400 Greatest Singles of the Nineties: #225-#201

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:


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


Black Coffee
Lacy J. Dalton
1990 | Peak: #15

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


Everytime I Cry
Terri Clark
1999 | Peak: #12

The downward spiral of abuse may be more dramatic when it climaxes with a burning house. It certainly makes for a heck of a song. But choosing to walk away, overcoming the weakness inside in the process, makes for a heck of a song, too. – Kevin Coyne

The Tips of My Fingers
Steve Wariner
1992 | Peak: #3

These days Bill Anderson is most known for co-writing Brad Paisley’s “Whiskey Lullaby” and George Strait’s “Give It Away”, but Steve Wariner’s “Tips of My Fingers” is yet another lonesome Anderson composition from the early nineties. The  soaring blend of Wariner’s lead and Vince Gill’s background vocals is the perfect combination to sell this song of self-inflicted heartache. – Leeann Ward

Don’t Rock the Jukebox
Alan Jackson
1991 | Peak: #1

Only Jackson could turn one “heartbroke” hillbilly’s simple request to hear some Jones into an endearing tagline for country music. – Tara Seetharam

Tanya Tucker
1993 | Peak: #2

They say that “someday never comes.” Such is the case with “Soon”, as Tucker’s character learns the hard way. – LW

Rumor Has It
Clay Walker
1997 | Peak: #1

The roses, the wine and his unexplainable smile are giving away Walker’s secret, but the only thing he cares about is whether or not his special someone shares the same secret. I find myself wanting to use the word “charming” every time I write about Walker, but that’s just what this is: a charming little record that he sings with sincerity. – TS

Sold (The Grundy County Auction Incident)
John Michael Montgomery
1995 | Peak: #1

I’m not sure how this scenario would play out in real life, but it makes for a part ridiculous, part ingenious toe-tapper. – TS

Angels Working Overtime
Deana Carter
1999 | Peak: #35

Is the driving force here God’s plan for the girl or the girl’s faith that God will provide? Does it matter, given the glorious result? – KC

I’ll Try
Alan Jackson
1995 | Peak: #1

On the surface, it seems like a halfhearted declaration of commitment, since we’re used to saying, “I promise to love only you.” However, anyone who’s in a committed relationship, even the strongest of relationships, learns that “I’ll try” is really the most honest promise one can make. – LW

If I Didn’t Have You
Randy Travis
1992 | Peak: #1

Randy Travis is really good at the up-tempo love songs. “If I Didn’t Have You” isn’t necessarily lyrically original, but the jaunty production and Travis’ vocal exuberance elevates the song from sappy to delightful. – LW


Whenever You Come Around
Vince Gill
1994 | Peak: #2

I stand by my belief that the best-written lyrics can’t touch the best-written melodies or the most expressive vocal performances. Case in point: “Whenever You Come Around,” in which Gill conveys through his vocal performance alone the intoxicating, paralyzing infatuation he has with a woman. He pays such careful attention to the synergistic rise and fall of the sentiment and melody that I’m convinced no combination of words could have told this story better. – TS

If I Know Me
George Strait
1991 | Peak: #1

It’s a simple song of commitment. He knows that no matter the argument, they’ll be back in each other’s arms when all is said and done. – LW

Tender When I Want to Be
Mary Chapin Carpenter
1994 | Peak: #6

Carpenter acknowledges that strength is an admirable quality, but a budding relationship shows her that a little tenderness isn’t a sign of weakness. – LW

Norma Jean Riley
Diamond Rio
1992 | Peak: #2

Diamond Rio shows off their tight harmonies and instrumental prowess in this goofy song  that celebrates the steps of sheer infatuation. – LW

Don’t Tell Me What to Do
Pam Tillis
1990 | Peak: #5

Tillis stands up for her right as an independent woman…to stay hopelessly in love with you. The drums drive it, the steel guitar defines it. A brilliant fusion of old and new in both theme and sound. This lady knew what she was doing. – DM

Blue Clear Sky
George Strait
1996 | Peak: #1

There he goes again, turning one of life’s simplest truths – that love, like the best things in life, comes when you least expect it – into a solid hit, made all the more charming by its Forrest Gump-inspired turn-of-phrase. – TS

Nowhere Bound
Diamond Rio
1992 | Peak: #7

How influential was sixties rock on nineties country? Diamond Rio did a country derivative on the Beatles classic “Nowhere Man” without compromising its integrity as a country record or cheapening the classic original. – KC

Hey Cinderella
Suzy Bogguss
1993 | Peak: #5

Bogguss understands the wiser, more mature version of the fairy tale; the one where the mundane details of life take center stage. – LW

Dust On the Bottle
David Lee Murphy
1995 | Peak: #1

My guess is that this spunky little record from the mid-90s is still in rotation today not just because it’s infectious ear candy, but because, like the best country songs, it uses a bite-size story to tell a timeless, life-size truth. – TS

I’m Alright
Kim Richey
1997 | Peak: Did Not Chart

“After all was said and done…there was nothing left to do.” The weary smile embedded in that opening line lingers through the song, which doesn’t make a big show out of getting over someone and persevering through the occasional pain. This is what real people sound like when they decide to overcome stuff, I think. (I am also assuming that real people have sunny banjo parts playing somewhere during such decisions.) – DM

Lead On
George Strait
1995 | Peak: #7

Two weary lovers who were burned in their youth find new hope in each other. Well, not so much hope as a willingness to believe that their potential future together might be better than being alone with the memories of love from days gone by. – KC

Lord Have Mercy On a Country Boy
Don Williams
1991 | Peak: #7

Williams wistfully longs for the country  life that he once enjoyed, but his beloved country surroundings has slowly transformed into a city, which is difficult for him to endure. Unlike many “I’m from the country songs”, this one lacks the bravado and, instead, conveys humble befuddlement. – LW


One of These Days
Tim McGraw
1998 | Peak: #2

Lays on enough sap to rival “Don’t Take the Girl”, but if you can sift through that, there’s a strikingly frank self-reflection here by a man with whom we might not normally think to sympathize. – DM

Marty Stuart
1991 | Peak: #5

Marty Stuart is respected for championing traditional country music today, but he wasn’t afraid to stray from the format at times back in the day. Listen to this song, and you hear some cool  old-time rock influences. – 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. No arguments here. I love both Carpenter entries, Bogguss’ “Hey Cinderella”, Clark’s “Everytime I Cry”, Dalton’s “Black Coffee” and Strait’s “Blue Clear Sky”.

  2. Re. “Passionate Kisses”–This is one of MCC’s few songs that really gets any airplay anymore on country radio, proof that really good, intelligent, and thoughtful songs like this are probably too good to be played on country radio (incidentally, Lucinda Williams wrote that song, I believe).

    Re. “I’m Alright”–Same situation with Kim Richey as it is with MCC, a song too good for the format by an artist who can’t fit in to only the country genre (IMHO).

  3. So many great songs from female singers — Dalton, Chapin Carpenter, Tillis, Bogguss.

    Those were the days.


  4. I like Kim Richey’s “I’m Alright”, which I have by Kathy Mattea and Terri Clark. I saw Kim open for Kathy Mattea in ’96 and as part of a songwriter show at the Bottom Line in ’01. Don’t know why she hasn’t had any chart success.

    I would have Suzy B’s “Hey, Cinderella” much higher. Other favorites in this group are the MCC songs, Terri Clark’s “Everytime I Cry” and “Black Coffee”, the Lacy J. Dalton song which I never heard before.

  5. Can’t believe “Hey Cinderella” wasn’t in the top 50, and that Lacy J song cuts strait to the bone. It’s one of my go to songs when I’m sad!!!

  6. More good ones on this list. While reading this, I just had to bring up iTunes and listen to “Everytime I Cry,” “Don’t Tell Me What to Do,” and “Tender When I Want to Be.”

    One of the things that I love about “Dust on the Bottle” is the symbolism that adds a special poetic touch to the song. It’s so nice that the song still gets played on country radio today. I wish Pam Tillis and Mary Chapin Carpenter were still getting more spins today.

  7. …i had almost forgotten about lacy j. dalton’s “black coffee”. even beats a starbuck’s hazelnut-cappuchino – and that’s quite a tough one to beat.

  8. Good heavens, “Chill of an Early Fall” is a terrific record. The title track is terrific, and aren’t ‘So Much Like My Dad’ and ‘Why Do Trains Make Me Lonesome?’ on that one? But “If I Know Me” is one of my all-time favorite George songs, which makes it among my all-time favorites.

    “Dust on the Bottle”, too — that’s one I always crank to the max when I hear it. Gorgeous.

    Keep up the great work. These lists kick butt, and we have a long way to go.

  9. I just wanted to thank you for this at the midway point. I checked out of country music when Garth broke through and paid little attention to country outside of the Dixie Chicks from then until the mid-2000s. It’s great to get a primer like this.

  10. ,i> Good heavens, “Chill of an Early Fall” is a terrific record. The title track is terrific, and aren’t ‘So Much Like My Dad’ and ‘Why Do Trains Make Me Lonesome?’ on that one?

    No, both of those songs are from Holding My Own. But you’re right, Chill of an Early Fall is a great album.

  11. No, both of those songs are from Holding My Own. But you’re right, Chill of an Early Fall is a great album.

    @ Razor X: Of course they are. I wasn’t thinking. I guess I really like ‘Holding My Own’, then – but this one is great, too. I think I have been making that mistake for years.

    Fortunately, George doesn’t know how to record BAD records. Just good ones and REALLY good ones.

  12. Leeann Ward says “The Tips of My Fingers” is an “Anderson composition from the early nineties”, which makes it sound like Anderson wrote it at that time, but it actually was already a hit four times before: First a #7 by Bill himself as early as 1960 with following versions by Roy Clark (1963, #10), Eddy Arnold (1966, #3) and Jean Sheppard (1975, #16).

  13. i am so glad to see lacy j. dalton black coffee mentonied she has one hell of a voice and this song fit her so well ihope hillbilly girl with the blues also gets a mention lacy is still one of the most talented people of the 80,s and 90,s

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