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

 

#224
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

 

#223
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

#222
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

#221
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

#220
Soon
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

#219
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

#218
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

#217
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

#216
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

#215
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

 

#214
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

#213
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

#212
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

#211
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

#210
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

#209
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

#208
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

#207
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

#206
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

#205
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

#204
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

#203
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

 

#202
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

#201
Tempted
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