The hits come from all over the place here. Breakthrough hits from Trace Adkins and Carlene Carter join one-hit wonders Brother Phelps and George Ducas. And alongside crafty covers of songs by sixties rock band The Searchers and nineties country artist Joy Lynn White, you can also find tracks from three diamond-selling country albums.
400 Greatest Singles of the Nineties: #200-#176
#200
Carrying Your Love With Me
George Strait
1997 | Peak: #1
A traveler gets through his lonely nights on the sheer strength of love. It’s perhaps a little too saccharine for some, but the sweet melody and Strait’s understated vocals make the record work. – Tara Seetharam
#199
Nothing’s News
Clint Black
1990 | Peak: #3
A man sits around in a bar “talking ’bout the good old times, bragging on how it used to be.” Standard premise, but Black’s melancholy performance lifts the record to Haggardly heights. – Dan Milliken
#198
Rockin’ Years
Dolly Parton with Ricky Van Shelton
1991 | Peak: #1
The lyric is unabashedly cutesy, but Dolly’s and Ricky’s way of leaning into the song with no shame makes it all okay and even endearing. – Leeann Ward
#197
We Can’t Love Like This Anymore
Alabama
1994 | Peak: #6
A beautiful requiem for a dying love. The man just needs to know it’s over for sure so he can begin to make peace with it coming to an end. – Kevin Coyne
#196
Daddy Won’t Sell the Farm
Montgomery Gentry
1999 | Peak: #17
The emotional and family roots are planted so deep that there’s no way that the family farm will be sold if father and son have anything to say about it. We’ve heard the sentiment before, but Montgomery Gentry’s take on the theme is a worthy addition. – LW
#195
Trouble is a Woman
Julie Reeves
1999 | Peak: #39
A firecracker of a song that pays tribute to the tenacity and steadfast determination of a woman who’s been done wrong. Reeves’ performance is as blazing as the woman she’s singing about. – TS
#194
What Kind of Fool Do You Think I Am
Lee Roy Parnell
1992 | Peak: #2
What’s that saying again?: “Fool me once, shame on you; Fool me twice, shame on me.” It seems that Parnell understands that concept rather well, as he plainly says, “You hurt me one time, I finally learned.” – LW
#193
Too Cold at Home
Mark Chesnutt
1990 | Peak: #3
A melancholy record about a man who finds himself stuck at a bar because it’s too hot outside and too cold at home. Sounding both dejected and wistful, Chesnutt does a superb job conveying his pain, and his vocal emphasis on “cold” is just gorgeous. – TS
#192
I’m On Your Side
Kathy Mattea
1997 | Peak: Did Not Chart
Jim Lauderdale sure knows how to write some catchy melodies and Kathy Mattea knows how to bring them to life. What’s more, this is actually a heartwarming, albeit fun, pledge of fierce loyalty. – LW
#191
Let Go
Brother Phelps
1993 | Peak: #6
Finally breaking free from anything that’s held you back is liberating, but comes with the bittersweet realization that you were free to go all along. – KC
#190
Livin’ On Love
Alan Jackson
1994 | Peak: #1
Jackson gave us so many strong neotrad ditties in the nineties that they can tend to run together and feel same-y, even when any one of them could have been a career highlight for a lesser artist. Like “Little Bitty” or “Gone Country” or “Chasin’ That Neon Rainbow,” “Livin’ On Love” more or less tells you in the title what you’re getting, and also like those songs, it delivers with charm and catchy hooks to spare. – DM
#189
When You Walk in the Room
Pam Tillis
1994 | Peak: #2
It was a quintessential crush song for the Searchers in the mid-sixties. Tillis adds a steel guitar to the classic guitar hook, but what sends the song to the stratosphere is her vocal. While the original had the lead singer matching the quiet tension of the backing music, Tillis lets loose toward the end, giving the song an added punch worthy of its lyric of unrequited love. – KC
#188
Tonight the Heartache’s On Me
Dixie Chicks
1999 | Peak: #6
The first of four Chicks singles that made our countdown, this one isn’t quite as lightweight as it appears on the surface. It’s satisfyingly self-pitying, but it’s also astute – from the clever spin on words in the hook, to the apt bite in Natalie Maine’s performance, to the sly line in the second verse: “I wonder if he told her she’s the best he’s ever known/The way he told me every night when we were all alone.” – TS
#187
We Shall Be Free
Garth Brooks
1992 | Peak: #12
Garth Brooks lost some airplay with this gospel-tinged piece of social commentary that was inspired by the Rodney King beating and the riots that followed. It, however, remains one of his most overtly substantive songs. – LW
#186
Two of a Kind, Workin’ on a Full House
Garth Brooks
1991 | Peak: #1
How many clichéd metaphors can you fit in one song? I counted over ten, and Brooks makes every one of them work in this raucous, hilarious tribute to his better half. – TS
#185
Time Marches On
Tracy Lawrence
1996 | Peak: #1
The passage of time seems like a broad, simple theme, but as the series of family vignettes in this song show, its impacts are specific and complicated. In an instance of brilliant songcraft, “Time Marches On” maintains a totally detached, matter-of-fact voice in touching on its characters’ developments, underscoring the point that time doesn’t make judgments or linger on particular moments the way we’re used to doing; it just keeps moving along, changing us without pause or permission. – DM
#184
I’m Over You
Keith Whitley
1990 | Peak: #3
There’s nothing like righteous indignation (Why they makin’ those stories up”?) fueled by denial (“I’m over you”). Whitley naturally emotes these common, conflicting responses with his signature tear-stained voice, which makes for an irresistible slice of hard core country music. – LW
#183
Every Light in the House
Trace Adkins
1996 | Peak: #3
Staunch conviction meets tender grief. Only Adkins could have made this as powerful a record as it is. – TS
#182
You’re Still the One
Shania Twain
1998 | Peak: #1
It’s hard to believe that the woman who filled a million wedding hall dance floors never had a true ballad hit until this instant standard was released. Finally, an anniversary song for those who didn’t have the support of their family and friends when they got married! – KC
#181
Lipstick Promises
George Ducas
1994 | Peak: #9
The Roy Orbison single you didn’t even know you were missing. Ducas won’t be falling for you and your deceitful cosmetics anymore, treacherous woman. – DM
#180
A Broken Wing
Martina McBride
1997 | Peak: #1
A rousing story of a woman who rose above the physical and emotional constraints of her spirit-crushing husband. Like the best inspirational hits in McBride’s catalogue, “A Broken Wing” also doubles as a powerful tribute to women everywhere who’ve been told that “only angels know how to fly.” – TS
#179
Walking Away a Winner
Kathy Mattea
1994 | Peak: #3
In 1994, Kathy Mattea made a calculated attempt at an explicitly commercial country record. It worked, thanks in large part to the album’s powerful title track. With surprisingly aggressive production behind her, she gives a performance that’s empowering to listen to even when you aren’t walking away from a bad situation. – KC
#178
I Fell in Love
Carlene Carter
1990 | Peak: #3
Carter falls in love and throws a freaking musical party for herself. The song begs to be hula hooped or limboed to. – DM
#177
Girls With Guitars
Wynonna
1994 | Peak: #10
Mary Chapin Carpenter might have written it, but it might as well be autobiography with the fiery authenticity that Wynonna rips into it. Bonus points for Lyle Lovett, who gives distinctive background vocals that nearly drown out fellow backup singer Naomi Judd. – KC
#176
On the Road
Lee Roy Parnell
1993 | Peak: #6
Sometimes you hit the road knowing that there’s probably nothing better on the other end of it. But getting gone is still better than sticking around where you’re no longer valued, as Parnell demonstrates through the desperation of a lonely housewife, a teenage kid dodging college, and an unhappily retired couple. – KC