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
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
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
A lot of songs from both ends of the charts here, including a husband-and-wife duet that spent six weeks at #1.
400 Greatest Singles of the Nineties: #250-#226
I Meant Every Word He Said
Ricky Van Shelton
1990 | Peak: #2
At least the third song on this list about a guy mulling over romantic gestures he wishes he’d made to his former love, and the most traditional among those songs. You could easily imagine this one being a minor classic by a 60’s or 70’s legend, so close is its replication of that style. – Dan Milliken
I’m So Happy I Can’t Stop Crying
Toby Keith with Sting
1997 | Peak: #2
My hard-and-fast rule for Toby Keith: The sadder he is, the happier the listening experience tends to be. He’s all kinds of sad in this snapshot of post-divorce melancholia, reflecting on everything from unfair custody protocol to the greater motions of the universe. Even a gratuitous Sting cameo can’t detract from the single’s gloomy grandeur. – DM
You Ain’t Much Fun
1995 | Peak: #2
Toby Keith is also funny, though. What’s a man to do? Sobering up ain’t all that it’s cracked up to be from is perspective. Ever since he’s done so, his wife has been taking advantage of his increased functionality by giving him honey-do lists that he wasn’t ably tackling pre-sobriety. It’s enough to drive a man to drink. – Leeann Ward
This section begins with a song about a farmer and his wife and ends with one about Mama. Doesn’t get much more country than this!
400 Greatest Singles of the Nineties: #275-#251
Somewhere Other Than the Night
1992 | Peak: #1
About a woman who only feels truly appreciated by her husband when they’re having sex. That kind of says it all, doesn’t it? – Dan Milliken
Looking Out For Number One
1993 | Peak: #11
From his rocking side, Tritt is tired of trying to please everyone around him, including his demanding lover. As a result, he brashly declares that he’s going to make some changes, which will include looking out for himself. Get out of the way, because his ferocious performance makes him seem quite serious about his epiphany. – Leeann Ward
Let That Pony Run
1992 | Peak: #1
Gretchen Peters wrote the gorgeous song and Pam Tillis, in turn, beautifully sings it. The song is about Mary, a woman who is forced to start a new life after her husband confesses his infidelities with no apologies. The story is sad, it’s resilient, and it’s hopeful. – LW
I Just Want to Dance With You
1998 | Peak: #1
Any monotony in the verses is overcome by the song’s completely enticing rhythm and flavor. How can you not get lost in this? – Tara Seetharam
The list continues with appearances from artists who first surfaced in the eighties and continued to thrive into the nineties, like Reba McEntire and Patty Loveless, along with new stars from the nineties who would find greater success in the next decade, like Toby Keith and Brad Paisley.
400 Greatest Singles of the Nineties: #300-#276
Does He Love You
Reba McEntire with Linda Davis
1993 | Peak: #1
This two-female duet was a gamble at the time of its release, but it offers such a brilliant fusion of perspectives that it’s hard to imagine why. The song fleshes out the range of emotions that the two women are experiencing –from pain to longing to self-doubt– and culminates in one shared question that they’ll never know the answer to: “does he love you like he’s been loving me?” – Tara Seetharam
A woman who can actually sing:
The first quarter of the countdown comes to a close, highlighted by excellent comeback attempts by T. Graham Brown, Emmylou Harris, and Willie Nelson.
400 Greatest Singles of the Nineties: #325-#301
He Would Be Sixteen
1992 | Peak: #31
Sometimes the choices that you make linger forever. Here, a woman in her thirties drives past a high school football game, and her mind wanders to the painful void left in her heart from the son she gave up for adoption. – Kevin Coyne
It Matters to Me
1995 | Peak: #1
Faith Hill’s sophomore album is a surprisingly deep set, filled with candid insights into different womens’ lives. The title track represents that spirit well, as a woman articulates the differences in her and her man’s relationship approaches with impressive precision. – Dan Milliken
A few should’ve been hits are mixed in with genuine smashes as the countdown continues.
400 Greatest Singles of the Nineties: #350-#326
How Do I Live
1997 | Peak: #2
When Yearwood and LeAnn Rimes released dueling versions of this song in 1997, it was apparently a wake up call to country listeners: “Hey, wait a minute. Trisha Yearwood is an amazing singer!” She elevates “How Do I Live” beyond its movie theme nature by adding layers of subtlety and nuance to the typical Diane Warren template. – Kevin Coyne
Boot Scootin’ Boogie
Brooks & Dunn
1992 | Peak: #1
I don’t claim to have any real knowledge of what it’s like to spend a night at the liveliest of honky-tonks, but I’ll be darned if this song doesn’t make me feel like I do. Because “Boot Scootin’ Boogie” isn’t really about a specific place where people go, and it isn’t even about the boogie itself; it’s about the universal thrill of busting out of the work week, kicking back and dancing your troubles away. From start to finish, Brooks & Dunn’s performance is a twangy blast of exhilaration, and that’s a feeling we can all relate to – outlaws, in-laws, crooks and straights alike. – Tara Seetharam
The second segment of our countdown includes the first appearances by Garth Brooks and Reba McEntire, two of the biggest-selling stars of the decade.
How Do I Get There
1997 | Peak: #1
It’s always a gamble when friends decide to take their relationship to the next level. “How Do I Get There” explores the struggle of following one’s heart, even though it’s taking a big emotional risk to do so. – Leeann Ward
If I Could Make a Living
1994 | Peak: #1
This song is either ridiculously cheesy or irresistibly cheesy depending on your taste, but there’s no denying Walker sells the heck out of it with charm and enthusiasm. – Tara Seetharam
It’s hard to believe that twenty years have passed since the nineties first began. Perhaps that’s because so many of the artists who broke through during that decade remain relevant on the music scene today, whether they’re still getting major spins at radio or not.
For many of us, it was the nineties when we discovered and fell in love with country music, and it’s the music and artists from that decade that represent the pinnacle of the genre. It may be debatable whether the nineties were the most artistically significant decade in the history of country music, but there’s no debating that country music never had more commercial success or cultural impact than it did in that decade.
It was a time that when the C-list artists could sell gold or platinum on the strength of one or two hits, and that 24-hour video outlets could give wide exposure to songs and artists that radio playlists could not. When the four writers of this feature got together and combined our favorite singles from the decade, it was clear that this retrospective had to run far deeper than the one we recently completed for the first decade of the 21st century. There were simply far more good singles to choose from.
A woman who can actually sing: Trisha Yearwood.