400 Greatest Singles of the Nineties: #300-#276

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:



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

The Hard Way
Mary Chapin Carpenter
1993  |  Peak: #11

The chorus is catchy, something that would work as a good audience participation song at a concert, so it’s possible to miss the message. “Show a little inspiration; show a little spark,” she implores. It might be work, even hard work, but a good relationship won’t last without it. – Leeann Ward

He Ain’t Worth Missing
Toby Keith
1993  |  Peak: #5

Toby acknowledges the woman’s feelings in this song, but offers her a little straight talk, along the way. Not only does he assure her that her ex isn’t worth missing, he lets her know that he’s more than willing to be the replacement. – LW

That Don’t Impress Me Much
Shania Twain
1998  |  Peak: #8

One of the campiest, sing-and-talk-a-longiest singles ever. Long after you’ve forgotten most of this year’s great serious songs, you’ll still remember the exact timing and inflection of, “OK, so you’re Brad Pitt.” – Dan Milliken

John Michael Montgomery
1996  |  Peak: #2

A record that hinges on two sad truths. First, a love affair has ended. Second, all friendships come to an end. – Kevin Coyne

Phones are Ringin’ All Over Town
Martina McBride
1996  |  Peak: #28

With the build up of the song, the frenzy that the repeat cheater is feeling is palpable. Even though he knows exactly why she’s left, he desperately tries to find her, which is why “phones are ringin’ all over town.” – LW

Patty Loveless
1990  |  Peak: #1

One of Loveless’ earliest hits, “Chains” revolves around a hook that’s as simple as they come, but therein lies its charm. – TS

Even the Man in the Moon is Crying
Mark Collie
1992  |  Peak: #5


Mark Collie is one of the casualties of the nineties country boom. Despite talent, he just couldn’t keep up with the big hit makers of the decade. “Even the Man on the Moon Is Crying” is one of his most memorable songs, however. From the moment he drops her off at the airport, he knows it’s over, despite putting on a brave front. It’s all so sad and final that even the man in the moon is crying. – LW


Right On the Money
Alan Jackson
1998  |  Peak: #1

If only Phil Vassar, one of the song’s writers, would record a song this cool. The best line? “She’s the best cook that’s ever melted cheese.” – LW


Walkin’ Away
Clint Black
1990  |  Peak: #1

“Walking away, I saw a side of you that I knew was there all along.” Oh, how I long for the days when his word craft described love gone wrong instead of right. – KC

Something Like That
Tim McGraw
1999  |  Peak: #1

On the surface, “Something Like That” is a fairly basic story of two teenagers’ first kiss. But the true value of this classic is spelled out in its bridge: “Like an old photograph, time can make a feeling fade/But the memory of the first love never fades away.” I’ve always viewed this song as a validation of puppy love: that no matter how trivial the details or circumstances –be it barbecue stains, miniskirts or skippin’ rocks on the river – the experience of your first love matters. – TS


On a Bus to St. Cloud
Trisha Yearwood
1995  |  Peak: #59

Haunted by the ghost of a love that she sees everywhere that she goes, she loves him some, hates him some, but misses him most. – KC

Easy Come, Easy Go
George Strait
1993  |  Peak: #1

Even though they’re saying goodbye, this song is as relaxed as the title suggests. If only the dissolution of all relationships were this calm. – LW

Tall, Tall Trees
Alan Jackson
1995  |  Peak: #1

George Jones and Roger Miller both recorded versions of this quirky number they co-wrote, but it was latter-day traditionalist Jackson who made it a hit. The ridiculous lyrics – about a lovestruck man who pledges to buy his girl trees, limousines, and all the planet’s ocean waters – are equal parts spoof and celebration of the blissful irrationality of new love. – DM

Clown in Your Rodeo
Kathy Mattea
1995  |  Peak: #20

In the contemporary Christian music world, Wayne Kirkpatrick wrote most of the lyrics to Michael W. Smith’s melodies. In country circles,  he is most known for his involvement in Garth Brook’s Chris Gaines project and, most recently, his contributions to Little Big Town’s career. Back in the mid-nineties, however, he was the writer of “Clown in Your rodeo”, a fun, sassy number from one of Kathy Mattea’s most popular albums. – LW

It’s Lonely Out There
Pam Tillis
1996  |  Peak: #14

One of her strongest vocal performances, as the casual indifference to a man threatening to leave quickly escalates into genuine fear. By the end, she’s begging him to stay, realizing  it’ll be just as lonely in here if he’s gone. – KC

You Lie
Reba McEntire
1990  |  Peak: #1

The modern heartbreak queen takes the weepy country ballad to spine-tingling heights that Kitty Wells and Tammy Wynette never dreamed of. – KC


Why Walk When You Can Fly
Mary Chapin Carpenter
1995  |  Peak: #45

Nowadays, a song with this title would probably be all about one person trying to work up the self-confidence to achieve some kind of worldly success – an elementary-school “believe in your dreams” thing. But in the nineties, it was a warm, understated challenge to us all to break free of our cyclical demons – selfishness, fear, pointless finger-pointing – for the good of humankind as a whole. We walk or we fly together. – DM


Nothin’ But the Taillights
Clint Black
1997 |  Peak: #1

Left on the side of the road by his lover, Black reflects on his sticky situation in this inescapably catchy number. – TS


Unbreakable Heart
Carlene Carter
1993  |  Peak: #51

Radio loved her when she was rowdy, but she’s just as good when she’s nakedly vulnerable.- KC

Burnin’ the Roadhouse Down
Steve Wariner with Garth Brooks
1998  |  Peak: #26

You’ve got to give them credit. Steve Wariner and his buddy, Garth Brooks, try to take an old fashioned sounding, western swing flavored song to mainstream country radio. Within the warm production, check out the cool guitar picking from Wariner, not to mention steel guitar aplenty. – LW


Who Needs Pictures
Brad Paisley
1999 |  Peak: #12

A man thinks about going to develop a roll of pictures (remember those?) featuring his ex, but figures it would be redundant: “who needs pictures with a memory like mine?”. Still one of Paisley’s best moments.  – DM


Whatever You Say
Martina McBride
1999  |  Peak: #2

New-millenium fans may not realize that there was a time when McBride’s whisper-then-BELT style actually seemed fresh. This ultimatum to a cold lover feels like a natural progression of the songs heartbroken women had always sung in country music, but the skyscraping vocal was McBride’s own twist on the model, and it was a truly cool innovation – until, of course, it became the insufferable norm. – DM


You’ve Got a Way
Shania Twain
1998  |  Peak: #13

Twain was often criticized for being a subpar vocalist, but the difference between Twain and, say, Taylor Swift is the former’s ability to use her instrument to express shades of emotion, working with instead of against her vocal imperfections. “You’ve Got a Way” is a perfect example, with Twain soulfully and stirringly filling every crevice of the acoustic arrangement. – TS


Two Sparrows in a Hurricane
Tanya Tucker
1992  |  Peak: #2

This is a straightforward, paint-by-numbers love story song, but one that manages to seem sweet and simple all the same. – 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. Some terrific, concise writing on this feature thus far, gang.

    “Whatever You Say” is the only single of McBride’s other than “Independence Day” that I revisit much at all, and it’s certainly the only other single in her catalogue on which her glorynote belting is truly in service to the song itself. And, much like inferior “issue” songs like “God’s Will” have done for the legacy of “Independence Day,” inferior songs like “Where Would You Be” and “How Far” have diminished the impact of “Whatever You Say.” McBride doesn’t seem to get the idea of “lightning in a bottle,” even though she’s caught it twice. I’d have “Whatever You Say” somewhere in my top 50, but I’m glad to see it included here.

    And I hope to see the underappreciated Carlene Carter turn up a few more times as the feature continues to unfold.

  2. I agree with everyone else: It’s nice to see some love for Carlene Carter. Mark Collie, too, for that matter.

    “On a Bust to St. Cloud” may rank as my favorite Trisha Yearwood song. Top 5 for sure.

  3. Loving the list so far. Shocked that Something Like That and Two Sparrows In A Hurricane are this low (I thought both were locks for the Top 50), but really loving the list.

  4. It’s a tricky decade to rank. Each writer did a 200-track personal list. I can put mine on shuffle and not notice a difference in quality than if it was played in rank order. When I made a playlist of our combined top 400, that didn’t really change. I’m amazed to find that I enjoy most of the songs that other writers included as well. I’ve even discovered some new favorites from their picks that I’d somehow managed to miss. It was a very rich decade.

  5. It’s good to see some Shania on this list. The blurb for “You’ve Got a Way” describes her very accurately. Her set of pipes might not have been as powerful as Martina’s, but Shania still brought her own unique set of gifts to the table. She displayed charm, charisma, and personality, and an ability to connect with the audience on an emotional level. The simple production always complemented her voice perfectly. It all goes to show that you shouldn’t judge a singer solely on her ability to hit high notes.

    Also happy to see more Trisha, Patty, and Mary Chapin – love ’em!

  6. Re. Trisha’s “On A Bus To St. Cloud”–it’s interesting, and unfortunately just a bit too unsurprising, that a lot of times when Trisha does deeper material and it gets released as a single, it stalls on the charts and at country radio. It’s partly because of this song’s lackluster radio and chart performance that I feel they still only think of her in terms of “She’s In Love With The Boy”, which is a dreadful misjudgment on their part (IMHO).

    Re. “That Don’t Impress Me Much”–this is part of what I meant in another thread when I said that Shania’s writing capacity hasn’t really caught up to what her voice can do, at least not quite yet. Whether it’s country or pop is not in and of itself the big deal, but the lyrics to me were too cutesy and clever here.

    Re. “Whatever You Say”–it’s hard not to like a lot of the things Martina does with this song, but I too wish on other songs that she would exert the same kind of vocal control that Trisha does, alongside being unafraid to challenger herself and her audience with tougher, harder-edged material, be it neo-traditional or rock-slanted.

  7. Another great Kathy Mattea song, just picked up this album a few months ago and I think it’s my favorite of the one’s I’ve heard of hers. Hopefully one of the great singles from Love Travels makes the list, that’s my favorite album of hers from the 90’s.

  8. I like what Eric said about wishing Martina would delve into some more harder-edged material. I remember reading that she thought that “Concrete Angel” wouldn’t do well at radio because she thought it was too over the top because it was so serious, but it did to well and it is one of my favorite songs of hers. She still has a great voice, but I think she needs to have a few more singles that are heartbreaking to balance out the mix of hopeful.

  9. The Chains video was my intro to Patty Loveless, and it is still one of my favorite PL songs. I consider it her “other” tongue-twister song (next to Blame it on your heart). I really like the “heart breakin’ love takin’ cold hard lonely makin’ chains” chorus, but especially the way she sings it.

    Also a big fan of Martina’s Whatever You Say and it sure doesnt hurt that the wonderful Sara Evans provides some strong backup vocals on the song!

  10. It’s a tricky decade to rank. Each writer did a 200-track personal list. I can put mine on shuffle and not notice a difference in quality than if it was played in rank order. When I made a playlist of our combined top 400, that didn’t really change.

    Yep, I feel the exact same way. There’s just an insane amount of good songs from the 90s. It really does come down to personal taste.

  11. To echo Paul up there, Jessica Andrews did do a recording of Unbreakable Heart that I thought was much more powerful than the Carlene Carter version. Of course, it could be because I was 19 in ’99 when it came out and my long time girlfriend had just moved across the country to go to college, but hey, still like Andrews’ version better.

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