400 Greatest Singles of the Nineties: #275-#251

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:


Somewhere Other Than the Night
Garth Brooks
1992 | Peak: #1

About a woman who only feels truly appreciated by her husband when they’re having sex. Practically literature, that. – Dan Milliken

Looking Out For Number One
Travis Tritt
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
Pam Tillis
1992 | Peak: #4

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
George Strait
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

Come Next Monday
K.T. Oslin
1990 | Peak: #1

The cheap-sounding keyboard production is actually a perfect fit for this plucky song about forgetting an old love…next week. Also a perfect fit for the song: the . – DM

Keep it Between the Lines
Ricky Van Shelton
1991| Peak: #1

The rich voiced, traditionally minded Van Shelton seems almost forgotten today. In turn, “Keep It Between the Lines” is one of his nearly forgotten hits, which is a shame, as it’s a heartbreaking, yet tender, father song that’s rarely recognized on the annual Father’s Day lists. – LW

I Can’t Do That Anymore
Faith Hill
1996 | Peak: #8

The sinking housewife is Faith Hill’s specialty role. If this Alan Jackson-penned confessional doesn’t have the striking vision of “Stealing Kisses”, it’s nonetheless powerful in its directness. – DM

Holes in the Floor of Heaven
Steve Wariner
1998 | Peak: #2

Over-the-top sad but wonderfully written, Wariner’s classic serves as both a touching homage to lost loved ones and a comfort to those they’ve left behind. – TS

Wish I Didn’t Know
Toby Keith
1994 | Peak: #2

Is ignorance bliss when it comes to cheating lovers? Keith wrestles with his conflicting feelings in this cleverly written song, proving once again that his gruff bravado is most effective when he’s expressing a multi-faceted sentiment. – TS

Why Didn’t I Think of That
Doug Stone
1993 | Peak: #1

Call it the mature version of Mark Chesnutt’s “It’s a Little Too Late” – same concept, but more introspective and wistful. – TS

Quittin’ Time
Mary Chapin Carpenter
1990 | Peak: #7

One of her earliest hits benefits from an aggressive vocal and escalating production that goes crazy with the drums in the final verse. – Kevin Coyne

Wrong Again
Martina McBride
1998 | Peak: #1

Nobody likes to be wrong, but poor Martina seems to have a knack for it. Just when she’s sure that she’s finally found “the one”, she discovers that she’s, once again, wrong. It’s one of Martina’s best songs, which, just about marks the end of her time of  best songs. – LW

One Way Ticket (Because I Can)
LeAnn Rimes
1996 | Peak: #1

There’s a distinct moment after every break-up when the pain subsides, the clouds part and there it is – a world of opportunities in front of you that you feel like you’re seeing for the first time. Rimes captures this experience perfectly in “One Way Ticket,” with a performance that exudes spirit and conviction. – TS

Down to My Last Teardrop
Tanya Tucker
1991 | Peak: #2

A snappy, energetic performance brimming with self-assurance. – TS

Sawmill Road
Diamond Rio
1993 | Peak: #21

In contrast to their very successful first few singles, this was  the first single of Diamond Rio’s to receive lukewarm radio reception. It is, however, a gem from their sophomore album that portrays a tight knit sibling group with ideal childhoods who all grew up to take vastly different paths as adults. – LW

You’re Easy on the Eyes
Terri Clark
1998 | Peak: #1

Good-looking men and women who are otherwise terrible people are among the key recurring characters in country music lore. This song about one such man has become so well-known that it’s easy to take for granted how well it actually upholds the tradition. – DM

Cheap Whiskey
Martina McBride
1992 | Peak: #44

Written by Emory Gordy, Jr. (Patty Loveless’ husband), “Cheap Whiskey” is a straight up country song that McBride mournfully tackles with complete success. The man chooses cheap whiskey over good love and he lives to regret it as a lonely, broken person. And who’s that guy singing in the background? Well, none other than Garth Brooks. – LW

The Day That She Left Tulsa (In a Chevy)
Wade Hayes
1997 | Peak: #5

A great modern heartbreak story narrated by one of our great modern heartbreak singers. You just can’t go wrong. – DM

Baby Likes to Rock It
The Tractors
1994 | Peak: #11

A bizarre, awesome, unique boogie-woogie record that somehow got to be a #11 country hit. My personal favorite part is how the lead singer’s riffs near the beginning of the song actually sound like a tractor revving. – DM

Out of My Bones
Randy Travis
1998 | Peak: #2

How do you know that Travis will get this woman out of his bones? Because his searing voice and the fiery fiddle combine to cut right down to them. – KC

Don’t Let Our Love Start Slippin’ Away
Vince Gill
1992 | Peak: #1

This song is essentially a plea to save a relationship, but I find it uplifting more than anything else, perhaps because the focus is kept on the couple’s underlying love. There’s a hopefulness to the song that’s woven into both Gill’s performance and the warm melody. – TS


When I Said I Do
Clint Black and Lisa Hartman Black
1999 | Peak: #1

Don’t look at me like that. Not all schmaltz is inherently evil, and when it’s as well-crafted and exceptionally well-sung as it is here, who’s going to complain about a little extra sentimentality dripping off?  – DM

Whatcha Gonna Do With a Cowboy
Chris LeDoux with Garth Brooks
1992 | Peak: #7

Garth Brooks gets to sing with one of his performing heroes and you can hear the joy in the recording as a result. The  comical, fiddle-laden song asks the unthinkable: “Whatchya gonna do with a cowboy when he don’t saddle up and ride away?” – LW

Thinkin’ Problem
David Ball
1994 | Peak: #2

Again, all you have know is the title to know why country fans like us love songs like this. – DM

Mama Knows the Highway
Hal Ketchum
1993 | Peak: #8

Country music chronicles a lot of trucking fathers, but the trucker in this song isn’t your typical truck driver character, but instead, a mama who knows the highway by heart, including its conditions at various points. – 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. “One Way Ticket” is one of my favorites. I remember my parents playin LeAnn’s “Blue” album in the kichen when I was about six years old. That song really brings back memories. Being older now, I can really appreciate now what a great song it is.

  2. The two songs from Martina in this segment illustrate what I said about here in the previous segment: that if she exerted vocal control and gave herself more challenging, harder-edged songs, whether their neo-traditional or rock-slanted, it would really enhance her standing as an artist. Being “little and loud” (as she likes to quote from Little Jimmy Dickens) really only gets you so far; and doing inoffensive material for country radio, as she has largely done since the 1990s, hasn’t exactly warmed me up to her…not yet, anyway.

  3. While it is a shame that radio has forgotten Rickey Van Shelton, his “Keep It Between The Lines” has been getting some airplay lately on the Sirius/XM channel Prime Country.

    I love the inclusion of “The Day She Left Tulsa (In A Chevy).” This is not a song that many would think of when looking back over his hits but it is easily one of his best.

    I’ll have to check out “Saw Mill Road.” I’ve near heard that Diamond Rio song before.

    I couldn’t agree more about “Wrong Again” being among the last of Martina’s great songs. Her EMOTION album was just okay and while I loved each of the new songs from 2001’s GREATEST HITS, it’s just been down-hill from there. A waste of a fantastic singer on mediocre songs.

    Also, GREAT Pam Tillis song. “In Between Dances,” was catchier, but “Let That Pony Run” ranks among the best of her introspective ballads. She is one of the main reasons why I love 90s country so much.

    It’s easy to take for granted just how stellar she really is but many females in Nashville today cannot even hold a candle to her.

    The slower version of “Quittin’ Time” from MCC’s Greatest Hits CD puts a whole other spin on the song. It’s funny; I’m more familiar with that version than the one that became a hit. Of course, MCC is great no matter what she does

  4. Not a batch that I’m overly crazy about but I do like the Toby Keith, Randy Travis, MCC and Diamond Rio selections. But after 15 years, I still can’t stand that Tractors song. :)

    I think the peak for Pam Tillis’ “Let That Pony Run” may need a correction. I believe she only had one #1 hit (Mi Vida Loca… unfortunately).

    I continue to enjoy the write ups and seeing the countdown roll out; I look forward to more!

  5. I’m not big on that particular Tractors song myself, but I really like the album from which that song comes, along with subsequent Tractors albums. They’re a pretty cool band.

  6. “Wrong Again” was definitely one of Martina’s best. I love how the song has a bit of a surprise ending, which gives a more positive ending to a mostly sad song.

    I love me some Pam Tillis! I hope I continue to see more of her on the list in the future.

  7. So many good songs. I don’t like to be one of those old farts who can’t give credit to anything new, but the nineties were far better than the oughties – and the eighties, seventies …

    I never understood why Wade Hayes did not become a big star. He sounds great on ballads and uptempo songs like “On a Good Night”.

    Love the MCC, Hal K, Pam T, Terri C and Doug Stone songs and like quite a few others.

  8. I agree, I think Wrong Again is one of Martina’s best. And this is another one, (like Whatever You Say) that features Sara Evans on harmony vocals which makes it even better in my book.

  9. …i like “keep it between the lines” as much as you do leeann – one of rvs finest.

    off-topic: good to see that all’s well with you steve from boston. i nearly started worrying a little when your nick didn’t come up for a while this spring.

  10. This portion of the list includes the two artists that became my first obsessions as a 6 year old kid, Terri Clark and Leann Rimes. Both of their listed songs are among my favorites from them and I’m hoping we see more of them (esp. Terri’s “If I Were You”).

    I’m also loving the inclusion of the Wade Hayes hit as well! Another great list of songs and I can’t wait to see more! I’m wondering if my other early obsession – The Wilkinsons – might the list.

  11. I love the K.T. Oslin song, for some reason I never seem to get tired of hearing it! I always wanted to find a video of her singing this live!

  12. @ Tom,

    I just felt I needed to take an extended break from posting, but thanks, all’s well and it’s good to be back.

  13. I’ll join the club that doesn’t think much of The Tractors entry, or the George Strait selection for that matter. But, I really like the Garth Brooks, Pam Tillis, K.T. Olsin, Toby Keith, and Martina McBride songs on this list. Like most other commenters, I discovered country music during the time most of these songs were current, and I am really enjoying the reminiscing of some tracks I had nearly forgotten.

  14. @Steve from Boston
    I agree. Adding Sara on harmony is always a perfect way to make a great song even better. The song “Wrong Again” also features Sara. I had heard that song countless times before I happened to read in the album liner notes that Sara was on backup. Then when I listened to the song again, I could hear her. I actually think I can hear Sara better on “Wrong Again” than on “Whatever You Say.”

  15. LOVE Martina’s “Wrong Again”… not sure if that’s a good thing or not. :-)
    I agree that Martina just seems capable of SO MUCH MORE than what she offers up. Every blue moon she puts out a song like this that validates every “best female vocalist” award. But then she puts out stuff like she has in recent years that sounds like it could be shoveled out by anyone else and I’m left wondering where Martina McBride went.

  16. Some great songs on this list. I graduated high school in Dallas in 1992 and college in Texas in 1996, so a lot of these are songs of my youth. I haven’t heard a lot of them for years.

    “Why Didn’t I Think of That” and “Wish I Didn’t Know” are two particular faces I haven’t heard. Looks like I might have to make an iTunes excursion before long. Damn you and your making me spend $$.

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