400 Greatest Singles of the Nineties: #250-#226

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:



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
Toby Keith
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

Tender Moment
Lee Roy Parnell
1993 | Peak: #2

Actions speak louder than words. – Kevin Coyne

Go Rest High On That Mountain
Vince Gill
1995 | Peak: #14

Every once and awhile an artist delivers a song so powerful that it seems to shatter all divides in its genre. A tribute to both the late Keith Whitley and Gill’s late brother, “Go Rest High On That Mountain” pairs deeply spiritual lyrics with a tender, emotion-soaked performance. The combination is magic. – TS

Dwight Yoakam
1995 | Peak: #20

Living up to its title, the Yoakam’s barren heart and soul are replicated in the arrangement of the song.  If emptiness has a sound, this is it. – KC

(Who Says) You Can’t Have it All
Alan Jackson
1994 | Peak: #4

Jackson more than earns his neo-traditional street cred thanks to this song. Just soak up that lonesome steel guitar! – LW

It’s Your Love
Tim McGraw with Faith Hill
1997 | Peak: #1

A good power ballad shot to greatness by its artists’ striking chemistry – palpable, fiery and so very genuine. More than just a hit single, “It’s Your Love” represents the moment in country music history at which we were introduced to one of its definitive couples. – TS

Grandpa Told Me So
Kenny Chesney
1995 | Peak: #23

Amidst a collection of country life lessons passed down from two generations back is one to live by: “There’ll be times that you want to hold on but you’ve got to let go.” – KC


Thank God For You
Sawyer Brown
1993 | Peak: #1

This man has a lot to thank God for, including stereotypical parental figures, but he’s most thankful for his girl. – LW


I Never Knew Love
Doug Stone
1993 | Peak: #2

An earnest, soulful confession of love. It’s hard to ignore the fact that it leans more in the adult-contemporary direction than that of anything else, but when a song is this moving, it’s also hard to care. – TS


What She’s Doing Now
Garth Brooks
1992 | Peak: #1

In an unusual tact for Mr. Brooks, he forgoes melodrama in order to allow the natural drama of pining for a lost love to speak for itself. The dialed down performance works in the service of the song, as the sadness appropriately penetrates through. – LW

Find My Way Back to My Heart
Alison Krauss & Union Station
1997 | Peak: #73

Some of the best songs from AKUS play on the home life that’s sacrificed by following the musical dream. Krauss remembers how she used to laugh at songs about the lonely traveling life, but she’s not laughing now. – KC


I Know
Kim Richey
1997 | Peak: #72

It takes more than self-awareness to mend a broken heart. – KC


Leave Him Out of This
Steve Wariner
1991 | Peak: #6

A man makes a soaring yet understated plea for his lover to let go of her past love. The song is made sadder by the touch of resignation in Wariner’s performance, which suggests the man knows he’s making his plea in vain. – TS


Just My Luck
Kim Richey
1995 | Peak: #47

Roba Stanley once sang about the joys of the single life and its simplicities.  Richey is about to leave it behind, and wonders just how lucky that makes her. – KC


What if I Do
Mindy McCready
1997 | Peak: #26

A whole song about deciding whether or not to go all the way with one’s movie date. McCready gives a fantastically entertaining performance, speak-singing her lines with a a bold campiness that most other gals wouldn’t dare. – DM

Chasin’ That Neon Rainbow
Alan Jackson
1990 | Peak: #2

Stories of would-be stars trying to make it big in Nashville are nothing too novel, but Jackson’s plucky earnestness gives this one an accessibility many of the others lack. – DM


Now That’s All Right With Me
Mandy Barnett
1996 | Peak: #43

The other great Barnett single of the era, fusing Patsy Cline-style vocal class, Pam Tillis-style production and Gloriana-style youthful exuberance. – DM


With You
Lila McCann
1999 | Peak: #9

Ten years before “You Belong With Me” made its splash, McCann set her sights on the same demographic with a song just as relatable, vibrant and passionate. That the song lacks Taylor Swift’s sharp perspective is perhaps what makes it such a great record: there’s something so pure about McCann’s fully unapologetic, headfirst fall into love. – TS


My Maria
Brooks & Dunn
1996 | Peak: #1

The rare country cover of a pop song that improves on the original. No offense, B.W. Stephenson. – DM


Boom! It Was Over
Robert Ellis Orrall
1992 | Peak: #19

How far can an amazing song title carry you? All the way to #229, that’s how far! – DM


Somewhere in My Broken Heart
Billy Dean
1991 | Peak: #3

So simple and plain in its heartbreak, and so understated and quiet in its delivery.  – KC


I Just Wanted You to Know
Mark Chesnutt
1993 | Peak: #1

Chesnutt makes a phone call to an old love that could be construed as creepy, pathetic or terribly sad – take your pick. I’m going with a mixture of all three, with a pinch of selfishness thrown in. Either way, “I Just Wanted You to Know” is a memorable slice of the-one-that-got-away reality.- TS


I’m Gonna Be Somebody
Travis Tritt
1990 | Peak: #2

In the twenty years that passed since the release of this song, the path to success in the music industry has morphed into something that looks very different than it used to. Unlike that of Bobby in the song, these days an artist’s journey can come in all shapes and forms, sometimes abrupt and sometimes completely unprecedented.

Think what you want about this paradigm shift, but here’s what I believe: regardless of how you shoot to the top, the only way you’ll achieve longevity and, most importantly, respect in country music is if you share the fire in Bobby’s eyes. This soul-stirring hunger and unshakable passion is the heart of “I’m Gonna Be Somebody” and the reason it remains a timeless classic. Here’s to hoping – and I’m optimistic – our modern artists are made of the same stuff. – TS


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. Another good bunch…

    Love the Yoakam, Jackson (“(Who Says) You Can’t Have it All”), AKUS, Barnett, Stone, Brooks and Chesnutt contributions.

    Absolutely NO recollection of the Robert Ellis Orrall number so I’ll have to go look that one up.

    I may be in the minority here, but I’ve never particularly cared for Gill’s “Go Rest High”.

    And I love the Toby Keith/Sting duet! He’s one of those artists who frustrates me. Kind of like Trace Adkins who I can love on a song like “I’m Tryin'” or “Then They Do”, but hate more than anyone else on some of their other material. “You Ain’t Much Fun” isn’t quite as bad as “American Ride”, “She’s a Hottie”, “High Maintenance Woman”, etc., but it’s still not one I’d ever desire to hear again.

  2. More great choices – the Travis Tritt selection is a particular favorite.

    I’m surprised, but not unpleasantly so, to see Lila McCann here. It’s too bad her singles for Broken Bow never seemed to take off. She’s apparently working on new music now.

  3. Nice to see Kim Richey represented here, and twice yet. I personally think she is underrated as a recording artist, and her music falls in that little crease between country and rock; but she is far better a singer than the public gives her credit for. And as a songwriter, she is way up there at or near the top (IMHO).

    In the case of “What If I Do”–it is really quite a tragedy to listen to Mindy on that song, realize how good she was becoming at that time, and how utterly far she has personally fallen since then. And to demonstrate how much potential was lost, “What If I Do” is on the same 1997 album (IF I DON’T STAY THE NIGHT) where she bravely covers Linda Ronstadt’s 1970 country-rock classic “Long Long Time.”

  4. Yes! One of Lila McCann’s songs made the list! That one happens to be one of my favorites. It’s a shame she didn’t enjoy a longer career.

    Another great bunch of songs! Can’t wait to see more.

  5. I really like Vince’s Go Rest High, and Patty Loveless and Ricky Skaggs harmony vocals really help that song to soar even more.

    I always liked B W Stephenson’s My Maria, dont know if I agree the B and D version improves on it, but they certainly do the song justice.

  6. …i just hope it wasn’t that skirt of mandy barnett that ultimately prevented her career from taking off the way it should have been. great singer, weird dresser.

  7. I too am surprized to see Lila McCann on the list. I met her in 07 and she is sooooo nice. Her “Lila”album came out when I was 12 and everyone my age loved and owned it. She was, in my opinion, the Taylor Swift of my generation except she can sing. I hope to see “Down Came A Blackbird” on the list later. We used to sing that song on the bus ride home from school. Good times!!!!!!!

  8. another interesting group of songs. I never heard the Mandy Barnett song. thanks. I like it. I didn’t know that B&D’s “My Maria” was a pop cover. I haven’t listened to pop radio in over 30 years.

    My favorites here are the songs by Lee Roy Parnell, Billy Dean and Garth Brooks. In fact, checking the I-Tunes count on my MacBook, I’ve played “What She’s Doing Now” more than any other song by Garth.

  9. Just seen Travis perform in my hometown last night and I gotta say he’s still got the fire, “I’m Gonna Be Somebody” was a real highlight of the set. Got to meet him as well, smaller guy than I thought.

  10. One of my fave Garth songs. I also like that cd because it was right before Garth became “Garth” and his music lost so much, IMHO.

    Really cool to see the Kim Richey shout-outs. One of my fave songwriters and when you see her live you think, “she wrote THAT?”.

    I always really liked Vince’s “Go Rest High…” and whenever I’ve seen him perform it, especially at memorials, it never ceases to get to me. It’s just one of those songs that seems to have been written for a divine purpose.

    Kenny Chesney: Don’t know the song but the cd cover in that little hat is worth the price of admission.

  11. My first concert was Tim McGraw and Faith Hill, and one of the best moments was when they sang “It’s Your Love.” That song is such a classic. I love their heartfelt performances, and I love the prominent steel guitar as well.

    I was a little surprised to see Lila McCann’s “With You” on this list. I like it, but I didn’t think it sounded like the kind of song that would get a spot on this list. It’s kind of like ear candy, but it’s tasty ear candy!

  12. Robert Ellis Orral was a talented songwriter whose career as a performer never took off. I am not sure what his greatest success as a writer was but the #1 Shenandoah hit “Next To You, Next To Me” immediately comes to mind.

    I’m glad to see that there’s someone else who doesn’t particularly care for Vince Gill’s “Go Rest High”. Bar bands in my area insist on resurrecting the song continuously

    One of the things I’m noticing with this list thus far is that I like most of these songs but love very few of them. That wouldn’t be true for a rundown of the 50s,60s or 70s

  13. I’m guessing that might change as we get to the higher ranked songs. I was actually surprised how many songs I liked when we were still in the 300s. Probably 80% of them.

  14. There’s no doubt that “Go Rest High” has a great impact and it’s one of Vince’s career songs, but it’s not among my personal favorite Gill songs either. It’s never done anything for me for some reason.

  15. I love the harmonies on “Go Rest High.” They really make the chorus soar the way that a song of this nature needs to.

    But I’ve always found the opening verse awkward. “You were no stranger to the rain” is a clumsy way to point out it’s a tribute to Whitley, IMO, and it compromises the universality of the sentiment a bit for me.

  16. Kenny Chesney in the 90’s may have had a “run-of-the-mill” 90’s sound, but man was he enjoyable to listen to. Not just a few singles worth of listenable, good material like Fall in Love or Me and You, but entire albums worth of good country. I wish for an album, hell a single, Kenny would rediscover his 90’s sound and allow us to hear Kenny Chesney, the talent, good, country artist.

  17. Love the Tim and Travis selections. I used to love Toby Keith- he’s gone so far off the deep-end it’s sad. He’s probably got the best male voice in country music.

  18. I agree, K. Toby Keith did some pretty good songs in the old days, but now he’s gone from “Should’ve Been a Cowboy” to “fat dog, skinny dog, little itty bitty dog…” It really is sad.

  19. Really pleased to see the Robert Ellis Orral song, that was always one of my favorites. Surprised that the Travis Tritt song didn’t make the T100, going to be very interested in seeing the rest of the list.

  20. It’s a shame that Sting got relegated to a “gratuitous” cameo on Keith’s version, as Sting’s original version blows it out of the water, and is far more country to boot. I can’t listen to Keith’s version because of it.

  21. I haven’t heard the Sting version. I’ll have to check it out. I’d never guess that his version might be better, since I actually don’t think he adds positively to Keith’s recording.

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