400 Greatest Singles of the Nineties: #75-#51

As might be expected, the subject matters are getting more intense as we edge closer to the top.  But there’s still room for some carefree moments here, thanks to the Chicks and Jo Dee Messina.

400 Greatest Singles of the Nineties:



When You Say Nothing at All
Alison Krauss & Union Station
1995 | Peak: #3

This Keith Whitley classic was recorded as part of a tribute album to the late country star. It became a hit all over again, perhaps because Krauss performed it in a near-whisper. The quiet arrangement matches the sentiment beautifully. – Kevin Coyne


Tracy Lawrence
1993 | Peak: #1

Lawrence dishes on his ex’s cheating ways to her new potential lover. How did she get that way? He reveals that he’s the one who taught her everything she knows from the cheater’s playbook. Moreover, he seems regretful of her corruption. – Leeann Ward

Cowboy Take Me Away
The Chicks
1999 | Peak: #1

In a modern world where life can so easily feel cold and mechanical, love remains earthy and exciting and mysterious. It’s a window into a different world, one where we’re not defined by the predictabilities of our routine – the same stresses, the same cars and buildings – but by our core nature as people, our place in the greater fabric of Earth and, perhaps, heaven. On the surface, “Cowboy Take Me Away” sounds like just a sugar-sweet love song – I’ve even heard it called “pre-feminist”  – but there’s something else going on here: a plea for life to have meaning again. – Dan Milliken

A Thousand Miles From Nowhere
Dwight Yoakam
1993 | Peak: #2

With it’s hypnotizing melody, one can’t help but feel for Yoakam as he reels from “the cruel, cruel words” that were said to him, which cause him to feel as though he’s far removed from reality at “a thousand miles from nowhere.” – LW

I’m Holding My Own
Lee Roy Parnell
1994 | Peak: #3

When an ex-girlfriend asks Parnell how he’s been getting by since their break-up, he responds with a fabulous, subtle mix of thoughtfulness and indignation. It takes a skilled artist to pull of the haughty emphasis on “holdin’” without compromising the maturity of the song. – Tara Seetharam

You Don’t Seem to Miss Me
Patty Loveless with George Jones
1997 | Peak: #14

This is one of those great records that could only work as a country song. The fiddle is her undying love, and the steel guitar is her painful worry that it’s no longer reciprocated. Just the instrumental track could tell most of the story. Throw in two of the finest vocalists in country music history, and you’ve got yourself a classic. – KC

A Bad Goodbye
Clint Black with Wynonna
1993 | Peak: #2

Should he stay or should he go? He knows that he should go, but guilt and, maybe, even some sort of co-dependency won’t let him make a clean break. He wants to avoid a bad goodbye, but unfortunately for him, such a thing rarely exists. – LW

Past the Point of Rescue
Hal Ketchum
1992 | Peak: #2

This level of self-awareness is dangerous when your heart is on the verge of being broken. – KC

Shut Up and Drive
Chely Wright
1997 | Peak: #14

A remarkably rational inner monologue by a woman finally driving away from her always-failing relationship. She knows she’s still susceptible to her own loneliness, but reminds herself, “you’ll only miss the man that you wanted him to be.” – DM

Thanks to You
Emmylou Harris
1994 | Peak: #65

Songs of salvation are a lot more interesting when the protagonist has a long way to go before they get there. – KC

Things Change
Dwight Yoakam
1998 | Peak: #17

Yoakam’s always getting left, so most of this record is just a very good version of what he normally gives us. But in that final verse, where he gets to turn the knife himself, he settles the score for one brief moment. – KC

If You Ever Have Forever in Mind
Vince Gill
1998 | Peak: #5

A slow-burning, jazzy, luscious record that Gill knocks out of the park. – TS

Almost Goodbye
Mark Chesnutt
1993 | Peak: #1

“Sometimes the most important words are the ones left unspoken”, Chesnutt observes. In this case, it’s a premature “goodbye.” It is a power ballad wrought with melodrama of epic proportions, but it’s just so good anyway. – LW

Wide Open Spaces
The Chicks
1998 | Peak: #1

A beloved, inescapable coming-of-age smash. – DM

Suzy Bogguss
1992 | Peak: #9

A woman who’d rather be right than wrong finally realizes that way of thinking is about to leave her alone and lonely. – KC

Never Again, Again
Lee Ann Womack
1997 | Peak: #23

Right out of the gate, Womack aces her traditional country exam: clever, frank, self-deprecating, sad, gorgeously sung. – DM

In My Next Life
Merle Haggard
1994 | Peak: #58

He’s spent his whole life trying to be her hero, and he’s set the bar so high in his mind, he doesn’t even realize that he cleared it by a long shot. – KC

You’d Think He’d Know Me Better
Bobbie Cryner
1996 | Peak: #56

It’s very difficult to be a thoroughly unlikable narrator and still garner sympathy, but Cryner pulls it off here. – KC

That’s Why I’m Here
Kenny Chesney
1998 | Peak: #2

Chesney paints a sympathetic portrait of a man who has owned the consequences of his alcoholism. – LW

Love Travels
Kathy Mattea
1997 | Peak: #39

Five and half minutes of Celtic-flavored bliss, and not a wasted second among them. – KC

All These Years
Sawyer Brown
1992 | Peak: #3

A husband catches his wife in bed with another man, and they finally share the candid, open conversation that could potentially save their marriage. – DM

I’m Alright
Jo Dee Messina
1998 | Peak: #1

With a lunch date between two old friends as its backdrop, “I’m Alright” dances around the details of a struggling artist’s life. It’s brilliant in its blend of realism and optimism, but above all, it’s insanely infectious. – TS

Godspeed (Sweet Dreams)
Radney Foster
1999 | Peak: #74

A lullaby of timeless beauty from a father unable to stay near his child. Deep love and deep sadness sound from every note. – DM

Here I Am
Patty Loveless
1994 | Peak: #4

The truth is revealed so slowly here that even after a thousand listens, it still comes as a surprise. Credit a brilliant lyric from Tony Arata and a masterclass vocal from Loveless for that. – KC

Worlds Apart
Vince Gill
1996 | Peak: #5

Gill quietly displays a sweet social conscience: “There’s nothing quite as ugly as two people full of hate/We’ll end up as equals when we stand at heaven’s gate/Love is still the answer/It’s the only place to start/Why do you and me have to be worlds apart?” Tragically, Gill’s question never stops being relevant. – 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. Given Chely Wright’s reemergence, I’ve been dipping back into her catalogue and have been pleasantly surprised — there was a lot of depth on her early albums. She was underrated.

    And I can never get enough of Lee Ann Womack and the Dixie Chicks.

  2. I’ve always thought it was funny that the guy that the woman is having an affair with must be present during the “candid conversation” in “All These Years”, since they don’t have him exit before that scene.

  3. Well I was wrong. I fully expected “Wide Open Spaces” to be #1. With all the love for the Dixie Chicks at Country Universe, and the importance of this song in their career, I thought it couldn’t loose.

    “Here I Am,” another song I thought would be top in the 10, is my favorite Patty Loveless song of all time. A masterclass vocal and killer lyric, the song is a modern day country classic.

    Also, my favorite Suzy Bogguss song, “Aces,” also made it this round. It’s a shame that song didn’t go higher than #9 on the country charts. Another modern day standard.

    The inclusion of “That’s Why I’m Here” proves Kenny Chesney is more than just a singer of island-theme party songs. He should go back and do more songs like these, which would make people take him more seriously and prove his worth as an artist.

    The biggest surprise, for me, is “Worlds Apart.” I love Vince Gill’s music but had forgotten about that song when thinking which of his classics should make this list. When it came out I was too young to full understand what he was singing about, but I get it now. It’s a great song when the lyric is as relevant today as it was in 1996.

  4. Jonathan,
    I was so ashamed/horrified that I totally skipped over “Worlds Apart” when I did my Favorite Songs by Favorite Artists on Vince. I must have had a total brain freeze, because it’s actually one of my favorite Vince songs.

  5. You Don’t Seem to Miss Me is one of the few Patty songs I’ve never been able to warm up to. Maybe it’s my childhood fear of George Jones. On the other hand, Here I Am is one of my all-time favorites.

    Past the Point of Rescue (where the heck *is* Hal Ketchum now?), Almost Goodbye, and When You Say Nothing At All are all on my iPod too. Another great installment! I can’t wait to see the top 10. I’m waiting for Strawberry Wine. Every girl in my middle school was obsessed with that song when it came out.

  6. Awesome group of songs. Chicks, AK, Patty, Lee Roy, Chely’s Drive song, Vince, Radney’s Godspeed, Hal K, …

    “Aces” was the first song I ever heard Suzy sing. I was hooked immediately. She followed with “Nightrider’s Lament” on some show with Jerry Reed.

    I remember being blown away by Wynonna & Clint’s “Bad Goodbye”, still one of my favorite country duets.

  7. Some awesome Patty Loveless and Dixie Chicks songs on here.

    “You Don’t Seem to Miss Me” makes me think of that Classic Rewind video I just saw on My Kind of Country of Johnny Cash and Linda Ronstadt performing together. In each instance, the two voices put together were so awesome that the combination could only produce something great.

    “Here I Am” just might be my favorite Loveless song (There have been a few that have taken turns as my favorite). It’s already an amazing song, and that was one of Patty’s greatest vocal performances. The soft bare-bones arrangement gives Patty’s voice plenty of room to shine. It shows that Patty’s producers had a level of well-placed confidence in her that many modern-day producers do not have in artists.

  8. Patty’s mainstream country albums for Sony from back then still blow me away. She was the only traditionalist back then that mixed things up enough to keep me interested. Each album had its own distinct sound. They really pushed the boundaries of traditional country music.

  9. I’ve really enjoyed this collection of 90’s songs, interested in the final 50 and top 10 especially. I had more disposeable income in the 90’s and bought more music than ever before in that decade. I’ve most all the songs listed.

    I’m sneaking up to 65th birthday in a few months, a comment about being in middle school in 90’s got me to thinking about when I was in middle school, Ricky Nelson, Elvis, Connie Francis, Annette Funicello, Paul Anka, Neil Sedaka, Buck Owens, Marty Robbins, Connie Smith, Kitty Wells, among others were who I heard on my transistor radio.

    If you all would be interested I could come up with a collection of the greatest singles of the 50’s and 60’s…

  10. Nice to see Bobbie Cryner on this list and I expect to see her a few more times. Someone who deserved more notoriety then she got. Sad really.

  11. I thought that Alison’s cover of “When You Say Nothing At All” and the Chicks’ “Wide Open Spaces” would be higher. Knowing how beloved the Chicks are at CU, I thought that they’d be a shoo-in for the top ten.

    I’m loving this segment, it’s nice to go back and revisit the music from my *early* childhood.

  12. Ditto. Of course, if “Am I The Only One (Who Ever Felt This Way)” was a single, I’d have had that pretty high on my personal list. But it’s hard for early Chicks to stack up well against so many other great artists who were in their prime. Funny how they went from a promising act at the end of one decade, to leagues above anything else the genre had to offer in the next one.

  13. I love the Chicks’ 90s stuff. I had five of their singles on my personal list, although “Wide Open Spaces” was the second lowest ranked of the five.

  14. My first reaction to this segment was to think that a few of these singles could have been ranked higher, but then I thought of some of the singles that haven’t turned up yet (including what would be my own #1 pick for the decade), and I don’t see a lot of wiggle room for things to move up all that much. The two Loveless singles and “Thanks to You” are really the only three that I might bump something else down for, but not without some hemming and hawing.

    The Chicks singles that I’ve actually liked from the aughts, I would rank ahead of those from the 90s, but there is a much greater quantity of singles of theirs I liked in the 90s. And “Am I the Only One Who Ever Felt This Way” is one of my absolute favorite entries in their catalogue. Maria McKee’s influence is all over Natalie Maines’ vocal style.

  15. I share the opinions expressed by Leeann, Kevin, and Tara. The Dixie Chicks put out some great mainstream country music in the late 90s, but it was mostly their 00s output, particularly the bluegrass-tinged “Home” album, that really made them shine.

    I’d be hard-pressed to choose which 90s Chicks hit was my favorite. It might be “Wide Open Spaces,” “Cowboy Take Me Away,” or “There’s Your Trouble.” Basically just about all of them.

  16. This conversation makes me want to give a shout-out to Paul Worley and Ed Seay. They were fantastic at getting some of the great female voices in country music off and running, working on the first handful of albums by Highway 101, Pam Tillis, Martina McBride, and the Dixie Chicks.

    I think some did better once parting with them and some did worse, but there’s no denying they all had a solid beginning with those guys.

  17. Love the Patty and Suzy songs off course, but was pleasntly surprised to see Kathy Mattea’s “Love Travels” on the list. I didn’t even know that song charted. It has always been my favorite song from the “Love Travels” CD!!!!! Also love, love, love ‘A bad Goodbye”, without Wynonna on that one it would suck. Also love the Vince song, I was 12 when it came out and everytime I here it it take me back to that place and time!!

  18. Those are my 2 favorite Dixie Chicks songs!! Ready To Run is my 3rd favorite, but I don’t think that one will be making the list.
    Love the Jo Dee Messina song too!
    Has “Callin’ Baton Rouge” by Garth appeared on this list?
    Looking forward to the top 50!

  19. It says a lot of good things about the folks here that the Chicks are still respected all around for their musicianship and their craft, as “Wide Open Spaces” and “Cowboy Take Me Away” demonstrated, and as their most recent work would attest to. The fact that they would eventually be thrown under the industry’s moving bus is something I hope that same industry lives to regret, because I doubt very much that there will ever be a phenomena like the Chicks again, either in country or, for that matter, in pop.

  20. I think country radio needs to find another good girl group to fill the void left by the Dixie Chicks. I know it’s unlikely that they’d be every bit as good as the Chicks, but still…

  21. It says a lot of good things about the folks here that the Chicks are still respected all around for their musicianship and their craft…

    Not trying to open a can of worms here, but honestly, I can’t imagine feeling any other way. It still boggles my mind. I’m just thankful that I lived in Austin during the bulk of the backlash, because if I had been anywhere else in this state, I would have gone a little crazy.

  22. This site wouldn’t exist if not for that backlash. One of my goals was to have a place where the Chicks were discussed in terms of their music, even though CU had a political element really early on (when nobody but a friend or two were reading it anyway.)

    I also wanted to have a place where nineties artists were still discussed, so two birds, one stone here, eh?

  23. Some radio DJ a few years back spliced together a version of When You Say Nothing At All from both Keith Whitley’s and Alison Krauss, making it a duet. It didn’t come out quite like a studio version but it was still a really good combination of soft (Krauss) and rough-edged (Whitley) voices, making for a cool fake duet.

  24. “Alibis” , “You Don’t Seem To Miss Me” and “Past The Point of Rescue” are my favorites among this group of songs. I’ve not really put together a parallel list but if I did, “Past The Point of Rescue” for sure would have been in my top ten

  25. Three of my absolute favorite 90’s songs are included in this portion. Lee Ann Womack’s amazing vocal on “Never Again, Again” is what made me a fan of hers from the start. It’s just brilliant.

    “You Don’t Seem to Miss Me” is just a classic song in my book. Patty and George together was pure brilliance!

    “Wide Open Spaces” well, it’s a Chicks song and I love anything they do!

    Another great portion of the list and can’t wait to see the rest!

  26. @ Paul:

    Re. “Past The Point Of Rescue”–I thought that was one of the more literate and intelligent country songs of the 90s. It’s a shame that this kind of songwriting that Hal Ketchum personified in that song is absent from the radio these days (IMHO).

  27. “You Don’t Seem to Miss Me is one of the few Patty songs I’ve never been able to warm up to.”

    ITA! Love Patty’s work on it but IMHO, George Jones ruins it. (There, I said it!) It’s reminiscent of the Sinatra duet albums where they could not be more fake, and truly sound like it. Jones sounds like he makes no effort in the song and showed up to basically echo Patty, and collect a paycheck. Patty Loveless deserved much better and way more respect.

    Still can’t listen to Clint Black. Man! That guys vocals are even more grating than Darius Rucker’s… and that says ALOT!

    Alison Krauss = Brilliant.

  28. @Erik North – While Hal Ketchum has written many great songs, “Past the Point of Rescue” is not one of them. It was solely written by Irish singer/songwriter Mick Hanly. One of Hal’s best solo writing efforts, “I Miss My Mary”, was from the “Past the Point of Rescue” album however it was not a single.

  29. Leeann Ward:
    Do you know that Patty’s producer is her husband, Emory Gordy Jr.?”

    (Belated reply) Yes, I do remember hearing that now that you mention it. The fact escaped my memory when I was leaving that comment. Emory has done a great job on his wife’s music. She should keep him around!

  30. Ha, Kevin! A little nineties country music humor for us all.:)

    Soul Miner’s Daughter,
    I absolutely don’t hear what you hear in George Jones’ performance. Even if that is what you hear, it’s kind of presumptuous for you to suggest that “Patty derserves more respect” as if he purposely didn’t respect her enough to give the compelling performance that you feel he should have given. It’s one thing not to like how he did it or even think he sounded like he was phoning it in, but it’s another thing to say that he actually purposely phoned it in out of a lack of respect for Loveless.

  31. I know Patty has a lot of respect for George Jones (her “first love”), so I’m sure she just felt honored to have him singing on a record with her, and I’m sure she was more than satisfied with the way it turned out.

    I’m sure George meant no disrespect, and I don’t hear any sign of it myself. I think that’s just his style of singing. Whether or not you like it (I do) just boils down to personal taste.

    And if Patty herself doesn’t feel disrespected, then I’m sure there’s no reason for any of us to become upset.

  32. Glad to see the Chicks on this list but I agree with sentiments expressed already , that im also suprised that Wide open spaces hasnt ranked higher on this list. :)

  33. You’re right Ben, Patty introduces You Dont Seem to Miss Me at her concerts with
    a lot of pride at having been able to record it with her hero George Jones.. and
    the respect is mutual. There is a Jones album (Cold Hard Truth I think is the name)that features liner notes that contain photos of him posing with some of his favorite artists, including Patty.

    The caption for that one reads “Patty Loveless, a real Country singer whom I love”.

    Also, Jones included You Dont Seem to Miss Me on his “40 Years of Duets” album.

    A lot of radio stations told Patty they wouldn’t play it unless she dropped the Jones harmony track. Patty fought for George (whom some were calling “no-show” at the time) called their bluff, and told them that she would not change the record. I think Patty made the right

    And Kevin, I know we’ve butted heads from time to time over the years and we seem to disagree more
    often than not, but I respect the many interesting and eloquent comments and articles you’ve made here at Country Universe. I think you’re encapsulation of “You Dont Seem to
    Miss Me” is especially brilliant, and we are in complete agreement! (but of course I would have put it at #2, right behind Nothing But the Wheel.;) )

    And on a personal note, this is the song that sparked a process of rediscovery in me that eventually led me to embrace Patty Loveless as my favorite artist. It will always be one of my favorites.

    Having said that, YDSTMM does seem to be a “love it or hate it” type polarizing song, even sometimes for Patty’s most devoted fans.

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