400 Greatest Singles of the Nineties: #325-#301

The first quarter of the countdown comes to a close, highlighted by excellent comeback attempts from T. Graham Brown, Emmylou Harris, and Willie Nelson.

400 Greatest Singles of the Nineties:



He Would Be Sixteen
Michelle Wright
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
Faith Hill
1995  |  Peak: #1

Faith Hill’s sophomore album is a surprisingly deep set, filled with candid insights into different women’s lives. The title track represents that approach well, with Hill’s protagonist speaking to the differences in her approach to love and her partner’s. Seems simple, but then again, people spend thousands in couples counseling trying to find a way to voice feelings this directly. – Dan Milliken


She’d Give Anything
Boy Howdy
1993  |  Peak: #4

A not-so-subtle depiction of how elusive true love can be for some women – even those who desperately seek it – that resonates not despite of but because of its blatancy. There’s a beautiful honesty to the song’s precise articulation of the mixture of frustration and strength that builds up within these women. – Tara Seetharam


The Trouble With the Truth
Patty Loveless
1997  |  Peak: #15

The trouble with the truth is that it is just so demanding. We think we want it, but it often requires some sort of action from us once we have it. Loveless struggles with this quandary: “The trouble with the truth is it always begs for more. That’s the trouble with the truth.” – Leeann Ward


Still Gonna Die
Old Dogs
1999  |  Peak: Did Not Chart

Waylon Jennings, Mel Tillis, Bobby Bare, and Jerry Reed united for an amazing live album dominated by Shel Silverstein songs. For anyone who read his brilliant poetry books for children, “Still Gonna Die” is the golden years equivalent: clever, frightening, and darkly hilarious.  KC

Alan Jackson
1990  |  Peak: #3

the hands of many male country artists, but it’s simply lovely in Jacksons’, ringing with sincerity and regret. – TS

Finish What We Started
Diamond Rio
1995  |  Peak: #19

While it’s not a part of the wedding song canon, this is a gorgeous declaration of commitment. – LW

Tryin’ to Hide a Fire in the Dark
Billy Dean
1992  |  Peak: #6

From the first strains of the song, we know this is going to be a dark one. While he hasn’t physically cheated yet, the thoughts of at least wishing to do so are spilling over, which begs the analogy of “It’s like trying to hide a fire in the dark.” – LW


She is Gone
Willie Nelson
1996  |  Peak: Did Not Chart

As with his classic recording of “Blue Eyes Crying in the Rain”, Nelson’s sad remembrance of a lost love glows with unspoken warmth, as the beauty of his good memories shines through the outer layer of melancholy. – DM

It Was
Chely Wright
1999  |  Peak: #11

An ode to the nonsensical mess of emotions that accompany falling in love, just contradictory enough to make sense. – TS

You Can Feel Bad
Patty Loveless
1995  |  Peak: #1

As deft a take down of a departing lover there’s ever been.  Not since “You’re So Vain” has a jilted lover struck back so powerfully by simply holding up a mirror. – KC

Till I Found You
Marty Stuart
1991  |  Peak: #12

With a Roy Orbison feel, “Til I Found You” is a sweet declaration of finally finding the right one. – LW

Blame it On Your Heart
Patty Loveless
1993 |  Peak: #1

A shameless radio bid delivered with more power and charm than such bids generally deserve. – DM

You Never Even Call Me By My Name
Doug Supernaw
1994 |  Peak: #60

Presenting the perfect Country & Western song! This is a great David Allan Coe cover with some alterations, including the exclusion of a stanza (which does water down the song a bit), changes to the spoken part, and additions of some special guests. – LW

Wine Into Water
T. Graham Brown
1998  |  Peak: #44

roken man struggling with his alcoholism asks Jesus to perform His first miracle in reverse. Brown’s rough and tumble voice is the best possible fit for this fine composition.- KC

High Powered Love
Emmylou Harris
1993  |  Peak: #63

The added punch to the production shows that Harris could do nineties country as well as anybody on the radio back then, which is quite the compliment, given who was getting airplay in 1993.  A perfect lament for a lover who won’t settle for skin deep treasures, she wonders, “Is there anyone left with teeth just a little uneven? Who won’t spend more time with a mirror than he does with me?” – KC

You Won’t Ever Be Lonely
Andy Griggs
1998  |  Peak: #2

Griggs creates a touching ballad out of one of the sweetest, simplest promises that comes with making a commitment to someone – that no matter the storm outside, you’ll never have to face it alone. – TS


A Door
Aaron Tippin
1997  |  Peak: #65

Instead of serving as a means to shut the other person out, the door that Tippin is suggesting is for the purpose of letting the other person in. “a door ain’t nothin’ but a way to get through a wall”, he sings. If they work together to create it, then they might be able to walk through it to meet each other halfway. – LW

Someday Soon
Suzy Bogguss
1991  |  Peak: #12

Suzy Bogguss takes this Ian Tyson cowboy folk song and makes it her own. She successfully breathes emotion into this wistful song that, once again, pits woman against rodeo. – LW


The River
Garth Brooks
1992  |  Peak: #1

Built on a poignantly written metaphor, “The River” gracefully weaves together elements of faith, inspiration and motivation. It’s a masterful single, from its poetic lyrics to its beautifully simplistic arrangement, but the heart and soul is Brooks’ gripping conviction – quiet yet fierce. On a personal note, this song contains one of my all-time favorite lyrics that I often revisit: “So don’t you sit upon the shoreline and say you’re satisfied/Choose to chance the rapids and dare to dance the tide.” – TS

Time Passes By
Kathy Mattea
1991  |  Peak: #7

Blessings are fleeting, and they’re best appreciated in the moment. It’s far more satisfying to celebrate them without the bittersweet tinge of regret. – KC

You Can’t Stop Love
Marty Stuart
1996  |  Peak: #26

To hear Marty Stuart tell it, there’s nothing more powerful than love. No matter what you do, you can’t stop it. True enough. – LW


Tim McGraw
1997  |  Peak: #1

McGraw’s character leaves behind a lifelong love interest and a little home town to explore the world. But instead of getting good closure, the poor guy starts seeing the girl he left in every place he visits, even long after she has married and had children. That these visions could feasibly represent both unresolved romantic feelings and the inescapable imprint of one’s roots is just country-delicious. – DM

You’re Beginning to Get to Me
Clay Walker
1998  |  Peak: #2

Walker’s falling head first for a girl, but he isn’t ready to take the plunge with the L-word just yet. In his catalogue of fabulous 90s hits, this understated “love” song gets overshadowed by some of the more distinct ones, but it’s nonetheless memorable. – TS

Help Me Hold On
Travis Tritt
1990  |  Peak: #1

Travis Tritt is one of few country artists who is as known for his rocking side as he is for being a strong balladeer. “Help Me Hold on” is a plea to his lover to help him salvage what’s left of their relationship, which doesn’t seem to be much, since she’s already packing a suitcase. – 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. Re. “High Powered Love”–yes, it did show that Emmy could do Nineties country as well as everyone, but I think this song made it known that she was going to do it HER way, country radio be damned.

    Re. “Someday Soon”–I think Suzy took her arrangement of that song from Judy Collins’ well-liked 1969 version of it, which, given Suzy’s musical background, wouldn’t be too shocking. But it does indicate how individual an artist Suzy is (IMHO).

  2. This is great – so many good songs. From a fan’s perspective, you want to see your favorites included but you don’t want to see them too soon. “Everywhere” is one of my favorite McGraw songs from the 90’s. Love the 3 Loveless songs, Suzy, Kathy, Billy Dean, Andy Griggs, TT. Of the country artists I haven’t seen in concert yet, Travis Tritt is at the top of my to-see list.

  3. Love the whole Cowgirl’s Prayer album from Emmylou and “Everywhere” is one of my favorite McGraw songs. This countdown has already been a ton of fun and the fact that songs as good as these are already showing up and we haven’t even reached the Top 300 yet, shows what an embarrassment of riches the decade was. When I compare it to the list of this most recent decade’s top singles, I can’t help but feel majorly disappointed with the state of today’s country radio. Looking at a current list of the Top 40 singles, I’m usually lucky if I like five of the songs. I don’t know if it’s the slower turnover now, or the nostalgia factor of growing up on these songs in the 90s, but most of today’s hits can’t even hold a candle to those from even less than 20 years ago.

  4. I like probally 90% of these songs-hopefully the top 20 will have some Loveless and Yearwood representation! I cant wait

  5. Love, love, love the Chely Track, that was my favorite song she recorded until, “Notes To The Coroner” came this year. I suggest watching the video for whoever didn’t see it, beautiful.

    “Someday Soon” happens to be my least favorite of Suzy’s actual hit songs.

    “A Door” was released as a single? I thought it was charting just from unsolicited plays? Maybe I’m getting my thoughts wrong it is 4 in the morning…

    Love Michelle Wright still waiting for another album 2006’s Everything and More was her last one too long to wait, then again still waiting for new Sara Evans from 2005….

    Can’t go wrong with Emmylou, and Patty Loveless all awesome tracks.

    Kathy as well…

    This list is making me go back and listen to Clay Walker’s older stuff as I forgot how good a lot of it was…”Only On Days That End In “Y”” anybody :P

    Just Listened to Faith’s album again yesterday, and it really was a great deep album, “I Can’t Do That Anymore” was the highlight for me. The only cut I don’t like was the Shelby Lynne duet, love them both but I could care less to hear that one again.

  6. If there ever was a quintessential 90’s country song, Everywhere by Tim McGraw is it, and I absolutely love that song; I often feel sad right along with Tim as he’s singing it, but still a really great piece of work.

  7. Perfect timing on the Chely Wright cut.

    I’ve been going back and reevaluating her output now that she’s in the news again.

    I keep repeating “It Was.” It’s such a perfectly constructed song, especially the last line of the chorus: “It did all the things love does, that’s how I knew it was.”

    So very original.

  8. Wow! Good stuff!
    Never been a huge McGraw fan but have always liked that song… cuz it makes ya think.

    STILL one of my fave Kathy Mattea songs.

    LOVE the Patty tunes. It’s no wonder she is still so highly regarded with a dedicated fan base.

    I remember when that Michelle Wright song came out and how “controversial” it was. Brilliant for her to record it just the same.

    MEGA KUDOS for the Old Dogs shout-out!!

  9. Michelle Wright has one hell of a voice, but, like Shelby Lynne and Cindy Murphy of Dixiana, she has a deep, husky alto that radio programmers just didn’t seem to go for.

    “It Matters to Me” is far and away my favorite vocal turn and single from Hill, and I would have it fairly high on my own list. There’s a little catch in her voice as she breaks into the second chorus that’s just terrific, lived-in singing.

    Cowgirl’s Prayer is a fantastic album, and I hope “Thanks to You,” which is one of Harris’ best singles, shows up on the list at some point.

    Great pick-ups on the Old Dogs and lesser-known Marty Stuart hits, too. Good stuff all around.

  10. Kathy, I’m going to try and review the Jerrod album soon. Until then, keep plugs for it on posts that are relevant to him.

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