400 Greatest Singles of the Nineties: #375-351

The second segment of our countdown includes the first appearances by Garth Brooks and Reba McEntire, two of the biggest-selling stars of the decade.

400 Greatest Singles of the Nineties:



How Do I Get There
Deana Carter
1997 |  Peak: #1

It’s always a gamble when friends decide to take their relationship to the next level. “How Do I Get There” explores the struggle of following one’s heart, even though it’s taking a big emotional risk to do so. – Leeann Ward


If I Could Make a Living
Clay Walker
1994  |  Peak: #1

This song is either ridiculously cheesy or irresistibly cheesy depending on your taste, but there’s no denying Walker sells the heck out of it with charm and enthusiasm. – Tara Seetharam

It Sure is Monday
Mark Chesnutt
1993  |  Peak: #1

Mark Chesnutt is one of the best male vocalists of the nineties, but there were many times when he did not always rise to the challenge of conveying the energy to elevate a decent song to a good one. Case in point: “Friends in Low Places”, which was eventually properly energized by Garth Brooks. “It Sure Is Monday”, however, is a positive example of Chesnutt actually making a song his own by demonstrating the ability to breathe life into a decent song and make it really good. – LW

Take Me as I Am
Faith Hill
1994  |  Peak: #2

What do you think – will you take Faith Hill as she is? I mean, I know she’s kinda ugly and stuff, but…she does tell, like, the best Drunken-Martina stories at parties. And her quiche is just beyond.

Joking aside, it’s really something how this hit manages to make a mature, realistic perspective on love sound so bubbly and optimistic. That Hill can sing lines like “Baby, don’t turn out the light / I want to see you look at me” and sound so effervescent doing it suggests that we don’t have to forfeit our Taylor-Swiftish enthusiasm for romance just because our outlook on it grows up. – Dan Milliken

What Mattered Most
Ty Herndon
1995  |  Peak: #1

Many nineties stars had their biggest hit right out of the box. Herndon’s debut single remains his finest moment, but don’t take that as a minimization of his talent. A carefully cataloged collection of little things noticed while missing the big picture, this single would be the finest moment of plenty a career. – Kevin Coyne


My Heart Has a History
Paul Brandt
1996  |  Peak: #5

Brandt’s debut album was a big hit stateside, thanks in large part to his stunning debut single. A finely crafted lyric, a production that makes room for a church organ, and the best baritone voice to surface in the mid-nineties.  His native Canada’s been smart enough to hold on to him. He still regularly reaches the top ten of the country charts  north of the border. – KC

We Really Shouldn’t Be Doing This
George Strait
1998  |  Peak: #4

The kind of song that can’t get over how great its own title is, but in this case it totally works. The nervy melody nails the rush of flirting with trouble. – DM

Don’t Laugh at Me
Mark Wills
1998  |  Peak: #2

Wills builds this socially conscious song around a deceivingly elementary message, but it’s the anecdotes that drive it home, simple and real. The most stinging line for me is the cripple’s “don’t think I don’t notice that our eyes never meet,” because it materializes the imaginary, unnecessary divide society creates between people that Wills is begging us to tear down. – TS

Then What?
Clay Walker
1997  |  Peak: #2

Friends don’t let friends throw their good lives away.Clay Walker’s catchiest song to date, “Then What?” is a straightforward attempt to caution his friend regarding the consequences of committing adultery. – LW

(Without You) What Do I Do With Me
Tanya Tucker
1991  |  Peak: #2

One of those beautiful heartbreak songs that works as well for a widow as it does for the recently divorced. – KC

It’s a Little Too Late
Mark Chesnutt
1996  |  Peak: #1

A catchy little tale of an oblivious man, a fed-up woman and a whole lot of things that he should’ve-would’ve-could’ve done to keep her. – TS


She Don’t Know She’s Beautiful
Sammy Kershaw
1993  |  Peak: #1

It’s refreshing that this song has had so much staying power on country radio, because nowadays it isn’t often the spotlight falls on women like this one – modest, grounded, and beautiful inside and out – or on the men who are special enough to recognize them. – TS


Walk On Faith
Mike Reid
1990  |  Peak: #1

Reid urges us to use faith as our compass as we travel through life, a theme that’s no stranger to country music but that’s rarely expressed so joyfully and hopefully. – TS


I Just Might Be
Lorrie Morgan
1996  |  Peak: #45

The awkward removal of a minor swear word ruined the rhythm of the chorus, which is as good a theory as any for why this excellent record didn’t fare too well at radio. She so casually dismisses the man who dismissed her that it’s easy to walk away thinking it was the wrongdoer, not the wronged, who got the shaft. – KC

Bye Bye
Jo Dee Messina
1998  |  Peak: #1

One of country music’s greatest break-up anthems, “Bye Bye” is an exhilarating rush of pride and newfound freedom. – TS

Can’t Break it to My Heart
Tracy Lawrence
1993  |  Peak: #1

With one of the best tear-soaked male voices of the nineties, Tracy Lawrence was adept at ringing out the emotions of the songs that he sang, no matter the tempo. While “Can’t Break It to My Heart” is set to a bouncy melody, Lawrence laments that he knows his relationship is over with palpable emotion. As a result, he can get it through his head, but he just can’t break it his heart. – LW

Mandy Barnett
1996  |  Peak: #65

Sometimes a singer sounds so great singing something that the song itself feels irrelevant. Mandy Barnett faces this problem a good deal of the time. – DM

Fallin’ Out of Love
Reba McEntire
1991  |  Peak: #2

One of her smartest and most emotionally resonant singles finds McEntire using the second person voice, perhaps as the inner monologue of the woman who slowly discovers that “nothing feels as good as letting go.” – KC

I Love the Way You Love Me
John Michael Montgomery
1993  |  Peak: #1

Montgomery delivers a love song that aptly balances sweet, telling details with the sweeping profession in its title. – TS

I Cross My Heart
George Strait
1992  |  Peak: #1

A passionate, straightforward vow of love – no bells or whistles needed. – TS

Every Once in a While
1994  |  Peak: #2

Well before Toby Keith got in touch with his inner swagger, BlackHawk released this stunningly arrogant record which assumes that the woman he left behind still revels in his memory, so lucky she was to have been with him for at least one moment in time. Stunningly arrogant, indeed, but somehow pretty darn charming, too. – KC

Now I Know
Lari White
1994  |  Peak: #5

It wasn’t written as an answer song to the BlackHawk record above, but it certainly would make an interesting rebuttal. White’s biggest hit was also her best.- KC

The Thunder Rolls
Garth Brooks
1991  |  Peak: #1

One of country music’s truly epic singles, masterful in how it captures the surreal mist of emotions that hangs over lives being played at their highest stakes. – DM


A Little Bit of You
Lee Roy Parnell
1995  |  Peak: #2

This is simply an honest-to-goodness declaration of infatuation. Who wouldn’t want to hear “There ain’t nothin’ that a little bit of you can’t cure”?
– LW

I’ll Think of a Reason Later
Lee Ann Womack
1998  |  Peak: #2

A delightful slice of catharsis for jealous ex-girlfriends everywhere, made extra amusing by the contrast of Womack’s sweet soprano against the vindictive lyrics. – 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. Fun moment related to #369:
    When George Strait sang “We Really Shouldn’t Be Doing This” on the CMA Awards, it was so out there and not what you’d expect from him. I’ll never forget the baffled look on Reba’s face when it was over:


  2. The Deana Carter, Ty Herndon, Lari White, Lee Roy Parnell, and Mike Reid tracks are my favorites that are listed here.

    I always was a big fan of Mike Reid, especially some of his songs that were penned for other artists (“I Can’t Make You Love Me”, “Forever’s As Far as I’ll Go”, “In This Life”, “Love Without Mercy”). I think he’s ventured more into classical music/operas, but he’s definately one of my favorite country music songwriters. He’s also in the College Football Hall of Fame as a player…and a fellow Penn State Grad (which might explain part of the reason as to why I’m a big fan…lol). Regardless…I’d love to see him venture into country music again.

    I also want to say that I really appreciate the amount of time and effort you put into these lists. For me, it seems like the 1990s were just yesterday, so it’s cool to go back and revisit songs that haven’t played on the radio in years. Thank to the writers for all of the work you put into this website.

  3. I’m so glad Paul Brandt’s “My Heart Has a History” made the list! That was one of my favorite songs as a kid! He’s debut album was one of my faves and might have been one of the first cd’s I actually bought with my own money. The first one was Terri Clark’s debut album which hopefully a track or two from here will make the list!

    Once again a great bunch of songs and can’t wait to see the rest of it!

  4. I want to think you guys for these lists. I’m not familiar with a good amount of the material on here, and I fully intend to make a playlist on Spotify and check a lot of them out later!

  5. Ty Herndon’s “What Mattered Most” is my favorite here. I would have had this song much higher but tastes differ. I saw Ty about 10 or 11 years ago at one of the Country Thursday free lunchtime concerts they used to hold at the WTC. Great singer – sounds better live than on cd.

    Glad to see Lee Roy Parnell and Lari White on the list. I’ve seen them recently and they still sound great.

  6. The 90s were my introduction to country music so this countdown is bringing a lot of that back. The only song on this installment that I don’t know is “Maybe” which is surprising since I’m well aware of Mandy’s music.

    I really enjoyed seeing “Walk On Faith” and “My Heart Has a History” on here. Songs like this defined my childhood, and I love that I’m not the only one who remembers them.

    I’ve always wondered why country radio continues to play, “She Don’t Know She’s Beautiful” all these years later. When an artist has so many good hits as Sammy has, you’d think they would play more than that one song. It is a great song, so that can’t hurt.

    I cannot wait to see what other songs make the list. I could never do this kind of countdown myself; it would be way too hard. I’m glad to see it include 400 songs since there are so many wonderful moments in country music history from the 90s.

    I’m glad to see you’ve put yourselves up to the task.

  7. I would’ve had “I Cross My Heart” much higher on my list probably. That Pure Country soundtrack is really good. Strait had that huge run of number one songs from 86 thru 89. However, the early 90’s hit and radio seemed to be moving towards a younger generation of singers and Strait’s airplay dwindled a little bit with his Holdin’ My Own album. Country radio was getting ready to leave him behind but then he releases that album and that song which became a wedding anthem and was dripping with the one thing so many country singers (especially now) lack- sincerity. That came through and it had the newer generation of country fans seeking out his back catalog and put him squarely on the same pedestal as the younger stars of the time.

    Not to mention it was the first album where he hooked up with Tony Brown who has been his producer since then

  8. Hey Brian…George has said in the past that PC put him on a higher level than ever before. I don’t think he ever “left” the scene but you’re right in that HMO wasn’t a huge “hit” album (although I happen to love it myself!). Anyway, once the music from PC (and the movie itself) was released, it was an instant hit, and King George has never looked back. It was only a matter of time before the CMHOF came calling, and, of course, ACM Artist of the Decade is not too shabby either…;) !! Oh, and did you see the report a few month back where Mediabase said Strait was the “most played artist of the 2000’s decade”??? That included ALL genres of music!!

  9. Love being reminded of so many of these songs. Great selections by Reba, Tanya, Mandy Barnett, Lorrie Morgan, Lee Ann Womack and Lari White! Thanks for all of the hard work you guys have put into this countdown. Sigh… the (mostly) good ole days of country radio.

  10. I can’t wait to see what’s in the Top 10. This is only the second installment, but I’ve already seen some good ones, most notably “She Don’t Know She’s Beautiful” and “I’ll Think of a Reason Later.”

  11. Really enjoying this list. Great to see songs like Walk On Faith and Every Once In a While make it. I would’ve ranked What Mattered Most much higher (like T50), and probably would’ve had I Cross My Heart in the T200, but otherwise I’m surprised how much i’m agreeing with the list.

  12. I’m loving this countdown. So many write-ups, but all thoughtfully written. I’m surprised to see “The Thunder Rolls” and “I Cross My Heart” so far down but hey, everybody’s got their own opinion. I’m not sure I’ve ever heard “Walk on Faith,” I’ll have to look that up.

  13. I’m loving this countdown. I’m also amazed at how “country” the music was in hindsight and how well so much of it has stood the test. Today’s “country music” is so incredibly bad that I find myself longing for even the country of the ’90s.

  14. I’m a little surprised ‘(Without You) What Do I Do With Me’ is ranked so high. It’s one of my favorites in the large Tanya Tucker catalog.

    ‘I Just Might Be’ is also one of my favorites from Lorrie Morgan, and I always thought it should have fared better at radio. I never thought of the removal of the word ‘damn’ from the chorus hurting it as much as its stripped-down, almost-acoustic sound. Either way, it’s a shame more country fans didn’t get to hear it.

    And man, do I miss Blackhawk. I had their Greatest Hits CD out the other day, and was seriously impressed with the quality of nearly every song.

  15. Soul Miner’s Daughter: Agree with you about the “country” sound of most of this. I still contend that for the most part in the crossover era of the 90’s that the music was still very country sounding and happened to cross over into pop.

    Today it is geared more for pop audiences and happens to cross over into country.

  16. I love “Bye Bye” and “I’ll Think of a Reason Later” … kinda surprised to see them this low on the list, but love ’em anyways

Leave a Reply

Your email address will not be published.

This site uses Akismet to reduce spam. Learn how your comment data is processed.