The list continues with appearances from artists who first surfaced in the eighties and continued to thrive into the nineties, like Reba McEntire and Patty Loveless, along with new stars from the nineties who would find greater success in the next decade, like Toby Keith and Brad Paisley.

400 Greatest Singles of the Nineties:

#300-#276

 

#300
Does He Love You
Reba McEntire with Linda Davis
1993  |  Peak: #1

This two-female duet was a gamble at the time of its release, but it offers such a brilliant fusion of perspectives that it’s hard to imagine why. The song fleshes out the range of emotions that the two women are experiencing –from pain to longing to self-doubt– and culminates in one shared question that they’ll never know the answer to: “does he love you like he’s been loving me?” – Tara Seetharam

#299
The Hard Way
Mary Chapin Carpenter
1993  |  Peak: #11

The chorus is catchy, something that would work as a good audience participation song at a concert, so it’s possible to miss the message. “Show a little inspiration; show a little spark,” she implores. It might be work, even hard work, but a good relationship won’t last without it. – Leeann Ward

#298
He Ain’t Worth Missing
Toby Keith
1993  |  Peak: #5

Toby acknowledges the woman’s feelings in this song, but offers her a little straight talk, along the way. Not only does he assure her that her ex isn’t worth missing, he lets her know that he’s more than willing to be the replacement. – LW

#297
That Don’t Impress Me Much
Shania Twain
1998  |  Peak: #8

One of the campiest, sing-and-talk-a-longiest singles ever. Long after you’ve forgotten most of this year’s great serious songs, you’ll still remember the exact timing and inflection of, “OK, so you’re Brad Pitt.” – Dan Milliken

#296
Friends
John Michael Montgomery
1996  |  Peak: #2

A record that hinges on two sad truths. First, a love affair has ended. Second, all friendships come to an end. – Kevin Coyne

#295
Phones are Ringin’ All Over Town
Martina McBride
1996  |  Peak: #28

With the build up of the song, the frenzy that the repeat cheater is feeling is palpable. Even though he knows exactly why she’s left, he desperately tries to find her, which is why “phones are ringin’ all over town.” – LW

#294
Chains
Patty Loveless
1990  |  Peak: #1

One of Loveless’ earliest hits, “Chains” revolves around a hook that’s as simple as they come, but therein lies its charm. – TS

#293
Even the Man in the Moon is Crying
Mark Collie
1992  |  Peak: #5

Listen

Mark Collie is one of the casualties of the nineties country boom. Despite talent, he just couldn’t keep up with the big hit makers of the decade. “Even the Man on the Moon Is Crying” is one of his most memorable songs, however. From the moment he drops her off at the airport, he knows it’s over, despite putting on a brave front. It’s all so sad and final that even the man in the moon is crying. – LW

 

#292
Right On the Money
Alan Jackson
1998  |  Peak: #1

If only Phil Vassar, one of the song’s writers, would record a song this cool. The best line? “She’s the best cook that’s ever melted cheese.” – LW

 

#291
Walkin’ Away
Clint Black
1990  |  Peak: #1

“Walking away, I saw a side of you that I knew was there all along.” Oh, how I long for the days when his word craft described love gone wrong instead of right. – KC

#290
Something Like That
Tim McGraw
1999  |  Peak: #1

On the surface, “Something Like That” is a fairly basic story of two teenagers’ first kiss. But the true value of this classic is spelled out in its bridge: “Like an old photograph, time can make a feeling fade/But the memory of the first love never fades away.” I’ve always viewed this song as a validation of puppy love: that no matter how trivial the details or circumstances –be it barbecue stains, miniskirts or skippin’ rocks on the river – the experience of your first love matters. – TS

 

#289
On a Bus to St. Cloud
Trisha Yearwood
1995  |  Peak: #59

Haunted by the ghost of a love that she sees everywhere that she goes, she loves him some, hates him some, but misses him most. – KC

#288
Easy Come, Easy Go
George Strait
1993  |  Peak: #1

Even though they’re saying goodbye, this song is as relaxed as the title suggests. If only the dissolution of all relationships were this calm. – LW

#287
Tall, Tall Trees
Alan Jackson
1995  |  Peak: #1

George Jones and Roger Miller both recorded versions of this quirky number they co-wrote, but it was latter-day traditionalist Jackson who made it a hit. The ridiculous lyrics – about a lovestruck man who pledges to buy his girl trees, limousines, and all the planet’s ocean waters – are equal parts spoof and celebration of the blissful irrationality of new love. – DM

#286
Clown in Your Rodeo
Kathy Mattea
1995  |  Peak: #20

In the contemporary Christian music world, Wayne Kirkpatrick wrote most of the lyrics to Michael W. Smith’s melodies. In country circles,  he is most known for his involvement in Garth Brook’s Chris Gaines project and, most recently, his contributions to Little Big Town’s career. Back in the mid-nineties, however, he was the writer of “Clown in Your rodeo”, a fun, sassy number from one of Kathy Mattea’s most popular albums. – LW

#285
It’s Lonely Out There
Pam Tillis
1996  |  Peak: #14

One of her strongest vocal performances, as the casual indifference to a man threatening to leave quickly escalates into genuine fear. By the end, she’s begging him to stay, realizing  it’ll be just as lonely in here if he’s gone. – KC

#284
You Lie
Reba McEntire
1990  |  Peak: #1

The modern heartbreak queen takes the weepy country ballad to spine-tingling heights that Kitty Wells and Tammy Wynette never dreamed of. – KC

 

#283
Why Walk When You Can Fly
Mary Chapin Carpenter
1995  |  Peak: #45

Nowadays, a song with this title would probably be all about one person trying to work up the self-confidence to achieve some kind of worldly success – an elementary-school “believe in your dreams” thing. But in the nineties, it was a warm, understated challenge to us all to break free of our cyclical demons – selfishness, fear, pointless finger-pointing – for the good of humankind as a whole. We walk or we fly together. – DM

 

#282
Nothin’ But the Taillights
Clint Black
1997 |  Peak: #1

Left on the side of the road by his lover, Black reflects on his sticky situation in this inescapably catchy number. – TS

 

#281
Unbreakable Heart
Carlene Carter
1993  |  Peak: #51

Radio loved her when she was rowdy, but she’s just as good when she’s nakedly vulnerable.- KC

#280
Burnin’ the Roadhouse Down
Steve Wariner with Garth Brooks
1998  |  Peak: #26

You’ve got to give them credit. Steve Wariner and his buddy, Garth Brooks, try to take an old fashioned sounding, western swing flavored song to mainstream country radio. Within the warm production, check out the cool guitar picking from Wariner, not to mention steel guitar aplenty. – LW

 

#279
Who Needs Pictures
Brad Paisley
1999 |  Peak: #12

A man thinks about going to develop a roll of pictures (remember those?) featuring his ex, but figures it would be redundant: “who needs pictures with a memory like mine?”. Still one of Paisley’s best moments.  – DM

 

#278
Whatever You Say
Martina McBride
1999  |  Peak: #2

New-millenium fans may not realize that there was a time when McBride’s whisper-then-BELT style actually seemed fresh. This ultimatum to a cold lover feels like a natural progression of the songs heartbroken women had always sung in country music, but the skyscraping vocal was McBride’s own twist on the model, and it was a truly cool innovation – until, of course, it became the insufferable norm. – DM

 

#277
You’ve Got a Way
Shania Twain
1998  |  Peak: #13

Twain was often criticized for being a subpar vocalist, but the difference between Twain and, say, Taylor Swift is the former’s ability to use her instrument to express shades of emotion, working with instead of against her vocal imperfections. “You’ve Got a Way” is a perfect example, with Twain soulfully and stirringly filling every crevice of the acoustic arrangement. – TS

 

#276
Two Sparrows in a Hurricane
Tanya Tucker
1992  |  Peak: #2

This is a straightforward, paint-by-numbers love story song, but one that manages to seem sweet and simple all the same. – 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