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

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

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

#325
He Would Be Sixteen
Michelle Wright
1992 |  Peak: #31

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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

#324
It Matters to Me
Faith Hill
1995  |  Peak: #1

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Faith Hill’s sophomore album is a surprisingly deep set, filled with candid insights into different womens’ 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

#323
She’d Give Anything
Boy Howdy
1993  |  Peak: #4

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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

#322
The Trouble With the Truth
Patty Loveless
1997  |  Peak: #15

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The trouble with the truth is that 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

#321
Still Gonna Die
Old Dogs
1999  |  Peak: Did Not Chart

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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

#320
Wanted
Alan Jackson
1990  |  Peak: #3

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An apology via a wanted ad could be disastrous in the hands of many male country artists, but it’s simply lovely in Jacksons’, ringing with sincerity and regret. – TS

#319
Finish What We Started
Diamond Rio
1995  |  Peak: #19

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

#318
Tryin’ to Hide a Fire in the Dark
Billy Dean
1992  |  Peak: #6

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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

#317
She is Gone
Willie Nelson
1996  |  Peak: Did Not Chart

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As in 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

#316
It Was
Chely Wright
1999  |  Peak: #11

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

#315
You Can Feel Bad
Patty Loveless
1995  |  Peak: #1

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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

#314
Till I Found You
Marty Stuart
1991  |  Peak: #12

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

#313
Blame it On Your Heart
Patty Loveless
1993 |  Peak: #1

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

#312
You Never Even Call Me By My Name
Doug Supernaw
1994 |  Peak: #60

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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

#311
Wine Into Water
T. Graham Brown
1998  |  Peak: #44

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A kneeling drunkard’s plea for the modern age.  A broken 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

#310
High Powered Love
Emmylou Harris
1993  |  Peak: #63

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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

#309
You Won’t Ever Be Lonely
Andy Griggs
1998  |  Peak: #2

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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

#308
A Door
Aaron Tippin
1997  |  Peak: #65

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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

#307
Someday Soon
Suzy Bogguss
1991  |  Peak: #12

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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

#306
The River
Garth Brooks
1992  |  Peak: #1

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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

#305
Time Passes By
Kathy Mattea
1991  |  Peak: #7

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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

#304
You Can’t Stop Love
Marty Stuart
1996  |  Peak: #26

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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

#303
Everywhere
Tim McGraw
1997  |  Peak: #1

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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

#302
You’re Beginning to Get to Me
Clay Walker
1998  |  Peak: #2

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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

#301
Help Me Hold On
Travis Tritt
1990  |  Peak: #1

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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

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