400 Best Contemporary Country Singles: #325-#301

The 400 Best Contemporary Country Singles
Part 4:
#325-#301

#325
“I Cross My Heart”
George Strait
1992
Peak: #1

Strait’s first single to be co-produced with Tony Brown became his signature ballad. This tender love song is still being danced to at weddings everywhere.

#324
“Little Good-Byes”
SHeDaisy
1999
Peak: #3

SHeDaisy became Nashville’s first answer to the phenomenon that was the Dixie Chicks, even though the Osborn sisters had been signed before the Chicks hit it big. One of the reasons this chick trio is so easily dismissed is that their material is usually lightweight, opting for clever wordplay whenever possible. This first single established that formula right off the bat – “Took the hourglass, left the sand, now you’ve got time on your hands” – and gave them a higher-charting debut single than the Chicks had earned a year earlier.

#323
“Poor, Poor Pitiful Me”
Terri Clark
1996
Peak: #5

Like many musical geniuses, Warron Zevon was at death’s door when suddenly everybody from David Letterman on down was showering him with praise. Linda Ronstadt had a moderate pop hit with this Zevon classic in the early 80’s, but it was a twanged-up cover by Canadian Terri Clark that made the song a bona fide hit in the mid-90’s. She growls the vulnerability right out of this one.

#322
“Whose Bed Have Your Boots Been Under?”
Shania Twain
1995
Peak: #11

Listening to the first Mutt Lange-produced Shania single, there’s no sign of the brilliant country-arena rock fusion that is going to break all sales records across the globe. Rather, this is a charming country shuffle, with more steel guitar and twin fiddle than you’d ever expect from this dynamic duo of producer husband and performer wife.

#321
“Speak”
Nickel Creek
2003
Peak: did not chart

Nickel Creek have had very little success at radio; this fantastic single from their gold-selling set This Side didn’t even chart. But the trio never sounded better on a single than they did on this one, with alternating lead vocals by the Watkins siblings and the always-flawless mandolin work by Chris Thile.

#320
“Sorry You Asked?”
Dwight Yoakam
1996
Peak: #59

Yoakam runs into an old friend at the bar who asks where his lady friend is, and he gives that friend an earful. A tongue-in-cheek and very funny running monologue, complete with Mariachi horns.

#319
“How Long”
Bryan White
2000
Peak: #56

In four short years, White went from the hot new thing in country music to a forgotten has-been. This sweet and longful single was supposed to get him back on track, but it stumbled at radio and remains his final appearance to date on the country hit parade.

#318
“I Am a Man of Constant Sorrow”
The Soggy Bottom Boys
2001
Peak: #35

This CMA Single of the Year defied all expectations, helping make the O Brother soundtrack a phenomenon at the beginning of the century. Bluegrass this blue and grassy isn’t supposed to be popular; for a short time, it had Music Row questioning their entire approach.

#317
“No One Needs To Know”
Shania Twain
1996
Peak: #1

Harmonica and acoustic guitar provide all the hooks and beat that Shania needs to create a catchy single about the early stages of a romance. Her affection for her new man is palpable in every beat and sigh on this record. She’s rarely sounded better.

#316
“It’s Your Love”
Tim McGraw with Faith Hill
1997
Peak: #1

Let’s be honest. When this lust-drenched ballad hit the airwaves eight years ago, we all thought it would be a matter of time before this hot couple went the George & Tammy route. In hindsight, it’s the first audio documentation of the defining creative and personal relationship modern country music. They simply sound great together.

#315
“I Keep Looking”
Sara Evans
2002
Peak: #5

Country music finally gets its own “I Can’t Get No Satisfaction.” Over a pulsating guitar, Evans laments how the grass is always greener, and how “as soon as I get what I want, I get unsatisfied.”

#314
“Love Can Build a Bridge”
The Judds
1991
Peak: #5

A lesser vocalist would make this song frustratingly maudlin, but in Wynonna’s control, it becomes a timeless appeal for love, hope and peace. I think her mom’s on the record, too.

#313
“Just To See You Smile”
Tim McGraw
1998
Peak: #1

Tim McGraw has a knack for finding songs that subtly reveal little life truths. This tale of a man who’ll do anything to make his woman happy has one of the best lyrical asides ever when she introduces him to her new lover – “I told you that I was happy for you, and given the chance I’d lie again – just to see you smile.”

#312
“Did I Shave My Legs For This?”
Deana Carter
1997
Peak: #25

It’s hard to imagine this blonde bombshell dolling herself up in a leaky trailer for a man who comes home and ignores her, but when her frustration leads her to ask “did I shave my legs for this?”, it’s fun to go along for the ride anyway.

#311
“It’s Getting Better All The Time”
Brooks & Dunn
2005
Peak: #1

Brooks & Dunn are best known for their bar anthems, but Ronnie Dunn’s voice is a perfect fit for bittersweet and mournful ballads. He rips out the listener’s heart with this lament on the aftermath of a painful breakup.

#310
“Mi Vida Loca (My Crazy Life)”
Pam Tillis
1995
Peak: #1

When Pam Tillis won the CMA Female Vocalist of the Year award in 1994, beating out four women with far more commercial success, it was on the strength of her flawless new album, Sweetheart’s Dance. That classic kicked off with this Bo Diddley-flavored Tex-Mex anthem for living on the wild side of life. One of many fantastic, distinctive singles she would release, this was the only hit she had that went all the way to the top of the Billboard singles chart.

#309
“She Is His Only Need”
Wynonna
1992
Peak: #1

In this homespun tale of life-long devotion, Wynonna tells the story of a man who’ll do anything to make his wife happy, who feels like she doesn’t deserve him because he always goes overboard with the gifts. It’s rambling song without a hook or even much structure, but the sincerity Wy brings to the table makes it soar.

#308
“You’re Not the Best”
Charlie Robison
1999
Peak: did not chart

Too politically incorrect for the late nineties, Robison tells how pretty girls have broken his heart, so he’s settled for an ugly woman who’s “not the best, but you’re the best that I can do.” A criminally overlooked gem that lacks the bravado that makes Toby Keith so grating when he does songs like this.

#307
“Goodbye Time”
Blake Shelton
2005
Peak: #10

A spot-on cover of a top ten hit for Conway Twitty in the 80’s, Shelton’s voice has never sounded more powerful and focused than it does on this recent hit.

#306
“I’m Not Strong Enough To Say No”
BlackHawk
1995
Peak: #2

Mutt Lange co-wrote this anthem for all those men who are too weak to not cheat, but are smart enough to avoid situations where they will. A roving eye has rarely sounded more virtuous than it does here.

#305
“We Just Disagree”
Billy Dean
1994
Peak: #9

It’s no surprise that this cover of a 70’s adult rock hit sounded like an original in the hands of Billy Dean. His roots were clearly in the singer-songwriters that populated AM radio during the flower-power era. He brings this classic up-to-date for the nineties country audience.

#304
“There Goes My Baby”
Trisha Yearwood
1998
Peak: #2

Yearwood’s greatest strength as a recording artist is letting the material shine through. She avoids showboat vocals, even though she can rip the roof off when she wants to. On “There Goes My Baby”, she wants to. Her vocals are a force of nature, as she builds to a final chorus that makes always-screaming Martina McBride sound like a poor little kitten.

#303
“Someone Else’s Dream”
Faith Hill
1996
Peak: #3

Hill sings about a young woman who’s “got 27 candles on her cake, and she needs to make her life her own before there’s 28.” This is a morality tale that warns about living your life solely to please others.

#302
“Hey Cinderella”
Suzy Bogguss
1994
Peak: #5

Life’s not a fairy tale, and Bogguss is longing to ask Cinderella just how long is “ever after”, and are you really happy? She wryly asks the princess, “Does the shoe fit you now?” Odd little songs like this just don’t come around as much these days, at least on mainstream radio.

#301
“She Don’t Know She’s Beautiful”
Sammy Kershaw
1993
Peak: #1

The most beautiful women have no idea how gorgeous they are. Kershaw’s song is for them and the men who love them, even when they’re shaking off a poor night’s sleep and their hair is a mess.