400 Best Contemporary Country Singles: #250-#226

The 400 Best Contemporary Country Singles
Part 7:
#250-#226

#250
“New Way Home”
K.T. Oslin
1993
Peak: #64

There’s been so many songs about love, finding it and losing it, that fresh perspectives are few and far between. K.T. Oslin found one, as she sings about finding a new route home so she doesn’t have to drive past the house of her former love: “Someday I’ll see something I don’t wanna see and it will only break my heart all over again/Can’t afford it my friend, this will have to end/It’s the only heart I got, and it needs a little more time to mend.”

#249
“No One Else On Earth”
Wynonna
1992
Peak: #1

Wynonna was at the peak of her popularity when this bluesy hit topped the charts. She gives a pitch-perfect performance as a woman who has always been too tough to fall in love, but suddenly is somebody’s fool, growling the question – “How did you get to me?”


#248
“Letting Go”
Suzy Bogguss
1992
Peak: #6

There are so many deep and meaningful relationships that are not romantic, but few songs are written about them. Suzy Bogguss did her part to remedy that problem with this tender tale of a young girl going off to college, and how it is hard for both her and her mother to be letting go. The incisive use of the line “She’s had 18 years to get ready for this day/She should be past the tears, she cries them anyway” to describe both mother and daughter in alternating verses is just damn good songwriting.

#247
“I Fell In Love”
Carlene Carter
1990
Peak: #3

After a long-dead career as a progressive country-rock star, Carter resurfaced in Nashville with a surprisingly successful country debut. This charming rocker skyrocketed Carter into the top five of the country hit parade, and the album that spawned it earned her a Grammy nomination.

#246
“I Still Believe In You”
Vince Gill
1992
Peak: #1

Gill’s powerful declaration of devotion to his wife is so sincere that it makes you assume that it was the woman’s fault the marriage didn’t last. That may not be true, but it’s a testament to the power of great music. Footnote: This was the 1993 CMA Song of the Year.

#245
“Everybody Knows”
Trisha Yearwood
1996
Peak: #3

Trisha has been dumped, and she’s sick of people talking about it. Everybody has advice, from moving back home to praying for guidance to just “forget the jerk”, but all she needs is for everybody to back off so she can handle the situation herself.

#244
“It Only Hurts When I Cry”
Dwight Yoakam
1992
Peak: #7

Yoakam wrote this classic honky-tonk hit with Hall of Famer Roger Miller, and the collaboration clearly brought out the best in both of them. Witty, sharp and dripping with self-deprecation, this is a career highlight for both men.

#243
“Grown Men Don’t Cry”
Tim McGraw
2001
Peak: #1

Tim McGraw is just about the only hat act who can sing a song like this and not be called a pansy. He’s brought to tears by a homeless family, dreams of a father-son relationship he never had, and finally by his own daughter saying “I love you, Dad.”

#242
“Me and Emily”
Rachel Proctor
2004
Peak: #13

A surprisingly upbeat number about an abused wife running away by car, baby in tow. The vivid imagery in the lyrics – “Floorboard is filled with baby toys and empty Coke bottles and coffee cups/Riding through the rain with no radio, trying not to wake her up” – makes the listener believe every word.

#241
“On The Road”
Lee Roy Parnell
1993
Peak: #6

“Me and Emily” isn’t the only great song about hitting the road to get away from your troubles. Lee Roy Parnell’s 1993 hit, drenched in his trademark slide guitar, tells the story of two retirees, a misfit rebel son and an ignored housewife all looking for answers down the highway.

#240
“If Something Should Happen”
Darryl Worley
2005
Peak: #10

If “Live Like You Were Dying” is the ideal fantasy about dealing with a potentially terminal illness, “If Something Should Happen” is a stone-cold dose of reality in the same situation. Worley’s vocal trembles with nervousness as he asks his friend to look in on his wife and son if he doesn’t make it. His biggest concern is not himself, but the absence his death would cause, and he wants to make sure his family’s needs will still be met in some way. This is Worley’s finest moment to date.

#239
“Killin’ Time”
Clint Black
1989
Peak: #1

Clint Black’s debut album was brilliant honky-tonk, from start to finish. The opening line – “You were the first thing that I thought of, when I thought I drank you off my mind” – is an immediate sign that this guy has Haggard in his veins.

#238
“Like We Never Had A Broken Heart”
Trisha Yearwood
1991
Peak: #4

Sure, “She’s In Love With The Boy” was a mega-hit, but attentive fans heard the real essence of Trisha Yearwood when her second single hit the airwaves. Intelligent lyrics, sparse production and a voice filled with nuance and subtlety, the arrival of a serious artist was announced with this classic ballad.

#237
“I Can Count On You”
Lorrie Morgan
2004
Peak: did not chart

It’s interesting that for an artist who had many hit singles, it was the ones that didn’t make it too far up the charts that were her best work. Morgan sings this heartbreaker with only the help of a piano, and she uses the lower register of her voice with remarable results. This track is from her most recent album, Show Me How, which is arguably the best of her career.

#236
“Whole Lotta Love On The Line”
Aaron Tippin
1994
Peak: #30

Aaron could have sang the phone book over this hook and still made the list – the repeating guitar riff is almost hypnotizing. Thankfully, it formed the basis for one of his best songs, a plea to his lover not to walk out on a love worth fighting for.

#235
“Don’t Tell Me What To Do”
Pam Tillis
1991
Peak: #5

After two failed attempts in pop and rock, and a dismal run of country singles for Warner Brothers in the late 80’s, Mel’s daughter Pam came out of nowhere to launch a high-voltage career as the flagship female artist on the newly-formed Arista Nashville label. Co-written by Harlan Howard, who also wrote her dad’s first #1 hit, Pam’s deceptive feminist anthem announced her arrival as a woman to be reckoned with.

#234
“Forever and For Always”
Shania Twain
2003
Peak: #4

She’s had more hits on the pop chart than many pop stars, but when Shania does country, she’s tough to beat. The warmth of the steel guitar on this record is almost overwhelming, and her voice has never sounded better than it does on this, the highest-charting hit from her Up! CD.

#233
“I Just Might Be”
Lorrie Morgan
1996
Peak: #45

Maybe country radio just didn’t want to hear a song with “damn” in the chorus – as in, “I just might be the best damn thing that you ever threw away. Radio ignored this breezy break-up song that had Morgan showing more confidence and independence than usual.

#232
“Does My Ring Burn Your Finger”
Lee Ann Womack
2002
Peak: #23

Womack’s anger, indignation and loneliness absolutely radiate off of this record. An intense and powerful performance of a timeless cheating song.

#231
“Streets of Heaven”
Sherrie Austin
2003
Peak: #18

Break out the Kleenex. Mama Sherrie is in Room 304 of a nameless hospital, by the bedside of her dying 7-year old daughter, and praying that God not take her daughter from her. Her concern: the streets of heaven must be awfully crowded, and she’s too young to cross by herself. Who will hold her hand?

#230
“Angels Working Overtime”
Deana Carter
1999
Peak: #35

An entirely implausible tale of a baby left at a Denny’s in Colorado, found by a prairie family that raises her but doesn’t understand her. So she takes a Greyhound bus, gets out for a smoke, and the bus leaves her. So she hitchhikes, finds a guy heading to L.A., gets pregnant and they get an apartment for the two/soon-to-be-three of them. All this, and a choir of children to sing the chorus at the end. This is songwriters and producers working overtime, but it’s campy fun.

#229
“Who’s That Man”
Toby Keith
1994
Peak: #1

Keith started writing this song as a play off of that old joke – What happens when you play a country song backwards? You get your house back, you get your wife back, you get your dog back. Ironically, it led to him writing a classic country song that became an example of the joke instead of a joke itself. Keith is a divorced man driving past his old house, and sees his wife, his car, his kids, his dog, and asks, “Who’s that man running my life?”

#228
“Now I Know”
Lari White
1994
Peak: #5

There was a brief moment when RCA seemed to completely committed to making Lari White a major star, and this was the high point of that attempt. “Now I Know” is a near-perfect tale of a woman surviving being left better than she ever thought she could – “I always wondered how I’d live without you. Now I know.”

#227
“Pass It On Down”
Alabama
1990
Peak: #3

At the mid-point of the first Bush administration, a year after praising southern Democrats with “Song of the South”, Alabama’s politics got contemporary with this appeal to save the environment. Done in a common man style – “How we gonna breathe without them trees?” – they make a case for stewardship of God’s creation that should get both sides of the political fence thinking about leaving “some blue up above us.”


#226
“Everywhere”
Tim McGraw
1997
Peak: #1
Two lovers in a small-town. He can’t wait to get out; she can’t see herself living anywhere else. So he goes on his journey around the world, alone. The problem is, he still sees her everywhere. A somber loner’s tale.

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