400 Best Contemporary Country Singles: #275-#251

The 400 Best Contemporary Country Singles
Part 6:

“Live Like You Were Dying”
Tim McGraw
Peak: #1

A mega-hit if there ever was one, this was the biggest hit of Tim’s career. A conversation between a man who was told he had a few months to live and another who asks what he did in response, leads to a laundry list of some fairly ridiculous actions – sky diving, mountain climbing and bull-riding when your days are already numbered? That’s just silly. But then there’s the line that’s all to real – “I gave forgiveness I’d been denying” – that is the song’s salvation.

“The Night’s Too Long”
Patty Loveless
Peak: #20

And now, the second of three songs originally on that 1988 Lucinda Williams CD. This twangy and irregularly rhymed story of Sylvia from Beaumont tells the tale of a woman who moves to the city to meet some fast men with such sharp detail – “With her back against the wall she can listen to the band, and she’s holding a Corona and it’s cold against her hand” – that you can actually feel the scene, not just picture it.

“He Feels Guilty”
Bobbie Cryner
Peak: #68

A brilliant writer and muddy river vocalist, sultry and thick and straight out of the swampland. All she needs is a bit of guitar to get her started, and she takes the listener right into the mind of a woman who just knows her man is cheating from the chill he’s sending out.

“That’s Why I’m Here”
Kenny Chesney
Peak: #2

This is the record that finally got Kenny some real recognition as a credible artist. A powerful tale of a man taking the step to join Alcoholics Anonymous, he really becomes the man in the song, as all great interpreters do.

“Is It Over Yet”
Peak: #6

You just don’t get weepers like this from women in the post-Shania world. Wy is watching as her man packs up to leave, and keeps asking herself “Is it over yet?” Her mind is telling her to be strong, but she doesn’t trust her heart – “I’d like to help you with a suitcase or two, but I’m afraid I’m gonna wind up down on my knees.” Her voice aches with hurt and vulnerability.

“Every Little Thing”
Carlene Carter
Peak: #3

Carlene Carter is one hell of a fiesty performer. The raw energy of this track, with the 60’s pop backup singers and driving drum beats, had more confidence and sexual energy than just about anything country radio ever let into heavy rotation in the male-dominated early 90’s.

Trace Adkins
Peak: #16

A surprisingly moderate hit, this haunting tune is from the perspective of a soldier who has just been buried in Arlington National Cemetery. He’s proud of his service, and has joined his grandfather at the holiest of sacred ground.

“How Do I Live”
Trisha Yearwood
Peak: #2

Trish won a Grammy for her pitch-perfect rendition of this Diane Warren song. Yes, it was remembered mostly for the sing-off between her and LeAnn Rimes, who was left sounding like a little girl singing about a lost doll when stacked against the vocal powerhouse that is Trisha Yearwood. But it’s a gorgeous love song and finally got those award shows to acknowledge the legendary talent who’d been overlooked for too long.

“What Mattered Most”
Ty Herndon
Peak: #1

Ty misses the “forest for the trees.” He knows everything about his now ex-lover, from her favorite song (“In My Life”) to her car and her clothes, but he paid no attention to what mattered most – that she was feeling unloved and not needed.

“Pocket Full of Gold”
Vince Gill
Peak: #7

Can you get more classic country than the opening line “He slipped the ring off his finger when he walked in the room”? He clearly pities the man he’s singing about, who would give anything for another man’s treasure, and thinks he’s rich because he has money in his pockets. When he reveals he was a cheater himself in the second verse, you realize just where that pity comes from.

“I’m Holdin’ On To Love (To Save My Life)”
Shania Twain
Peak: #17

The eleventh and final single from the 20x platinum Come On Over was one of the best. Twain has never sounded more intelligent or clever, with a machine-gun speed list of all the crutches she doesn’t need – from psychics to Dr. Ruth to the internet – because she’s getting by on love.

“Jenny Come Back”
Helen Darling
Peak: #69

This is a tale about a girl who was smart, and determined, and beautiful, but changed to please and older guy in school. She ends up dropping out, and her sort-of friend sees her selling movie tickets for a career. It perfectly captures the dangers of selling yourself short to please others.

“Girls With Guitars”
Peak: #10

Maybe if Jenny had played guitar, she never would have followed some dumb guy around. Wy growls her way through this Mary Chapin Carpenter-penned saga about a girl who doesn’t take shit off of anybody, and only talks to boys who play the guitar. Her fierce confidence has her hitting the Big Apple and blowing away the guy who’s checking out her legs with her undeniable talent. Somehow you just know that a girl with a guitar answers only to herself.

“He Gets That From Me”
Reba McEntire
Peak: #7

Reba showed surprising restraint by recording this tearjerker with an acoustic production and no vocal acrobatics. Her conversation with her dead husband about how their son is getting her through the pain needs no bells and whistles to help the message along.

“What a Crying Shame”
The Mavericks
Peak: #25

The Mavericks were able to make retro cool in country music, for a few months at least. Raul Malo is one of the best voices to ever bless the genre, and his band’s sound was so distinctive that they received two Vocal Group awards without ever hitting the top ten at radio.

“When You Need My Love”
Darryl Worley
Peak: #15

Darryl’s debut single marked the arrival of a top-notch singer-songwriter, as he tells the woman he loves that someday he won’t be there for her when she’s been dumped by the man she really loves. With his delivery, you almost suspect even he doesn’t believe there will ever be a day that he’s not there for her, but it just makes him feel good to picture his heart letting go.

“Good-Hearted Man”
Tift Merritt
Peak: did not chart

Tift finally finds a man who loves and respects her, and she’s confused because she’s not sure how to handle the real thing. Her cynicism gives in to optimism as the song progresses. She sounds like she’s channeling Dusty Springfield.

“Let Go”
Brother Phelps
Peak: #6

While on haitus from The Kentucky Headhunters, the two Phelps brothers from that band put out two albums as a duo. This was the only hit, an song that inspires you to let go of all the things that are weighing you down.

“High-Powered Love”
Emmylou Harris
Peak: #63

Harris’ last attempt to please country radio was a forceful rocker about needing to find a love with more fire and energy, instead of just settling for guys who are all show and no heart. It’s hard not to smile when she asks, “Is there anyone left with teeth just a little uneven, who won’t spend more time with a mirror than he does with me?”

“Redneck Woman”
Gretchen Wilson
Peak: #1

Wilson’s in danger of becoming a cliche already, but when this song hit, it was a breath of fresh air. Their was just something universally appealing about Wilson’s comfort in her own skin; I don’t think you had to be a redneck or a woman to be yelling “Hell Yeah!” right back to her; you just had to he happy with who you are.

“Down On My Knees”
Trisha Yearwood
Peak: #19

Trisha has always been content to let the song shine; she saves her vocal power only for songs that deserve it. Because she uses her belting abilities so sparingly, the emotional punch is that much stronger when she does go full force, as she does on this power ballad from the early 90’s.

“I’m Just Talkin’ About Tonight”
Toby Keith
Peak: #1

This back and forth between a man who wants a one-night stand and a woman who wants a man for life is light, entertaining and very funny.

“Baby Likes To Rock It”
The Tractors
Peak: #11

There was this brief period of anything goes in the mid-90’s, and no act exemplified that better than the suddenly double platinum-selling Tractors, who somehow found a home in country music with this bizarre, random hit, complete with scat.

“How Your Love Makes Me Feel”
Diamond Rio
Peak: #1

Diamond Rio’s harmonies are some of the best in country music history. This up-tempo description of how love feels manages to talk about ice cream and wandering cows along the way.

“I Saw The Light”
Peak: #1

No, it’s not a cover of the Hank Williams gospel classic. Rather, Wy drops by her lover’s house and sees two shadows getting it on through the window. “They say that love is blind, but baby not this time.” She can’t be bothered to play the victim this time, so she’s going to hit the town in her red dress and find her own shadow to dance with.

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