400 Best Contemporary Country Singles: #300-#276

The 400 Best Contemporary Country Singles
Part 5:

“Lipstick Promises”
George Ducas
Peak: #9

One- hit wonders are still something of an anomaly in country music, though they’ve certainly become more common since the 90’s boom began. Country artists are supposed to have long careers, once they break through with that one hit song. George Ducas seemed poised for stardom when he put out this irresistible Roy Orbison homage – let’s be honest, Ducas’ entire career was warmed-over Orbison – but this was the only hit he ever had.

“Timber, I’m Falling In Love”
Patty Loveless
Peak: #1

It’s okay to be corny in country music, so long as you’re sincere enough to pull it off. This Kostas-penned hit would probably be laughed off the radio today, but in the years before the New York media was paying attention, it was still okay to be this hokey. Even today, it’s hard not to get swept up in her joy of new-found love when Patty yells “Timber…”

“My Next Thirty Years”
Tim McGraw
Peak: #1

No mid-life crisis here. Tim takes a moment to reflect on his first thirty years and map up the next thirty years, which he want to spend laughing more, crying less and hanging out with his wife. With Faith Hill by your side, how can you not look forward to the rest of your life?

“Every Once In A While”
Peak: #2

One of the most cocky songs to ever pose as a sensitive one, a casual listener might miss the arrogance and gloating driving the lyrics. Who knew you could be so snarky with mandolin and three-part harmony?

“Getcha Some”
Toby Keith
Peak: #18

If Keith released this song today, it would be a monster. A low-baritone drawl speaks over a funky harmonica during three verses of looking for sex, money and babies. Keith has never been more charming on record.

“I Sure Can Smell The Rain”
Peak: #9

Some of the best country songs put a down-home spin on universal themes. Randy Travis built a whole song around that with “Deeper Than A Holler.” Here, the boys of BlackHawk sense impending doom about a woman they know is ready to leave, even though she’s saying things are fine – “I can’t see a single storm cloud in the sky, but I sure can smell the rain.”

“Nobody Love, Nobody Gets Hurt”
Suzy Bogguss
Peak: #63

A man tries to rob a convenience store at 4 in the morning, and tells the clerk that she better do exactly as the note says. As the title indicates, he made a slight speling error that revealed a larger truth. “You know what I meant,” he says, and she replies, “Yeah, but that’s not what you said.” Written by the incomparable Bobbie Cryner.

“We Tell Ourselves”
Clint Black
Peak: #2

Before Clint Black started writing endless love songs for his wife, he was the master of the bitter and insightful breakup song. Here, he’s aware his lover and him are just going through the motions – “Somehow we sell ourselves on love, I just don’t think I’ll believe my heart this time.” A driving beat and relentless guitar build up the tension until it explodes into an extended instrumental breakdown that ends the record.

“I Never Cared For You”
Willie Nelson featuring Emmylou Harris
Peak: did not chart

Daniel Lanois produced the landmark Emmy album Wrecking Ball, which unfortunately didn’t send any singles to country radio or video outlets. So while that masterpiece cannot be represented on this list, this fantastic follow-up collaboration with Willie Nelson is nearly as good. Nelson truly is a genius, and this is a fresh take on one of his oldest compositions.

“My Give A Damn’s Busted”
Jo Dee Messina
Peak: #1

Wonderfully in-your-face. She’s the perfect messenger for a brand-new way to say you’ve had enough.

“I Wish I Could Have Been There”
John Anderson
Peak: #4

Country music’s own take on “Cat’s In The Cradle”, Anderson misses the birth of his daughter and his son’s first home run because he’s on the road. In retirement, his kids miss their parents’ anniversary party. Poignant.

“Like We Never Loved At All”
Faith Hill
Peak: #5

John Rich just writes one great song after another. Here, Hill laments that she’s still missing her man, and he’s moved on and doesn’t seem to miss her at all. One of her best.

“I Got It Honest”
Aaron Tippin
Peak: #15

Nobody does a blue-collar anthem better than Aaron Tippin. This is a beautiful and passionate testament to making an honest living, and not putting a price tag on your name. I believe your life’s work is a reflection of who you are as a person, not just what you did to pay the bills. This song reminds me of why I do what I do when there’s too much month at the end of the money.

Rebecca Lynn Howard
Peak: #12

Don’t cheat on this woman; she’ll tear you a new one.

“How Can I Help You Say Goodbye”
Patty Loveless
Peak: #3

One of those classic three-act country plays that ends up with somebody dying. Loveless can wail when she wants to, but she has the good taste to let the lyrics shine and not get in the way. This was the one that took her to the next level.

“When You Come Back To Me Again”
Garth Brooks
Peak: #21

Inspired by the death of his mother, and the aimlessness he felt in the aftermath, Brooks put out his most achingly personal single. I tear up every time.

Carolyn Dawn Johnson
Peak: #25

When men leave in country songs, the hit the bar. When women leave, they it the road. Johnson takes a tour of the southeast trying to drive her man off her mind. Her first and best single.

“I’m Alright”
Jo Dee Messina
Peak: #1

Messina sings for all those of those waiting for dreams to come true, and the rest of us who are pulling for them to succeed, even if it means we don’t see them that often. A bright sunshine bolt of optimism.

Travis Tritt
Peak: #1

Tritt can pull off a sensitive ballad better than anybody, in between all of those honky tonk rave-ups. I don’t think he’s ever sounded better than he does here.

“Crescent City”
Emmylou Harris
Peak: did not chart

Lucinda Williams may not have had much success at the time with her self-titled 1988 album, but many women in Nashville took the songs from that album for their own. This is the first of three covers from that album on this list; Harris wraps a Cajun twang around this charming tale of New Orleans life.

“Three Mississippi”
Terri Clark
Peak: #30

I love the twin fiddles. I love her honky-tonk wail. I love the counting in the chorus. I love the line “My bones are aching from the weight I’m holding down.” I love this single.

“I Hope You Dance”
Lee Ann Womack featuring Sons of the Desert
Peak: #1

There’s a melancholy to Lee Ann Womack’s music that made this single a strange choice for her, until I realized that the mother singing may be wishing for her daughters to dance because she never did. It certainly would explain all those minor chords if that was the case. I still like her woe-is-me material better, but the impact of this song is undeniable.

“I’m So Happy I Can’t Stop Crying”
Toby Keith with Sting
Peak: #2

Rather than just cover this Sting song, Toby got him to sing it with him. It’s the second best divorce song Toby ever did.

“Holes in the Floor of Heaven”
Steve Wariner
Peak: #1

Wariner made a major comeback with this tale of dead family members crying in heaven because they’re missing family gatherings; hence, the rain. Sweet, and touching, and more than a little cheesy. In other words, classic country music.

“Dance With The One That Brought You”
Shania Twain
Peak: #55

See, here’s the thing: even if Shania had never met Mutt, she still would have made this list. This beautiful waltz, written by Gretchen Peters, was one of the best should’ve-been hits of the early 90’s. It still has a timeless quality to it that suggests it might be a hit for someone else in the future.

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