400 Best Contemporary Country Singles: #100-#76

The 400 Best Contemporary Country Singles
Part 13:
#100-#76

#100
“Nobody Wins”
Radney Foster
1992
Peak: #2

Pride can be crippling. Sometimes you win the fight but lose the one you love. In the end, you win nothing at all. Radney gets that, and makes a passionate appeal to his lover to stop the fighting and just remember that the love they have is more important than any argument between them.

#99
“Quittin’ Time”
Mary Chapin Carpenter
1990
Peak: #7

Sometimes, however, fights signify that things aren’t as good as they used to be, but you stick around because you remember how good it used to be. Here, Chapin appeals to her lover to give up the fight, since it’s clear that their love is a thing of the past.


#98
“Cry”
Faith Hill
2002
Peak: #12

It’s never fun being the one who gives more than they take. To be the one who is the better person, who gives until they can’t give anymore while overlooking the failings of the other person, and still be left in the end? That’s not fun at all. Faith Hill demands that her leaving lover give her at least a few tears to justify all of the sacrifices that she has made on his behalf; she deserves that much.

#97
“You Win Again”
Mary Chapin Carpenter
1990
Peak: #16

I’ve never heard a more harrowing tale of desperation, of being trapped in a one-sided relationship where you’re being emotionally exploited – “I can’t stand up when I’m always kneeling at your altar or at your throne, you could show just a little feeling for who I am, baby you win again.” Desperation at its most fervent.

#96
“It’s Lonely Out There”
Pam Tillis
1996
Peak: #14

The grass ain’t always greener. The brilliance of this record is how Pam starts off coldly indifferent to her lover’s desire to find someone new, then slowly reveals her desire for him to stay, to the point that she’s finally pleading for him not to leave. At the beginning, “it’s lonely out there” is a cold reminder; by the end, it’s a desperate plea for him to stay.

#95
“He Would Be Sixteen”
Michelle Wright
1992
Peak: #31

A woman is haunted by the baby she gave up for adoption 16 years ago. Her need to know how the son she never knew is doing reveals a mother’s love is eternal, even if she doesn’t raise her child.

#94
“Whiskey Lullaby”
Brad Paisley & Alison Krauss
2004
Peak: #3

Who knew a double-suicide song could be a hit? Paisley is a very ordinary artist, but the extraordinary vocal talents of Alison Krauss and songwriting talents of Jon Randall & Bill Anderson give him his finest moment on record.

#93
“Keep Your Distance”
Patty Loveless
2005
Peak: did not chart

Some people just aren’t good for your system. If they can’t commit to you completely, you’re better off staying away from them completely. Loveless captures this in this fantastic single, which appeals to an ex-lover to keep their distance, since “with us, it must be all or none at all.” My favorite line in a song this year was “I played and I got stung, now I’m biting back my tongue and sweeping out the footprints where I strayed.”

#92
“Come From The Heart”
Kathy Mattea
1989
Peak: #1

If you let your head rule your heart, you won’t take the chances necessary to find real happiness. Sometimes you have to be willing to make an ass out of yourself.

#91
“Bring On The Rain”
Jo Dee Messina with Tim McGraw
2001
Peak: #1

Jo Dee tends to O.D. on the inspirational songs, but this one resonates with me more than the others. Don’t just deal with adversity; invite it. “Tomorrow’s another day, and I’m thirsty anyway, so bring on the rain.” A powerful motivation to survive.

#90
“Portland, Oregon”
Loretta Lynn with Jack White
2004
Peak: did not chart

Loretta meets Jack White on his own turf and shines on this honky-tonk rocker. She absolutely radiates from the speakers. She’s old enough for Social Security and I still want to take her home.

#89
“Feed Jake”
Pirates of the Mississippi
1991
Peak: #15

They take the classic joke about country songs about dogs, and use it to make biting social commentary. The chorus sings about feeding Jake, a good dog. The verses tackle homelessness, poverty and anti-gay bigotry. A stroke of brilliance.

#88
“I Don’t Call Him Daddy”
Doug Supernaw
1993
Peak: #1

This was a surprise hit, perhaps because it finally gave a voice to Sunday fathers who love their children but can’t fully provide for them. “He’s quite a little man, growing up as fast as he can, and I don’t get to see him half as much as I had planned.” Your heart breaks with the father when you hear his ode to his son.

#87
“You’ve Got A Way”
Shania Twain
1999
Peak: #13

There was something almost indignant about ending her pop crossover phenom Come On Over with this stripped-down country ballad. Here, Twain proves she can outclass all those folkies in the coffee shops when she wants to; she’s just chosen to please the masses instead.

#86
“Yard Sale”
Sammy Kershaw
1992
Peak: #17

A brilliant way of showing the aftermath of a broken home, Kershaw sings about the yard sale selling off all of his memories. “They’re sorting through what’s left of you and me”, he warbles, capturing pure country heartbreak in the most mundane of weekend activities.

#85
“Shut Up and Drive”
Chely Wright
1997
Peak: #14

The best woman leaving by driving away country song ever. Wright provides the voice of strength for every woman stuck in a relationship that makes her weak, and speaks an obvious truth: “He’s the one who will be missing you, and you’ll only miss the man that you wanted him to be.”

#84
“All These Years”
Sawyer Brown
1993
Peak: #3

A man comes home early and sees his cheating wife in bed with another man. No moral grandstanding here; the conversation they have lays blame on all sides. “She said you’re not the man you used to be, and he said neither is this guy. She said there’s some things you refuse to see, but I guess sometimes so do I.” You actually believe the marriage will be stronger after this incident than it was before, because honesty is finally on the table.

#83
“Drugs or Jesus”
Tim McGraw
2005
Peak: #14

Has there ever been a more honest explanation of why people use drugs? You do want that escape from reality, that hope that everything will be okay. Hey, that’s why some people go to church, too. Is that okay to put in a country song? McGraw thought so, and captured both situations without judgement and with sympathy.

#82
“Come Some Rainy Day”
Wynonna
1998
Peak: #14

All those good old days you’re hoping to revisit are already a thing of the past. Don’t wait for the rainy day; appreciate what you have while it’s still there.

#81
“Love, Me”
Collin Raye
1991
Peak: #1

Go ahead. Try not to cry as the grandfather kneels and tells his wife who has died that he’ll meet her when his chores are through.

#80
“Angry All The Time”
Bruce Robison
1998
Peak: did not chart

Tim McGraw had a #1 hit with this, but it’s Robison’s original version, with passionate harmony from Kelly Willis, that fully captures the voice of a man whose “reasons that I can’t stay don’t have a thing to do with being in love.” A stark and powerful story about how married life can fail to meet your expectations.

#79
“Just My Luck”
Kim Richey
1995
Peak: #47

A brilliant voice makes herself heard on her own terms, telling how her independence has been compromised by falling for a new man, and wondering if that’s good luck or bad luck. The jangly guitars still sound great ten years later. This should have been a #1 hit.

#78
“Things Change”
Dwight Yoakam
1998
Peak: #17

Dwight is dealing with a bitchy lover who no longer loves him, even though he “still feels the same.” She mocks his failure to understand how time changes things, but when she comes crawling back, he uses her own words against her.

#77
“Three Wooden Crosses”
Randy Travis
2002
Peak: #1

I can’t believe a #1 country hit started out with the line “A farmer and a teacher, a hooker and a preacher.” But more Baptists need to listen to how a prostitute can be the one who leads others to salvation. Too many Christians overlook the fact that Jesus bypassed the temples and hung out with the bottom-feeders of society. God’s love is not discriminating, and neither should ours be.


#76
“Perfect”
Sara Evans
2004
Peak: #2
I remember feeling frustrated that I wasn’t doing everything the right way, and I was being nailed at work for it. Then this song came on as I drove home and it was a reminder that nobody’s perfect, and if you surround yourself with people who know you’re trying your best, you will better yourself without all the extra guilt. I’m thankful for this song because it helped me find greater perspective and appreciation for myself.

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