Top Fifty CMA Single of the Year Winners, Part Four: #20-#11

Our countdown of CMA Single of the Year winners continues with #20-#11.

Top Fifty CMA Single of the Year Winners

Part One: #50-41 | Part Two: #40-#31 | Part Three: #30-#21

Part Four: #20-#11 | Part Five #10-#1

#20
“I May Hate Myself in the Morning”
Lee Ann Womack

2005

Lee Ann Womack’s second CMA Single of the Year lovingly recreated the warmth and intimacy of Sammi Smith’s definitive recording of “Help Me Make it Through the Night,” revisiting that classic’s theme with a modern day woman’s point of view.  There’s no submission here to external pressure. Instead, she submits to her internal longing, knowing in the morning that she will have to take responsibility for her choice. Great as the lyric is, “I May Hate Myself in the Morning” further distinguishes itself with an extended instrumental outro that I still maintain is the best showcase of country music instrumentation that we’ve heard this century. – Kevin John Coyne

#19
“When You Say Nothing at All”
Alison Krauss & Union Station

1995

Krauss shocked everyone by running the table at the 1995 CMAs on the strength of her cover of Keith Whitley’s ballad. The single has become a standard in the years since, a credit to its open-hearted sentiment and Krauss’ lovely, understated interpretation. For all of her continued popularity and acclaim, it’s astonishing that this single technically qualifies her as a One Hit Wonder. – Jonathan Keefe

#18
“Chattahoochee”
Alan Jackson

1993

Penning a good-time party anthem is no easy task — look at all the half-baked versions recorded over the last decade by Bryan, Aldean, Shelton, Chesney, etc. “Chattahoochee” is in a different league, and not just because they successfully rhymed “Chattahoochee” with “hoochy-coochee” without batting an eye. There’s an innocence in Jackson’s and Jim McBride’s lyrics that’s absent from contemporary songs, putting the emphasis fun with friends instead of getting your girl to shake it on the tailgate of your pickup truck. A good guitar riff is never to be underestimated, either. – Sam Gazdziak

#17
“I am a Man of Constant Sorrow”
The Soggy Bottom Boys

2001

#16
“Wide Open Spaces”
Dixie Chicks

1999

How prophetic Natalie Maines’ repetition of “She knows the high stakes” would be. The musical and political fearlessness that would later define country music’s greatest band hadn’t surfaced yet, but there’s a restlessness underlying the innocence and hope of “Wide Open Spaces” that gives the record greater depth in retrospect.  And yes, I did just call the Dixie Chicks country music’s greatest band. The genre still hasn’t recovered from their exile, which left the spaces for women in country music anything but wide open.- KJC

#15
“Eighteen Wheels and a Dozen Roses”
Kathy Mattea

1988

Kathy Mattea’s most beloved single is a sweet and hopeful celebration of a retiring truck driver who is looking forward to spending his retired life with his good wife. Mattea’s clear, warm performance elevates this retirement anthem with a subject that could be perceived as very specific to something that we all want to relate to. – Leeann Ward

#14
“Hurt”
Johnny Cash

2003

Grief for a lost legend might have been the fuel for Cash’s first CMA wins since 1969, but in choosing “Hurt” as the best Single of the Year, the CMA got it right.  His stark reading of Trent Reznor’s harrowing tale of addiction is transformed into a requiem for Cash’s public persona, the dying regrets of the old man who once sang about having stripes and having both the cocaine and Folsom Prison Blues.  That public persona, so perfectly lionized in the film Walk the Line, was never who Cash really was. But with “Hurt,” he once again proved how easily he could slip into a lost soul and make it his own. – KJC

#13
“A Boy Named Sue”
Johnny Cash

1969

Due to the live performance, the recording of “A Boy Named Sue” is perfectly imperfect. Johnny Cash talks and sort of sings his way through the tale of a man whose father gave him a name that forced him to be a fierce opponent. Shel Silverstein’s farfetched lyrics, Cash’s whimsical performance and his signature rhythm section all somehow work together. However, the live audience is what successfully completes the package. Without that audience responding to hearing the song for the first time, the song still would have been fun, but likely not the classic that it’s become. – LW

#12
“Strawberry Wine”
Deana Carter

1997

I did my undergrad at a small liberal arts college with a renowned English department. I once had to explain to a good friend who was a creative writing major— a poet, even— that the line, “I was thirsting for knowledge/And he had a car,” was not, in fact, a non-sequitor. Carter’s phenomenal, longing performance of one of Matraca Berg’s finest compositions remains a shining example of country music at its poetic best. – JK

#11
“Good Hearted Woman”
Waylon & Willie

1976

The original Outlaw Country movement was one of those times where mainstream country and critically acclaimed country collided, and this song helped send the Wanted: The Outlaws album to the top of the charts. This supposed “live” song was actually created in a studio, with the cheering crowd and Nelson’s vocals added onto Jennings’ version. You can still be an Outlaw and use a little studio trickery. – SG