Revising My Top-300 Country Song List of All-Time

Ten years ago on Super Bowl weekend, I put together a list of my 150 favorite country songs of all-time, ranking them chronologically from #1 to #150.  That was a fun exercise and I figured a decade later it was worth a revisit and an expansion.  This year I originally did a list of 250 of my favorite country songs singled out, but since I found myself with so many more songs I'd classify as "great" that I expanded it to 300 songs in my second edit.  I also arranged the list differently.  I'll go through cycles where one song really hits me and I find it to be the best thing ever recorded, while other songs I loved at their peak can burn out for me and lose their magic.  With that in mind, I didn't want to do a pecking-order list this time, so instead decided upon a chronological listing of the songs that comprise my top-300 list, going from oldest to newest.  Here's the list, with some additional commentary at the end....
 
Sixteen Tons--Tennessee Ernie Ford (1955)
Walk the Line--Johnny Cash (1956)
The Battle of New Orleans--Johnny Horton (1959)
Sink the Bismarck--Johnny Horton (1960)
Big Bad John--Jimmy Dean (1961)
I've Been Everywhere--Hank Snow (1962)
Ring of Fire--Johnny Cash (1963)
Six Days on the Road--Dave Dudley (1963)
King of the Road--Roger Miller (1965)

Don’t Come Home A-Drinkin’ (With Loving on Your Mind--Loretta Lynn (1966)
Wichita Lineman--Glen Campbell (1968)

Mama Tried--Merle Haggard (1968)
A Boy Named Sue--Johnny Cash (1969)
Galveston--Glen Campbell (1969)
Snowbird--Anne Murray (1970)
Take Me Home, Country Roads--John Denver (1971)
Coat of Many Colors--Dolly Parton (1971)
Burgers and Fries--Charley Pride (1971)
The Man in Black--Johnny Cash (1971)

Billy Dee--Kris Kristofferson (1971)

Uneasy Rider--Charlie Daniels Band (1973)
The Most Beautiful Girl in the World--Charlie Rich (1973)
Danny's Song--Anne Murray (1973)
Jolene--Dolly Parton (1973)
If We Make it Through December--Merle Haggard (1973)

Smoky Mountain Memories--Mel Street (1975)
Convoy--C.W. McCall (1975)
One Piece at a Time--Johnny Cash (1976)

Lucille--Kenny Rogers (1977)
Rollin' with the Flow--Charlie Rich (1977)
Don't It Make My Brown Eyes Blue--Crystal Gayle (1977)

Luckenbach, Texas--Waylon Jennings and Willie Nelson (1977)
Here You Come Again--Dolly Parton (1977)
There Ain't No Good Chain Gang--Waylon Jennings and Johnny Cash (1978)
Sleeping Single in a Double Bed--Barbara Mandrell (1978)
Tulsa Time--Don Williams (1978)
The Gambler--Kenny Rogers (1978)
Why Have You Left the One You Left Me For?--Crystal Gayle (1978)
Back on My Mind Again--Ronnie Milsap (1979)
The Devil Went Down to Georgia--Charlie Daniels Band (1979)
Shadows in the Moonlight--Anne Murray (1979)
Sail Away--Oak Ridge Boys (1979)
Family Tradition--Hank Williams, Jr. (1979)
Missing You--Charley Pride (1979)
Broken Hearted Me--Anne Murray (1979)
Coward of the County--Kenny Rogers (1980)
Like We Never Said Goodbye--Crystal Gayle (1980)
He Stopped Loving Her Today--George Jones (1980)
Drivin' My Life Away--Eddie Rabbitt (1980)
The Legend of Wooley Swamp--Charlie Daniels Band (1980)
Good Old Boys Like Me--Don Williams (1980)

Do You Wanna Go to Heaven?--T.G. Sheppard (1980)
Tumbleweed--Sylvia (1980)
Smoky Mountain Rain--Ronnie Milsap (1981)
Who's Cheatin' Who?--Charly McClain (1981)
Tight Fittin' Jeans--Conway Twitty (1981)
Drifter--Sylvia (1981)
Angel of the Morning--Juice Newton (1981)

Louisiana Saturday Night--Mel McDaniel (1981)
Somebody's Knockin'--Terri Gibbs (1981)
Seven Year Ache--Rosanne Cash (1981)
I Loved 'Em Every One--T.G. Sheppard (1981)
Queen of Hearts--Juice Newton (1981)
Rainbow Stew--Merle Haggard (1981)
I Wouldn't Have Missed it for the World--Ronnie Milsap (1982)

Lord, I Hope This Day is Good--Don Williams (1982)
Blue Moon with a Heartache--Rosanne Cash (1982)
Nobody--Sylvia (1982)
16th Avenue--Lacy J. Dalton (1982)
Mountain of Love--Charley Pride (1982)

A Country Boy Can Survive--Hank Williams, Jr. (1982)
Kansas City Lights--Steve Wariner (1982)
Mistakes--Don Williams (1982)
Like Nothing Ever Happened--Sylvia (1983)
Inside--Ronnie Milsap (1983)

Amarillo by Morning--George Strait (1983)
Pancho and Lefty--Willie Nelson and Merle Haggard (1983)
He's a Heartache--Janie Frickie (1983)
Stranger in My House--Ronnie Milsap (1983)
Highway 40 Blues--Ricky Skaggs (1983)
The Ride--David Allan Coe (1983)
The Sound of Goodbye--Crystal Gayle (1984)
Still Losing You--Ronnie Milsap (1984)
God Bless the USA--Lee Greenwood (1984)
The City of New Orleans--Willie Nelson (1984)
Angel in Disguise--Earl Thomas Conley (1984)
Some Fools Never Learn--Steve Wariner (1985)
Old Hippie--Bellamy Brothers (1985)
Meet Me in Montana--Dan Seals and Marie Osmond (1985)
I Don't Know Why You Don't Want Me--Rosanne Cash (1985)
Don't Call it Love--Dolly Parton (1985)
The Highwaymen--Willie Nelson, Kris Kristofferson, Waylon Jennings, and Johnny Cash (1985)
Nobody Falls Like a Fool--Earl Thomas Conley (1985)
Back to the Heartbreak Kid--Restless Heart (1985)
Never be You--Rosanne Cash (1985)
Bop--Dan Seals (1986)
Guitar Town--Steve Earle (1986)
Hold On--Rosanne Cash (1986)
Everything That Glitters Is Not Gold--Dan Seals (1986)
In Love--Ronnie Milsap (1986)
You Can't Stop Love--SKO (1986)
80s Ladies--KT Oslin (1987)
Baby's Got a New Baby Now--SKO (1987)
The Weekend--Steve Wariner (1987)
The Pride is Back--Kenny Rogers and Nickie Ryder (1987)
In Another World--Gary Morris and Crystal Gayle (1987)
The Way We Make a Broken Heart--Rosanne Cash (1987)
A Sure Thing--Foster and Lloyd (1987)
Midnight Girl in a Sunset Town--Sweethearts of the Rodeo (1987)

One Step Forward--Desert Rose Band (1987)
Tennessee Flat Top Box--Rosanne Cash (1988)
Where Do the Nights Go?--Ronnie Milsap (1988)

I Wouldn’t be a Man-Don Williams (1988)
It's Such a Small World--Rodney Crowell and Rosanne Cash (1988)

If It Don’t Come Easy--Tanya Tucker (1988)
Eighteen Wheels and a Dozen Roses--Kathy Mattea (1988)
I Told You So--Randy Travis (1988)
She's Crazy for Leaving--Rodney Crowell (1988)
The Bluest Eyes in Texas--Restless Heart (1988)
Runaway Train--Rosanne Cash (1988)
Don't Close Your Eyes--Keith Whitley (1988)
Addicted--Dan Seals (1988)
Song of the South--Alabama (1988)
Big Dreams in a Small Town--Restless Heart (1989)
Much Too Young (To Feel This Damn Old)--Garth Brooks (1989)
Bayou Boys--Eddy Raven (1989)
My Arms Stay Open All Night--Tanya Tucker (1989)
She Don't Love Nobody--Desert Rose Band (1989)
Where've You Been?--Kathy Mattea (1989)
I'm Gonna be Somebody--Travis Tritt (1990)
Two Dozen Roses--Shenandoah (1990)
Little Things--Marty Stuart (1990)

Dumas Walker--Kentucky Headhunters (1990)
Hard Rock Bottom of Your Heart--Randy Travis (1990)
Bordertown--Dan Seals (1990)
Sticks and Stones--Tracy Lawrence (1991)
Unanswered Prayers--Garth Brooks (1991)
In a Different Light--Doug Stone (1991)
Hurt Me Bad in a Real Good Way--Patty Loveless (1991)
Tempted--Marty Stuart (1991)
Hooked on an Eight-Second Ride--Chris LeDoux (1991)
Fancy--Reba McEntire (1991)
Feed Jake--Pirates of the Mississippi (1991)

Straight Tequila Night--John Anderson (1991)

Neon Moon--Brooks and Dunn (1992)
The Thunder Rolls--Garth Brooks (1992)

Billy the Kid--Billy Dean (1992)
Cafe on the Corner--Sawyer Brown (1992)
Aces--Suzy Bogguss (1992)

Nowhere Bound--Diamond Rio (1992)
Maybe it was Memphis--Pam Tillis (1992)
Past the Point of Rescue--Hal Ketchum (1992)
I'm in a Hurry (And Don't Know Why)--Alabama (1992)
Boot Scootin’ Boogie--Brooks and Dunn (1992)

Seminole Wind--John Anderson (1992)
Letting Go--Suzy Bogguss (1992)
When She Cries--Restless Heart (1992)
He Would be Sixteen--Michelle Wright (1992)
Tell Me Why--Wynonna (1993)
When You Leave That Way You Can Never Go Back--Confederate Railroad (1993)

I’d Rather Miss You--Little Texas (1993)
Chattahoochee--Alan Jackson (1993)

Let Go--Brother Phelps (1993)
Every Little Thing--Carlene Carter (1993)
Nobody Wins--Radney Foster (1993)
The Hard Way--Mary Chapin Carpenter (1993)
Mama Knows the Highway--Hal Ketchum (1993)
Holdin' Heaven--Tracy Byrd (1993)
On the Road--Lee Roy Parnell (1993)
What's it to You?--Clay Walker (1993)
Reckless--Alabama (1993)
My Baby Loves Me--Martina McBride (1993)
Someplace Far Away--Hal Ketchum (1993)
Wild One--Faith Hill (1994)

I Just Wanted You to Know--Mark Chesnutt (1994)
He Thinks He'll Keep Her--Mary Chapin Carpenter (1994)
Hey Cinderella--Suzy Bogguss (1994)
Live Until I Die--Clay Walker (1994)
Oh What a Crying Shame--The Mavericks (1994)
Words by Heart--Billy Ray Cyrus (1994)

Holding My Own--Lee Roy Parnell (1994)
Unbreakable Heart--Carlene Carter (1994)
Little Rock--Collin Raye (1994)
I Wish I Didn't Know Now--Toby Keith (1994)
How Can I Help You Say Goodbye?--Patty Loveless (1994)
I Take My Chances--Mary Chapin Carpenter (1994)
Daddy Never was the Cadillac Kind--Confederate Railroad (1994)

Foolish Pride--Travis Tritt (1994)
Spilled Perfume--Pam Tillis (1994)
The Cheap Seats--Alabama (1994)
Independence Day--Martina McBride (1994)
I Sure Can Smell the Rain--BlackHawk (1994)
She Thinks His Name was John--Reba McEntire (1994)

Calling Baton Rouge--Garth Brooks (1994)
Has Anybody Seen Amy?--John and Audrey Wiggins (1994)
Now I Know--Lari White (1994)
What They're Talking About--Rhett Akins (1994)

Southbound--Sammy Kershaw (1994)
Lipstick Promises--George Ducas (1995)
That's How You Know When You're in Love--Lari White (1995)
House of Cards--Mary Chapin Carpenter (1995)

Cain’s Blood--4-Runner (1995)
My Heart Will Never Know--Clay Walker (1995)
If I Were You--Collin Raye (1995)
That's Just About Right--BlackHawk (1995)

And Still--Reba McEntire (1995)
My Girl Friday--Daron Norwood (1995)
Just My Luck--Kim Richey (1995)
She Can't Love You--Boy Howdy (1995)
In Between Dances--Pam Tillis (1995)
That Ain't My Truck--Rhett Akins (1995)
Dust on the Bottle--David Lee Murphy (1995)
If the World Had a Front Porch--Tracy Lawrence (1995)
Heaven Bound (I’m Ready)--Shenandoah (1995)
Heart Half Empty--Ty Herndon and Stephanie Bentley (1995)
No News--Lonestar (1996)
The River and the Highway--Pam Tillis (1996)
She Said Yes--Rhett Akins (1996)
Miracle Man--Smokin' Armadillos (1996)
Living in a Moment--Ty Herndon (1996)

Home Ain’t Where His Heart is Anymore--Shania Twain (1996)
When Cowboys Didn't Dance--Lonestar (1996)

One Way Ticket--LeAnn Rimes (1996)
King of the World--BlackHawk (1996)
Where Corn Don't Grow--Travis Tritt (1997)

Cold Outside--Big House (1997)
Dark Horse--Mila Mason (1997)
A Dozen Red Roses--Tammy Graham (1997)
Everywhere--Tim McGraw (1997)
The Fool--Lee Ann Womack (1997)
Thank God for Believers--Mark Chesnutt (1997)
One Solitary Tear--Sherrie Austin (1997)
Postmarked Birmingham--BlackHawk (1997)
Bye, Bye--Jo Dee Messina (1998)
Matches--Sammy Kershaw (1998)
Dream Walkin'--Toby Keith (1998)
Innocent Man--Sherrie Austin (1998)
Holes in the Floor of Heaven--Steve Wariner (1998)

Don't Laugh at Me--Mark Wills (1998)
Honkytonk America--Sammy Kershaw (1998)
How Do You Sleep at Night?--Wade Hayes (1998)
I'll Think of a Reason Later--Lee Ann Womack (1999)
Please Remember Me--Tim McGraw (1999)

Fool I’m a Woman--Sara Evans (1999)
Give My Heart to You--Billy Ray Cyrus (1999)
Your Own Little Corner of My Heart--BlackHawk (1999)
You Were Mine--Dixie Chicks (1999)
Something Like That--Tim McGraw (1999)
He Didn't Have to Be--Brad Paisley (1999)
Smoke Rings in the Dark--Gary Allan (1999)
Goodbye Earl--Dixie Chicks (2000)
I Hope You Dance--Lee Ann Womack (2000)

Feels Like Love--Vince Gill (2000)
The Little Girl--John Michael Montgomery (2000)
Just Another Day in Paradise--Phil Vassar (2000)
The Hunger--Steve Holy (2001)
Go Back--Chalee Tennison (2001)
Why They Call it Falling--Lee Ann Womack (2001)

Rose Bouquet--Phil Vassar (2001)
There You'll Be--Faith Hill (2001)
Only in America--Brooks and Dunn (2001)
Austin--Blake Shelton (2001) 
No Fear--Terri Clark (2001)
Real Life--Jeff Carson (2001)
Riding with Private Malone--David Ball (2002)
That's When I Love You--Phil Vassar (2002)
Ol' Red--Blake Shelton (2002)
The Impossible--Joe Nichols (2002)
Life Happened--Tammy Cochran (2002)
Waitin' on Joe--Steve Azar (2002)
When You Think of Me--Mark Wills (2003)
Brokenheartsville--Joe Nichols (2003)
Three Wooden Crosses--Randy Travis (2003)
One Last Time--Dusty Drake (2003)
What Was I Thinking--Dierks Bentley (2003)

Long Black Train--Josh Turner (2003)
On Your Way Home--Patty Loveless (2003)
Texas Plates--Kellie Coffey (2004)
Whiskey Lullaby--Brad Paisley and Allison Krauss (2004)
Me and Emily--Rachel Proctor (2004)
Trip Around the Sun--Jimmy Buffett and Martina McBride (2004)
My Better Half--Keith Urban (2005)
If Heaven--Andy Griggs (2005)
Don't Ask Me How I Know--Bobby Pinson (2005)

He Oughta Know That by Now--Lee Ann Womack (2005)
Kerosene--Miranda Lambert (2006)
What Hurts Most--Rascal Flatts (2006)
I Loved Her First--Heartland (2006)
I Keep Comin' Back--Josh Gracin (2007)
I Don't Want To--Ashley Monroe (2007)

Love Lives On--Mallary Hope (2008)

Man of the House--Chuck Wicks (2009)
Need You Now--Lady Antebellum (2009)
Till Summer Comes Around--Keith Urban (2009)
American Honey--Lady Antebellum (2010)
Raymond--Brett Eldredge (2010)
Guinevere--Eli Young Band (2010)
Turning Home--David Nail (2010)
From a Table Away--Sunny Sweeney (2011)

Back to December-Taylor Swift (2011)
Let it Rain--David Nail (2011)
I Don't Want This Night to End--Luke Bryan (2011)
Amen--Eden's Edge (2011)
The Sound of a Million Dreams--David Nail (2012)
Tornado--Little Big Town (2013)
Mama’s Broken Heart--Miranda Lambert (2013)

Blowin’ Smoke-Kacey Musgraves (2013)
Sunny and 75--Joe Nichols (2013)
Drunk on a Plane--Dierks Bentley (2014)

What We Ain’t Got-Jake Owen (2014)

Biscuits-Kacey Musgraves (2015)
Song for Another Time--Old Dominion (2016)

So what's on the list....

Original Songs Released As Singles That Charted--Some were big hits, others were flops.  But they all hit the charts.  And there are plenty of outstanding remakes of classics that deserve a separate list, but even though I prefer Lonestar's 2003 version of "Walking in Memphis" to any other version I've heard, it wasn't their song and shouldn't be held up as such.  There are exceptions to the rule though.  If an artist turned an otherwise low-profile song from another performer into their own hit, and managed to own the song in a way that virtually nobody knows the song wasn't theirs originally--such as Willie's "The City of New Orleans"--then I'll put them on the list.

Mid-90s Awesomeness Abounds--Most people are sentimentally partial to the music of their most formative years and I'm no exception.  But it's not just nostalgia in play here.  The first half of the 1990s was a truly stunning era in country music with an exciting wave of new artists making the charts bringing fresh sounds and a different style of lyrics to country music.  At the time, the old-timers grunted about country music's transformation into something they didn't recognize, but I think now most people have come to appreciate what a great and diverse period in country music it was before the pretty boys in cowboy hats singing "sensitive" love songs took over in the second half of the 90s and the creative momentum came to an abrupt halt.

Sad And Depressing--All too often, critics of country music wrinkle their noses at the format because "it's just too depressing".  There's very little in the way of songs of that caliber on the country music airwaves in the 2010s, but I wish there was!  I have the utmost respect for the country music that successfully takes me to an emotional ditch, either with straight up tear-in-my-beer depressing lyrics or story songs with emotionally charged lyrical and vocal flourishes.  My list is packed with these types of songs.

Songs That Are Unique in Sound or Lyric--I've always sought out songs that are a little outside the box and even push the envelope a little bit.  This can go too far as I'm not likely to go for the new wave of autotuned EDM rock, hip-hop, and beatboxing fused into modern country, but I loved how country embraced rock as a natural component of its sound with escalating frequency in the 1980s and 1990s, along with saxophones and synthesizers.  I love the traditional sound of country music, but so long as a good song kept one foot planted in that traditional sound, I'm more than happy to entertain and reward some experimentation. Likewise with the lyrics.  If the lyrics say something different or controversial and say it well, I'm more often than not a fan.


What's Not on the List.....

Really Old Stuff--I've long said that the golden era for country for me was 1975-1995, and I added up to see that 188 of these 300 songs come from that timespan.  There was plenty to like from the preceding generation of country, but not a ton to love.  I like to think I've given the original era of commercial country music a fair shake and, while there are certainly some diamonds to be found, the production values generally aren't high enough for me to be viscerally drawn to.  And a fair percentage of the music is just straight-up dreadful, even worse than the laughably shallow Thug Country era we're suffering through today.  But even among what was considered the best music of the era, I like Hank Williams and Patsy Cline, but the sound and the lyrics are just intangibly dated for me in a way that I can't qualify them among the ranks of my all-time favorites.  I'm sure if I was a generation older, I'd have a completely different viewpoint.

The New Stuff--There are a number of issues in play as to why this list has so few entries from songs from the 2010s.  The primary problem is that the music has gone downhill in a big way.  The lyrics are shallower, the artists are less distinguished, and the musical arrangements are far less sophisticated.  Last night I listened to a dozen or so songs from the early-to-mid-90s on this list that I hadn't heard for a while and that really provided a reinforcement to what comparative thin gruel you get listening to an hour's worth of today's country radio. Beyond that, I've always found it hard to judge contemporary songs with "the classics" and have always felt I need five years removal from a song's chart reign to appreciate its worthiness.  Even by that standard, I don't suspect we're looking at a future groundswell of songs from the 2010s saturating this list, but perhaps in time, more songs will hold up well enough to seem worthy of the greats of yore.

A Lot of Beloved Artists Got Short-Changed--When compiling a list of this nature, it's always amazing how quickly you get to the magic number and realize you're out of slots.  There are a number of singers like Tanya Tucker, Mark Chesnutt, and Waylon Jennings I've always held up as above-average crooners with above-average material, but in all three cases, only two of their songs qualified for this list.  If I added 100 songs to the list, all three would likely get more than one new entry each, but that's just the way the cookie crumbled.  Other very high profile artists had their share of good material over their long careers and will turn the sound up on the radio when they come on, but there was little from Alan Jackson or Vince Gill that I absolutely LOVED.  Some artists you just don't connect that closely with.  Ditto for the likes of George Strait, Kenny Chesney, and Carrie Underwood, superstars I've never fully connected with.  I don't dislike them per se, but even after combined decades worth of collective songs from the three of them, there's little that makes me jump out of my skin.