| Year | Artist | Work | Nominees |
| 1965 | Roger Miller | "Dang Me" | - Bobby Bare – "Four Strong Winds"
- Johnny Cash – "I Walk the Line"
- George Hamilton IV – Fort Worth, Dallas or Houston
- Sonny James – You're the Only World I Know
- Hank Locklin – Hank Locklin Sings Hank Williams
- Buck Owens – "My Heart Skips a Beat"
|
| 1966 | Roger Miller | "King of the Road" | - Eddy Arnold – "Make the World Go Away"
- Bobby Bare – "Talk Me Some Sense"
- Carl Belew – "Crystal Chandelier"
- Jim Reeves – "Is It Really Over?"
|
| 1967 | David Houston | "Almost Persuaded" | - Ben Colder – "Almost Persuaded No. 2"
- Jack Greene – "There Goes My Everything"
- Charley Pride – "Just Between You and Me"
- Jim Reeves – "Distant Drums"
|
| 1968 | Glen Campbell | "Gentle on My Mind" | - Jim Ed Brown – "Pop a Top"
- Jack Greene – "All the Time"
- Charley Pride – "Does My Ring Hurt Your Finger"
- Porter Wagoner – "The Cold Hard Facts of Life"
|
| 1969 | Johnny Cash | "Folsom Prison Blues" | - Glen Campbell – "I Wanna Live"
- Henson Cargill – "Skip a Rope"
- Roger Miller – "Little Green Apples"
- Porter Wagoner – "The Carroll County Accident"
|
| 1970 | Johnny Cash | "A Boy Named Sue" | - Clay Hart – "Spring"
- Bobby Lewis – "From Heaven to Heartache"
- Charley Pride – "All I Have to Offer You (Is Me)"
- Jerry Reed – "Are You from Dixie ('Cause I'm from Dixie Too)"
|
| 1971 | Ray Price | "For the Good Times" | - Johnny Cash – "Sunday Mornin' Comin' Down"
- Merle Haggard – Okie from Muskogee
- Charley Pride – Charley Pride's 10th Album
- Jerry Reed – "Amos Moses"
|
| 1972 | Jerry Reed | "When You're Hot, You're Hot" | - Freddie Hart – "Easy Loving"
- Johnny Paycheck – "She's All I Got"
- Ray Price – "I Won't Mention It Again"
- Charley Pride – "Kiss an Angel Good Mornin'"
|
| 1973 | Charley Pride | Charley Pride Sings Heart Songs | |
| 1974 | Charlie Rich | "Behind Closed Doors" | - Tom T. Hall – "(Old Dogs, Children and) Watermelon Wine"
- Kris Kristofferson – "Why Me"
- Charley Pride – "Amazing Love"
- Johnny Russell – "Rednecks, White Socks and Blue Ribbon Beer"
|
| 1975 | Ronnie Milsap | "Please Don't Tell Me How the Story Ends" | |
| 1976 | Willie Nelson | "Blue Eyes Crying in the Rain" | - Glen Campbell – "Country Boy (You Got Your Feet in L.A.)"
- John Denver – "Thank God I'm a Country Boy"
- Freddy Fender – "Before the Next Teardrop Falls"
- Waylon Jennings – "Are You Sure Hank Done It This Way"
- Ray Stevens – "Misty"
|
| 1977 | Ronnie Milsap | "(I'm A) Stand by My Woman Man" | - Mac Davis – "Forever Lovers"
- Larry Gatlin – "Broken Lady"
- Waylon Jennings – "Are You Ready for the Country"
- Willie Nelson – "I'd Have to Be Crazy"
|
| 1978 | Kenny Rogers | "Lucille" | - Larry Gatlin – "I Don't Wanna Cry"
- Waylon Jennings – "Luckenbach, Texas (Back to the Basics of Love)"
- Ronnie Milsap – "It Was Almost Like a Song"
- Jerry Jeff Walker – "Mr. Bojangles"
|
| 1979 | Willie Nelson | "Georgia on My Mind" | - Waylon Jennings – "I've Always Been Crazy"
- Ronnie Milsap – "Let's Take the Long Way Around the World"
- Johnny Paycheck – "Take This Job and Shove It"
- Elvis Presley – "Softly, as I Leave You"
- Kenny Rogers – "Love or Something Like It"
|
| 1980 | Kenny Rogers | "The Gambler" | - Willie Nelson – "Whiskey River"
- Charley Pride – "Burgers and Fries/When I Stop Leavin' (I'll Be Gone)"
- Eddie Rabbitt – "Every Which Way but Loose"
- Hank Williams Jr. – "Family Tradition"
|
| 1981 | George Jones | "He Stopped Loving Her Today" | - George Burns – "I Wish I Was Eighteen Again"
- Johnny Lee – "Lookin' for Love"
- Willie Nelson – "On the Road Again"
- Eddie Rabbitt – "Drivin' My Life Away"
|
| 1982 | Ronnie Milsap | "(There's) No Gettin' Over Me" | |
| 1983 | Willie Nelson | "Always on My Mind" | - Ronnie Milsap – "He Got You"
- Jerry Reed – "She Got the Goldmine (I Got the Shaft)"
- Kenny Rogers – "Love Will Turn You Around"
- Ricky Skaggs – "Heartbroke"
|
| 1984 | Lee Greenwood | "I.O.U." | - Ray Charles – "Born to Love Me"
- Earl Thomas Conley – "Holding Her and Loving You"
- Vern Gosdin – "If You're Gonna Do Me Wrong (Do It Right)"
- Ronnie Milsap – "Stranger in My House"
- Kenny Rogers – "All My Life"
|
| 1985 | Merle Haggard | "That's the Way Love Goes" | - Lee Greenwood – "God Bless the USA"
- Willie Nelson – "City of New Orleans"
- Ricky Skaggs – "Country Boy"
- Hank Williams Jr. – "All My Rowdy Friends Are Coming Over Tonight"
|
| 1986 | Ronnie Milsap | "Lost in the Fifties Tonight (In the Still of the Night)" | - Lee Greenwood – "I Don't Mind the Thorns (If You're the Rose)"
- Mel McDaniel – "Baby's Got Her Blue Jeans On"
- Willie Nelson – "Forgiving You Was Easy"
- Ricky Skaggs – "You Make Me Feel Like a Man"
|
| 1987 | Ronnie Milsap | Lost in the Fifties Tonight | |
| 1988 | Randy Travis | Always & Forever | |
| 1989 | Randy Travis | Old 8x10 | - Rodney Crowell – Diamonds & Dirt
- Lyle Lovett – "Pontiac"
- Dan Seals – "Addicted"
- Dwight Yoakam – Buenas Noches from a Lonely Room
|
| 1990 | Lyle Lovett | Lyle Lovett and His Large Band | - Clint Black – "Killin' Time"
- Rodney Crowell – "After All This Time"
- Randy Travis – "It's Just a Matter of Time"
- Keith Whitley – "I'm No Stranger to the Rain"
|
| 1991 | Vince Gill | "When I Call Your Name" | - Garth Brooks – "Friends In Low Places"
- Doug Stone – "I'd Be Better Off (In a Pine Box)"
- Randy Travis – "Hard Rock Bottom of Your Heart"
- Dwight Yoakam – "Turn It On, Turn It Up, Turn Me Loose"
|
| 1992 | Garth Brooks | Ropin' the Wind | - Billy Dean – "Somewhere in My Broken Heart"
- Vince Gill – Pocket Full of Gold
- Alan Jackson – "Don't Rock the Jukebox"
- Travis Tritt – "Here's a Quarter (Call Someone Who Cares)"
|
| 1993 | Vince Gill | "I Still Believe in You" | - Garth Brooks – The Chase
- Billy Ray Cyrus – "Achy Breaky Heart"
- Randy Travis – "Better Class of Losers"
- Travis Tritt – "Lord Have Mercy on the Working Man"
|
| 1994 | Dwight Yoakam | "Ain't That Lonely Yet" | - Garth Brooks – "Ain't Goin' Down ('Til the Sun Comes Up)"
- Alan Jackson – "Chattahoochee"
- George Jones – "I Don't Need Your Rockin' Chair"
- Aaron Neville – "The Grand Tour"
|
| 1995 | Vince Gill | "When Love Finds You" | - David Ball – "Thinkin' Problem"
- John Berry – "Your Love Amazes Me"
- John Michael Montgomery – "I Swear"
- Dwight Yoakam – "Pocket of a Clown"
|
| 1996 | Vince Gill | "Go Rest High on That Mountain" | - John Berry – "Standing on the Edge of Goodbye"
- Alan Jackson – "Gone Country"
- John Michael Montgomery – "I Can Love You Like That"
- Dwight Yoakam – "A Thousand Miles from Nowhere"
|
| 1997 | Vince Gill | "Worlds Apart" | - Clint Black – "Like the Rain"
- Junior Brown – "My Wife Thinks You're Dead"
- Lyle Lovett – "Private Conversation"
- Dwight Yoakam – "Nothing"
|
| 1998 | Vince Gill | "Pretty Little Adriana" | - Clint Black – "Something That We Do"
- Johnny Cash – "Rusty Cage"
- Willie Nelson – "Peach Pickin' Time Down In Georgia"
- George Strait – "Carrying Your Love with Me"
|
| 1999 | Vince Gill | "If You Ever Have Forever in Mind" | - Clint Black – "Nothin' but the Taillights"
- Garth Brooks – "To Make You Feel My Love"
- Steve Wariner – "Holes in the Floor of Heaven"
|
| 2000 | George Jones | "Choices" | - Vince Gill – "Don't Come Cryin' to Me"
- Lyle Lovett – "That's Right (You're Not from Texas)"
- Tim McGraw – "Please Remember Me"
- Dwight Yoakam – "Crazy Little Thing Called Love"
|
| 2001 | Johnny Cash | "Solitary Man" | - Vince Gill – "Feels Like Love"
- Billy Gilman – "One Voice"
- Tim McGraw – "My Best Friend"
- Dwight Yoakam – "A Thousand Miles from Nowhere (live)"
|
| 2002 | Ralph Stanley | "O Death" | - Ryan Adams – "Lovesick Blues"
- Johnny Cash – "I Dreamed About Mama Last Night"
- Lyle Lovett – "San Antonio Girl"
- Tim McGraw – "Grown Men Don't Cry"
- Willie Nelson – "Maria (Shut Up and Kiss Me)"
|
| 2003 | Johnny Cash | "Give My Love to Rose" | - Pat Green – "Three Days"
- Alan Jackson – "Where Were You (When the World Stopped Turning)"
- Joe Nichols – "The Impossible"
- Brad Paisley – "I'm Gonna Miss Her"
|
| 2004 | Vince Gill | "Next Big Thing" | - Ray Benson – "Annabelle"
- Lyle Lovett – "My Baby Don't Tolerate"
- Tim McGraw – "She's My Kind of Rain"
- Joe Nichols – "Brokenheartsville"
- Randy Travis – "Three Wooden Crosses"
|
| 2005 | Tim McGraw | "Live Like You Were Dying" | |
| 2006 | Keith Urban | "You'll Think of Me" | - George Jones – "Funny How Time Slips Away"
- Toby Keith – "As Good as I Once Was"
- Delbert McClinton – "Midnight Communion"
- Willie Nelson – "Good Ol' Boys"
- Brad Paisley – "Alcohol"
|
| 2007 | Vince Gill | "The Reason Why" | - Dierks Bentley – "Every Mile a Memory"
- George Strait – "The Seashores of Old Mexico"
- Josh Turner – "Would You Go with Me"
- Keith Urban – "Once in a Lifetime"
|
| 2008 | Keith Urban | "Stupid Boy" | - Dierks Bentley – "Long Trip Alone"
- Alan Jackson – "A Woman's Love"
- Tim McGraw – "If You're Reading This"
- George Strait – "Give It Away"
|
| 2009 | Brad Paisley | "Letter to Me" | - Trace Adkins – "You're Gonna Miss This"
- Jamey Johnson – "In Color"
- James Otto – "Just Got Started Lovin' You"
- George Strait – "Troubadour"
|
| 2010 | Keith Urban | "Sweet Thing" | - Trace Adkins – "All I Ask for Anymore"
- Billy Currington – "People Are Crazy"
- Jamey Johnson – "High Cost of Living"
- George Strait – "Living for the Night"
|
| 2011 | Keith Urban | "'Til Summer Comes Around" | - Jamey Johnson – "Macon"
- Toby Keith – "Cryin' for Me (Wayman's Sang)"
- David Nail – "Turning Home"
- Chris Young – "Gettin' You Home (The Black Dress Sang)"
|
