Grammy Flashback: Best Male Country Vocal Performance

Updated for 2008

While the Grammys have honored country music from the very first ceremony in 1959, they did not begin honoring by gender until 1965, when the country categories were expanded along with the other genre categories. We’ll take a look back at the early country category after recapping all of the modern categories in a later Grammy Flashback.

In a continuation of our Grammy Flashback series, here is a rundown of the Best Country Vocal Performance, Male category. It was first awarded in 1965, an included single competing with albums until the Best Country Album category was added in 1995. When an album is nominated, it is in italics, and a single track is in quotation marks.

As usual, we start with a look at this year’s nominees and work our way back.


  • Dierks Bentley, “Long Trip Alone”
  • Alan Jackson, “A Woman’s Love”
  • Tim McGraw, “If You’re Reading This”
  • George Strait, “Give it Away”
  • Keith Urban, “Stupid Boy”

This is the most mainstream lineup this category has seen in eons. The last time that all five nominees in this race were all top ten hits was 1995. Frequent winner Vince Gill is absent from the race this year. Of the remaining nominees, two have never won (Alan Jackson, George Strait) and two have won just once (Keith Urban, Tim McGraw.) It’s worth noting that the Bentley, McGraw and Strait tracks also scored nods for Best Country Song, which may give them an edge. I’m guessing that Tim McGraw’s popularity with NARAS and the emotional impact of “If You’re Reading This” will carry him to victory, after confused voters scan repeatedly for Vince Gill’s name and finally realize he’s not in the running.


  • Dierks Bentley, “Every Mile a Memory”
  • Vince Gill, “The Reason Why”
  • George Strait, “The Seashores of Old Mexico”
  • Josh Turner, “Would You Go With Me”
  • Keith Urban, “Once in a Lifetime”

Vince Gill returned to win in this category for a ninth time with “The Reason Why.” Not only is he, by far, the most honored artist in this category, his wins here account for half of the eighteen Grammys currently on his mantle.


  • 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”
  • Keith Urban, “You’ll Think of Me”

Urban’s biggest and probably best hit launched his second album to triple platinum and established him as a crossover artist. He gave a killer performance of the song on the show. The only mystery to me is how it was nominated two years in a row.


  • Johnny Cash, “Engine One-Forty-Three”
  • Lyle Lovett, “In My Own Mind”
  • Tim McGraw, “Live Like You Were Dying”
  • Willie Nelson, “You Are My Flower”
  • Keith Urban, “You’ll Think of Me”

McGraw’s biggest hit won him his first Grammy in this category. His other wins have been for his collaborations with wife Faith Hill.


  • Ray Benson, “Annabelle”
  • Vince Gill, “Next Big Thing”
  • Lyle Lovett, “My Baby Don’t Tolerate”
  • Tim McGraw, “She’s My Kind of Rain”
  • Joe Nichols, “Brokenheartsville”
  • Randy Travis, “Three Wooden Crosses”

My vote would’ve gone to Randy Travis, who was nominated with his finest single in years, but Gill remained the voter’s favorite. Travis did, however, win two Grammys in the gospel categories, this and the previous year.


  • 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 (The Fishin’ Song)”

I fully expected Jackson to win here, but his understated performance lost out to one of the only gems on Cash’s fourth American project. Voters wisely acknowledged Jackson in the Best Country Song category, at least.


  • 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)”
  • Ralph Stanley, “O Death”

This was one of those times where you are just thankful the Grammys exist. Stanley’s “O Death” was the most powerful track on the storied O Brother soundtrack, but without a video, it was only known to those people who listened to the album all the way through. That NARAS had the good taste to both nominate it and vote it the winner is one of their best country victories ever.


  • 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” (Acoustic)

Grammy voters listening to this category couldn’t get a more drastic difference in male voices than the withered-with-age Cash and the prepubescent Gilman. “Solitary Man” was one of the most inspired covers Cash ever did with Rick Rubin, and it deserved the gold.


  • Vince Gill, “Don’t Come Cryin’ to Me”
  • George Jones, “Choices”
  • Lyle Lovett, “That’s Right (You’re Not From Texas)”
  • Tim McGraw, “Please Remember Me”
  • Dwight Yoakam, “Crazy Little Thing Called Love”

Jones won his first Grammy in twenty years for his harrowing “Choices”, which became oddly prescient as it was released in the aftermath of his near-death in an alcohol-related car crash.




  • Clint Black, “Nothin’ But the Taillights”
  • Garth Brooks, “To Make You Feel My Love”
  • Vince Gill, “If You Ever Have Forever in Mind”
  • Steve Wariner, “Holes in the Floor of Heaven”

Gill won a record-setting fifth year in a row, a domination that no country category has seen before or since. After being nominated for three years in a row, Black hasn’t been cited since.


  • Clint Black, “Something That We Do”
  • Johnny Cash, “Rusty Cage”
  • Vince Gill, “Pretty Little Adriana”
  • Willie Nelson, “Peach Pickin’ Time Down in Georgia”
  • George Strait, “Carrying Your Love With Me”

NARAS was so sure that Strait would get his first Grammy that they invited him to perform on the show, and he agreed. Unfortunately, sickness required Vince Gill to fill in for him, and Gill won.


  • Clint Black, “Like the Rain”
  • Junior Brown, “My Wife Thinks You’re Dead”
  • Vince Gill, “Worlds Apart”
  • Lyle Lovett, “Private Conversation”
  • Dwight Yoakam, “Nothing”

A strong lineup, the Grammy went to my favorite Vince Gill single to date; he also picked up a collaboration award the same evening.


  • John Berry, “Standing on the Edge of Goodbye”
  • Vince Gill, “Go Rest High on That Mountain”
  • Alan Jackson, “Gone Country”
  • John Michael Montgomery, “I Can Love You Like That”
  • Dwight Yoakam, “A Thousand Miles From Nowhere (Live)”

Strong entries from Jackson and Berry, plus a well-known song that was a hit for All 4 One after topping the charts for Montgomery, couldn’t stop Grammy powerhourse Gill from winning again.


  • David Ball, “Thinkin’ Problem”
  • John Berry, “Your Love Amazes Me”
  • Vince Gill, “When Love Finds You”
  • John Michael Montgomery, “I Swear”
  • Dwight Yoakam, “Pocket of a Clown”

The Grammys were getting dull, with Gill winning his third in this category the same evening that Mary Chapin Carpenter picked up her fourth in the Female category.


  • 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”
  • Dwight Yoakam, “Ain’t That Lonely Yet”

An astonished Yoakam accepted his Grammy on the live telecast, his only victory in this category in ten nominations.


  • Garth Brooks, The Chase
  • Billy Ray Cyrus, “Achy Breaky Heart”
  • Vince Gill, I Still Believe in You
  • Randy Travis, “Better Class of Losers”
  • Travis Tritt, “Lord Have Mercy on the Working Man”

Gill was the last artist to win this category for a full-length album. The same set won Album of the Year at the CMA’s.


  • 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)”

Despite breaking records, Brooks was left out of the big categories at the 1992 Grammys. He did win for his only nomination that evening, over a field that shows just how excellent commercial country was getting in the early nineties.


  • Garth Brooks, “Friends in Low Places”
  • Vince Gill, “When I Call Your Name”
  • 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”

Gill wins. Get used to it.


  • Clint Black, Killin’ Time
  • Rodney Crowell, “After All This Time”
  • Lyle Lovett, Lyle Lovett & His Large Band
  • Randy Travis, “It’s Just a Matter of Time”
  • Keith Whitley, “I’m No Stranger to the Rain”

Lovett is another frequent nominee in this category who has only actually won once. It pains me to see that the excellent work by Black, Crowell and Whitley was overlooked, but the Lovett album features his cover of “Stand By Your Man”, so I’ll let it go.



  • Rodney Crowell, Diamonds and Dirt
  • Lyle Lovett, Pontiac
  • Dan Seals, “Addicted”
  • Randy Travis, Old 8×10
  • Dwight Yoakam, Buenas Noches From a Lonely Room

Not one of Travis’ better albums, but who doesn’t enjoy “Deeper Than the Holler”? Fun fact: Seals’ only nomination in this category is for a Cheryl Wheeler cover.



  • Steve Earle, Exit O
  • George Strait, “All My Ex’s Live in Texas”
  • Randy Travis, Always & Forever
  • Hank Williams, Jr., Born to Boogie
  • Dwight Yoakam, Hillbilly Deluxe

Grammy partially redeems itself for overlooking Travis, Earle and Yoakam the previous year; Travis’ second album is almost good as his legendary debut.


  • Steve Earle, Guitar Town
  • Ronnie Milsap, Lost in the Fifties Tonight
  • Randy Travis, “Diggin’ Up Bones”
  • Hank Williams, Jr., “Ain’t Misbehavin’”
  • Dwight Yoakam, Guitars, Cadillacs, Etc., Etc.

Three of country’s most artistically significant newcomers lose to the album home of the previous year’s winning entry. The most charitable explanation I can come up with is they split the vote.


  • Lee Greenwood, “I Don’t Mind the Thorns (If You’re the Rose)”
  • Mel McDaniel, “Baby’s Got Her Blue Jeans On”
  • Ronnie Milsap, “Lost in the Fifties Tonight”
  • Willie Nelson, “Loving You Was Easy”
  • Ricky Skaggs, “You Make Me Feel Like a Man”

Against this field, Milsap’s win is a lot less painful, but I’ve just never understood the appeal of that particular song.



  • Lee Greenwood, “God Bless the U.S.A.”
  • Merle Haggard, “That’s the Way Love Goes”
  • Willie Nelson, “City of New Orleans”
  • Ricky Skaggs, Country Boy
  • Hank Williams, Jr., “All My Rowdy Friends are Coming Over Tonight”

Haggard finally wins in this category, with one of his very best ballads.



  • 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)”
  • Lee Greenwood, “I.O.U.”
  • Ronnie Milsap, “Stranger in My House”
  • Kenny Rogers, “All My Life”

As Greenwood songs go, not too bad. As album covers go, by blog has been sullied. I’d have gone with Gosdin.



  • Ronnie Milsap, “He Got You”
  • Willie Nelson, “Always On My Mind”
  • Jerry Reed, “She Got the Goldmine (I Got the Shaft)”
  • Kenny Rogers, “Love Will Turn You Around”
  • Ricky Skaggs, “Heartbroke”

I friggin’ love the Reed track, but Nelson’s performance is timeless, a high water mark in his storied career.



  • John Anderson, “I’m Just an Old Chunk of Coal”
  • George Jones, “Still Doin’ Time”
  • Ronnie Milsap, “(There’s No) Gettin’ Over Me”
  • Willie Nelson, Somewhere Over the Rainbow
  • Eddie Rabbitt, “Step by Step”

Milsap again. A shame when they could’ve gone for Jones again or newcomer Anderson.



  • George Burns, “I Wish I Was Eighteen Again”
  • George Jones, “He Stopped Loving Her Today”
  • Johnny Lee, “Lookin’ For Love”
  • Willie Nelson, “On the Road Again”
  • Eddie Rabbitt, “Drivin’ My Life Away”

Well, obviously.



  • Willie Nelson, “Whiskey River”
  • Charley Pride, Burgers & Fries
  • Eddie Rabbitt, “Every Which Way But Loose”
  • Kenny Rogers, “The Gambler”
  • Hank Williams, Jr., Family Tradition

Rogers has won for both of his signature songs in this category. This is the only one that’s led to T.V. movies.



  • Waylon Jennings, I’ve Always Been Crazy
  • Ronnie Milsap, “Let’s Take the Long Way Around the World”
  • Willie Nelson, “Georgia On My Mind”
  • Elvis Presley, “Softly As I Leave You”
  • Johnny Pacycheck, “Take This Job and Shove It”
  • Kenny Rogers, Love or Something Like It

Nelson’s biggest-selling album Stardust gets its due as the Grammy goes to one of the album’s highlights.



  • Larry Gatlin, “I Don’t Wanna Cry”
  • Waylon Jennings, “Luckenbach, Texas”
  • Ronnie Milsap, “It Was Almost Like a Song”
  • Kenny Rogers, “Lucille”
  • Jerry Jeff Walker, “Mr. Bojangles”

The Rogers hit that hasn’t led to T.V. movies, but is responsible for a hell of a lot of drunken sing-a-longs.



  • Mac Davis, Forever Lovers
  • Larry Gatlin, “Broken Lady”
  • Waylon Jennings, Are You Ready For the Country
  • Ronnie Milsap, “(I’m a) Stand By My Woman Man”
  • Willie Nelson, “I’d Have to Be Crazy”

Near-sighted Grammy voters meant to check off Jennings, but scribbled in the wrong box.



  • Glen Campbell, “Country Boy (You’ve 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”
  • Willie Nelson, “Blue Eyes Crying in the Rain”

Even classics by Fender and Jennings can’t touch the Nelson masterpiece.



  • Glen Campbell, “Bonaparte’s Retreat”
  • Roy Clark, The Entertainer
  • Waylon Jennings, “I’m a Ramblin’ Man”
  • Ronnie Milsap, “Please Don’t Tell Me How the Story Ends”
  • Charley Pride, Country Feelin’

Covering Kristofferson is a good way to get a Grammy. Just ask Ray Price and Sammi Smith.



  • Tom T. Hall, “Old Dogs, Children and Watermelon Wine”
  • Kris Kristofferson, “Why Me”
  • Charley Pride, “Amazing Love”
  • Charlie Rich, “Behind Closed Doors”
  • Johnny Russell, “Rednecks, White Socks and Blue Ribbon Beer”

Of course, Kristofferson recording his own work didn’t lead to a Grammy. In another year, it might have, but Rich is the stuff of legend here.


  • Merle Haggard, “It’s Not Love (But it’s Not Bad)
  • Waylon Jennings, “Good Hearted Woman”
  • Jerry Lee Lewis, “Chantilly Lace”
  • Charley Pride, Charley Pride Sings Heart Songs
  • Charlie Rich, “I Take it On Home”

The album home of “Kiss an Angel Good Morning” get the Grammy that the single lost the previous year.



  • 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 Morning”
  • Jerry Reed, “When You’re Hot (You’re Hot)”

Again, I friggin’ love the Reed single. I’m glad it won, though all five nominees were just as worthy.



  • Johnny Cash, “Sunday Morning Coming Down”
  • Merle Haggard, Okie From Muskogee
  • Charley Pride, Charley Pride’s 10th Album
  • Ray Price, “For the Good Times”
  • Jerry Reed, “Amos Moses”

The other way to lose a Grammy with a Kristofferson song? Be nominated against another Kristofferson song! In another rock-solid set of nominees, Price’s classic rendition of “For the Good Times” takes the gold, even though Cash had won the previous two years.



  • 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”

I spent many years wondering what was being bleeped in “A Boy Named Sue.” I had imagined something filthier, but it’s just “I’m the son of a bitch that named you Sue.”



  • Glen Campbell, “I Wanna Live”
  • Henson Cargill, “Skip a Rope”
  • Johnny Cash, “Folsom Prison Blues (Live)”
  • Roger Miller, “Little Green Apples”
  • Porter Wagoner, “The Carroll County Accident”

It was already one of his best songs, but performed live for the inmates of Folsom Prison, it’s mind-bogglingly good.



  • Jim Ed Brown, “Pop a Top”
  • Glen Campbell, “Gentle On My Mind”
  • Jack Greene, “All the Time”
  • Charley Pride, “Does My Ring Hurt Your Finger”
  • Porter Wagoner, “Cold Hard Facts of Life”

Campbell just doesn’t do it for me. I’d be torn between Jim Ed Brown and Porter Wagoner, but ultimately vote for the latter.



  • Ben Colder, “Almost Persuaded No. 2″
  • Jack Greene, “There Goes My Everything”
  • David Houston, “Almost Persuaded”
  • Charley Pride, “Just Between You and Me”
  • Jim Reeves, “Distant Drums”

The classic anthem for those who almost cheat went all the way at the Grammys, at least.



  • Eddy Arnold, “Make the World Go Away”
  • Bobby Bare, “Talk Me Some Sense”
  • Carl Belew, “Crystal Chandelier”
  • Roger Miller, “King of the Road”
  • Jim Reeves, “Is it Really Over?”

Can’t you hear those sweeping strings and Arnold’s soaring vocals as soon as you look at the words “Make the World Go Away”?



  • 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
  • Roger Miller, “Dang Me”
  • Buck Owens, My Heart Skips a Beat

One of my favorite Miller hits takes the first-ever Grammy in this category.


  1. Grammy voters have made many many errors in this category. Let’s count them off

    1967 was a tossup between “Almost Persuaded” and “There Goes My Everything”
    1972 the Pride, Paycheck and Hart selections all would have been better choices
    1977 mediocre set of selections with Gatlin’s “Broken Lady” the pick of the litter
    1982 should have been a repeat win for the Possum
    1984 I agree – it should have been Gosdin’s year
    1985 The Hag got the Grammy that Johnny Rodriguezz should have been nominated for in 1975. My least favorite Hag recordings. Skaggs should have won
    1987 Travis followed by Earle and Yoakam – an inexplicable Grammy result
    1994 Jones got robbed
    1995 I like Vince Gill but I do not understand the Grammy’s obsession with him – this song was easily the weakest of the nominees
    1997 Junior Brown’s only shot in this category should have netted him the trophy
    1998 How cool would it have been for Willie to pick off the Grammy with a Jimmie Rodgers song? As it was I’d have Strait at 1 & Nelson at 2
    1999 Again Gill wins with the weakest of the nominees. I think Wariner, whom I don’t generally like, should have won this Grammy
    2004 “Brokenheartsville” is the song that will be remebered from this year
    2007 Yet again Gill wins with the weakest song of the bunch – does he have incriminating photos on someone ???
    2008 This year should see a George Strait victory

  2. Vince’s domination make sense when you consider that the Grammy voting bloc is all musicians, recording artists, songwriters and producers. Vince’s ability to be all of those gives him an edge. The big Grammy country winners – Gill, Alison Krauss, Dixie Chicks, Ricky Skaggs, Chet Atkins – all have the multi-layered talent thing going for them.

  3. True enough, but those are extraneous considerations that should have no bearing on the awards – it certainly does not justify giving a weak song or a mediocre album a Grammy – the song or album should be weighed on its own merits – period – and too often the Academy does anything but that

  4. its kidna funny not to see vince in this catagory for once. But considering that he is missing I think the award should go to Dierks or George, Dierks for the mostmemorable performance of a song (although if You’re Reading This is a close second) and George because he has been the most consistant and enjoyable male country artist even after “his time”.

  5. Have to say I think this is George’s year for the Grammy. He is overdue and he really has been on a roll lately at these awards shows.

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