Grammy Flashback: Best Male Country Vocal Performance

Updated for 2009

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. This year, the 45th trophy for Best Male Country Vocal Performance will be awarded.

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, and included singles 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. Be sure to vote in My Kind of Country’s Best Male Country Vocal Performance poll and let your preference for this year’s race be known!

2009

• Trace Adkins, “You’re Gonna Miss This”
• Jamey Johnson, “In Color”
• James Otto, “Just Got Started Lovin’ You”
• Brad Paisley, “Letter to Me”
• George Strait, “Troubadour”

As with the album race, this year’s contenders for Best Male Country Vocal Performance are a combination of unrecognized veterans and promising newcomers. In fact, none of this year’s nominees have won in this category, and only one of them – Brad Paisley – has a Grammy at all.

First, the veterans. Paisley has numerous ACM and CMA victories to his credit, including two each for Male Vocalist.  Although he’s been nominated for this award twice before, this is the first time he’s contended with a cut that can’t be dismissed as a novelty number. The touching self-penned “Letter to Me” is his best shot yet at taking this home.

Trace Adkins has been at this a bit longer than Paisley, but this is his first Grammy nomination. His crossover exposure from Celebrity Apprentice might help him out here, along with the fact that the song was considered strong enough by voters to earn a nomination of its own.

But the real veteran to watch out for is George Strait. After being nominated only twice for this category in the first 25 years of his career, voters have now given him three consecutive nominations. This is one of four nods he’s earned for the 2009 ceremony, and “Troubadour” is essentially the story of his epic career distilled into a radio-length song. It would be the perfect way to honor the man and his music in one fell swoop.

However, there’s a newcomer that might be a Grammy favorite already.  We just haven’t found out yet. Not James Otto, of course, who is nominated for his charming romantic romp “Just Got Started Lovin’ You”, but rather, Jamey Johnson. The recent Nashville Scene critics’ poll further confirmed the depth of his support among tastemakers, and his nominations for Best Country Song and Best Country Album indicate that he’s very much on the academy’s radar. It helps that he has the most substantial track of the five, and it’s the obvious choice for traditionalists, who have little reason to split their votes in this category. If voters aren’t considering legacy when making their selections, he has a great shot at this.

2008

• 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”

The often offbeat Grammy voters have been surprisingly mainstream in this category for the past three years, a trend best exemplified by this lineup, which was the first in more than a decade to feature only top ten radio hits. Tim McGraw and Keith Urban were the only two who had won this before, and it was Urban who emerged victorious. “Stupid Boy” was a highlight of his fourth studio album, and this was the only major award that the impressive collection would win.

2007

• 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 nine of the nineteen Grammys currently on his mantle.

2006

• 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. Toby Keith was a first-time nominee here, and while he publicly groused that the Grammys put too little emphasis on commercial success in picking their nominations, he lost to the only track that was a bigger hit than his own.

2005

• 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.  To the Grammy voters’ credit, they have been reluctant to shower Johnny Cash with posthumous Grammys, so his predicted win here for a mundane effort didn’t come to pass.

2004

• 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.

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 (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, making him one of the few artist-songwriters to sweep the industry songwriting awards with one composition.

2002

• 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, which was a welcome surprise.

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” (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.

2000

• 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 experience in an alcohol-related car crash.

1999

• 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.

1998

• 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 the award, allowing him to acknowledge the memory of the young girl who inspired the song.

1997

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

Amid a strong lineup, the Grammy again went to Vince Gill.   This time around, he won for a tender plea for harmony within families and among all races and creeds.   A very inspiring song that was written while eating grilled cheeseburgers with Bob DiPiero at Rotier’s in Nashville.

1996

• 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. Patty Loveless and Ricky Skaggs provided the soaring harmonies.

1995

• 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.

1994

• 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. It’s also one of the few hits he had that was neither self-written nor a cover of another artist’s hit.

1993

• 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.

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)”

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 in the early nineties.

1991

• 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”

It would eventually become a yearly tradition, but when Vince Gill won his first Grammy, it was after more than a decade in the recording industry.

1990

• 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.  The album includes his cheeky cover of the Tammy Wynette classic “Stand By Your Man.”

1989

• 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”?  Seals’s only nomination in this category is for a song written by popular folk star Cheryl Wheeler, who also penned the Suzy Bogguss hit “Aces.”

1988

• 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.

1987

• 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.

1986

• 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”

Milsap, ever the Grammy favorite, hit the sweet spot of nostalgic voters with this swooning throwback to fifties pop that borrowed heavily from “In the Still of the Night.”

1985

• 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, and with one of his very best ballads.   He would later cover the song with Jewel, back when she was first contemplating making the jump to country music.

1984

• 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”

Lee Greenwood’s triumph here with “I’m Just a Gigolo” “I.O.U.” came just months after being named Male Vocalist at the CMA awards.   Surprisingly, he was not a winner of the Grammy for Best Album Package.

1983

• 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”

Willie Nelson’s career has been one with many zeniths.   Commercially speaking, “Always on My Mind” was the highest one.   It’s no surprise that it earned him a Grammy.

1982

• 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. It was a shame, since they could’ve gone for Jones again or for newcomer John Anderson.

1981

• 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. It’s not only Jones’s biggest hit ever, it’s arguably the greatest country single of all time.

1980

• 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 one that led to several  made-for-television movies.

1979

• 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.

1978

• 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”

This is the signature Rogers hit that hasn’t led to made-for-television movies, but it does boast a singalong chorus.   Who knows how many people have told off Lucille in the past thirty years?

1977

• 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”

Less than a decade after Tammy Wynette won a Grammy for “Stand By Your Man”, Milsap’s male spin on the theme earned him a trophy.

1976

• 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.

1975

• 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.

1974

• 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.

1973

• 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” gets the Grammy that the single lost the previous year.

1972

• 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)”
  

Reed won against a collection of classic recordings.   This was one of those years where a victory by any of the nominees would be justified.

1971

• 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.

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”
  

Cash became the second artist to win this two years in a row.   That both of his victories were recorded live in prison is pretty remarkable in itself.

1969

• 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 after hearing it performed live for the inmates of Folsom Prison, the original recording sounds almost quaint.

1968

• 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”
  

Glen Campbell’s crossover success would help him win several Grammy awards in 1968 and 1969.  Wagoner’s cited here for his best single.

1967

• 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”

David Houston emerged victorious with a classic anthem for those who almost cheat.   Perhaps Colder came in second.

1966

• 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 read the words “Make the World Go Away”?   Anyway,  not only did “King of the Road” win several Grammys in 1966, the parody “Queen of the House” even won the female trophy.

1965

• 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

Miller won the first trophy in this category, one of eleven victories in just two years.