Once again.  I’ve selected the five artists that I believe are most deserving of an Entertainer of the Year nomination.  But first, let’s take a look at last year’s race:

Entertainer of the Year (2009)

• Kenny Chesney
• Brad Paisley
• George Strait
• Taylor Swift
• Keith Urban

Swift was victorious in her first nomination in this category.  She competed against three previous winners:  Kenny Chesney, who has gone 4 for 8 in this category;  Keith Urban, who is 1 for 5; and the incomparable George Strait, who is 2 for 17.  Brad Paisley lost for the fifth year, tying Kenny Rogers for the most nominations without a win.

As the numbers above show, this has been a largely static category for the past ten years.  Only thirteen artists earned nominations from 2000-2009. The CMA noms can be very predictable.

But looking at radio and retail these days, there’s been a big changing of the guard.  I think that this category more than any other should reflect that.  I’m putting my personal tastes aside here, as there are only two artists I list that I actually listen to regularly.

Entertainer of the Year (2010)

The nominees should be:

Lady Antebellum

Their second album has already spent 25 weeks at #1, and “Need You Now” was such a big hit that it’s led to pop airplay for “I Run to You”, the award-winning hit from their debut album.  It would be an early nomination in terms of their career, but Alabama and Dixie Chicks were elevated to this category even faster, so there’s precedent for vocal groups.

Miranda Lambert

She’s always had the critical success, and she’s always sold records.  But she’s selling them a heck of a lot faster these days and radio is suddenly, shockingly, spectacularly on board.  It’s time for the CMA to catch up with the ACM, who have been away ahead in acknowledging this artist.

Taylor Swift

Being nominated the year after winning is not a given, but it’s the norm.  While it was common in the seventies, it’s been very rare in recent years.  Shania Twain (1999) was the last winner to not receive another nomination the following year, with the others being:  Dolly Parton (1978), Mel Tillis (1976), John Denver (1975), and Charlie Rich (1974).

So she’s probably a lock for a nomination, and she deserves one. Though things have been quiet on the Swift front for the past couple of months, she had a massive tour and sold a ton of records during the eligibility period.

Carrie Underwood

She really should be enjoying her third nomination this year, but a (flimsy) case could be made for her not making the ballot in 2008 and 2009. But no nomination this year would be inexcusable. She had a very successful tour, continued to dominate radio, and her third album is quickly approaching double platinum.  At this point, she shouldn’t just get a nomination. She should win.

Zac Brown Band

Their live performances are well-regarded, radio is fully on board, and their first major label album is double platinum.  A case could be made for Brad Paisley getting this spot, but sales of his new album have fallen quite a bit short of previous efforts.  The same goes for other perennial nominees Keith Urban, George Strait, and Kenny Chesney.

So those are my five choices. What are yours?

Where does this leave Crystal Gayle, younger sister of Loretta Lynn and owner of 32 top ten hits, 18 of which went #1? As the first female country artist to sell platinum, her impact was quite big back in the day. But aside from her signature classic “Don’t It Make My Brown Eyes Blue”, her music has been largely forgotten.  Perhaps this is because she peaked during an era that is often looked down upon as too crossover for its own good. Unlike Parton and Cline, there is virtually nothing for traditionalists to celebrate within Gayle’s catalog of hits. But much like Hill and Newton-John, the woman recorded some wonderful songs that deserve rediscovery.  Here are a dozen of the best.

“I’ll Do It All Over Again” from the 1976 album Crystal

Gayle typically avoided purely victim stances in her lyrics. Here, she’s been left but is aware that her heart will mend and that she’ll love again.

“Ready For the Times to Get Better” from the 1976 album Crystal

Country singles recorded in a minor key are quite the rarity, but the arrangement undercuts the misery of the lyric, even as she’s clearly ready to move on to happier times. This just might be her finest moment.

“Don’t It Make My Brown Eyes Blue” from the 1977 album We Must Believe in Magic

This classic won her a Grammy and the first of two CMA Female Vocalist trophies. If the piano sounds familiar, that’s because it’s the same player that powered Charlie Rich’s “Behind Closed Doors” to similar success on both the country and pop charts.

“Talking In Your Sleep” from the 1978 album When I Dream

Proving that her appeal wasn’t limited to one big hit, this hit launched what would become Gayle’s second consecutive platinum album.

“Why Have You Left the One You Left Me For” from the 1978 album When I Dream

Her first really big uptempo hit defied expectations and broke her out of the ballad mold.  It didn’t hurt that it was ridiculously catchy.

“Half the Way” from the 1979 album Miss the Mississippi

Another hook-laden hit, powered by an infectious string section and quite a bit more wailing than she’s usually known for.

“Too Many Lovers” from the 1980 album These Days

What sounds like a quiet bar ballad in the first few seconds soon turns into an uptempo message of caution to women looking for love in all the wrong places.

“You Never Gave Up On Me” from the 1981 album Hollywood, Tennessee

There aren’t too many anniversary songs that essentially say, “Thanks for loving me even when I didn’t love you.”  Romantic songs like to pretend that both partners are equally kind and loving, when that isn’t always the case. I like ones like this more.

“‘Til I Gain Control Again” from the 1982 album True Love

Crystal Gayle was hardly the predictable vehicle for this intricate Rodney Crowell composition that had been previously cut by Emmylou Harris.  Even she didn’t think she could pull it off. Thankfully, producer Jimmy Bowen coaxed her into it, and the result was a #1 hit that was also among her most sophisticated performances.

“Baby, What About You” from the 1982 album True Love

Not much more to say about this one than it’s a slice of pop-country perfection.

“The Sound of Goodbye” from the 1983 album Cage the Songbird

One of Hugh Prestwood’s first great moments as a writer was this hit. Much like his material later pushed Randy Travis into a more ambitious production approach (“Hard Rock Bottom Of Your Heart”), the sonic landscape of this #1 hit pushed Gayle and country radio into far more interesting territory.

“Cry” from the 1986 album Straight to the Heart

Given that she’s in the grand tradition of those Nashville Sound ladies, it’s no surprise that Gayle not only covered Lynn Anderson’s #3 hit effectively, she even took it two slots higher up the chart.

Chesnutt’s greatest commercial and radio successes came early on. His first three studio albums went platinum and his fourth went gold. He’d earn an additional platinum record with a hits collection assembled from those sets.

While he remained a consistent presence on radio for the entire decade, his sales tapered off. His last big hit was his 1999 cover of Aerosmith’s “I Don’t Want to Miss a Thing,” which went to #1. In more recent years, he’s limited his covers to The Marshall Tucker Band and Charlie Rich.

Ten Essential Tracks:

“Too Cold at Home”
from the 1990 album Too Cold at Home

Chesnutt’s first twelve singles reached the top ten, starting with this pure country hit that finds him hiding out in a bar on a sweltering summer day. “It’s too hot to fish, too hot for golf, and too cold at home.”

“Brother Jukebox”
from the 1990 album Too Cold at Home

He’s still at the bar for this hit, his first to top the charts. This time, the woman has left him, and his only family left are the jukebox, wine, freedom, and time.

“I’ll Think of Something”
from the 1992 album Longnecks & Short Stories

A bone-chilling cover of a very old Hank Williams Jr. single. His nuanced vocal digs deeper than Williams did on the 1974 original.

“Bubba Shot the Jukebox”
from the 1992 album Longnecks & Short Stories

This was one of the first singles forced by radio, as unsolicited airplay pushed it on to the charts while MCA was still working “I’ll Think of Something.” Songwriter Dennis Linde also penned Chesnutt’s #1 hit “It Sure is Monday.”

“Almost Goodbye”
from the 1993 album Almost Goodbye

It begins like a domestic epic worthy of George Jones, complete with the swelling of the strings for heightened emotional effect. But cooler heads prevail as they realize how much they’d have to lose if they said the word goodbye. After all, “Sometimes the most important words are the ones that you leave unspoken.”

“I Just Wanted You to Know”
from the 1993 album Almost Goodbye

One side of what must be an incredibly awkward telephone conversation, with the woman’s implied silence at the other end of the line making things just a little more uncomfortable.

“Goin’ Through the Big D”
from the 1994 album What a Way to Live

The nineties equivalent of “She Got the Goldmine (I Got the Shaft.)”

“Trouble”
from the 1995 album Wings

Covering Todd Snider. The coolest thing that Mark Chesnutt has ever done. “A woman like you walks in a place like this and you can almost hear the promises break.”

“It Wouldn’t Hurt to Have Wings”
from the 1995 album Wings

Essentially the title track to Chesnutt’s finest major label album, it was also the set’s only big hit.

“Thank God For Believers”
from the 1997 album Thank God For Believers

In a decade that brought several powerful new perspectives on alcoholism, this was one of the best, as the man who struggles with his addiction can’t believe the strength and the faith of the woman who stays beside him.

Two Hidden Treasures:

“Strangers”
from the 1995 album Wings

Take your pick from this album – perhaps you’d prefer “As the Honky Tonk Turns” or “King of Broken Hearts” – but my favorite is the closing track, where strangers that meet in the evening will be strangers again the next morning.

“A Hard Secret to Keep”
from the 2004 album Savin’ the Honky Tonk

This is the best moment of Chesnutt’s strongest album, the independent release Savin’ the Honky Tonk. It’s an album that more than lives up to its title, especially on this tale of cheater’s paranoia.

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.

Presenter Charlie Rich fanned the flames of an ongoing battle between country music’s traditional artists and the pop singers making waves in Nashville when he presented the Entertainer of the Year trophy in 1975.

Rich opened the envelope, read it, and then lit a cigarette lighter and burned the envelope. He announced the winner, “My friend, Mister John Denver.” Though he claimed he had overmedicated, Rich’s presentation appeared to be a strong statement against the pop sensibilities of Denver and his counterparts. Denver, accepting via satellite, was unaware of Rich’s actions, and spoke briefly and humbly about his triumph. Furious, industry insiders never again showed outward support to Rich (he had won five CMA awards in the past). His career cooled considerably after the incident. Even though he continued to produce albums frequently until his semi-retirement in 1981, he never added to his list of five #1 albums.

Neither Denver nor Rich ever received another CMA award. Rich failed to earn another nomination (and was not invited back to the ceremony the next year), and he died at the age of 63 in 1995. Denver was recognized in the Vocal Event of the Year category in 1989, and passed away in an airplane crash in 1997.

Charlie Rich, live performance, “Behind Closed Doors”

2009

• Kenny Chesney
• Brad Paisley
• Darius Rucker
• George Strait
• Keith Urban

Just like in the Entertainer category, 80% of this race for the past three years had been Kenny Chesney, Brad Paisley, George Strait, and Keith Urban. This year, Darius Rucker took the fifth slot that was occupied by Alan Jackson in 2008 and Josh Turner in 2007.  Brad Paisley went on to win his third Male Vocalist prize.

2008

• Kenny Chesney
• Alan Jackson
• Brad Paisley
• George Strait
• Keith Urban

After so many years on the sidelines, Paisley began to dominate the category, scoring his second consecutive Male Vocalist award. Meanwhile, Kenny Chesney tied Willie Nelson for most nominations without a win, though his seventh loss was accompanied by his fourth win for Entertainer.

2007

• Kenny Chesney
• Brad Paisley
• George Strait
• Josh Turner
• Keith Urban

This was the year that Brad Paisley finally won, with his seventh nomination in eight years. The stars aligned for him, with a very successful tour, a new album that is selling strongly, and a continued hot streakat radio that was nearly unmatched. He still hasn’t had a single miss the top ten since “Me Neither” in 2000, a claim that even radio favorites like George Strait, Toby Keith, Brooks & Dunn, Tim McGraw and Rascal Flatts can’t call their own.

2006

• Dierks Bentley
• Kenny Chesney
• Alan Jackson
• Brad Paisley
• Keith Urban

Urban became the first artist to win Male Vocalist three years in a row since George Strait did it in 1996-1998, right after Vince Gill’s 1991-1995 run. His acceptance letter, read by Ronnie Dunn, was the emotional highlight of the evening’s show.

2005

• Kenny Chesney
• Alan Jackson
• Brad Paisley
• George Strait
  
• Keith Urban
  

No surprises here, as another multi-platinum year full of radio hits and a high-profile appearance at Live 8 kept Urban fresh on voter’s minds. The big shock was him walking away with Entertainer of the Year later that night.

2004

• Kenny Chesney
• Alan Jackson
• Toby Keith
• George Strait
• Keith Urban
  

Urban hadn’t even been nominated for any CMA Awards in 2002 and 2003, after winning Horizon in 2001, but he came back with a bang, taking home Male Vocalist of the Year over the four other superstars in the category. He joined Chesney as the only other man in the running who had never won before; Chesney got the wonderful consolation prizes of Entertainer and Album of the Year the same night.

2003

• Kenny Chesney
• Alan Jackson
• Toby Keith
• Tim McGraw
• Brad Paisley
• George Strait

Things were getting tight in this category in 2003, with so many worthy contenders that ties resulted in six nominees, instead of the usual five. Still, voters chose to stick with last year’s winner, Alan Jackson, a sure indicator of his enduring popularity among CMA voters.

2002

• Kenny Chesney
• Alan Jackson
• Toby Keith
• Brad Paisley
• George Strait

The other four men were merely placeholders, there to create a list around the obvious winner, Alan Jackson. As he swept the awards on the strength of his post-9/11 “Where Were You” and autobiographical “Drive”, the only real shock was that he was winning Male Vocalist for the first time, a result of the ridiculously slow turnover in this category during the 1990′s.

2001

• Alan Jackson
• Toby Keith
• Tim McGraw
• Brad Paisley
• George Strait

Toby Keith has been a vocal critic of the CMA because he feels they’ve overlooked him, but he’s been up against some tough competition, with his popularity peaking at the same time that Alan Jackson, Kenny Chesney and Keith Urban were making a huge impact on the charts and at the CMA’s. Thankfully, he’s at least won in this category, so he won’t go down in history with Willie Nelson and Conway Twitty as one of the best male singers to never win it.

2000

• Vince Gill
  
• Alan Jackson
• Tim McGraw
• Brad Paisley
• George Strait

On the same evening that his wife was crowned Female Vocalist, McGraw walked away with his second consecutive Male Vocalist award.

1999

• Vince Gill
• Alan Jackson
• Tim McGraw
• George Strait
• Steve Wariner

Early on in his career, when McGraw was selling tons of records but being excluded from this category, he humbly said that he didn’t think he was a good enough singer to be nominated. His talents grew over the years, and he finally won in 1999.

1998

• Garth Brooks
• Vince Gill
• Tim McGraw
• Collin Raye
• George Strait
  

Strait matched Vince Gill’s record of five wins in this category, defeating Gill and three other nominees who had yet to win in the category.

1997

• Vince Gill
• Alan Jackson
• Collin Raye
• George Strait
• Bryan White

With no turnover in the category from the previous year, Strait won for the fourth time, again defeating his fellow mega-winner Gill, and three other stars who had never won before.

1996

• Vince Gill
• Alan Jackson
• Collin Raye
• George Strait
  
• Bryan White

Jackson was already long overdue, and Collin Raye and Bryan White broke into the category for the first time. Nobody expected Gill to win for the sixth year in a row, but many were surprised to see former two-time winner George Strait collect a Male Vocalist award for the first time in ten years.

1995

• John Berry
• Vince Gill
  
• Alan Jackson
• John Michael Montgomery
• George Strait

Even Gill was expecting to lose, so when his name was called out for the fifth year in a row, he was gamely applauding backstage for the winner, before suddenly realizing it was him and rushing out to the stage.

1994

• John Anderson
• Vince Gill
  
• Alan Jackson
• George Strait
• Dwight Yoakam

Vince won for the fourth year in a row, even though fellow nominees John Anderson, Alan Jackson and Dwight Yoakam were seen as likely spoilers.

1993

• John Anderson
• Garth Brooks
• Vince Gill
• Alan Jackson
• George Strait

Vince not only won his third Male Vocalist award this year, he also took home four other awards: Entertainer, Album, Song and Vocal Event.

1992

• Garth Brooks
• Joe Diffie
• Vince Gill
• Alan Jackson
• Travis Tritt

A bunch of hot young stars dominated the ballot this year, with Gill emerging triumphant for the second time. Though they would continue to score hits for many years, Joe Diffie and Travis Tritt received their only nominations to date in this category.

1991

• Clint Black
• Garth Brooks
• Vince Gill
• Alan Jackson
• George Strait

After Garth swept the ACM’s earlier that year, he was expected to do the same at the CMA’s, and he came close, winning Entertainer, Single and Album. But industry favorite Vince Gill took home Male Vocalist, an award that Garth Brooks would never receive, though he would win Entertainer a record four times.

1990

• Clint Black
  
• Garth Brooks
• Rodney Crowell
• Ricky Van Shelton
• George Strait

For the second year in a row, the previous year’s Horizon winner took home Male Vocalist. Clint Black won easily over very distinguished competition.

1989

• Rodney Crowell
• Ricky Van Shelton
• George Strait
• Randy Travis
• Keith Whitley

After winning Horizon in 1988, platinum-selling Ricky Van Shelton graduated into a Male Vocalist winner only one year later. Keith Whitley received a posthumous nomination; he won Single of the Year that same evening.

1988

• Vern Gosdin
• Ricky Van Shelton
• George Strait
• Randy Travis
• Hank Williams, Jr.

It’s hard not to wince at the knowledge that the peerless Vern Gosdin only received one nomination in this category, but there was no stopping Travis from collecting his second win.

1987

• George Jones
• Ricky Skaggs
• George Strait
• Randy Travis
  
• Hank Williams, Jr.

In a lineup that was a traditionalist’s dream, new star Randy Travis took home the trophy.  At the time, he was breaking sales records, enjoying a quadruple-platinum studio album in Always & Forever.

1986

• George Jones
• Gary Morris
• George Strait
• Randy Travis
  
• Hank Williams, Jr.

Strait won his second consecutive Male Vocalist award on the strength of another huge year at radio and retail.

1985

• Lee Greenwood
• Gary Morris
• Ricky Skaggs
• George Strait
• Hank Williams, Jr.

George Strait won the first of a record-matching five Male Vocalist awards, also taking home Album of the Year that same evening.

1984

• Lee Greenwood
• Merle Haggard
• Gary Morris
• Ricky Skaggs
• George Strait

Greenwood’s Vegas vocals won him the award for the second time.

1983

• John Anderson
• Lee Greenwood
• Merle Haggard
• Willie Nelson
• Ricky Skaggs

Greenwood looks pretty shabby against these other four nominees, taking home Male Vocalist in the same year Janie Fricke won for Female Vocalist. Is there a year in the history of the CMA’s where the winners of those two categories were collectively less impressive?

1982

• Merle Haggard
• George Jones
• Ronnie Milsap
• Willie Nelson
• Ricky Skaggs

Pulling off the astonishing feat of winning both Male Vocalist and Horizon award, Emmylou Harris’ former bandmate was hugely rewarded for bringing bluegrass to the masses.

1981

• George Jones
  
• Ronnie Milsap
• Willie Nelson
• Kenny Rogers
• Don Williams

It’s taken for granted that Jones is the greatest living male vocalist in country music; few would dare to argue otherwise. No surprise, then, that he won for the second year in a row.

1980

• John Conlee
• George Jones
  
• Willie Nelson
• Kenny Rogers
• Don Williams

Nominated for the first time in his career, George Jones walked away with Male Vocalist of the Year, along with Single of the Year for “He Stopped Loving Her Today”.

1979

• John Conlee
• Larry Gatlin
  
• Willie Nelson
• Kenny Rogers
• Don Williams

It’s hard to believe that the legendary showman never won Entertainer of the Year, but he did take home a much-deserved Male Vocalist award, at least.  Unfortunately, fellow nominee John Conlee would never be recognized at all, losing his first of two shots at this award.

1978

• Larry Gatlin
• Ronnie Milsap
• Willie Nelson
• Kenny Rogers
• Don Williams

One of the most underrated artists in country music history got a well-deserved pat on the back, winning over four larger personalities in 1978.

1977

• Larry Gatlin
• Waylon Jennings
• Ronnie Milsap
• Kenny Rogers
• Don Williams

Milsap set a record when he won for the third time in this category, which would stand until 1994, when Vince Gill won his fourth trophy.

1976

• Waylon Jennings
• Ronnie Milsap
• Willie Nelson
• Conway Twitty
• Don Williams

After losing to Jennings the previous year, Milsap returned to collect his second Male Vocalist trophy in 1976. Conway Twitty lost again in his final appearance in the category.

1975

• John Denver
• Freddy Fender
• Waylon Jennings
  
• Ronnie Milsap
• Conway Twitty

There was no love lost between Waylon Jennings and the CMA – he loathed the organization so much, he didn’t even show up at his Hall of Fame induction. This was the first of several CMA wins for Jennings, though the only one in this category that he would receive.

1974

• Merle Haggard
• Waylon Jennings
• Ronnie Milsap
  
• Charlie Rich
• Cal Smith

Blind singer-songwriter and pianist Ronnie Milsap won for the first time; with Olivia Newton-John winning Female Vocalist the same night, pop was the flavor of the evening.

1973

• Merle Haggard
• Tom T. Hall
• Charlie Rich
  
• Johnny Rodriguez
• Conway Twitty

The Silver Fox won on the strength of a great year at radio. He’s still considered one of the era’s finest and most under-appreciated vocalists.

1972

• Merle Haggard
• Freddie Hart
• Johnny Paycheck
• Charley Pride
• Jerry Wallace
  

Charley Pride became the first artist to repeat in the category, winning for the second year in a row.

1971

• Merle Haggard
• Ray Price
• Charley Pride
• Jerry Reed
• Conway Twitty

The CMA had a wealth of great male vocalists to choose from in the early years of the awards, and they finally got around to acknowledging Pride, who had been nominated four times already.

1970

• Johnny Cash
• Merle Haggard
  
• Charley Pride
• Marty Robbins
• Conway Twitty

Merle Haggard dominated the show in 1970, winning Entertainer, Male Vocalist, Single and Album of the Year.

1969

• Glen Campbell
• Johnny Cash
  
• Merle Haggard
• Sonny James
• Charley Pride

Cash was a huge winner in 1969, taking home five awards: Entertainer, Male Vocalist, Single, Album and Vocal Group (with wife June Carter Cash). He wouldn’t win again until after his death in 2003, when he took home another three awards.

1968

• Eddy Arnold
• Glen Campbell
• Johnny Cash
  
• Merle Haggard
• Charley Pride

Crossover star Glen Campbell won in a year that is so impressive, all five nominees are now in the Hall of Fame. He also took home Male Vocalist the same evening.

1967

• Eddy Arnold
• Jack Greene
  
• Merle Haggard
• Sonny James
• Buck Owens

Few casual country fans would recognize him today, but Jack Greene will forever go down in history as the first Male Vocalist winner at the CMA’s. He won on the strength of his signature hit “There Goes My Everything”, which also won Single of the Year and was the title track of his Album of the Year winner that same night.

Facts & Feats

Multiple Wins:

• (5) – Vince Gill, George Strait
• (3) – Ronnie Milsap, Keith Urban
• (2) – Lee Greenwood, Alan Jackson, George Jones, Tim McGraw, Brad Paisley, Charley Pride, Randy Travis

Most Consecutive Wins:

• (5) – Vince Gill (1991-1995)
• (3) – George Strait (1996-1998), Keith Urban (2004-2006)

Most Nominations:

• (24) – George Strait
• (16) – Alan Jackson
• (11) – Merle Haggard
• (10) – Vince Gill
• (9) – Brad Paisley
• (8) – Kenny Chesney
• (7) – Ronnie Milsap, Willie Nelson
• (6) – Keith Urban, Don Williams
• (5) – Garth Brooks, George Jones, Charley Pride, Kenny Rogers, Ricky Skaggs, Conway Twitty

Most Nominations Without a Win:

• (8) – Kenny Chesney
• (7) – Willie Nelson
• (5) – Garth Brooks, Conway Twitty
• (4) – Hank Williams, Jr.
• (3) – John Anderson, Larry Gatlin, Gary Morris, Collin Raye
• (2) – Eddy Arnold, John Conlee, Rodney Crowell, Sonny James, Bryan White

Winners in First Year of Nomination:
Clint Black (1990), Glen Campbell (1968), Vince Gill (1991), Lee Greenwood (1983), George Jones (1980), Toby Keith (2001), Ronnie Milsap (1974), Charlie Rich (1973), Ricky Skaggs (1982), Randy Travis (1987), Keith Urban (2004)

CMA Male Vocalists of the Year Who Have Never Won the ACM Award:
Johnny Cash, Jack Greene, Waylon Jennings, Charley Pride, Ricky Van Shelton, Ricky Skaggs, Randy Travis, Don Williams

ACM Male Vocalists of the Year Who Have Never Won the CMA Award:
Garth Brooks (1990 & 1991), Kenny Chesney (2003), Larry Gatlin (1980), Mickey Gilley (1977), Freddie Hart (1972)

CMA Male Vocalists Who Have Also Won the Grammy for Best Country Vocal Performance, Male:
Glen Campbell, Johnny Cash, Vince Gill, Lee Greenwood, George Jones, Tim McGraw, Ronnie Milsap, Brad Paisley, Charley Pride, Charlie Rich, Kenny Rogers, Randy Travis, Keith Urban

Winners of the Grammy for Best Country Vocal Performance, Male Who Have Never Won the CMA Male Vocalist Award:
Garth Brooks, David Houston, Lyle Lovett, Roger Miller, Willie Nelson, Ray Price, Jerry Reed, Ralph Stanley, Dwight Yoakam