I couldn’t let this day end without using my humble little corner of the internet to celebrate some of his favorite songs.  A love for country music was something that my father shared with my mother, and thanks to long car trips as  child, this love eventually rubbed off on me.  This morning, my mother put on the country classics Music Choice channel and it was playing their song: “Blanket on the Ground” by Billie Jo Spears.

It’s one of those songs that always seemed to be on the mix tapes that my parents listened to.  But there are a wealth of country hits that I associate with just Dad.  Some of them I always loved. Some of them I didn’t care for at the time. Some I openly disdained and wished he’d never play again.  All of them are now among my favorites because they remind me of him.

So in honor of Father’s Day, here are some of my Dad’s favorite country songs.  Share your dad’s favorites in the comments!

Alan Jackson, “Livin’ On Love”

From my mom’s point of view, K.T. Oslin’s “Hold Me” perfectly encapsulated their marriage.  For my dad, it was “Livin’ On Love.”

Clint Black, “Nobody’s Home”

My dad loved Clint Black, especially his first two albums.  This was the hit he played to death when Killin’ Time was his album of choice.

Johnny Cash, “(Ghost) Riders in the Sky”

Sure, my dad loved “Sunday Morning Coming Down” and “Five Feet High and Rising.” But he also loved Cash’s campier hits, like “One Piece at a Time” and this chestnut.

Dixie Chicks, “Travelin’ Soldier”

No matter what was going on in the room, my dad would stop what he was doing to watch this video.  As a Navy veteran, this song really hit home for him.

Dwight Yoakam, “A Thousand Miles From Nowhere”

Another guy that Dad couldn’t get enough of.  This was a song that I thought he played too much, never caring for it at the time. Now it’s one of my favorites of his.

John Anderson, “Seminole Wind”

He bought the album for “Straight Tequila Night”, but this quickly emerged as one of his all-time favorite songs.

John Conlee, “Common Man”

I do believe that I’d never have discovered this great vocalist if his greatest hits set wasn’t one of the very first CDs my father purchased. I still remember the “Priceless Music Priced Less” logo on the front.

Johnny Horton, “Sink the Bismarck”

Another hits collection dad played the heck out of. I always thought this was Horton’s biggest hit because Dad played it so much. I remember being shocked to find “Honky Tonk Man”, which I knew as a Dwight Yoakam song, was on there, too.

Kenny Rogers, “The Gambler”

He didn’t care for the man’s love songs or most of his pop hits, but he had this album on vinyl and I only remember hearing him play the title track.

Willie Nelson & Merle Haggard, “Pancho and Lefty”

Another one of Dad’s first CD purchases. I always thought the opening music sounded like a TV theme song.

Marty Robbins, “Big Iron”

Dad loved the Western subgenre of country music, at least as performed by Marty Robbins.

And finally, it’s not a country song, but it was his favorite song, and I’ll forever associate it with him. Amazing how I used to groan when I heard him playing it on our living room jukebox again, and now I never get tired of it because it’s him.

The Beach Boys, “Sloop John B.”

I think that the strongest feature of the iPod is the ability to create playlists.  I currently have over 16,000 songs, so playing it on pure shuffle is interesting but not likely to result in hearing a string of my favorite songs.

I have dozens of playlists, but the one that I visit the most is called “Repeat.” It’s an ever-shifting playlist of songs that I don’t tire of.  Currently, there are 131 songs on the list.

I’m sharing the first ten that play on shuffle from the list. Share your favorite playlist and ten of its tracks in the comments!

Ten Tracks from “Repeat”:

• Miranda Lambert, “Kerosene”
• Nickel Creek, “Helena”
• Roxette, “Spending My Time”
• Pam Tillis, “When You Walk in the Room”
• John Conlee, “Rose Colored Glasses”
• Madonna, “Devil Wouldn’t Recognize You”
• Clint Black, “Burn One Down”
• Dixie Chicks, “Bitter End”
• Patty Loveless, “Keep Your Distance”
• Cyndi Lauper, “Time After Time”

Predictably and justifiably, the list is topped by “He Stopped Loving Her Today”, a George Jones classic that tops many a classic country list, including one of our own.  There’s also a pretty high body count -- four outright deaths and one by implication.  Country songs sure do like to kill people off, don’t they?

So what are the saddest country songs ever? My first instinct was to mention “Where’ve You Been”, but that Kathy Mattea classic has a ray of hope. It’s really about a perfect relationship meeting its natural end.

For real, heartbreaking sadness, all hope must be vanquished, with only regret remaining. Bonus points if somebody dies.  Here are two that I think are tragic, one with death and one without:

Dixie Chicks/Patty Griffin, “Top of the World”

A man realizes after his death that he did nothing but hurt the woman he loved, and now it’s too late to go back and change it:

John Conlee, “Backside of Thirty”

Something similar, though the man is still alive. He had everything he ever wanted -- a beautiful wife and son -- and somehow messed it up. He’s now living alone in an apartment, drinking away his rent money, “back on the bottom with no will to climb.”

What do you think are the saddest country songs ever?

Is it Porter Wagoner & Dolly Parton’s “I Get Lonesome By Myself”, with a plot line that should lead to child endangerment charges by the first verse?

How about the horrific cautionary tale “Drunken Driver” by Ferlin Husky?

Or, if you’ll just hand me my crayons, I’ll write down the reasons why the mental home classic “I Don’t Remember Loving You” is John Conlee at his best:

What are your favorite over-the-top country classics? Share in the comments. Remember, if you want to embed a video from YouTube, you need only add a “v” after the http at the beginning of the url. (i.e., httpv://www.youtube.com…)

#20

Taylor Swift, “You Belong with Me”

Teen-pop perfection, bursting with personality and unshakable hooks. – Dan Milliken

#19

Keith Urban, “‘Til Summer Comes Around”

There’s nothing quite as lonely as a carnival that has shut down, except for being alone at a carnival, surrounded by everyone but the love who has left you behind. – Kevin Coyne

#18

Lady Antebellum, “I Run to You”

Sheer passion and pulsing energy from start to finish. – Tara Seetharam

#17

The Civil Wars, “Poison & Wine”

How perfect a song for this duo, whose harmonies make the most venomous of lyrics go down as sweet as cherry wine. – KC

#16

Oh, Alexis!, “Strugglin’”

The perfect jukebox number for the early morning hours, with a voice that makes you long for the whiskey and beer that has settled on its breath. – KC

#15

Ryan Bingham, “Country Roads”

I say if our country tent is big enough for The Civil Wars and Taylor Swift, we can certainly make a little room in it for Bingham’s wide-open stomp ‘n’ roll. This is one of his best, too, an ode to elected homelessness that sounds tailor-made for its singer’s chimney-stack vocals. – DM

#14

Dolly Parton, “Backwoods Barbie”

A fascinating self-portrait of sorts that Parton tackles with honesty, heart and that ever so rare quality of effervescent, unabashed self-confidence. – TS

#13

Heidi Newfield, “What Am I Waiting For?”

No maudlin whining or cheesy mood-uppers here – just a long, honest look in the mirror by a woman struggling for the courage to get out of her own way. – DM

#12

Zac Brown Band, “Highway 20 Ride”

“Highway 20 Ride” is a sweet, but sad, message from a father to his son who is separated from him as a result of divorce. – Leeann Ward

#11

Reba McEntire, “Consider Me Gone”

Her most irresistible single since “The Fear of Being Alone”, with the same clear-eyed confidence that fueled that classic hit. This is country music by adults and for adults. More, please. – KC

#10

Lee Ann Womack, “Solitary Thinkin’”

A shining example of the kind of song that makes me go genre-blind – because who honestly cares if a song is pop or blues or country when it’s so masterfully on-the-money? Womack wrings this smooth, slow-churning lounge tune of every last drop of boozy resignation and shameless self-pity. – TS

#9

Carrie Underwood with Randy Travis, “I Told You So”

Nearly twenty years later and a classic country hit is reborn, thanks to a perfectly imperfect pair of voices and personas. The rough-and-pure quality of the duet is captivating enough, but it’s the deeper entanglement of  Travis’ understated, almost doubtful monologue and Underwood’s poised, heart-on-her-sleeve confession that turns this song into a memorable – and perhaps historical – moment in country music. – TS

#8

Chris Young, “Gettin’ You Home (The Black Dress Song)”

Much like Billy Currington does with contemporary country music, Young infuses this refreshingly traditional hit – about a stuffy night out that just ain’t going to last – with just enough sexual tension to make it feel flirtatiously rousing, without resorting to sleaze. His rich, charismatic vocal performance is second to none among the male country singles of the year. – TS

#7

Sugarland, “It Happens”

Starting with an unshakably catchy guitar riff, “It Happens” is a joyous celebration of life and its ups and downs. – LW

#6

Taylor Swift, “Fifteen”

What starts out sounding like a big-sister advice session slowly reveals itself as the narrator’s attempt to understand and accept her own past self. She was young and foolish, too starry-eyed to protect herself and a dear friend from the cruel disillusionments of life, and it’s only because time has passed that she’s found any relief from the shame of those failures. Like Swift in general, the song isn’t for everyone, but don’t let the high school setting fool you: “Fifteen” is anything but kid’s stuff. – DM

#5

Patty Loveless, “Busted”

I didn’t think that anyone could ever rival the John Conlee version, but Loveless can channel the voice of the Appalachian poor just as effectively as Conlee can channel the voice of the blue-collar worker. – KC

#4

Willie Nelson & Asleep at the Wheel, “Hesitation Blues”

“Hesitation Blues” is a blues standard that was revived by Willie Nelson and Asleep at the Wheel and adapted into a cool Western Swing gem. As is the case with the entire album from which this song comes, the production is both refreshing and organic. While the sound is crisp, it also finds a way to sound properly dated. A difficult balance to successfully strike, to be sure. – LW

#3

Brad Paisley, “Welcome to the Future”

In a genre that so often falls over itself idealizing the past, it’s refreshing to hear a major artist stick up for progress. The first two verses flirt with Boring thanks to Paisley’s typical reliance on quotidian details (“I was on a video chat this morning”), but the soaring arena-rock arrangement hooks you in long enough to get to the game-changing third verse, a moment of sincere, hard-earned joy for humanity that ties all the previous little details together and cements “Welcome to the Future” as one of the most significant singles of the year. – DM

#2

Jamey Johnson, “High Cost of Living”

There’s nothing pretty about Jamey Johnson’s appearance, his voice or this song. That’s one of the fascinating aspects of Johnson’s appeal. “High Cost of Living” doesn’t boast a pretty ending; it’s just blunt, raw and a dang fine piece of country music as a result. – LW

#1

Alan Jackson, “Sissy’s Song”

A great song, but an even better record. The way that Jackson essentially recites the conflicted verses that reveal his doubts about what he proclaims in the chorus with a gospel melody is brilliant. It’s not certain whether he truly believes that “she flew up to heaven on the wings of angels” and is “smiling, saying, ‘Don’t worry ’bout me.’”  But it’s what he has to tell himself he believes to make the grief manageable down here on earth. Sometimes faith comes from weakness and doubt, rather than strength and certainty. – KC

“Why Not Me” wasn’t a great title. To get a really good record, you’ve gotta write a hell of a song when you’re dealing with a title that average. The only thing I know to do with songs like “Why Not Me” and “Busted” – which I never thought was a good title – is to put the title in there often so that people remember it. The weaker the title, the more you gotta hear it.”

“Why Not Me” earned the Judds the Country Duo/Group Grammy and the CMA award for Single of the Year. “Busted” was hit for both Johnny Cash with the Carter Family in the sixties and John Conlee in the eighties. Both songs feature the titles repeated endlessly.

I think this quote is fascinating because it provides a window into how two songs from different eras were crafted by the same writer. I never noticed the similarities before reading the quote.

I’d also add that the Little Texas hit “My Love” and the Brooks & Dunn hit “That’s What It’s All About” show how the rule can be taken too far, in my opinion, and turn into just an annoying song.

What do you think?

Thankfully, my amazing writing staff has made my absence unnoticeable, but as I make my return, I’m thinking tonight about songs that capture that “I need a break” feeling.   Here are some of my favorites:

Keith Urban, “Raining on Sunday”

John Conlee is always good.

And just because it’s my site and I can indulge in my favorite non-country artist:

What are your favorite “Gimme a Break!” songs?

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 has been Kenny Chesney, Brad Paisley, George Strait, and Keith Urban. This year, Darius Rucker takes the fifth slot that was occupied by Alan Jackson in 2008 and Josh Turner in 2007.  Though there could be a surprise, it seems like Brad Paisley is the presumptive favorite 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