The Grammy Award for Best Male Country Vocal Performance was first handed out to Roger Miller in the year 1965 for his hit single “Dang Me”. For the first two years after its inception the award was known as Best Country & Western Vocal Performance – Male, in 1968 it was changed to Best Country & Western Solo Vocal Performance, Male. From 1969 to 1994 it was awarded as Best Country Vocal Performance, Male and in 1995 the Recording Academy came up with the title Best Male Country Vocal Performance, which is still in use today. Vince Gill is the most honored artist in this category with a total of 8 wins. The list of winners over the years is given below.

Winners: Grammys Best Male Country Vocal Performance

Year
Winner/s
Song
2010
Keith Urban
Sweet Thing
2009
Brad Paisley
Letter to Me
2008
Keith Urban
Stupid Boy
2007
Vince Gill
"The Reason Why"
2006
Keith Urban
You'll Think of Me
2005
Tim McGraw
Live Like You Were Dying
2004
Vince Gill
"Next Big Thing"
2003
Johnny Cash
"Give My Love to Rose"
2002
Ralph Stanley
"O Death"
2001
Johnny Cash
"Solitary Man"
2000
George Jones
"Choices"
1999
Vince Gill
"If You Ever Have Forever in Mind"
1998
Vince Gill
"Pretty Little Adriana"
1997
Vince Gill
"Worlds Apart"
1996
Vince Gill
"Go Rest High on That Mountain"
1995
Vince Gill
"When Love Finds You"
1994
Dwight Yoakam
"Ain't That Lonely Yet"
1993
Vince Gill
I Still Believe in You
1992
Garth Brooks
Ropin' the Wind
1991
Vince Gill
"When I Call Your Name"
1990
Lyle Lovett
Lyle Lovett and His Large Band
1989
Randy Travis
Old 8x10
1988
Randy Travis
Always & Forever
1987
Ronnie Milsap
Lost in the Fifties Tonight
1986
Ronnie Milsap
"Lost in the Fifties Tonight (In the Still of the Night)"
1985
Merle Haggard
"That's the Way Love Goes"
1984
Lee Greenwood
"I.O.U."
1983
Willie Nelson
"Always on My Mind"
1982
Ronnie Milsap
"(There's) No Gettin' Over Me"
1981
George Jones
"He Stopped Loving Her Today"
1980
Kenny Rogers
"The Gambler"
1979
Willie Nelson
"Georgia on My Mind"
1978
Kenny Rogers
"Lucille"
1977
Ronnie Milsap
"(I'm a) Stand By My Woman Man"
1976
Willie Nelson
"Blue Eyes Crying in the Rain"
1975
Ronnie Milsap
"Please Don't Tell Me How the Story Ends"
1974
Charlie Rich
"Behind Closed Doors"
1973
Charley Pride
Charley Pride Sings Heart Songs
1972
Jerry Reed
"When You're Hot, You're Hot"
1971
Ray Price
"For the Good Times"
1970
Johnny Cash
"A Boy Named Sue"
1969
Johnny Cash
"Folsom Prison Blues"
1968
Glen Campbell
"Gentle on My Mind"
1967
David Houston
"Almost Persuaded"
1966
Roger Miller
"King of the Road"
1965
Roger Miller
"Dang Me"