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100

John Conlee

“Rose Colored Glasses”

The mortician-turned-singer struck gold in 1978 with this beautiful tear-jerker.
Listen on YouTube


 

99

Mel McDaniel

“Louisiana Saturday Night”

Don Williams wrote this ode to dancing in the kitchen till the morning light, but McDaniel skyrocketed with it.


 

98

Earl Thomas Conley

“Holding Her, Loving You”

One of countless country songs about being with one person yet loving another. Few are as moving as this 1983 hit.


 

97

Emmylou Harris

“If I Could Only Win Your Love”

Harris has dabbled in so many genres, it’s easy to forget her honky-tonk background. This is a reminder from her incredible 1975 record, Pieces of the Sky.


 

96

Don Williams

“I Believe in You”

Williams’ easygoing vocal style and poetic lyrics perfectly married on this 1980 hit.


 

95

Waylon Jennings

“Ain’t Livin’ Long Like This”

Ha!—Jennings outsmarted this `70s staple by living a nice, long and extremely meaningful life.


Rodney Crowell version


 

94

Alan Jackson

“Drive (For Daddy Gene)”

If Father’s Day had an anthem, it would be Jackson’s 2002 nod to dear old dads.


 

93

Burl Ives

”(Ghost) Riders in the Sky”

This song rose only to No. 21 in 1949. Over time, artists and fans began to appreciate the strange tale of fire-breathing cattle getting chased by ghostly cowboys, and many singers covered it, including Johnny Cash, Duane Eddy and, of course, the band Riders in the Sky.


Johnny Cash with the Muppets version


 

92

Sons of the Pioneers

“Tumbling Tumbleweeds”

This 1934 song, chugged out by the famous cowboy group that featured Roy Rogers, made such an impact that it inspired a Gene Autry movie.


 

91

Charley Pride

“Kiss an Angel Good Morning”

One of the few black male singers in country music had his profile heightened considerably with this insanely catchy 1971 chart-topper, which won Pride the Country Music Association’s Entertainer of the Year award.


(best available video quality)


 

90

Johnny Cash

“I Still Miss Someone”

No other version of this song can match the haunting and emotionally numbing reading Cash gave it on his appropriately named 1958 album, The Fabulous Johnny Cash.


 

89

Merle Haggard

“My Favorite Memory”

Hag’s sweetest, most melancholy song.


 

88

Bobbie Gentry

“Ode to Billie Joe”

This was a 1967 B-side, but DJs sniffed a hit and played it, catapulting it to No. 17 on the country charts and to No. 1 on the pop charts, turning the singer into a superstar.


 

87

The Oak Ridge Boys

“Ya’ll Come Back Saloon”

The Oaks’ official switch from gospel to country paid off big time with this 1977 hit.


 

86

George Jones & Tammy Wynette

“Golden Ring”

“Golden Ring” is NOT the song you want played at your wedding, despite its optimistic title.


 

85

Johnny Cash

“Hurt”

You can’t get grimmer than Nine Inch Nails, but Cash did in 2002, with his bare-bones reading of this NIN heartbreaker.


 

84

Alan Jackson

“Don’t Rock the Jukebox”

Not exactly one of Jackson’s more pensive moments but still a lot of fun.
Video


 

83

Dixie Chicks

“Am I the Only One (Who’s Ever Felt This Way)”

The Chicks have marvelous taste in covers, such as their devastatingly believable cover of this Maria McKee song.
Video of Maria McKee version


 

82

Brooks & Dunn

“Neon Moon”

A wonderfully written ballad, with that unforgettable refrain, “watch your broken dreams dance in and out of the beams.”


 

81

Dixie Chicks

“Travelin’ Soldier”

This bittersweet tale of a young girl whose love is killed in Vietnam is one of the Chicks’ finest moments.


 
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