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80
Lefty Frizzell
“Long Black Veil”
A 1959 hit for the country music icon, and the song most closely associated with his legendary status.
Bruce Springsteen version
79
Alabama
“Love in the First Degree”
This single contains more legal lingo than an episode of “Law & Order” but still manages to be sweet, in a cornball sort of way.
78
Toby Keith
“Get Drunk and Be Somebody”
Keith’s anthemic opener from his 2006 White Trash With Money epitomizes a faction of blue-collar life—folks who work without reward and find what they need in their friends and their bottles.
77
Tim McGraw
“Please Remember Me”
McGraw’s melodramatic plea is undeniably touching.
76
Clint Black
“A Better Man”
The first single from his 1989 debut, “Killin’ Time,” was prophetic: With each new record, Black got better.
75
The Judds
“Grandpa (Tell Me ‘Bout the Good Old Days”
A simple and pretty ballad about the changes time inevitably brings.
74
The Louvin Brothers
“When I Stop Dreaming”
A beautiful country-gospel song, released in 1955, that would later become one of the most covered country songs ever.
73
The Oak Ridge Boys
“Elvira”
Slightly silly, with lyrics like “oohm bop a mow, mow” and “hi yo silver away!” Still, it became one of the Oaks’ biggest songs. You’re humming it right now.
72
Reba McEntire
“Whoever’s in New England”
Thought by many fans to be McEntire’s answer to Barry Manilow’s “Weekend in New England,” this song about a husband messing around in New England earned the singer her first Grammy.
71
Dwight Yoakam
“I Sang Dixie”
Rumored to be based on any number of Yoakam associates who died of alcohol abuse, this could easily be about anyone who has suffered that fate.
70
Loretta Lynn
“You Ain’t Woman Enough (To Take My Man)”
Lynn made it a habit to spit in the face of Nashville, but here, she was spitting in the face of a woman who was flirting with her husband.
69
Johnny Horton
“Battle of New Orleans”
Born in Los Angeles but raised in East Texas, Horton found success with this 1959 unlikely success story, one of his many saga songs. It was sort of like Yes without the drum solos.
68
Buck Owens
“Together Again”
The king of Bakersfield country released this wildly influential gem in 1964, paving the way for so many followers.
67
Mickey Gilley
“Stand By Me”
Gilley’s complete overhauling of Ben E. King’s classic was not just a high point of the “Urban Cowboy” soundtrack but also a highlight of `80s country music.
66
Vernon Dalhart
“Wreck of the Old 97”
Dalhart’s wonderfully compelling 1924 song about the real-life derailment of the Southern Railway Fast Mail train No. 97. Also gave a certain Dallas alt-country band a good name.
65
George Strait
“The Fireman”
Full of hilarious, perhaps intentional cliches (“I can cool `em down while they’re smolderin’ hot”), this 1984 single was one of the gazillion Strait would eventually have. But this was the most rambunctious fun.
64
Emmylou Harris & Gram Parsons
“Love Hurts”
Both Parsons and Harris specialized in country-rock arrangements, though in vasty different ways. On this 1974 duet, their dissimilar styles mesh hauntingly well.
Emmylou Harris & Elvis Costello version
63
Brooks & Dunn
“My Maria”
The best covers are sometimes the ones that sound absolutely nothing like the originals. That’s not the case with B&D’s reworking of B.W. Stevenson’s pop hit: It’s pretty much a note-for-note retry, but an exceptionally good one.
62
Trace Adkins
“I’m Tryin’”
Simple but effective song about trying to put your life back together after a divorce. Love the line “still ain’t used to putting `ex’ in front of `wife.’ ”
61
Vince Gill
“Take Your Memory With You”
Back before he got all gooey-hearted—you know, before he married Amy Grant—Gill churned out several terrific spitball fireballs, including this 1991 kiss-off.
