Country music as we know it today goes back almost 100 years. While the history of the genre goes back much further, the commercialization of country music began with the Bristol Sessions—a set of recording sessions held in Bristol, Tennessee in the summer of 1927. Since then, the genre has evolved and changed many times. However, when fans talk about classic country, they’re usually talking about songs recorded between the late ‘40s and early ‘60s.
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This era of country music saw the dominance of Western influences, the early days of honky tonk, and the rise of Owen Bradley’s “Nashville Sound.” The songs in the list below serve as a starting point for those who want to dig deeper into the classic era of country music.
[RELATED: Forgotten Country Music Stars of the 1950s That Deserve to Be Rediscovered]
1. “I’m So Lonesome I Could Cry” by Hank Williams (1949)
There is no better place to start your journey into classic country music than this song—or any of the other songs—from Hank Williams. While artists like Jimmie Rodgers, the Stonemans, The Carter Family, Roy Acuff, and others rose to prominence before Williams, he remains one of the most influential artists in the genre’s long history. At the same time, he’s the perfect gateway into classic country music.
Williams wrote “I’m So Lonesome I Could Cry” and released it in 1949. It was the B-side to the more upbeat “My Bucket’s Got a Hole in It.” However, this track would go on to be one of Williams’ signature tracks. Its combination of early honky tonk and blues makes it the perfect heartbreak song and an example of the kind of music that made the Hillbilly Shakespeare a cornerstone artist.
2. “It Wasn’t God Who Made Honky Tonk Angels” by Kitty Wells (1952)
The title “Queen of Country Music” gets tossed around pretty often these days. Fans, critics, and journalists regularly lay the title on artists like Dolly Parton, Loretta Lynn, and Reba McEntire. While they’re all phenomenal and influential artists, those who know the genre’s history would likely name Kitty Wells the true Queen of Country Music. She paved the way for Parton, Lynn, Patsy Cline, Tammy Wynette, and other women in country music.
Wells was more than a pretty face with a great voice. She was also bold. The classic country song “It Wasn’t God Who Made Honky Tonk Angels” is proof of that boldness. It was an answer to Hank Thompson’s “The Wild Side of Life” in which a jilted lover says to his ex, I didn’t know God made honky tonk angels / I might have known you’d never make a wife. In Wells’ reply, penned by Jay Miller, she sings about how unfaithful men cause their significant others to stray and laments that women get all the blame. It was a progressive sentiment for the time and set the stage for the future ladies of country music.
“It Wasn’t God Who Made Honky Tonk Angels” made Wells the first solo female artist to have a No. 1 single on the Billboard country charts.
3. “There Stands the Glass” by Webb Pierce (1953)
Modern country music is full of drinking songs but there’s something about the classics that just hit differently. Webb Pierce’s “There Stands the Glass” is a perfect example. This song about drinking away a broken heart will grab you from the opening notes. Pierce’s crystalline vocals drive the heartbreak home like few could.
While country music, drinking, and heartaches go hand-in-hand, “There Stands the Glass” found some controversy upon release. Some say it promoted or glorified alcoholism. However, that didn’t stop it from topping the Billboard Country chart for 12 weeks and bringing Pierce his fifth career No. 1.
Russ Hull, Mary Jean Shurtz, and Audrey Grisham co-wrote the song and Blaine Smith was the first to record it in 1952. Several other artists including Patty Loveless, Van Morrison, Hoyt Axton, and Loretta Lynn all recorded versions of the song. However, nothing matches Pierce’s heart-rending rendition.
4. “Crazy Arms” by Ray Price (1956)
“Crazy Arms” wasn’t just a career-making hit for the legendary Ray Price. It also changed the face of country music forever. Price used the song to introduce the world to his Texas Shuffle sound. It included fiddle, pedal steel, and a “walking” bassline played on an electric bass guitar. However, the major shift came with the song’s swinging beat.
Charles Seals co-wrote the song with Ralph Mooney. If the latter name sounds familiar, he played pedal steel for Wynn Stewart and Waylon Jennings.
5. “She Thinks I Still Care” by George Jones (1962)
George Jones is often hailed as the greatest country singer to ever live for good reason. Any of his songs would be a great gateway into the classic country music era. His early work, mostly produced by Pappy Daily, had a strong blend of country and rockabilly. Later in his career, though, he started working with the legendary producer Owen Bradley who pioneered what would come to be called the “Nashville Sound,” incorporating string arrangement and troops of backup singers.
“She Thinks I Still Care” walks the line between the two distinct styles. It packs pedal steel, a beautiful piano arrangement, and what sounds like a choir singing behind Jones.
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