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The 20 Greatest Country Songs from the 1920s, Part I


Early recorded country music was a mixture of jazz, blues, and Southern Appalachian fiddle based material. The first commercial country records were released in 1922 by Texas based fiddler Eck Robertson, accompanied by Henry Gilliland, on their Victor recordings “Arkansaw Traveler” and “Turkey in the Straw.” Vernon Dalhart had the first national country hit in 1924 with “Wreck of the Old 97,” but it was “The Singing Brakeman” Jimmie Rodgers who became the first true superstar of the genre. Below I’ve listed part one of my version of the twenty greatest country songs from the 1920s with listenability being considered, as well as historical significance.

20. “Soldier’s Joy,” Gid Tanner and His Skillet Lickers. Gid Tanner was a Georgia based fiddler and chicken farmer who recorded over 100 songs from 1926 to 1931 with his incomparably named Skillet Lickers. It is believed that “Soldier’s Joy” dates back to 1760 as a traditional Scottish and Irish reel or country dance song and was referred to as “Payday in the Army” during the American Civil War era. On this 1929 recording, Skillet Licker Clayton McMichen introduces the number by stating, “I want you to grab that girl, shake her foot and moan.” Blind lead singer Riley Puckett, one of the least photogenic frontmen in music history, ponders an economic decision between morphine and beer while the fiddles saw away.

19. “Hobo from the T&P Line,” Almoth Hodges with Bob Miller’s Hinky Dinkers. Songs about hobos or “ramblin’ men” and their railroad adventures were an important genre an early country music, providing rich imagery about the hardships and putative rewards of the untethered lifestyle. There is little historical information to be found on Almoth Hodges and the only thing I know about Bob Miller’s Hinky Dinkers is that they also backed up vocalist Bill Baker on his 1929 recording “The Wild and Reckless Hobo.” On this story song, the narrator falls in love with his boss’s sixteen-year-old daughter. After the love affair is discovered, he’s sent packing to bum his way on the Texas and Pacific line.

18. “Frankie and Johnny,” Gene Autry. The origins of “Frankie and Johnny” are murky and it has been written with many different verses. Although not all scholars agree, it is believed to have been originally written by St. Louis balladeer Bill Dooley in 1899, after a real life affair resulted in a murder in St. Louis. “The Singing Cowboy” Gene Autry was known as the apotheosis of white bread, wholesome entertainment during his long career in radio, films, and as a recording artist. Given his image, it’s pretty startling to hear Autry singing about “pimps and whores” on this 1929 release. Autry also recorded another sex song that was more than racy for its time, alternately known as “Bye Bye Cherry,” ”Bye Bye Boyfriend,” or “Bye Bye Blackbird.” No matter the title, it will raise your eyebrows.

17. “Down on Penny’s Farm,” The Bently Boys. These North Carolina banjo strummers recorded this sharecropping tale in 1929, yet sonically the recoding holds up very well. Bob Dylan later re-wrote the song (well, basically wrote new lyrics over the tune) for “Hard Times in New York.”

16. “He Rambled,” Charlie Poole with the North Carolina Ramblers. Charlie Poole, with his guitar/fiddle/banjo unit the North Carolina Ramblers, recorded over sixty songs for Columbia Records between 1926 and 1930. His work was considered to be a major influence on both Bill Monroe and Hank Williams and he also somewhat created the archetype of the hard drinking, hard living, rootless country singer (although not songwriter, he was primarily a cover artist). The tune of “He Rambled,” sometimes known as “Didn’t’ He Ramble,” comes from an English folk song “The Derby Ram.” How this song transformed from a tale about a mythical animal of biblical proportions to an unlucky rambling, gambling man is a mystery for the ages.

15. “Wildwood Flower,” The Carter Family. The Virginia based Carter Family, comprised of A.P. Carter, his wife Sara, and his sister-in-law Maybelle Carter, reportedly sold over 300,000 records during the 1920s. A.P. took the lead in the group as a songwriter or finding material, Maybelle’s variation of the flat picking guitar style provided the signature sound. “Wildwood Flower” evolved from a piano based parlor song written in 1860 by Joseph Webster and Maud Irving titled “I’ll Twine ‘Mid the Ringlets.” This poetic tale of unrequited love has become a country standard, later covered by Bob Dylan and The Band, as well as included on the landmark 1972 Nitty Gritty Dirt Band album “Will the Circle be Unbroken.” “Wildwood Flower” was also a jaunty instrumental hit for Hank Thompson and His Brazos Valley Boys with Merle Travis on lead guitar, going to #5 on the country charts in 1955.

14. “Fishing Blues,” Henry Thomas. A country blues singer from Big Sandy, Texas, Thomas rode the rails as a young man and was in his mid-50s when he recorded 23 songs for Vocalion Records in the late 1920s. For the instrumental breaks, Thomas played the quills, a set of cane pipes, that originated in the early 1800s as an instrument played by slaves. “Fishing Blues” has been covered by the Lovin’ Spoonful, Taj Mahal, the Nitty Gritty Dirt Band, and a host of other lure losers.

13. “Waiting for a Train,” Jimmie Rodgers. Rodgers was a Mississippi native who worked as a railroad water boy as a teen, when he wasn’t organizing traveling music shows. He worked as a railroad brakeman before being diagnosed with tuberculosis at the age of 24. He became country music’s first true superstar in the late 1920s, with his trademark hair raising yodeling which once resulted in him being described as “half man, half antelope.” “Waiting on a Train” describes a hobo’s nightmare – a thousand miles from home without a penny in his pocket.

12. “Stealin’, Stealin’,” Memphis Jug Band. Jug bands were known for, of course, using a jug as a musical instrument, but also employing homemade instruments such as spoons, washtubs, and gourd guitars. The bands were typically comprised of African Americans, with a background in vaudeville or medicine shows, and they often gave street performances for tips. The Memphis Jug Band added a kazoo to their musical equation and performed, with frequently personnel changes, for over three decades. “Stealin’, Stealin’,” which was covered by The Grateful Dead in 1966, seems to be about a man who has connected with an old flame, one that wears a ring from another. “Walk Right In” by the Cannon Jug Stompers is another standard from this era that could have been included on this list.

11. “Lovesick Blues,” Emmett Miller. Emmett Miller and His Georgia Crackers. Now generally known as a country song due to the Hank Williams 1949 Emmett Miller inspired cover version, “Lovesick Blues” was written as a show tune by Cliff Friend and Irving Mills. Emmett Miller, one of the last performers in the blackface/minstrelsy tradition, recorded the song on two occasions, making full use of what Nick Tosches refers to as his “trick voice.” Bob Wills and Merle Haggard paid tribute to Miller by covering his 1936 recording “I Ain’t Got Nobody.” According to Haggard, Miller was buried in an unmarked grave in Macon, Georgia, due to local outrage about his marriage to a black woman. Haggard paid for his headstone.


  1. Ron on October 25, 2020 at 9:06 pm

    Really enjoyed what I’ve read so far. Look forward to more. My Dad played backup guitar for local bands in Nebraska

  2. Michael J. on April 21, 2022 at 2:24 pm

    Bro. Where r the other ten ?????

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