Best Songs of the 1920s: #10 – 1

10. “In the Jailhouse Now” by Jimmie Rodgers

The greatest country music songs often contain an element of comedy, which is why Jimmie Rodgers’ “In the Jailhouse Now” remains one of the finest in the genre’s history. The lyrics tell about the humorous misadventures of Ramblin’ Bob, a degenerate gambler destined for the hoosegow. Yet the tale wouldn’t be so amusing if it wasn’t for the excellent musicianship — and yodeling — that carries the song through.

9. “Travelin’ Blues” by Blind Willie McTell

Half-spoken, half-sung, Blind Willie McTell’s “Travelin’ Blues” chugs along at a frenetic pace. Stream-of-consciousness lyrics pair with omnipresent rhythms to create one of the most innovative blues songs of the decade. There’s so much information packed into the song’s three-minutes-19-seconds that an entire essay could be written on its wide-ranging musical complexities. But since we’re strapped for space, I’ll simply say this: it’s some of the best music that the 1920s has to offer.

8. “West End Blues” by Louis Armstrong

The unaccompanied trumpet fanfare that opens Louis Armstrong’s “West End Blues” signified that jazz had officially arrived. All of a sudden the burgeoning genre ascended to the highest order of musical expression, even surpassing classical in its ability to convey raw emotion. Recorded in 1928, “West End Blues” was a true turning point in musical history. The song’s innovations in rhythm and harmony, coupled with Armstrong’s tender scat singing, made it an immediate classic whose influence can still be felt to this day.

7. “Frankie” by Mississippi John Hurt

Although Mississippi John Hurt grew up near the Delta, his hometown of Avalon is located in hill country, which explains his folk-influenced style. “Frankie” is Hurt’s greatest song, featuring all the things that he did better than anyone else: innovative acoustic guitar, melodic vocals not typical of a bluesman and a matter-of-fact narrative that doesn’t pass judgment on any of its fundamentally flawed characters.

6. “Statesboro Blues” by Blind Willie McTell

Blind Willie McTell’s 12-string acoustic guitar is a thing of wonder. In fact, it’s almost unbelievable that he is able to generate so much sound from a single instrument. “Statesboro Blues,” McTell’s finest composition, is a superb example of his singular style. The lyrics flow in free association, with a non-linear narrative held together by the ambiguous titular theme, an unexplained condition of which all McTell’s unnamed family members suffer from. Meanwhile, the dazzling guitar props up the circular storyline, or is it vice versa? The beauty of McTell’s method is that no musical element is more important than the other.


Blind Willie Johnson - Dark Was the Night, Cold Was the Ground

5. “Dark Was the Night, Cold Was the Ground” by Blind Willie Johnson

The Voyager Golden Record was launched into space in 1977 to give extraterrestrials some idea of what life on Earth sounds like. Mixed among the compositions of Bach, Mozart and Stravinsky was Blind Willie Johnson’s 1927 recording of “Dark Was the Night, Cold Was the Ground.” Despite its relative obscurity, it might be the most universal song on the entire LP.

Johnson’s wordless vocal, which runs concurrent to his eerie slide guitar, seems to encompass all of humanity. He grunts, groans and wails a ghostly melody, snaking through the form and void, searching for a place to rest in the dark. It’s a song about struggle and, like most early blues recordings, a song about death. As a result, “Dark Was the Night, Cold Was the Ground” is relatable to all life forms, on this planet or elsewhere.

4. “In a Mist” by Bix Beiderbecke

“In a Mist” is Bix Beiderbecke’s most advanced composition. Drawing from classical impressionism and hinting at bebop, the solo piano tune features a combination of lush, melancholic chord progressions and a swinging tempo, which creates a dynamic tension that points the way directly toward modernism.

3. “Ain’t Misbehavin’” by Fats Waller

The star pupil of James P. Johnson and the preferred pianist of Al Capone, Fats Waller was respected by everyone and loved by all. His infectious personality is why his music still resonates to this day (and why he features so prominently in the Colin’s Review Best Songs of the 1920s and 1930s). “Ain’t Misbehavin'” is warm and comforting, marrying Waller’s trademark stride piano with swingin’ melodies. Unsurprisingly, it’s been a huge success for every artist who has ever covered it, a disparate list that includes everyone from Django Reinhardt to Johnnie Ray.

2. “East St. Louis Toodle-Oo” by Duke Ellington

Bubber Miley’s growling trumpet is a perfect complement to the song’s sinister backbeat, but after the first stanza “East St. Louis Toodle-Oo” transforms its jilted melodies into joyous celebration. Incredibly arranged by Duke Ellington and impeccably performed by his Washingtonians, “Toodle-Oo” is early evidence that jazz was constantly transforming. Even in 1927, the song couldn’t be categorized — it isn’t stride, stomp or Dixieland. Instead, it can only be called for what it is: a convincing argument that Ellington was the greatest and most influential jazzman who ever lived.

1. “Stardust” by Hoagy Carmichael

Not only the greatest song of the 1920s, but one of the greatest (and most famous) songs of all time, “Stardust” remains timeless to this day, a testament to its eternal longevity and endless adaptability. The original 1927 recording by singer, songwriter and occasional pianist Hoagy Carmichael is an instrumental version you’ve probably never heard, yet after one listen it’ll likely be the only interpretation you’ll ever need to hear again.

Carmichael’s song is beautiful and melodic, with jazzy overtures and interludes that tug at the heartstrings. But “Stardust” touches on an even deeper level — it encapsulates the dreams and desires and spirit of longing that comes with simply existing. The song is glorious and tragic, joyous and melancholic. Like the cosmic particles alluded to in the title, “Stardust” is everything.


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