10. “Sing, Sing, Sing” by Benny Goodman
Benny Goodman and his 14-piece big band took swing to the next level with their eight-minute recording of “Sing, Sing, Sing.” The improvised solos harkened back to the days of Dixieland, while the extended runtime pointed the way toward the genre’s expressive future. Driven by a relentless beat, “Sing, Sing, Sing” rocks harder than any jazz song before or after. And if you’re looking for an even more bacchanalian version, listen to the 12-minute showstopper from The Famous 1938 Carnegie Hall Jazz Concert.
9. “I’m Gonna Sit Right Down and Write Myself a Letter” by Fats Waller
One of Fats Waller’s most relaxing songs, “I’m Gonna Sit Right Down and Write Myself a Letter” is a masterpiece of popular melody. The song contains one of Waller’s greatest vocal performances: smooth and steady, yet filled with ambiguous emotion. Is the tune supposed to be sad? The tender singing and lonely lyrics indicate yes, but the cheerful music and sparkling piano solos would say otherwise. The contradictions coupled with the catchiness is what makes the song so special.
8. “Cross Road Blues” by Robert Johnson
Robert Johnson’s guitar is capable of producing a world of sound. It slides, plucks, strums and chugs; always delivering a constant thrust of forward momentum. When Keith Richards first heard his music decades later, he turned to Brian Jones and asked, “Who is the other guy playing with him?” In terms of legendary talent, Johnson is only equalled by Jimi Hendrix.
Of course, the story goes that Johnson gained his otherworldly abilities by selling his soul to the Devil at the crossroads (fellow blues musician Son House attested that it was the only explanation for how Johnson got so good so fast). Whether or not the Faustian tale is true, “Cross Road Blues” remains the ultimate Johnson guitar showcase.
7. “We’ll Meet Again” by Vera Lynn
Vera Lynn’s 1953 re-recording of “We’ll Meet Again” is featured at the end of Dr. Strangelove, accompanied by visuals of nuclear explosions. But the seminal version of the song — the one that became Britain’s unofficial national anthem during World War II — was released in 1939. Instead of a lush orchestra and full choir, the 22-year-old Lynn is backed by the Hammond Novachord, the world’s first polyphonic synthesizer. When combined with Lynn’s characteristically low vocals, the song takes on a peaceful yet haunting quality. In a sense, it’s the first (and most famous) example of synthpop. But in terms of emotional impact on a national scale, “We’ll Meet Again” means so much more.
6. “Moonglow” by Benny Goodman
Benny Goodman was best known for his big band ensembles, but some of his best work came when he scaled back. On the 1936 recording of “Moonglow,” Goodman was joined by drummer Gene Krupa, pianist Teddy Wilson and vibraphonist Lionel Hampton. Each musician brought their own signature style to the composition, yet the end result was synchronous with what the track required. Krupa’s relaxed backbeat propped up Wilson’s sophisticated elegance, while Hampton’s tremolo’d reverberations provided the perfect counterpoint to Goodman’s commanding tone. Together, the (first) integrated quartet crafted the dreamiest song of the 1930s.
5. “Dance of the Octopus” by Red Norvo
“Dance of the Octopus” is a very strange tune. It might as well be classified as “swing,” but it’s far too modernist to be considered “pop.” In fact, the end result is almost avant-garde. Red Norvo plays atonal xylophone melodies backed by bowed double bass and an unexpected appearance from Benny Goodman on bass clarinet. The second half of the tune is eerily melodic, with an acoustic guitar joining the mismatched quartet.
Like Bix Beiderbecke before him, Norvo was a hero of the cool jazz underground before such a thing even existed. The curiously titled “Dance of the Octopus” was decades ahead of its time.
4. “In a Sentimental Mood” by Duke Ellington
Duke Ellington’s “East St. Louis Toodle-Oo” was the fourth-best song of the 1920s; he repeated the feat the following decade. But “In a Sentimental Mood” is vastly different: an elegant and emotional mood-setter that swings at a stately tempo. The song contains some of Ellington’s most beautiful passages (specifically the bridge, which is reprised twice, first by the full wind ensemble and then later as a trumpet solo). In fact, you could probably say that “In a Sentimental Mood” is Ellington’s greatest song, which by default makes it one of jazz music’s finest achievements.
3. “Midnight, the Stars and You” by Ray Noble & Al Bowlly
“Midnight, the Stars and You,” performed by the partnership of British bandleader Ray Noble and South African singer Al Bowlly, is famously featured at the end of Stanley Kubrick’s The Shining (the second Kubrick connection in the Top 10 Songs of the 1930s), during the mind-bending fadeout of Jack Torrance’s 1921 photograph in the Gold Room. This has given “Midnight” a haunting connotation ever since, despite the fact that it was originally written as a love song. Yet even when separated from the film, the song still retains an eerie quality. It’s a ballroom swing number that is surprisingly spare — a pop song that possesses a ghostly gracefulness.
2. “Body and Soul” by Coleman Hawkins
“Body and Soul” was a jazz standard originally written in 1930 and then popularized by Louis Armstrong and Paul Whitehead. It wasn’t until Coleman Hawkins covered it in 1939 that the song revolutionized jazz history. In Hawk’s version, the original melody of “Body and Soul” is foregone. Instead, his tenor sax improvises around the outskirts, steering clear of swing clichés and inventing bebop in the process. In terms of history, the song represented a seismic shift akin to Armstrong’s Hot Five and Hot Seven Sessions — a new kind of solo showmanship that stood in stark contrast to the bombast of the big band era.
Yet as a singular work of art, “Body and Soul” remains timeless. It’s the rarest of songs — one that demands close and careful listening while remaining immensely soothing and relaxing.
1. “Moonlight Serenade” by Glenn Miller
The most famous song of the swing era, Glenn Miller’s “Moonlight Serenade” has been inducing swoons and captivating the hearts of listeners for the past 85 years. How has it remained so effective for so long? In short, it’s a perfectly constructed pop song: extravagant yet never excessive; sentimental yet never saccharine. It was destined to become an international phenomenon from the moment it was written.
In a way, “Moonlight Serenade” is the perfect representation of the 1930s, rising up from the doldrums of the Great Depression with a slow, swaying melody that remains unchanged and unscathed, patiently progressing in a calm and coherent manner before rousing to a passionate fervor, finally breaking the trance. It’s the most romantic song of all time, one that signifies the love of life itself.
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