A tremendous source of frustration in my life concerns the following sequence of events.

I’ll be playing an early recording of a Cole Porter song from the late 1920s or early 1930s, or perhaps a daring song from a soundtrack from an outrageous Busby Berkeley movie.

I’ll be absolutely thrilled at the sheer radicalism of the text and the beat, the edginess of the topic which covers issues considered “adult only” today, and I love to imagine the world being born in that period and how utterly new and startling it must have been. Such a window into a time not unlike our own!

Technology was reaching the world in a new way and composers and singers were reveling in the new opportunities. It was only two generations earlier when pop music was a Souza march or a filiopietisic love song played on a piano at home. Back then, the only serious innovations in popular music (ragtime) were found in places you weren’t supposed to be.

But in the 1920s-30s, there was this explosion of artistic energy, all tied up with protesting the regimentation of the world with socialism, fascism, and prohibitionism. Music was a sphere of freedom. It was bound up with dance and free association of persons, with a love of life despite the growth of despotism all around. It reflected urbanism, the desire of the new generation to escape the world their parents inhabited, to explore new forms of art and life, to embrace and live prosperously, and, above all, to decline to comply with the growing restrictiveness of regime politics.

I hear all of this in this music. It thrills and delights me.

But when I play it for others, the reaction is usually rather disappointing: “that sounds old.”

Well, it sort of does sound old. But old is not old-fashioned. Not if you listen carefully. There is liberation in this music and style. It cries with with a love for freedom despite what was happening to the world with the rise of every form of tyranny. Indeed, music was a great American contribution to the world.

Our dance music and jazz annoyed dictators all over the world (the Nazi’s ridiculous “war on jazz” was about as successful as the U.S. war on drugs.)

What song from this period is the best to illustrate what was going on and why it matters? My vote is the Benny Goodman performance of “Sing, Sing, Sing,” from 1937, featuring Gene Krupa on drums. The song itself was written a year earlier and first recorded by Louis Prima. Goodman went to Hollywood for his recording and the results are nothing short of classic.

It also represented a big push forward in technology. It was pressed on a 78-rpm record, one that you had to turn over to hear the entire song. The usual big-band chart of the time was 3 minutes long, a limitation of what could be distributed. But Goodman went all out with a version that lasted 8 minutes and 43 seconds. Nothing like this had been done until that point.

The song features every conceivable musical effect, many just outrageous. The trumpets use what’s called flutter tonguing to achieve a growling and animal-like sound. Descending passages in one side-melody employ a two-against-three motif that seems designed to capture the feeling of inebriation. The solos are long and dream like, and clearly improvised. There are moments that seem absolutely primal, with brass that nearly scream with excitement and abandon. Every new section seems to yell “you can’t control me” with ever more intensity.

Then there’s the speed of the song itself. It is very quick, so much so that dancing to it requires some real expertise. You have to stay cool but doing much in the way of turns and flips calls upon real physical energy and stamina. But the song is so upbeat and happy, the adrenaline that emerges makes it possible.

Underneath it is the driving, primitive drum beat provided by the great Gene Krupa. The drum in this song becomes an extended solo instrument, on par with any other. It seems to be waking something up within us, something calling on the broadest range of human experience.

More than any other feature of this song, the persistent, daring, pushy, and innovative drum work suggests a busting out of the confines in which the politics of the time were trying to place us. As freedom in the external world was declining, this music and this song in particular seem to be recreating the joy and liberty of life in musical form.

Consider the amazing distance, the vast gulf, that separates this song in 1937 from the music of 50 years earlier. There was nothing else like this in existence only a couple of generations earlier. It called on new talents, new sensibilities, a new way of dancing, a sense of daring defiance against the status quo.

Public life was becoming ever more restricted, censorious, regimented, and even tyrannical. But musical life was going in the exact opposite direction, as if to underscore that freedom, progress, and love of life cannot be crushed no matter what governments say.

“Sing, Sing, Sing” embodies this spirit more than any song of the period. It goes way beyond the comparatively stodgy “Pennsylvania 6500” and “Chattanooga Choochoo” of Glen Miller and other bands at the time. Even now it strikes the ear as radical, revolutionary, and insanely fun. This is why it has been featured in dozens of films, shows, games, and commercials over the last decades.

It’s a masterpiece, and maybe the most radical song ever performed.