In Praise of the Greatest Swing Song Ever -or- Sing Cubed is Not Square

I’m not a musical historian, but I play one on this blog, and I think the Golden Age of Swing in American music ran from the late 1930s through the end of World War II. A host of incredible musicians wrote and recorded songs that still capture ears and imagination almost a century later.

I’d be hard-pressed to come up with a favorite tune from that era, but I’m pretty sure Sing, Sing, Sing would be in the running. This post is a tribute to that musical gem.

Louis Prima wrote and recorded Sing, Sing, Sing (With A Swing) (hereafter referred to as S3 to save my typing fingers) in 1936. The record was a 78 rpm and ran just a tad longer than four minutes, which was pushing the limit on that medium. Here’s Prima’s recording, via YouTube:

I don’t know if the original version was a huge hit for Prima, but the song’s popularity shifted into high gear when Benny Goodman got hold of it the following year. A fellow named Jimmy Mundy — a saxophonist who was associated with jazz luminaries such as Count Basie and Lionel Hampton — created an arrangement for Goodman that extended the tune to almost nine minutes, taking up both sides of a 12-inch 78 rpm platter.

Here’s a video of Benny Goodman’s orchestra’s performance of S3 in the 1937 movie Hollywood Hotel.

I watch this clip and as an exceedingly average clarinetist whose improvisational skills are about as developed as my self-levitation skills, I can’t think of a better experience than being one of the sax players sitting behind Goodman during his solo (starting at around the one minute mark). What a gig!

Now, in 1938 Goodman’s orchestra took the stage in Carnegie Hall and the resulting performance of S3 became a part of music lore. This 13-minute version also featured Gene Krupa on drums and Harry James on trumpet. The piano solo was performed by Jess Stacy, who improvised the riff on the spot, not having been given the spotlight for this tune prior to this concert.

Sidenote: That’s Gene Krupa on drums. For you kidwinks who never heard of him, Krupa was likely the first drummer to combine flair and skill and get a showcase in a commercially successful band. He and another somewhat skillful (ha!) drummer named Buddy Rich used to do the dueling drummer thing, much to the delight of audiences. Here’s an excerpt from a 1956 interview of both men. It’s fascinating reading, especially the part where Rich takes on the so-called “cool music” of the day, and the way he felt it excluded musicians of his ilk:

I have a definite and very set opinions about the so-called modern school of music and drummers. Whereas in the days when it was necessary to swing a band, where a drummer had to be a powerhouse, today more or less the “cool school” has taken over, and I don’t believe there’s such a thing as a “cool drummer.” You either swing a band or don’t swing a band and that’s what’s lacking today. There aren’t any guys who get back there and play with any kind of guts. And I like a heavyweight. I’m not a flyweight. I like-in my fighting, I like heavyweights and in my music I like emotionally good, strong heavyweight type of jazz. And it’s just lacking today.

And speaking of their drum battles, here’s another YouTube clip of one that was broadcast on the Sammy Davis, Jr. Show in 1966. The tune will be recognizable, I think:

Now, where were we? Oh, yeah…S3. Now, while these old recordings are wonderful (and it’s truly a blessing that these performances have not been lost), there’s really no substitute to hearing this song performed live by a skilled group of musicians. There aren’t a lot of venues in our area where you can experience this, but one of them is just 90 miles down the road from where I live, in San Antonio to be exact.

In the Pearl District, just north of downtown and adjacent to the northern end of the famous River Walk, there’s a nightclub/restaurant called Jazz Texas. It features live music every night; during the week the music may range in genre, but on the weekends it’s primarily jazz, courtesy of Brent (Doc) Watkins and his orchestra. You can visit Doc’s website to see his complete bio, but for our purposes it’s sufficient to say that he’s one of the most gifted pianists and music arrangers you’ll ever encounter, and he surrounds himself with equally gifted musicians.

In March, 2020 — just before COVID brought the world to its knees — Debbie and I spent a weekend in San Antonio, and we spent Saturday night dining at Jazz Texas and enjoying the music. It’s a relatively small venue, and while we were seated toward the back of the room, we were still only a few yards away from the band. Suddenly, the signature sound of the drum solo that kicks off a certain song began, and I fired up the iPhone. Here’s the result:

“Sing Sing Sing” – The Doc Watkins Orchestra from Eric Siegmund on Vimeo.

I wish I could identify all the individual musicians featured in that video, but I can tell you that the drummer is Brandon Guerra and the incredible clarinetist is Bill King.

(Incidentally, I have strong opinions about people who go to a jazz club and then ignore the music, but I won’t share them here.)

If you made it all the way through this screed, thanks for your patience and attention. I suspect that we share an affinity for good music, regardless of genre…but this big band stuff is the bee’s knees!

Categorized as Music


  1. Kinda thought you might approve of this song, Sam. 😉
    The Jazz Texas performance I recorded wasn’t nearly as impressive as the one we got to experience together, where we were practically on the bandstand, but I think it still captured the same spirit.

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