Sing Sing Nights

IMG_1499 (2)The Drink

We can almost see the warden, the captain of the guards, and a couple of gentlemen in striped coveralls singing “Sweet Adeline” and imbibing the Sing Sing Nights Cocktail devised by Harry Stephen Keeler.

Shake with 3 Ice Cubes till at least Half of the bulk of the Cubes has dissolved.

-From So Red the Nose

* =shot

For the grain alcohol I used Everclear because, well, you know. It’s what’s at the store, and I’m not quite to the point of raiding the medicine cabinet yet. Simple syrup can be made easily enough, and the juice was squeezed right from the fruit into my cocktail shaker, as per Keeler’s instructions. If you do make this drink, take that part about the ice cubes seriously; grain alcohol of any brand isn’t something to mess around with.

As a vehicle for getting needlessly strong liquor into your bloodstream without skinning your tongue, Sing Sing Nights works about as well as anything else. But if you’re looking for actual tastiness, I think The Canary Murder Case is the superior potent, citrus drink based on a mediocre murder mystery.

The Book
Or, The Strange Adventure of America’s Best Worst Writer*


“Well gentlemen…We’ve got something like nine hours to live. What shall we do with ourselves on this glorious evening which the State of New York has so kindly consented that we spend in each others’ company?”

-From Sing Sing Nights


The 1934 movie’s plot was “suggested” by Keeler’s frame story.

One dead body. Three convicted killers. Two bullets. One blank governor’s pardon and exactly one night to figure out which man will get to use it to save his own life.

Amazing set-ups with disappointing payoffs are going to be a theme for Harry Stephen Keeler’s Sing Sing Nights. 

In fact, these three killers are not even our main characters, but rather part of a Canterbury Tales– style framing device for three short stories. Whichever of our three prisoners tells the most entertaining, elaborately-plotted tale (that he just now thought up) wins the pardon and his freedom.

The first story, appropriately enough, is a murder mystery. “The Strange Adventure of the Giant Moth” starts off promisingly with characters of unclear motivations, a series of strange but connected coincidences, and the delightfully bizarre plot device of an elaborate moth costume.

The second tale, “The Strange Adventure of the Twelve Coins of Confucius” is a murder…thriller? Our journalist hero doesn’t really do much sleuthing, but there is a lot of intrigue based around a murdered Chinese launderer, a beautiful Chinese princess, a completely bullshit legendary Chinese treasure, and just a general butchering of an ancient and noble culture.

Our final tale, “The Strange Adventure of the Missing Link” is about a man who switches brains with an ape. Huh.


A second film, based on the middle story, was also released in 1934. Holding to the spirit of Keeler’s racial sensitivity, it stars Bela Lugosi as a Chinese shopkeeper.

So this all sounds amazing so far, right? Well, like I said above, Keeler is great at constructing elaborate and intricate plots (he called it “webwork”), but not as much at connecting all those threads into a satisfying conclusion. I mean, the mystery story actually ends with “the butler did it.”

This, of course, extends to the frame story as — spoiler alert — there’s a cop-out at the end and no best story is chosen. Even though “Missing Link” is clearly the best, if for nothing else than giving us the image of an depressed ape strolling through a London slum in a too-tight suit. The fact that Keeler decided to take such a far left turn from standard whodunnits into preposterous speculative fiction delights me enough to overlook the story’s old-timey tendency to have pages and pages of boring science explanation.

Also, I’m trying not to talk about the racism in these books anymore — since I’ve realized that I would have to with, like, all of them — but some writers really slap you in the face with it. Sing Sing Nights is an OK read as it goes, but I don’t know if it’s really great enough to have to work through whatever weird issues Keeler had with Asian people (Did you villanize them? Sexually fetishize them? Exoticize them? Keeler your prejudices are more mysterious than your plots.).

Forgotten Classic or Better Left in the Past?

All that said, I do acknowledge that Sing Sing Nights is just barely outside the line for me. I can’t honestly state it is worse in any objective sense than, say, something like Bring ‘Em Back Alive. It’s just that the latter hits my particular fun buttons enough to overlook the bullshit. I can certainly see many people thinking Sing Sing Nights is entertaining enough to skip over horribly offensive tangents about interracial breeding and/or date rape via mind switching being portrayed as a “happy ending.” 

keelerAnd some of those people may be Keeler’s currently-existing fan club, The Harry Stephen Keeler Society. You see, in comparatively recent years, Keeler has become a cult figure by the usual way: from loosing his damn mind. Always a bit strange and complicated,  in the years after So Red the Nose was published, Keeler’s stories became ever more meandering, fantastical, convoluted, and just plain batshit. I’ve seen him called the “Tommy Wiseau” or “Ed Wood” of literature in online reviews. His special brand of brilliant nonsense even inspired an episode of Futurama (whoah, all my worlds colliding).

So this book is another one that was more fun to research than to read. Would I recommend 1927’s Sing Sing Nights? Not really. But would I recommend 1936’s X. Jones of Scotland Yard, about a little person who dresses as a baby and murders people via helicopter? You bet your shiny metal ass.

*Title blatantly stolen.

Sing Sing Nights is available in Kindle or or used form on Amazon.

Next time:



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