Work in progress (WIP) as I gather my notes, thoughts, editing, braindump, etc.
A list built around the constellation of two archetypal symbols that sometimes appear together in art and real life.
I first came across this connection between death and fools in Mark Dery's essay "Cotton Candy Autopsy: Deconstructing Psycho-Killer Clowns." In the medieval and renaissance period there was a connection between these two entities as seen in the Durer woodcut banner image (see also The Decameron). Dery's essay gives various examples of this death-jester connection: the serial killer John Wayne Gacy (who worked as "Pogo the Clown"), the dead jester Yorick in Hamlet and memento mori, horror rapper's Insane Clown Posse and their "dark carnival," Batman's enemy The Joker.
You can find earlier symbolism in ancient cultures: Hermes as both "divine trickster" and guider of souls to the underworld. The connections between wisdom/life and folly/death in the Book of Proverbs. Examples can obviously be multiplied.
Similar to the philosophy of Gilbert Durand, Hans Blumenberg, and Ernst Cassirer, I tend to use this imagery and symbolism as a "philosophical heuristic" (as a heuristic it sometimes works, and sometimes doesn't). If either of the fantastic imagery manifests itself, I start looking for connections to the other symbolism:
(1) If I see jesters, fools, tricksters, etc., then I am thinking what is their connection with death? ("It's just a prank bro")
(2) If I see death-like entities, then I ask what is their connection to fools and tricksters?
As an example of (2), notice that warfare is tied up with stratagems, ruses, cover-ups, madness, stupidity, etc. Similar to the behavior of classic trickster myths. Sun Tzu: "all warfare is based on deception". See also the first few paragraphs in Nick Land's essay "Philosophy in a War-Zone," which opens with:
"In a reality at war, things hide. The alternative is to become a target, a casualty, and thus – in the course of events – to cease to be. When war reigns, ontology and occultation converge. The oldest of all alliances binds survival to the shadows."
I am interested in reading more about either symbol in order to produce more connections while thinking.
Other random things to research:
Connection between conmen/grifters and the collapse of businesses/economies.
Other iconographical connections: death and love, order and chaos.
Other iconography and symbolism lists: