A few words on the significance of Cicero as the Jester
We know the story: Ciceroās last job was to assassinate a flamboyant jester, who laughed until the moment he died; this obviously had a lasting psychological impact on dear sweet Cicero⦠but itās never fully delved into what sort of impact this had and why it was so poignant, nor why Cicero chose to take on the role as a Jester, himself, other than mentioning that he did so to cope with the silence and isolation within the dark brotherhood.
Itās important to note that Cicero is very much a rebellious figure, and he pokes fun at Astridās Dark Brotherhood chapter because of the way it deviates from the original, and this is where the character of the Jester becomes not just fun, but deeply political.
Historically, letās break down the elements of a court jesterās outfit, because itās deeper than you think.
Poulaines and Pointy Caps
Letās start with his poulaines - pointy boots. The typical court jester would wear long and exaggerated pointy shoes because pointed shoes were a symbol of wealth among elites: this was to mock the impractical nature of upper class fashion - he could be foreshadowing Astridās betrayal of the Listener and faux assassination plot of the Emperor by wearing what appears to be a combination of exaggerated rich fashion and the dark brotherhood colours, painting a portrait of the Dark Brotherhood āsucking upā to the Emperor and Solitude Guards (since they also share the same colour scheme).
The double points on his jesterās cap are made to mimic an āassā or a hare, and this is because donkeys were symbolic of stupidity and stubbornness, and rabbits, cowardice.
Bells and Ruffs
The star ruff mimics real ruffs worn by the upper classes, again mocking rich fashion, but the bells on the end of each point held a different and more blasphemous connotation: the bells were something historically associated with priests. This is openly mocking the church; in Ciceroās case, he is mocking what he thinks is a bastardisation of the faith and tenets of the dark brotherhood.
The bells also symbolise āfoolish chatterā and meaningless noise - perhaps his dancing and loud manner of speaking was to cope with isolation to begin with, but the second he steps into the Falkreath Sanctuary, it becomes a mockery of the treasonous plots that are about to ensue and Astridās ridiculous arguments over (and obsession with) leadership whilst the Night Mother is right there.
(But this is in fanart depictions of him where he has bells; he doesnāt typically wear them in the game because he does still need to sneak around. Still. I love the bells when theyāre added.)
Dual Tones and Chaotic Patchwork
The chaotic patchwork in a typical jesterās outfit often symbolised being āoutcastā in society and mental fragmentation, and bi-coloured clothing was typically legally reserved for criminals or mentally ill individuals; Cicero gets away with wearing bi-coloured clothing because he is mentally ill, but to then wear a two-toned jesterās outfit in the colours of the Dark Brotherhood pokes fun at the fact that theyāre all criminals.
Jester Status and Artificial Fools
āJester Statusā allows Cicero to get away with mockery because Jesters were not seen as people; they were seen as property - in this case, property of Astrid, and property of the Emperor. Kings rarely executed their jesters because they would be seen as stupid if they were offended by a āthingā; this is why Astrid falls into idiot territory the second she begins her shenanigans with Cicero. Because she is offended by him. She does react in a disproportionate way when her authority is questioned, even playfully.
āNatural Foolsā were usually people with facial deformities or learning disabilities; since it is clear that Cicero has neither, that puts him into the category of āArtificial Foolā⦠and artificial fools were usually highly skilled performers; hence why you should never underestimate Cicero as a character and why heās one of the best - if not the best - companion to bring along with you.
To Conclude
Cicero is making some very bold statements with his choice of attire and persona; not only does it bring him comfort, and not only does his āJesterā status allow him to mock Astrid and the Emperor⦠he can do it whilst wearing their fucking clothes.
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