Sunglasses of the Prophet

GPI: Cue Journey’s “Any Way You Want It”. (Problem Sleuth, p. 1666)

Long before the Dead Cherub’s dramatic speaking debut, there was already speculation that an alternate Calliope might speak with lowercase red text. Mirroring the quirk Caliborn took when he stole Calliope’s typing style was the main reason, of course, but another potential parallel was seen as particularly exciting.

When the Dead Cherub types in pure red and all lowercase, she almost exactly imitates the typing style of Dave Strider. Which would be perfect, if only she had a set of black shades to match.

The reason Calliope might have been expected to show up with Ben Stiller shades on is mainly because of her perceived parallels to various incarnations Problem Sleuth’s Pickle Inspector. In Problem Sleuth the shades were prominently worn by Godhead Pickle Inspector, whose catchphrase “fondly regard creation” has been read by some as being synonymous with the phrase that makes up Calliope’s title “Muse of Space”. Pickle Inspector’s temporal replicsimile ability that eventually has him literally become creation has also been seen as in line with the role of a Muse of Space; and of course Problem Sleuth’s Death, who shares a build and manner with the Inspector, shares the Dead Cherub’s job of overlooking the afterlife.

(Homestuck, p. 311)

The significance of these shades to the Muse of Space role isn’t limited to just the fact that they briefly touched the Godhead’s weird, kind of gaunt face, either. Andrew comments on their galactic glint - a callback to the same shine seen in Problem Sleuth on page 1667 - in Homestuck: Book 1;

The Stiller shades, presumably the exact same ones that made the whole trip through Problem Sleuth, were witness to every event that took place the history of the universe when they went through a black hole. They still bear this cosmic imprint, much like a kind of photographic film. This detail remains startlingly insignificant to the story in HS though.

All of that aside, though, the shades and the Dead Cherub have their own special connection within Homestuck itself. Because while getting the shades to Dave was a pretty simple process for John pre-Scratch, Dave Strider’s relationship with Ben Stiller post-Scratch was far more involved.

DAVE: what happened to ben stiller
DIRK: He was deemed a heretic, and was crucified on the Washington Monument by some clowns.
DAVE: wow
DIRK: Due to his dedication to freedom and peace, he came to be seen as a martyr, and then a holy figure.
DIRK: He was left on the monument as an example to all, but thousands of faithful gathered below to gaze up at his pious, sort of gaunt face.
DIRK: For years thereafter, his followers would carve stone busts of him in his memory, capturing the piercing glare of his final expression.
DIRK: But they were all smashed to pieces by the presidential church.
DIRK: That religious movement didn’t last very long.
DIRK: Rumor has it the batterwitch had a lot of experience crushing righteous insurrections.

This whole exchange serves to establish Ben Stiller as parallel to Alternia’s Signless, who was also martyred on a stone obelisk. This establishes an ongoing legacy from character to character, across universes; from Kankri to Stiller to Dave, who apparently received the sunglasses from Stiller personally.

(Also note that it provides a direct connection to the shades’ origins in Problem Sleuth).

This is relevant to the Dead Cherub because it forms a link between each generation of characters dressed in the colour red; Ben Stiller in the post-Scratch timeline specifically dons a red shirt for his role as Sweet Bro in Dave’s SBaHJ films. By taking red for her own, the Dead Cherub is not merely dressing herself in the colour of her defeated brother and becoming more Davelike; she is specifically becoming part of an established legacy of like characters.

(Homestuck, p. 7069)

The fact that the Dead Cherub isn’t wearing sunglasses when we finally see her face might not actually be important. Her pitch black eyes - which have no other in-text explanation - evoke them visually, and follow her when she hops into another body in the same way Dave “lifts the shades off [his] corpse, and puts them on his face” when he moves into his robot body. Davepeta represents their sunglasses with the letter B, associated with the number 8; directly opposite to the letter O and the number 0, which Aradia repeatedly uses in emotes like 0_0 to represent her white ghostly eyes.

They also notably form “black holes” in her face, in the same way Sollux’ - who has also at one time held the universe(s) in his sunglasses - did after being attacked with Eridan’s white wand. This association with black holes only makes sense, given that black holes represent the pockets in Caliborn’s pool session, where Lord English’s eyes are the pool balls themselves; and again, this ties back to the Stiller shades and the transformation they went through after they went through a black hole.