FanficRecs Comment by Roo
One of the old fics from back when A Sailor Moon Romance was the go-to place for Sailor Moon fanfic, Secondary Characters is a Black Comedy Crack Fic that still stands out as of the weirdest, most surreal fics the franchise has ever inspired, being alternately hilarious and disturbing (in a good way). The story begins with the Senshi all dead and telling each other dirty jokes in the afterlife while Usagi is off fighting Galaxia, and it only gets more surreal from there, after they're returned to life — and yet, even while deconstrucing and at times lightly mocking the Sailor Moon universe and characters, the fic stays sympathetic to them. And even with all its surreal strangeness, everything comes together and actually makes perfect sense in the end.
FanficRecs Comment by Dune
Seconded by Dune. Even though I still don't agree with the ending (I'm the whiny kid in the reviews), it's a really well-written and interesting story. Every character gets a new depth, and the final chapter or so are really suspenseful.