Throughout the city, SUPERSTRUCTURES has encountered some surprising and sinister figures glaring down from parapets and facades. And not just on Halloween, but every day of the year. They menace our team with leering looks wrought in terra cotta, cast iron, and stone. The culprits? Gargoyles and grotesques.

These harmless characters have a long history of inhabiting buildings—from medieval cathedrals to their heyday in 19^th century revival structures. Here are a few fun facts about their history:

• What makes a gargoyle a gargoyle? While the term is often applied to any type of fantastic figure adorning a building, there’s an important caveat: gargoyles serve as downspouts, while grotesques don’t. Originally, gargoyles functioned as decorative disguises for roof drainage, directing water away from facades like that of Notre Dame Cathedral in Paris.
• In medieval church architecture, they also served as part of a dense decorative program meant to instruct—and terrify—the illiterate masses. From demonic beasts to pagan “green men,” they helped promote the power of the Church.
• Some modern renditions celebrate industry, while others memorialize building patrons, incorporating a biographical element into the built environment. There are even nods to pop culture, like the “Alien” gargoyle added to Scotland’s Paisley Abbey during its restoration in the 1990s.

From Collegiate Gothic to Art Deco facades, here are some of our favorite gargoyles and grotesques encountered in our work on New York’s buildings (and beyond):

From left, top row: Two downspout gargoyles on a chimney at City College’s Compton-Goethals Hall; A toothy grotesque from the MacIntyre building; A pensive figure of a scholar from Westinghouse High School. Middle row: A stern beaver from the seal of New York on the Manhattan Municipal Building; A fiendish terra cotta face from 345 Adams Street, Brooklyn; An avatar of electrical invention from the Graybar Building. Bottom row: One of numerous pupil figures from Haaren Hall; A sly green man from the Hotel Beacon; A chimeric gargoyle on Yale University’s Sheffield-Sterling-Strathcona Hall.