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Fytherley Undercliffe was a former headmaster of Hogwarts School of Witchcraft and Wizardry during the 1500s. His portrait was painted and dated 1531, which was closer to the end of his time at the school. Prior to his position as headmaster, he served as Slytherin Head of House for at least a decade. While he may not have been the most memorable of headmasters to have graced the castle grounds, Undercliffe has many duplicate portraits hanging aside from the one in the Headmaster’s office; two of the most prominent being in the Grand Staircase and near the entrance to the Astronomy Tower.

The inscription on Undercliffe’s portrait frame reads “Virtutes, Archangeli, Angeli, Principatus, Dominationes, Seraphin, Cherubin, Throni.” These are the eight hosts of angels in Christian angelology and the inscription was added to the frame years after the final portrait was finished. The reason for this was that Undercliffe devoted his life after retirement to delve into a study on a possible connection between Muggle tales of contact with angels and a seer’s communication with spirits. His studies later inspired the medium and possible charlatan Edward Kelley to proclaim that angels communicated with him through an Enochian (angelic) language, which eventually led Kelley to work with John Dee, a famous alchemist and astronomer. Undercliffe never lived to see his work used for this purpose as he died in 1560, when Kelley was only five years old.