Headmasters and Headmistresses
In the United Kingdom, a headmaster or headmistress is the man or woman who heads the staff members and facility of a school (in the United States, this person would be known as the principal).
Portraits of the former headmasters and headmistresses of Hogwarts hang in Dumbledore's office. Although they often appear to be snoozing, they actually listen to everything that is going on. They are duty bound to assist the current headmaster or headmistress in any way they can, which may include traveling to their portraits in other places and reporting on what they see or delivering messages. After Dumbledore died, his portrait was magically hung in his office: "Dumbledore was slumbering in a golden frame over the desk, his half-moon spectacles perched upon his crooked nose, looking peaceful and untroubled" [HBP29].
The following is the known list of headmasters and headmistresses of Hogwarts. In addition, a portrait of one former headmistress - a "gimlet-eyed witch with a stout birch-rod-like wand" - hangs in the Headmaster/mistress's office, but we don't know her name.
Black, Phineas Nigellus - a former headmaster of Hogwarts who is dead [and said to be the least popular one that Hogwarts ever had); his full name is Phineas Nigellus Black; he is a clever-looking old wizard with a pointed beard; he is the great-great-grandfather of Sirius Black; his portrait hangs in both the Headmaster/mistress's office and number 12 Grimmauld Place, so he can travel between his portraits [OOTP6, 23, 37; HBP13, 17].
Derwent, Dilys [1741-1768] - a former headmistress of Hogwarts and a renowned Healer; she is dead; she has long, silver ringlets; her portrait hangs in both the Headmaster/mistress's office and St. Mungo's Hospital, so she can travel between her portraits [OOTP22].
Dippet, Armando - a former headmaster of Hogwarts who is dead; he was headmaster before Professor Dumbledore and was there when Tom Riddle was a student; his portrait hangs in the Headmaster/mistress's office [COS13, OOTP22, HBP20].
Dumbledore, Albus Percival Wulfric Brian - a former headmaster at Hogwarts who is dead; he was one of the most respected and powerful wizards in the world; his portrait now hangs in the Headmaster/mistress's office [HBP29]
Everard - a former headmaster of Hogwarts who is dead; his portrait hangs in both the Headmaster/mistress's office and the Ministry of Magic, so he can travel between his portraits [OOTP22, HBP29].
Fortescue - a former headmaster of Hogwarts who is dead; he is fat and has a red nose; his portrait hangs in the Headmaster/mistress's office [OOTP22]; he actually took out an ear trumpet to hear Dumbledore's and Harry's conversation better [HBP23].
Gimlet-eyed witch with a stout birch-rod-like wand - a portrait of this former headmistress of Hogwarts hangs in the Headmaster/mistress's office [OOTP22].
McGonagall, Minerva - she became the headmistress of Hogwarts for a short period after Dumbledore died [HBP29], and then again after Severus Snape died [JKR Interview].
Snape, Severus - Snape, Severus - appointed headmaster of Hogwarts by Voldemort in August 1997, usurping Minerva McGonagall [DH11].
Umbridge, Dolores Jane - she was first given the title "High Inquisitor of Hogwarts"; the Ministry of Magic briefly appointed her as headmistress of Hogwarts but Dumbledore's office refused to admit her, and she had to use her old office; she was removed at the end of Harry's fifth year [OOTP15, 28].
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