Headmaster portraits

Headmaster portraits are mounted in the Headmaster's office at Hogwarts School of Witchcraft and Wizardry. Each portrait represents a previous Headmaster or Headmistress, and they are honour-bound to serve the current Headmaster]] at all times. The portraits also talk to the current Headmaster]]. In the books on more than one opportunity, Harry has walked into the office and the portraits have fallen silent. They also have a tendancy to pretend to be asleep when something interesting is happening that doesn't involve them. The only known person to have served as Headmaster who does not have a portrait is Professor Dolores Umbridge.

History
During the Second Wizarding War, Albus Dumbledore used the portraits to relay messages to other locations where other portraits of the subject were kept, such as keeping in contact with 12 Grimmauld Place using the portrait of Phineas Nigellus Black. After his death, Dumbledore via his portrait gave instructions to his successor, Severus Snape; which, thereby allowed Dumbledore to continue his machinations and efforts to help Harry Potter defeat Lord Voldemort once and for all.

Known Headmaster portraits

 * Albus Dumbledore
 * Ambrose Swott
 * Armando Dippet
 * Basil Fronsac
 * Dexter Fortescue
 * Dilys Derwent
 * Eoessa Sakndenberg
 * Everard
 * Heliotrope Wilkins
 * Newton Scamander
 * Phineas Nigellus Black
 * Phyllida Spore
 * Portrait of a bearded man holding a book
 * Quintin Trimble
 * Severus Snape
 * Vindictus Veridian
 * Vulpus
 * Walter Aragon
 * Unidentified chessmasters Heads of Hogwarts
 * Unidentified Hogwarts Headmaster
 * Unidentified Hogwarts Headmistress

Behind the scenes

 * It is possible that Dolores Umbridge does not have a portrait, because Hogwarts did not recognise her as Headmistress. For example, she was denied access to the Headmaster's office.
 * It is assumed that by the year 2017, a portrait of Minerva McGonagall hung in the office.

Appearances

 * Harry Potter and the Chamber of Secrets
 * Harry Potter and the Chamber of Secrets (film)
 * Harry Potter and the Chamber of Secrets (video game)
 * Harry Potter and the Goblet of Fire
 * Harry Potter and the Goblet of Fire (film)
 * Harry Potter and the Order of the Phoenix
 * Harry Potter and the Order of the Phoenix (film)
 * Harry Potter and the Order of the Phoenix (video game)
 * Harry Potter and the Half-Blood Prince
 * Harry Potter and the Half-Blood Prince (film)
 * Harry Potter and the Deathly Hallows
 * Harry Potter and the Deathly Hallows: Part 2
 * Harry Potter and the Deathly Hallows: Part 2 (video game)
 * LEGO Harry Potter: Years 1-4
 * LEGO Harry Potter: Years 5-7
 * Harry Potter: A Pop-Up Book
 * Harry Potter Trading Card Game