Headmaster portraits

The Headmaster portraits are a set of portraits mounted in the Headmaster's office at Hogwarts School of Witchcraft and Wizardry. Each portrait represents a previous Headmaster or Headmistress, though not every person to hold the office is immediately granted a portrait. They are honour-bound to serve the current Headmaster at all times. Several of these portraits have counterparts in other prestigous magical insitutions, such as the British Ministry of Magic Headquarters, St. Mungo's Hospital for Magical Maladies and Injuries, and the Black family home at 12 Grimmauld Place.

A trait shared by many of the portraits is that they spend most of the time asleep or pretending to be asleep, though most of them, with the occasional exception of Phineas Nigellus Black, will immediately awaken when addressed.

1995-1996 school year
When Arthur Weasley was attacked by Nagini on 18 December, Albus Dumbledore called upon several of the portraits to relay or provide information on the event. Everard was sent to his portrait at the Ministry of Magic to make sure Arthur was found, Dilys Derwent was sent to St. Mungo's to monitor his arrival there, and Phineas Nigellus Black was sent to 12 Grimmauld Place to inform Sirius Black that Harry Potter and the Weasley children would be arriving there by Portkey.

The portraits witnessed Cornelius Fudge's attempt to arrest Dumbledore later that year, and did not sham sleep that night, but instead outright supported him against the Ministry, with one or two even gave Fudge a rude hand gesture.

1997-1998 school year
After the death of Albus Dumbledore, then-Head Severus Snape continued to be advised by, and take orders from, his portrait. It was under these orders that Snape delivered Godric Gryffindor's Sword to Harry Potter, and arranged for Harry to view several of his memories.

Following the defeat of Lord Voldemort at the Battle of Hogwarts, the portraits cheered on Harry when he visited the Headmaster's office. Dumbledore in particular complimented Harry, and supported his decision to discard the Resurection Stone and return the Elder Wand to the White Tomb.

Knowledge of portaits
Headmaster portraits are capable of interaction with the living world. The headmaster or headmistress is painted before they die. When the portrait is completed, it is kept in a cupboard in the castle, and the headmaster or headmistress can teach their portrait to act and behave like themselves. Additionally, they can impart specific information and knowledge that can be shared down the centuries with their successors.

Known Headmasters with 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 she is still alive and is currently in Azkaban. Most headmasters only receive their portraits once they die. Moreover Hogwarts did not recognise her as Headmistress, as she was forcibly interjected by the Minister, and was denied access to the Headmaster's office. Also considerable factors are that her term lasted from the middle of the year to near the end of that same year, and that she was dismissed with suspicions on her conducts.
 * According to J. K. Rowling, all of the Headmaster portraits depict deceased individuals. As such, though it is never directly stated, it can be assumed that a Headmaster who leaves the position for other reasons will not have their portrait added until after their death.
 * Snape did not get a portrait at first due to his, at the time, questionable allegiance. However, with Harry Potter convincing Minerva McGonagall, he got Snape's portrait into 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
 * Pottermore