For the bulk of the Harry Potter series, Dumbledore was the Headmaster of Hogwarts, and for many fans he will always be the most iconic witch or wizard to lead the school. However, even within the original series, there were a few others that took on the role over the years. Dolores Umbridge, Severus Snape, and Minerva McGonagall all held the position during Harry"s time at school (or when he should have been at school, but was off chasing Horcruxes).
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A few other Headmasters are mentioned in the series, too. Dumbledore"s predecessor, Armando Dippet, gets a few mentions, and others who occupy their portraits in the Office also appear, such as Phineas Nigellus Black. But based on the entire Harry Potter canon, which of the known Headmasters are worth remembering (and which are just background portraits)?
Nothing is known about this Headmaster, not even their name - but they get a mention for two reasons. First, because none of the four founders themselves were ever Headmaster, although each was "head" of their own house (obviously). Second, because there was a statue of the first headmaster at the school, which is mentioned in passing. Even if he didn"t have many other achievements, being the first Headmaster is worth something!
10 Elizabeth Burke
Elizabeth Burke was Headmistress of Hogwarts, and was one of the few Slytherins to take the job. She may have been related to the Burke of Borgin & Burkes, and was known to favor her own house, and to encourage her students to be "nasty to Mudbloods". From the DVD extras and games, it is known that her portraits hung over the entrances to shortcuts to and from the dungeons, that Slytherins could use with a password.
Dilys Derwent is described in the series itself as one of "Hogwarts’s most celebrated Heads. Their renown is such that both have portraits hanging in other important Wizarding institutions". She was Headmistress from 1741 - 1768, a Healer who left a job at St Mungo"s to take up the post. She is mentioned in the series, as her portraits at Hogwarts and St Mungo"s are used to send messages when needs be (such as when Arthur Weasley is attacked).
Everard is the second Headmaster mentioned alongside Dilys as one of the "most celebrated". Unlike Dilys, though, his portrait is not at St Mungo"s, but at the Ministry of Magic.
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He was also involved in important communication between Dumbledore and the others when Arthur Weasley was attacked, as well as between the Ministry and McGonagall when Dumbledore was killed. What he did to become so celebrated, though, is unknown.
Quentin isn"t mentioned in the series as many of the other more notable Headmasters, but like many, he was also an author. Previous Headmasters have been known to write many books on magic, but Trimble"s is definitely the most significant accomplishment, as he wrote the textbook that would later be used by every student in Defense Against The Dark Arts: "The Dark Forces: A Guide to Self-Protection".
6 Phineas Nigellus Black
Harry Potter fans are very familiar with Phineas Black, because he is not only the last Slytherin headmaster by the time of the series, he is related to Sirius Black, and his portrait hangs in Grimmauld Place. Not a whole lot is known about his time as Headmaster, other than the fact that he was not popular, and his House. During the events of the series, though, he is a reluctant ally to the Order of the Phoenix.
Headmaster Dippet was Headmaster when Dumbledore was working at the school, and his immediate predecessor. He was also Headmaster during the time that Tom Riddle went to Hogwarts, and when he opened the Chamber of Secrets. Fans will also know Dippet as the man who expelled Hagrid (although they may not forgive him for that!). Dippet was clearly a capable wizard, as he had a book written about him (by Rita Skeeter, admittedly), and he also had a chocolate frog card, but his specific achievements are not mentioned.
4 Albus Dumbledore
Dumbledore is, of course, referred to as the "greatest headmaster" of Hogwarts, and is one of the most powerful wizards of all time. He is certainly considered to be the most powerful wizard of his own time - although much of this may be down to his possession of the Elder Wand.
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It"s difficult to sum up Dumbledore"s time, as he is such a huge figure in the series. But as Headmaster, he is usually well-liked and respected, and apart from some brief (and well-documented) periods, most of the wizarding world regards him with respect, and mourned his passing.
Professor Umbridge barely counts as a true Headmaster, as she announced herself as Headmistress when Dumbledore fled after Dumbledore"s Army was revealed. While he was on the run, Umbridge became one of the most hated Heads of all, with everyone (teachers and students alike) attempting to undermine her. Peeves had a field day, of course, as did Fred and George Weasley, and the Headmaster"s Office refused to admit her.
2 Severus Snape
After Dumbledore"s passing, Snape was instated as Headmaster - an appointment that was clearly arranged by Voldemort, who was very much in control at this point in time. Snape"s time as Headmaster would be short-lived, though. After it was revealed that he was the one to kill Dumbledore, the other teachers drove him out, and he fled to Voldemort, and to his death during the Battle of Hogwarts.
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Minerva McGonagall is acting Headmistress more than once in the series, and then takes up the position permanently at the end of the original books. She also received the Order of Merlin, and a Chocolate Frog Card. In The Cursed Child, McGonagall is still Headmistress, and unsurprisingly, continues to run the school the way she did her classroom and her house - firmly, but fairly.