Albus Dumbledore's journey, in order
To watch Albus Dumbledore's story in order, start with Fantastic Beasts: The Crimes of Grindelwald, then Fantastic Beasts: The Secrets of Dumbledore and Harry Potter and the Philosopher's Stone. That's 10 out so far, about 24 hours, ending with Harry Potter and the Deathly Hallows: Part 2.
Dumbledore is played by Jude Law as a young man in Fantastic Beasts, then by Richard Harris and Michael Gambon as Hogwarts' headmaster. In story order, his past with Grindelwald comes first.
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Albus Dumbledore's story in order

Fantastic Beasts: The Crimes of Grindelwald
A young Dumbledore, who can't move against Grindelwald himself.

Fantastic Beasts: The Secrets of Dumbledore
Dumbledore and Grindelwald's past, and their duel.

Harry Potter and the Philosopher's Stone
Headmaster of Hogwarts when Harry arrives.

Harry Potter and the Chamber of Secrets

Harry Potter and the Prisoner of Azkaban

Harry Potter and the Goblet of Fire
Voldemort returns, and Dumbledore starts to prepare.

Harry Potter and the Order of the Phoenix
Dumbledore is forced out of Hogwarts.

Harry Potter and the Half-Blood Prince
Dumbledore teaches Harry about Voldemort's past.

Harry Potter and the Deathly Hallows: Part 1
Harry learns about Dumbledore's own past.

Harry Potter and the Deathly Hallows: Part 2
The truth about Dumbledore's plan.
Questions
What order should I watch Albus Dumbledore's story in?
Start with Fantastic Beasts: The Crimes of Grindelwald, then Fantastic Beasts: The Secrets of Dumbledore and Harry Potter and the Philosopher's Stone, and follow the list above: 10 in all, ending with Harry Potter and the Deathly Hallows: Part 2.
How long does it take to watch all of Albus Dumbledore's story?
About 24 hours for the 10 out so far.
Who plays Dumbledore?
Richard Harris in the first two Harry Potter films, Michael Gambon from Prisoner of Azkaban on, and Jude Law as the younger Dumbledore in Fantastic Beasts.
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