The Oracle: Candy?
Neo: D'you already know if I'm going to take it?
The Oracle: Wouldn't be much of an Oracle if I didn't.
Neo: But if you already know, how can I make a choice?
The Oracle: Because you didn't come here to make the choice, you've already made it. You're here to try to understand why you made it. I thought you'd have figured that out by now.
Neo: Why are you here?
The Oracle: Same reason. I love candy.

So I'm curious as to what school of Phiolosphy this originates from. Any ideas?

Neo is questioning determinism (per his usual m.o.), and the Oracle is playfully ignoring his questions because they aren't relevant to his purpose.  Instead she constantly reiterates variations on the theme of 'know thyself', which of course has several philosophical origins.  That convo is roughly Plato arguing with Siddhartha.

Incidentally, while the films spend a lot of energy making overt Looking Glass references, the Oracle herself is a specific nod to both the Delphic Sibyl and the Delphic Oracle Pythia, right down to the riddle-speak, the orange/green color scheme of her kitchen and apron, the smoking, the "temet nosce" inscription, etc.

As a personal speculation, I've always found the red candy bit to be the Oracle's thinly veiled method of telling Neo to stop asking stupid questions and remember why he took the red pill.

"We are the music makers... and we are the dreamers of dreams."

Uhm, yeah .... determinism.

The Oracle: Candy?
Neo: D'you already know if I'm going to take it?
The Oracle: Wouldn't be much of an Oracle if I didn't.
Neo: But if you already know, how can I make a choice?
The Oracle: Because you didn't come here to make the choice, you've already made it. You're here to try to understand why you made it. I thought you'd have figured that out by now.
Neo: Why are you here?
The Oracle: Same reason. I love candy.

So I'm curious as to what school of Phiolosphy this originates from. Any ideas?

Personally I dont think its so much Philosophy as psychology.

I think its more about understanding why we do something then the behavior itself.

I don't think it was just a matter of the Oracle loving candy like Mr. Wonka did. But I quite agree with the character being analogous to Alice in Wonderland's Caterpillar.

There is a lot of imagery like this surrounding the Oracle in the movies, such as the sign above the kitchen door (Temet Nosce). It was a nod to the ancient Greek's Oracle at Delphi (although, given how she is known to Redpills, I rather think that sign is something that she herself would have done instead of it just being a plot function).

The inspiration for her character came from, I believe, the story of Sophia, whom, in Gnosticism, is represented as "A Feminine figure, analogous to the human soul but also simultaneously one of the Feminine aspects of God and the Bride of Christ, she is considered to have fallen from grace in some way, in so doing creating or helping to create the material world."  (http://en.wikipedia.org/wiki/Sophia_%28wisdom%29)

Her character is echoed here, also from Wikipedia, "In most, if not all versions, of the gnostic religion, Sophia brings about an instability in the Pleroma, in turn bringing about the creation of materiality," and her story is parallel to the one in this passage, "Sophia's fear and anguish of losing her life (just as she lost the light of the One) caused confusion and longing to return to it. Because of these longings, matter (Greek: hyle, ‘υλη) and soul (Greek: psyche, ψυχή) accidentally came into existence through the four elements: fire, water, earth, and air. The creation of the lion-faced Demiurge (Smith) is also a mistake made during this exile, according to some Gnostic sources as a result of Sophia trying to emanate on her own, without her male counterpart (The Architect). The Demiurge proceeds to create the physical world in which we live, ignorant of Sophia, who nevertheless managed to infuse some spiritual spark or pneuma into the creation of the Demiurge."

Sadly, we still do not know whether we can trust this Oracle or not. With the immense power that she has of calculating all possibilities and then choosing the most probable one, she can manipulate anything into to behaving the way she wants it to. This was evident with Neo, as is illustrated by Brett Watson from the Nutter's Log:

"If The Oracle really did have such immense foreknowledge of Neo's actions under all possible circumstances, then did Neo himself really have any free will in doing what he did subsequently? It was her intention, obviously, that Neo discover his abilities as The One, and this he did. Was this a journey that he undertook himself, as master of his own fate? Or was he merely the puppet of The Oracle, doing her will, and treading a path that she had determined for him?"

For that matter, aren't we all?

The candy was a test, one that Neo passed; albeit blithely. "If you already know, how can I make a choice?"

The Oracle was just another layer of the system of control. I can't for the life of me understand how people still try and debate that.

Yes, she is an exile. But an "Allowed Exile" because it allows her to play her role in the overlaying system.

Which in the end, means she has a purpose, which means she isn't an exile, she's a program with a cover " />