Here is a casting idea: Freddie Highmore (Charlie, Charlie and the Chocolate Factory) as Tip. While I believe Freddie could play the role when he's a bit older, I believe Charlie and Tip are two very different characters.
TIP is a young boy (probably in his early teens) who doesn't know the exact truth of his past, but he is bold and is not afraid to speak his mind. He takes hold of his own destiny and makes his own decisions. A very independent young man. It turns out that he is really Princess Ozma under an enchantment. Even though he would prefer to remain a boy, he puts aside what he wants for the good of the people of Oz and becomes their rightful ruler.
CHARLIE is an even younger boy (preteen?) who lives with his family. In fact, he is a bit more comparable to my take on Dorothy than Tip. He respects and cares about them, even though it's just his parents, and four older people. He resists the temptations to misbehave in Willy Wonka's chocolate factory, and thus turns out be the only kid who won a golden ticket who wasn't "rotten." He is then bequeathed the Factory.
So, as you see, they are different characters, but the same actor could play them. I just think we'd better wait 'till Freddie's a little older.
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