re: Who should have played Anakin?

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Anakin was the stubborn child. His character demanded that he butted heads with the parental figure/mentor.

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I'm not exactly sure about that. Personally I think that Obi Wan should have been somewhat of an outcast in the Jedi Order. He had unorthodox ways of the Force, and he was shunned for it. He finds Anakin and finds that he's attuned to the Force, and very gifted at that. The two form a fast friendship, and Obi Wan offers to teach Anakin in the ways of the Force. Despite what his superiors and equals tell him, he goes through with it. Obi Wan would be blind to the fact that Anakin is really only going through with the Jedi training for the title and making himself as powerful as he possibly can be. Anakin goes through his training lustfully, is found out, and kicked out of the Jedi Order. Eventually he kills one of the members of the Jedi out of rage (Mace Windu if there were a reboot), and eventually both Obi Wan and Anakin have to very reluctantly fight to the death.

Anakin's and Obi Wan's friendship should have been the primary thing they focused on, not a teacher and student relationship. I never bought that the two were friends, despite the ridiculous backtracking in Episode 3 where Lucas realized he fricked all this up. The thing is Anakin was a heavily unorthodox student that Obi Wan thought he could control simply out of friendship and the fact that Anakin meant well, but he denied that Anakin had a power hungry and lustful nature to him, which led to Anakin's and the Jedi Order's doom. You didn't have to have Anakin killing kids in the prequel trilogy, since 20 years without eating, drinking, or sex from a former hedonist is more than enough to make him a mass murdering psychopath. That's the direction they should have gone with the character.