He never really got much of a character in the prequels except for "guy who doesn't really like what's going on" - that's about it. I think the closest he got to being an actual character was Attack of the Clones, where he was a detective. But even then - it was sorta thrown away (as was most of the movie)
And I'm only through Season 3 of The Clone Wars - but he's not much better there. He's kind of an arrogant asshole even when he's the nicest guy on the screen.
The longer I stick around in the Prequel Era, the less I like either Anakin OR Obi-Wan. They're just not written to be endearing in the least. And I get WHY they're not, but there's gotta be a better way to write these guys to end up at their tragic endpoints.
As my good friend GentlemanCrow alluded to earlier in the thread, use X-Men: First Class as a model for their friendship. We watched it together recently, and while it is a very solid if unremarkable film overall, it nails Xavier and Magneto's brotherly relationship perfectly and manages to do more in one film than the prequels did in three.
Some observations/ideas:
- James McAvoy as Xavier would be an ideal young Obi Wan type- effortlessly mature and classy even in youth, but warm and possessing a cheeky sense of humour. He even looks like he could be a young Alec Guinness when bearded.
- Michael Fassbender as Magneto is a physically imposing man in his prime (a la Vader), nomadic, a man of few words but innately sympathetic and likeable. Fassbender is masculine and has shown that he has the acting chops to suddenly and convincingly turn "bad" within the space of one film- perfect for Anakin (although this turn should ideally span two films).
- Anakin is an adult and has a dark past from the off, like Magneto. Replace the Nazi camp with a slaver camp, and only allude to it sparingly. Like First Class or Star Trek '09, Anakin's troubled childhood could perhaps be addressed in a brief prologue and then cut to present day. We don't need to dwell on it.
- Anakin could initially be on a quest to hunt down his former slaver and exact his revenge. He has had inexplicable force powers since childhood and works as a smuggler in adulthood.
- Obi Wan crosses paths with Anakin and helps him to develop his burgeoning force powers as a Jedi in Episode I, but cautions him not to seek revenge. He offers support and guidance, but he is his equal, not a disciplinarian.
- Anakin is seduced by the Emperor and fully buys into his ideology. He is not tricked.
- By the end of Episode II, Anakin is Vader and wears the familiar black costume sans helmet, breathing mask and chest panel in battle. Through Episode III, he works on behalf of the Emperor. Obi Wan has been aware of this for some time, and faces his old friend as a last resort. He confronts him and eventually defeats him on Mustafar, knocking him into sulphuric waste or such like, the toxic fumes impairing his breathing. Obi Wan is chased away by Imperial forces that arrive on the scene, as Vader crawls out of the waste and is rescued by the Emperor. The helmet and breathing mask are organic and essential additions to his suit.
One of the biggest caveats with the above proposal is to not merely transplant First Class's tone (which is sombre and naturalistic and would be inappropriate for Star Wars), but approximate the general feel of Xavier and Magneto's relationship dynamic in that film. You'd have to tackle an innately dark character like Anakin with care and maintain enough levity and snappy banter throughout these alternate prequels to make it consistent in tone with OT.