I'd love to see Capitan Mal playing the Tin Man, now that I think of it.
And again!
Spider-man:
Peter Parker:
Joseph Gordon-Levitt
Mary Jane:
Bryce Dallas Howard
Aunt May:
Maggie Smith
Uncle Ben:
Stan Lee
Harry Osborn:
Ryan Gosling
Norman Osborn:
David Strathairn
Flash Thompson:
Chris Evans
First off, Toby McGuire isn't much of an actor. Sorry, but he really isn't. He worked in pictures like Plesantville mostly because the roll asked for an awkward guy that looks surprised a lot. If you're casting a roll as monumental as Parker/Spider-man, you need raw talent. Joseph Gordon-Levitt ("10 Things I Hate About You", "Manic", "Brick", "Shadowboxer", "Stop-Loss") has the experience in acting and the ability to pull off one of the biggest roles out there.
Bryce Dallas Howard is really, really hot. And a very, very capable actress. I like Dunst, don't get me wrong, but she's not classically beautiful in a way that can pass as a popular model. And she always seemed like she was phoning in the role, especially in the last movie (not that I blame her). In order for Spiderman to work, you need a cast that loves their job. You need devotion. You need passion. Bryce Dallas Howard was outstanding in the Village, an otherwise subpar film. She didn't just make the film watchable, she made the film great. Better still, she's a natural redhead.
I first saw Maggie Smith in Hook, and she was the quintessential mother/grandmother. She's sweet, she's old but she's aged quite gracefully, and she's got the acting chops most actors couldn't earn in three lifetimes. And it would be perfectly fitting for Stan Lee to make the jump from cameo to serious roll for his greatest creation. He's said the line, "With great power comes great responsibility" so many times, he has it down to an art. IIRC, he's about the same age as Maggie Smith.
Looking past the fact that even a level 1 comic book nerd knows that the Green Goblin has no business being in the first Spiderman movie, the Osborns needed to be a bit more serious and a bit less cheek-bony. James Franco can act, he was great in Milk, but for whatever reason he was too cool for school when he took the roll of Harry Osborn. He was either passive and light or he was waaay overplaying his brooding. Ryan Gosling was going to end up in one of my recastings because of Lars and the Real Girl, and this seems to be the best fit, especially with dramatic powerhouse David Strathairn playing his father, Norman Osborn.
Lastly, Flash Thompson was supposed to be Peter Parker's arch nemesis, to match his superhero persona's more colorful rouges gallery. That's not a bit part, or at least it shouldn't be. There needs to be legitimate torment, there needs to be hatred, there needs to be jealousy, there needs to be that spark that we've seen with the great bullies in film. That requires an actor. Chris Evans was outstanding in Sunshine, he totally took me by surprise.