With Daredevil leading the pack in 1992 (for reasons mentioned in my What If? DareDevil fancast) followed by The Punisher in 1993, Spiderman is going to take it to the next level. Up to this point there has been no evidence that DD and Punisher share the same universe. Spiderman and his cast pull them all together with more to come.
Sean Maguire (18 years old) as Spiderman
starring in Eastenders and Dangerfield as a young teen but is recognizable today as the star of The Class; Krod; Meet the Spartans
He seems to be both a dork and a heartthrob at the same time. Parker would be a senior getting bit and going off to college in this movie. I hate when older adults play teens as they look to old in later movies
Reese Witherspoon (18 years old) as Gwen Stacey
The Man in the Moon; Jack the Bear
As the sweet Gwen Reese's smile is a winner. An amazing actress as well. Both of these movies won her awards. She has a heavy burden, you have to really be upset when she's killed off in a sequel
Julie Andrews (59) as Aunt May
Sound of Music; Mary Poppins
I've always hated how old and decrepit Aunt May and Uncle Ben were. I deaged them slightly and I needed a real mother type. She was 1 out of 5 and she won obviously.
Robert Duvall (63) as Uncle Ben
Godfather's 1 and 2; Apocalypse Now
He ALWAYS plays such pivotal roles and Ben is sooo important to who Peter becomes
Joaquin Phoenix (19) as Harry Osborne
Parenthood; To Die For (nominated for both)
Try and think about this 1 before you dismiss it. he wasn't always as thick as he is now and who better to play the troubled college roommate and best friend of the spider
Larry Drake (44) as Otto Octavious
Darkman 1 and 2; Dr. Giggles
In 1992, I saw Giggles and I thought, not knowing, that Doc Ock was based on his look; so why not pick him now? He does not yet become Doc Ock but, at the end of the film, he has the accident setting up the sequel. He works for Osborne
Kris Kristofferson (58) as JJJ
Paper Hearts; Knights
I struggled with this one by almost using Allen Arkin however, I think kris would deliver a much more believable JJJ rather than an over the top character
***the return of John Malkovich (40) as Norman Osborne (as seen in What If? Punisher)
After seeing him work treacherously with HammerHead we now see him working someone even bigger as a way of double crossing HammerHead. Whatever it takes to finance his dubious activities. His build to villainy will be the longest
Bill Pullman (41) as Kurt Conners
Sommersby; Wyatt Earp
Another build from young family man to... (you know)
Robert De Niro (51) as Kraven
It's freakin' De Niro
Don't discredit him as the Russian hunter. He is a true actor's actor and can play all roles. He was also in phenomenal shape when a role called for such. He is the mane villain hunting the neighborhood wall-crawler
...and the crossover character tying (in addition to Osborne) DD to this
Frank Langella (56) as Kingpin
The man whom Osborne conspires with