Peter Parker and Aunt May/Tom Holland and Marisa Tomei
Well, these two are a given. I'm leaving out the 3rd confirmed cast member, Zendaya, because who knows, maybe she really is just playing some girl named Michelle?
Gwen Stacy/Ariel Winter
Yes, I know we just saw Emma Stone give an immensley popular preformance as Gwen, but I don't think it's the right idea to skip her in the new series. Peter's story works for the best with the Stacys in it. And as a talented up and coming actress capable to portray both the intelligence of Gwen and match Holland's Peter with witty banter, Winter is more than capable of endearing audiences to the character once again.
Cpt. George Stacy/Enrico Colantoni
You can't have Gwen without her father. As one of Spidey's biggest defenders, Captain Stacy was really done a disservice by the Amazing Spider-man films, so it's up to Marvel to once again fix Sony's mistakes. Stepping into the role, I have Enrico Colantoni, a brilliant and underrated actor who would easily be able to juggle the streetwise veteran cop, doting father to Gwen, and mentor to Peter.
J. Jonah Jameson/Timothy Omundson
Perhaps the biggest task facing Marvel's casting director for Spider-man is finding someone who can fill the massive shoes left by J.K. Simmons. The best answer to that is to take a new direction. As defining as Simmons was in the part, JJJ is so much more than just a blowhard comic relief. Marvel should instead highlight the more serious side of the character, the hardened investigative journalist. Sure this is the guy who hates Spidey more than some of his villains, but this is also the guy who published a self-incriminating report he was blackmailed with even after the leverage was destroyed. With his knack for both intensity and a scathing dry wit, Omundson could become the defining JJJ for a new generation and elevate the character to new heights.
Joe Robertson/Ernie Hudson
Yet another character who got the short end of the stick at Sony, Joe is the perfect second half to JJJ, the calming, logical influence to the firebrand chief editor. A beloved talent such as Ernie Hudson is just the sort of talent Marvel loves to bring on board their films, and he would perfectly embody Joe's role as another sorely under-utilized mentor to Peter, perhaps the only one that doesn't end up dead or a super villain.
Randy Robertson/Shamiek Moore
Speaking of the Robertsons, we get to Randy. Marvel wants to ensure Peter's group of friends is diverse, so he's the clear place to start. Rising star Shameik Moore is just the type of talent Marvel should be populating Midtown High with.
Flash Thompson/Charlie Rowe
After just missing out on being the franchise star, Charlie Rowe takes over a resident Midtown bully, Flash Thompson. And he's in luck, because if Marvel plays their cards right, and Sony doesn't screw things up, he'll have his own spinoff film coming up in a few years. With a future franchise lead on the line, Marvel needs to take extra thought with casting Flash this time, why not go with someone who clearly already impressed them?
Norman Osborn/Ken Watanabe
Over the years on film, Norman Osborne has donned a green Power Ranger suit, driven his son crazy as a ghost, died without leaving his bed, and had his head stuck in a jar. So Marvel certainly has some room to improve, especially now that Norman has the whole MCU at his fingertips. They need someone who distinguish himself from past versions, can maintain a building threat over the long haul before hopefully menacing the Avengers themselves in a Dark Reign adaptation. Ken Watanabe is the man for job, everyone knows he can easily handle the foreboding schemer and, having seen him on Broadway in "The King an I", I can vouch for his ability to handle the manic eccentricities of the Green Goblin.
Harry Osborn/Ryan Potter
Faring slightly better than his father in past films when it comes to character development, Harry is nonetheless a core part of Peter's life. He may not need any huge improvements, but he will need an actor capable of making the character their own. Ryan Potter has already worked with Disney to great acclaim and could excell, this time in live action, as the outwardly confident yet insecure boy genius Harry Osborne.
Mysterio/Neil Patrick Harris
Now for the villains: We know Marvel plans to use a never-before seen foe for the debut film, and Mysterio is the best fit. As a flamboyant entrepenuer, he's the perfect crux point for the birth of the super-criminal in the MCU. Combining flamboyant imagry with the small-scale story Marvel desires, he's everything the studio could ask for. And who better to embody the villainous showman than Niel Patrick Harris. Capable of sliding between manic flamboyance and menace at the drop of a hat, he brings another big name to the debut feature, with hopes of returning down the line for the Sinister 6.
Shocker/Riz Ahmed
My first pick for this part would be Aaron Paul but, as I try not to create conflicts in my fancasts and greatly prefer Paul as Guy Gardner, I'm going with Ahmed here. In my vision, he wouldn't have become Shocker yet, instead serving as a technician for Mysterio, only donning his own suit in the sequel. With Shocker, you need someone likeable, and Ahmed is certainly that, as well as adding more of the diversity Marvel is looking for.
Beetle/Dule Hall
And as the opening, one-fight, introductury villain:The Beetle. The perfect fit, not a big threat, but impressive enough visually to leave a mark in the audience's memory. And you get two birds with one stone! A snazzy victory for Spidey and a Thunderbolts mainstay locked up in time for a part in a brand new franchise! (Plus paving the way for Janice Lincoln to take the identity down the line) Much like Shocker, you need a likeable guy for Abe Jenkins, one you want to root for despite his criminal actions. In that case, former Psych star Dule Hill is an excellant choice for the job!
Roderick Kingsley/Michael Keaton
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Lots of names have been tossed around as the identity of Michael Keaton's villainous role in the upcoming film. For him, I've selected Kingsley, an eccentric villain holding a unique place in Spidey's Rougues gallery perfectly tailored for the former Batman star's talents. Setting up the Hobgoblin mystery with Kingsley as a respected public figure in this first film ensures Marvel will get plenty of work out of a great actor for their new franchise.