I'd go with this
1. Scorpion (Shocker as secondary antagonist)
2. Death of Jean DeWolff storyline with Mysterio replacing Sin-Eater.
3. Venom
4. Carnage
5. Kraven
6. Hobgoblin
I like it, but Marvel is better than Sony at introducing multiple villains at once, so we could see several introduced or nodded to in one movie.
In that case, let me elaborate/expand.
The series starts out when Peter has just graduated college and started working at The Daily Bugle. Norman Osborn killed Gwen Stacy which caused Peter to kill Norman and Spider-Man is now painted as a dangerous vigilante who killed a billionaire. This past is shown in flashbacks/nightmares that Peter has. He's currently in a long-term relationship with Broadway stage actress MJ Watson who's now moved in with Peter and May. Harry Osborn is now the CEO of Oscorp as Norman's heir. He likes Peter but hates Spider-Man.
The series would be titled The Sensational Spider-Man
Part one should also have Mach as a minor villain in the first scene of the film. Scorpion believes himself to be the real hero and fights Shocker just like Spider-Man does before Scorpion rebels. The post credits scene features Shocker, Mach and Scorpion all being recruited by Baron Zemo to tease Thunderbolts. They all work differently. Mach is just meant to kick the film off with some great special effects. Shocker is nothing more than a professional thief who Spider-Man is hunting down and when Mac Gargan becomes Scorpion, he also starts hunting down Shocker. He's a crook but the audience wants to root for him since he's so good at surviving. Scorpion is a corporate sponsored superhero who starts out being proud to provide some accountability for super heroes, likes working with authority figures, etc. He turns against JJ Jameson and Harry Osborn when he learns that Oscorp's process that turned him into Scorpion is slowly killing him and there is no cure but Oscorp is working on it REALLY HARD. Mac's response is to stage attacks on the Daily Bugle and Oscorp and it's up to Spider-Man to stop him.
The Sensational Spider-Man: The Death of Jean DeWolff. Have Sin-Eater and Mysterio in the second film. Mysterio is a red herring who frames an (not-so) innocent woman as Sin-Eater. The plot would be an adaptation of The Death of Jean DeWolff. After the events of Infinity War, Spider-Man now has the symbiote attached to him. Sin-Eater is a serial killer who murdered a police officer who's known to be a friend to Spider-Man and keeps the force from arresting him. Mysterio is thief who burglarizes corporations for his own profit and frames other criminals for his crimes. This time around, he's framed Felecia Hardy as Sin-Eater simply because she's beaten him to committing his last few heists. Ed Brock is also a tertiary antagonist since he buys into the false clues that Mysterio left. Daredevil would play his normal role in the story and Luke Cage and Black Cat would play the role that the Fantastic Four did in removing the symbiote. Brock resigns in disgrace after publishing that Felecia is Sin-Eater before the Daily Bugle is forced to retract the story and Peter winds up getting the credit for outing the REAL Sin-Eater. After the credits, Brock bonds with the symbiote.
The Sensational Spider-Man: Separation Anxiety. Venom works well enough on his own that there shouldn't be a secondary antagonist. The story would be based around Todd McFarlane's run on Amazing Spider-Man. Venom is obsessed with revenge and blames Peter for ruining his career. He stalks Peter throughout the entire film and shows up at random places to start fights. He winds up arrested and placed in The Raft where he's declared insane and Doctor Ashley Kafka is working with him as his therapist while his cell mate is Cletus Cassady. After the credits, the Symbiote is shown in containment at Oscorp and winds up breaking out on it's own.
The Sensational Spider-Man: Maximum Carnage. The symbiote rebonds to Brock in his cell where a tiny piece also bonds to Cassady. Venom starts out seeking revenge but the fight between the two is cut short when a news report states that Cletus Cassady has raided The Raft and staged a jailbreak across New York. Spider-Man and Venom need to put their differences aside to stop dangerous criminals from creating terror across New York. Captain America also cameos to assist Spider-Man in handling the jailbreak. Peter can't contact MJ throughout the film. After the credits, we see the two reunited.
The Sensational Spider-Man: Kraven's Last Hunt. Sergei Kravenov is an eccentric Russian oligarch who poaches dangerous predators. He has his eyes on coming to America to kill Spider-Man just for the thrill of the hunt. He succeeds in not only defeating Spider-Man but leaving him for dead and wearing his mask as the new, "Superior Spider-Man." He vows to do the things that Spider-Man can't do, namely he shoots Tombstone and Hammerhead to death. The third act has Peter revealed to still live despite being buried alive. He bests Kraven in their rematch and Kraven proceeds to kill himself.
The Sensational Spider-Man: Shadow of Evils Past. Hobgoblin is kind of like Venom in the sense that he's interesting enough for his own film. Roderick Kingsley breaks into Oscorp and injects himself with the Goblin formula while stealing Norman Osborn's weaponry. Peter is left wondering if Harry is getting his revenge on him for murdering his father, if Hobgoblin is Norman Osborn resurrected or if he's an entirely new threat. Unlike Osborn, Peter notes that Hobgoblin is perfectly sane and far more calculating than Green Goblin was.
Happy? That's all but two films who have more than one villain now.

Winter Soldier in particular used several Cap villains. Nobody (with any credibility, at least) compares that to, say, Spider-Man 3. GotG also effectively pulled off multiple villains from the comics.
I'd say there's a difference between having 3 iconic Spider-Man villains with more complex origins introduced in one film than 1 brainwashed guy and a bunch of regular humans or just a bunch of aliens that don't need explanation.
I'd say there's a difference between having 3 iconic Spider-Man villains with more complex origins introduced in one film than 1 brainwashed guy and a bunch of regular humans or just a bunch of aliens that don't need explanation.
Oh ok, I misinterpreted your original post.The Kangaroo in a Batroc the Leaper-esque opening villain fight, followed by a Green Goblin story where he's taking over the New York crime scene with Ox, Montana, and Fancy Dan as his hired muscle. Boom. Comic loyal Spidey story with not one, not two, not even three, but five comic villains, and it could work. It's all about making the right choices. That's what I was getting at. Winter Soldier did a great job picking multiple villains that could be done justice in supporting roles. Spider-Man 3 and The Amazing Spider-Man 2 threw everything in a pot and hoped it would work. Harry Goblin, Sandman, and Venom was never going to work in Spidey 3. Norman Goblin and the Enforcers, with a minor villain for a fun action opening before the main plot kicks in (doesn't have to be Kangaroo, just throwing out a villain who'd never lead a movie) could work, though.
Mysterio & Rhino.
I quite like it![]()
YW.
Also, if assuming that there's room for three more sequels...
The Sensational Spider-Man: Ends of the Earth. A rogue AIM cell named The Sinister Six run by Otto Octavius plans on testing out their new plan for a new type of nuclear weapon that has the power to destroy the entire Eastern Seaboard and when detonated will level Boston, New York and Philadelphia along with most of New Jersey. The other five members are Electro, Speed Demon, Vulture, Override and Mister Negative. Spider-Man saves the day with the help of rogue AIM scientist Spencer Smythe who sacrifices himself so Spider-Man will have time to defuse the bomb. After the credits, we see Smythe's son meet with Doc Ock as he vists him in prison and asks how his father died.
The Sensational Spider-Man: Invasion of the Spider-Slayers. Alistair Smythe falsely believes that Spider-Man killed his father. Led on by the incarcerated Otto Octavius, Smythe dubs himself the "Ultimate Spider-Slayer" and builds autonomous killing robots which are programmed to kill Spider-Man but backfire horribly and wind up killing anyone of Peter's approximate height and weight. After seeing how much destruction he's caused as well as how easily Spider-Man destroys his machines, Smythe deactivates his robots and builds himself a suit of armor meant to be the ultimate weapon.
I'm not sure which should be the subtitle for the ninth film. I'm torn between Torment, Feral and Shed. Regardless, enough time will have passed to reboot Lizard. Curt Conners comes up with a plan to reconstruct his arm which instead turns him into a mindless man-eating animal.
Assuming that since Sony is distributing, we're able to get more films than other franchises, I'm expecting the first film to hit in Phase 3 in 2016 or 2017 and then a new Spider-Man film every other year.
All of your ideas sound better than anything Sony had planned for the future. Weren't they planning to release a Spidey flick like every other year prior to TASM2's release?
Nope. They were planning on releasing one every single year. They wanted annual Spidey films.
I actually think it could work but not the way Sony was going about it. An annual film series could work if you did it in a three year cycle (solo film, team up film, spin off film) like so:
2017: Spider-Man
2018: Spider-Man & Daredevil
2019: Black Cat
2020: Spider-Man 2
etc.
If marvel gains control over sony's spiderman, I'd hope at some point they try that again. They can have their own spiderman slate to coincide with the main MCU slate, with spin offs and team-ups and what not. It could work,if handled with care. I'd trust marvel to find the right people and make that work. I think an agent venom film could work well too.
Just move Drew Goddard from Sinister Six to Spider-Man & Daredevil. He was supposed to do Daredevil on Netflix, plus he loves both characters. Cabin in the Woods was really good, so I'd certainly trust him as the director (he is most certainly not the problem with Sinister Six).
Why Rhino? I know Giamatti's version was polarizing (I liked it), but why would you want to see him again so soon?
Winter Soldier in particular used several Cap villains. Nobody (with any credibility, at least) compares that to, say, Spider-Man 3. GotG also effectively pulled off multiple villains from the comics.
I have plenty of ideas for a new Spiderman franchise, they just don't all fit together in a realistic and linear manner. Somewhere along the line I'd like to see:
The Spectacular Spiderman This would be the first MCU Spidey film. Peter is already Spiderman, dating Gwen, doing freelance work for the Bugle and is about to graduate high school. He and Gwen are at the top of their class, and are both taking college science classes taught by Dr. Otto Octavious. Harry is a year older than them, and already goes to college. Anyway, the main villain is Mysterio, who, inspired by the increasingly crazy world, is convinced that the future of crime in New York is theatrics. Ultimately, Spidey defeats him, but Dr Octavious' beloved wife is killed during one of Mysterio's crimes. Guest appearances by Herman Schultz, who helps design Mysterio's tech, and Kingpin, who appears in the post credits scene, recruiting Schultz.
The Spectacular Spiderman: Superior Since the events of the last film, Dr. Octavious has amped up his work in honor of his wife, now convinced that Spider-man is a menace. Working along with Dr. Spencer Smythe, funded by Oscorp, he is designing a new generation of law enforcement technology to aid NYPD Captain George Stacy in combatting the new "super-villains". Case in point: The Enforcers, Kingpin's new team, lead by Shocker. The Enforcers beat Spiderman on their first encounter. Peter, meanwhile, is invited, along with Harry, to work on the Superior Project with Octavious and Smythe. Jameson discovers the project, and convinces the scientists that Spiderman should be the first target. The night before the grand unveiling, however, Peter and Harry discover that someone has uploaded military hardware onto the robotic drones. Against Otto and Harry's wishes, he warns Captain Stacy, who shuts the program down. Furious and betrayed by his surrogate son, Otto dons his tentacles, storms the lab and unleashes the drones. However, chaos erupts as the "Spider-Slayers" leave a trail of destruction as they hunt their targets: The Enforcers (whom are quickly overwhelmed) and Spiderman (Not so easily beaten). Dismayed, Otto attacks Oscorp, revealing Smythe's arsenal of robotic weapons, stollen from the other scientests at the college. This includes the Scorpion suit, which he himself dons. A three-way fight ensues between Ock, Scorpion, and Spidey. Smythe/Scorpion is killed and Otto sacrifices himself to shut down the drones. The movie ends with the surviving Enforcers being locked up in the Raft and approached with plans for the Thunderbolts. JJJ is guilt ridden over his involvement with Smythe, and destroys all evidence of their correspondence. And Otto's body is taken away by a mysterious ambulance, and it is shown that he is still alive.
Since the prospect of Mysterio as the first villain is looking likely, does anyone here have a favorite Mysterio story from the comics?
I feel like him framing spidey is the obvious choice, but for good reason. There was also an interesting daredevil story where he drugs daredevil and makes him go insane through delusions and hallucination and what not. that could be something interesting they could do with spidey (there was also the time mysterio made peter think aunt May died, they could probably tie that into the drugging)