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See here for Spider-Man 3 specific Wild Massive Guessings.

The trilogy takes place in the same universe as the Marvel Cinematic Universe at some point before The Avengers.
It kind of makes sense. The Human-Enhancer Formula that Oscorp was developing in the first film was yet another attempt to recreate the super soldier formula. And just like with the Hulk, it didn't work out exactly right. The powered armor that the military almost invested in instead of Oscorp's stuff? Someone else trying to cash in on Stark's inventions. Oscorp investing in Dr. Octavius's fusion-based energy reactor? They are trying to match the arc reactors with their own power generating solution. As for why Spider-Man doesn't run into any of these other heroes? They aren't in New York at the moment. Tony Stark lives on the west coast, Steve Rogers is frozen, Bruce Banner is on the run in South America and/or Asia, Thor was in Asgard or hanging out in the desert with his new friends, and Natasha and Clint were doing whatever awesome spies and assassins do when working for SHIELD. As for why no one in SHIELD ever considered Spider-Man as part of the Avengers Initiative, they probably did briefly and dismissed him as a possibility for being 1) too young, 2) more territorially-based than the others, or 3) someone didn't think he'd fit into the group dynamic for some reason.

Not to mention that J. Jonah Jameson briefly mentions Dr. Strange in Spider-Man 2 who is recently getting a movie in the Marvel Cinematic Universe.

  • Jossed. The Marvel Cinematic Universe has already introduced its own version of Spider-Man who is not Tobey Maguire.
    • Though the Sam Raimi series was considered to be part of the MCU; at least Kevin Feige intended to include Spider-Man earlier. An early script of Iron Man mentioned that Tony Stark created Dr. Octavius' tentacles; and the alternate take on the post-credit scene has Nick Fury mentioned "radioactive bug bites". Also, director Louis Leterrier wanted Maguire to cameo as Peter Parker in The Incredible Hulk. Although J. K. Simmons does reprise his role as Jameson in the MCU. Additionally, we'll see the Raimiverse versions of Doctor Octopus and Green Goblin in Spider-Man: No Way Home.
    • And No Way Home gave all the proof to bury this theory, showing the Raimi trilogy took place in its own universe.

In the films, Peter Parker is so poor because...
Of his organic web shooters, he uses most of his money buying extra food to replace the protein he loses uses from using those things.
  • Being always broke was a major part of the early Ditko-era Spidey stories.
    • Yes, but that was generally because he had to pay for web-fluid. Since he has organic shooters in the films, he doesn't have this problem.
      • Things are more expensive nowadays.
    • And even before the spider-bite, he and his family had money problems. That's why he took the wrestling gig— even though at that point he was still using stolen borrowed lab equipment from his school lab to make web-shooters, thus paying nothing for them.
  • Because he doesn't work for Iron man, but he may if he will join the Avengers.

Spoilers for Venom (2018):
After his defeat (it's a superhero film, of course that's not a spoiler), the Goblin's grenade left the symbiote shriveled and dehydrated instead of incinerated. Eddie Brock splattered, and the symbiote plus his blood plus a new host will be Carnage (or more likely Karnage) in the fifth film. The now-Anti-Hero Venom may return as one of the bits that got disconnected during the fight before the goblin grenade flashbanged Blonde EricForeman and the majority of the symbiote, or the Venom movie that's in the works could be an alternate continuity depending on who has which rights for what.
  • CONFIRMED! (Sorta...) - David S. Goyer claims that, through a pile of red tape the size of a Humvee, and royalties that could buy California's debt, Venom will be the same one from Spider-Man 3 - also; he's not dead and isn't going to become Carnage. Carnage isn't even planned for the Venom movie at this point - no villain (life foundation) has (Life Foundation) been named yet (LIFE FOUNDATION!).
  • Jossed, as it is now confirmed the SSU and the Raimiverse are seperate worlds.

The next film (or the one after) will feature the Chameleon.
And Sam Raimi, or whoever's in charge by then, will cast Gary Oldman in the part.

Tobey Maguire's back injury severely hampered his acting.
We've seen Tobey act in other movies, he's usually not that bad. But his acting in Spider-Man 2 and 3, especially when he's supposed to be having chemistry with Mary Jane, is just painful. No doubt the pain killers from his back injury are to blame. Or YMMV and he was awesome.

The second film was a Hollywood History allegory for the history of communism.
A thinking man, Doctor Octopus, (Karl Marx) devises a new way, a “better” way of generating power (goods). This technology (system) will be ready when it is ready; this new way (communism) is a plan for when the next opportunity arises to put it into action (some revolution that could be coming after 1848). It requires very careful monitoring to control this great power (government control over the means of production must be balanced). The tests go awry. The stipulated limit on waiting for a revolution is lost when the control chip shorts out (the model of agitation in Russia); now there is an urgency to implement this model that becomes a serious obsession (widespread revolutionary attitudes).

This obsession eventually gets hold of the fuel (property) and the apparatus (government). There is no respect for the effect this will have on the environment, cities, and human lives; it is an system that must be implemented at all costs, including the lives of innocent millions. Just as the initial tests went, however, there is no way to control the system (the markets) sufficiently and still bring about the desired results (prosperity for all). Having a change of heart, there is a call for outside help, so in the end, a Red-White-and-Blue American hero sinks the whole operation. For now. In the next one, he’ll be having to face an internal conflict.

In the movie universe, the "cartoon" theme song was composed originally by The Ramones.
And, for that, they're being offed one by one by supervillains. First Joey, then Johnny...

In the movies, Peter becomes such a jerk in the third movie because he never had to deal with the death of his first love in the first movie.
Without such a grievous mistake, he never learns to actually keep himself in check. So instead of just being a thrillseeker when he gets the black suit, he becomes an all around jerk ass. We get to see what happens when he is forced to become a hero, but not that his powers are dangerous if not kept in check.
  • That actually makes sense. Erm... What about Foe Yay? Can Harry count as a... If that is the case then... You know, he'll stop being a jerk.

Subway Station Guitarist got hugely ripped off.
Popular singers are using his song by the third movie, and he never gets a dime.

Subway Station Guitarist is hugely rich.
Royalties. Gotta love 'em.

In the second film, Peter Parker deliberately associates himself only with obnoxious people, because he doesn't want to endanger anyone who's nice.
The first film ends with, "Now matter how hard I try, the ones I love will always be the ones who pay." So, in the sequel, who has Peter chosen to hang around and interact with? His "best friend," who is always insulting him and even slaps him; Mary Jane, a slut who never listens to Peter's side of the story, and who has no care for the feelings of the men she plays games with; and, of course, his obnoxious boss. (His Aunt May is a kind woman, but he could not help being related to her.) And what of the people who are nice to Peter? The blonde girl who brought him cake when he was down: didn't even get a thank you. The secretary who saved his job ("Parker you're fired." "Sir, the planetarium meeting!" "Good point. Get back here Parker, you're un-fired."): doesn't get a thank you either. The black co-worker, who stands up for Spider-Man, Peter ignores him. Peter's intentions are clear; he will only allow himself to get close to jerks, and avoid interacting with nice people so as not to put them in danger.

In the movie series, Robbie knows Peter is Spider-Man
He certainly noticed that Spider-man showed up somewhere Peter "just so happened" to be during Dr. Octavius's experiment in the second film...

Throughout the Raimi series, the true Big Bad is Mysterio or otherwise an illusionist.
Whoever they are has rigged up hidden speakers and a screen in the mirror. In the first movie, they take advantage of Norman Osbourn's already strained mind by creating a state-of-the-art 3D image of him on the mirror, and pretending to be his alter ego. In the second and third movies, they again use the tech to make Harry think his father is talking to him from beyond the grave. Whoever it is, and whatever they want, it's likely they want any heroes in New York out of the picture, either dead or switching sides.Also, it's possible that Osbourn found out about this deception off-camera, and wanted in on it. Perhaps he survived the impaling, like in the comics, got together with this puppeteer, and acted as himself in Harry's visions in an attempt to make him 'a proper son'. In this case, his last words (Don't tell Harry), could have been said because he knew that Harry would blame Spider-Man and thus be angry at Peter to begin with. He and the illusionist then threatened his butler under pain of death not to reveal the truth, explaining why he kept it a secret for so long.

Bruce Campbell was playing Quentin Beck
After letting his arena be robbed, ring announcer Quentin Beck developed a vendetta against Spider-Man and determined to make his life miserable. Since he could easily figure out who Peter Parker was, he inserted himself into his life in the most unusual places, such as at Mary Jane's play, and at the restaurant where Peter planned to propose. Had the series kept going, we could have seen this escalate to Beck becoming Mysterio.

This incarnation of Spider-Man died in Spider-Verse.
He was referenced in the comic as a Spidey who looked like "the guy from Seabiscuit", but never appeared after that. (On the same page, a Spidey who looked like "the guy from The Social Network" was also mentioned, so he died too.)

There actually would have been two movies after Spider-Man 2.
The third movie would have involved only the symbiote controlling Peter, Harry's amnesia, and the Sandman. The symbiote came to Earth via John Jameson's space mission. There would be a subplot of Jameson hiring Eddie Brock to spy on Peter to learn how he get those pics of Spider-Man and for Mary Jane leaving his son at the altar. The rest of the movie would more or less be the same, and ends with the symbiote falling onto Eddie Brock and Harry regaining his memory. The fourth movie would feature Venom and Harry teaming up, and possibly Peter and MJ's wedding.

Aunt May deduced Peter was Spider-Man after the bank robbery in the second movie.
She seems understandably suspicious when Spider-Man says "we sure showed them". Later on she gives Peter a speech on people needing Spider-Man back, especially their young neighbor almost in a guilt-tripping way. In the third film she is disturbed at the news of Sandman being killed by Spider-Man.

The Green Goblin would have been Back from the Dead.
The serum brought Osborn back to life. But the Green Goblin persona completely takes over, and the original Norman persona died when he got impaled by his glider. The Goblin would pretend to be Norman and takes control of Oscorp, claiming his death was greatly exaggerated. He still wants revenge on Spider-Man for rejecting his We Can Rule Together offer as well as for his death. Also, it's revealed that he's been a wandering spirit all through the movies, which only Harry can see so he wasn't an hallucination after all. He became furious at his/Norman's son for being weak for helping Spider-Man and Mary Jane. When Spider-Man tries to get through to Norman, he'll say "Osborn is dead! There is only the Green Goblin!"; and when he tries to use Harry as a Morality Pet, he'll say "he was weak like his old man!". The movie (or story arc) would be loosely based on his post-Back from the Dead storyline from the comics.

Dr. Octavius is a fomori.

Banes possessed the AI tentacles at some point before the reactor accident. Octavius was so traumatized by the reactor failure, the death of his wife, and the carnage at the hospital that his psyche was vulnerable to bane possession. Empowered by their physical and spiritual bond to Octavius, the banes directed him to build a new reactor that they knew would malfunction. The death, suffering, and ecological devastation that would result from the reactor malfunction would feed their fellow banes and empower the Wyrm. Fortunately, Octavius regained enough autonomy to resist the banes and stop the reactor at the end of the film.

Doctor Strange
When J. Jonah Jameson says this name was already taken, he refers to a Noodle Incident in which Strange magicked himself from the MCU, into the universe of the Spider-Man Trilogy.

Had this film series got a fourth movie, Roderick Kingsley would have appeared.
With both Norman and Harry gone, Kingsley took advantage of this to buyout Oscorp and modify the goblin serum so the side-effect of insanity would be a thing of the past. It would be revealed that the military stopped buying the original formula because of that side-effect. In the end, Norman would be revealed to be alive and, through the use of shell companies, the holder of 51% of Kingsley, Inc. stocks. He just let Kingsley think he had the non-absolute majority.

Had Mr. Aziz and Mr. Ditkovich found out that Peter Parker is Spider-man,
They would have accused Peter of high treason, and terrorism and do everything in their power to not only expose him, they would have ether had him arrested, thrown out of the city, state, or country for good, or worse had him executed. And they would have been famous.
  • Uh, what???

Eventually Tobey Maguire will appear in the MCU during Doctor Strange and the Multiverse of Madness
Bonus points if J. K. Simmons reprises his role here as Raimi's J. Jonah Jameson and it explains how Jameson knew about a Doctor Strange in Spider-Man 2.
  • Confirmed. J.K. Simmons has reprised his role as Far From Home. As for Maguire, we don't know whether or not he will reappear in the MCU.
  • Uh, no it's not confirmed? This WMG is specifically for Multiverse of Madness, where we don't know if the Raimiverse JJJ or Peter will appear.

Alternatively, Tobey Maguire will appear in the MCU during Spider-Man: No Way Home
Since Alfred Molina's Doctor Octopus and Willem Dafoe's Green Goblin are appearing in this film, the Maguire Spider-Man is going to help Holland Spidey.
  • Confirmed.

Dennis Carradine will appear in No Way Home
Given that he at least was one of the villains who died while battling Spider-Man, he might appear in No away Home.
  • Jossed.
The Unseen Vulture will appear in No Way Home
Given that Doctor Octopus, The Green Goblin, Sandman, will appear in No Way Home as Alternate Villains, The Vulture can appear as an Alternate Villain since he didn’t appear in the fourth Spider-Man film due to it being cancelled.
  • Jossed.

Black Cat will appear in No Way Home
Given that she barely even made her appearance as Black Cat, it can be possible for her to appear as Black Cat in No Way Home.
  • Jossed.

Gwen and MJ are still friends
Despite MJ being shocked at Peter kissing Gwen, it is heavily implied that since Gwen felt bad for MJ being cheated on, they are still friends even after what happened
  • Do they even know each other?

Spider-Man 4 will Happen
Given that fans were happy to see Tobey Maguire as Spider-Man again in No Way Home, it is implied that Spider-Man 4 will happen.
  • How is fans liking Maguire implications that ther will be a SM 4?

Bruce Campbell's characters were one person, and a watcher, similar to Stan Lee in the MCU

With Sam Raimi set to direct the next Doctor Strange film, he could be given another cameo.

  • Only Raimi's intentions were for him to be Mysterio, who already appeared in the MCU. But he could be someone else.

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