If Spider-Man 4 being canceled, fans thought they’d seen the last of the character. However, that now doesn’t appear to be the case.

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So we’ll now take a look back at the Raimi trilogy and list Maguire’s top 10 moments as the webhead so far.

His First Swing

Spider-Man first swing

Peter is bitten by a spider while on a school trip during 2002’s Spider-Man blockbuster, with the student then noticing his powers the next day. After realizing he’s now super strong, doesn’t need glasses, and is capable of climbing walls without any equipment, he takes to the rooftops to test whether he’d be able to swing from one building to another.

This was the moment many had been waiting to see on the big screen and Maguire brought comedy to the scene. He goofily tries a number of different methods without any success, before finally cracking the code. Amusingly, he swings straight into a nearby building - making him realize he needs a lot more practice if he’s to make it a regular habit…

Uncle Ben’s Death

Tobey Maguire Crying in Spider-Man

The best superhero actors are capable of nailing the emotional moments - and Maguire does this during the 2002 movie when he learns of the death of Uncle Ben. Ben Parker is ruthlessly shot while waiting to collect his nephew and perishes on the streets, cue cinema-goers reaching for the tissues.

Not only does Maguire excellently portray the feelings of grief, but his anger also seems realistic. Peter chases down Dennis Caradine, who then tumbles to his death while under pressure. It wouldn’t be until two movies later that the webhead learns Caradine wasn’t responsible, and that Flint Marko was instead.

Mary Jane Upside Down Kiss

Spider-Man Mary Jane Peter Parker Kiss

There have been several MCU. But before the pair was Kirsten Dunst, who played Mary Jane during the Raimi trilogy and was involved in one of, if not the most-iconic kisses in Hollywood history.

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We are, of course, referring to their upside-down kiss - which takes place after Peter has just battered a gang of thugs who were targeting her. Mary Jane is far from happy, however, when Maguire’s character kisses Gwen Stacy in an identical fashion in Spider-Man 3. And we can’t say we blame her.

Defeating Norman Osborn

The Green Goblin lectures Spider-Man on the New York rooftop.

Peter is pushed to his limits during the 2002’s Spider-Man movie, with Norman Osborn proving to be a pretty difficult villain to beat. Fortunately, in the film’s final battle, he’s able to prevent the Green Goblin from causing yet more mayhem by getting the better of him. Norman attempts to kill Spidey using his glider but the student merely jumps over it, meaning the Oscorp kingpin kills himself instead.

It’s a turning point for Peter, showing he’s got what it takes to win against the very best bad guys in the game. It’s also significant for the trilogy itself, setting the tone for what’s to follow. Norman’s death isn’t really the end of the Goblin and merely the beginning, with Harry Osborn following in his father’s footsteps two movies later.

Accepting Peter Parker

Spider-Man No More cover art recreated in Spider-Man 2

In Spider-Man 2, Peter’s mission to stop Doctor Octopus from destroying New York is made trickier when he loses his powers. This happens because of the amount of stress in his life, with financial troubles, Mary Jane, Aunt May, Harry Osborn, and Otto Octavius all on his mind. This then leads Peter into having to get his life in order.

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And Maguire shows Peter’s struggle brilliantly with arguably his best performance as the character. Never before has somebody who can swing from building to building felt so relatable and we get to really see the other side to the superhero, which is certainly refreshing. Past directors often chose to focus on big action sequences rather than character studies and this was the exception to the norm.

Taking Back His Powers

Spider-Man fighting Doc Ock on a train in Spider-Man 2

But while we enjoyed seeing Maguire as a powerless Peter, Spider-Man 2’s best action moments come when he’s back in the game. Hilariously, and again ironically, Peter wastes no time in returning to his second job - stealing his suit from the Daily Bugle office and J. Jonah Jameson himself. He then heroically takes the fight to Doc Ock, despite the odds being stacked against him.

This then leads to the sensational fight on top of a moving train, a sequence that had fans on the edge of their seats. It’s probably the most memorable moment in Spider-Man 2 and that speaks volumes given it’s been 16 years since the movie came out.

"Go And Get Them Tiger"

Toby Maguire and Kirsten Dunst standing close together in Spider-Man 2

It seems as though Peter and Mary Jane are destined to be together when the latter decides she wants to give dating Spider-Man a go, despite the obvious challenges involved. As Mary Jane and Peter start to open up about their feelings, a police alert goes off. This forces Spider-Man into leaving, with Kirsten Dunst’s character saying "go get them Tiger" as he leaps off his balcony and towards the danger.

But Maguire’s obliviousness towards Mary Jane’s true feelings is a clear hint at what’s to follow. The pair’s relationship is on the rocks during the events of Spider-Man 3, which brings us to our next point…

His Angry Phase

Emo Peter Parker in a jazz club in Spider-Man 3

A symbiote comes to Earth during the early stages of the final Raimi movie and, with Peter’s anger rising, latches itself onto Spider-Man. This then changes our hero, who becomes different in more ways than one.

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He becomes way too confident and arrogant, sports all-black attire, and also gets himself a gothic haircut. While it’s Meme-able content over the years, it’s refreshing seeing another side to Peter’s character - even if it makes for some uncomfortable viewing at times. It takes great strength to shed the symbiote and Peter is only just able to get out of its clutches, with the mysterious substance then latching itself onto Eddie Brock.

"I Forgive You"

Sandman desintegrates into the wind in Spider-Man 3

It takes true strength to toe a line as a hero. And Peter demonstrates this at the end of the Spider-Man 3, showing incredible heart to forgive Flint Marko for murdering Uncle Ben years previously - and teaming up with Venom.

Peter could have been forgiven for wanting to kill Sandman, especially in the moments after close friend Harry Osborn is impaled by his own glider. Instead, he takes the moral high ground and shows that everybody has a choice, that doing evil things only brings more evil into the world. This inner strength is why everybody loves the character, and why the ending of Spider-Man 3 is handled magnificently.

Asking Mary Jane To Dance

Mary Jane Watson Spider-Man 3

Superhero movies usually end on a positive note, with the good guys defeating the bad guys and everybody living happily ever after. However, Spider-Man 3 instead closes on a somber note. Harry Osborn dies and Peter, shortly after the funeral, extends his hand to Mary Jane.

This, again, is a testament to the character’s mental strength and irable attitude. Even after everything that’s happened, and after everything he’s done wrong, he knows he must make a stand and rectify things. In asking Mary Jane to dance, he’s not just attempting to fix their relationship - he’s also taking the first steps to forgiving himself.

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