The multiverse has cracked open, thanks to the events of Spider-Man: No Way Home, finally allowing fans to revisit the Spider-Man that started it all with the return of Tobey Maguire. Well over a decade after hanging up the mask, Maguire has returned to once again reignite fan interest in his trilogy of Spider-Man movies.
Tobey Maguire's Peter Parker wrote the book on the pain that comes with heroism, suffering through more than his fair share of trials and tribulations during his time as Spider-Man. Some of these moments were absolutely formative in the hero that he would become.
Almost Losing Mary Jane
Much of Sam Raimi's Spider-Man trilogy is a love story between Peter Parker and Mary Jane Watson. Though the two have their ups and downs, it seemed as though they were on track to get married in Spider-Man 3. That is, until Peter's erratic behavior and constant battles with supervillains put a strain on their relationship.
Peter and Mary Jane go through their toughest relationship trials in Spider-Man 3, and Peter even lashes out and hits MJ at one point while under the influence of the Venom symbiote, striking her in anger. By the film's end, it was somewhat unclear whether the couple would get back together, though No Way Home finally revealed that they eventually worked out their issues.
The Train Incident
Though not everything about Sam Raimi's Spider-Man films aged well, one scene that has absolutely stood the test of time is the battle on the train in Spider-Man 2. After Doctor Octopus destroys the track, Spider-Man must use every ounce of strength in his body to stop the speeding train from hurtling to the ground and killing everyone inside.
Though Peter manages to accomplish this feat, he very nearly dies in the process. The physical exertion required to stop a train traveling at that speed with nothing but his own strength was enough to nearly kill even a superhero. Nevertheless, Peter's strength and perseverance allowed him to win the day, and emerge a better hero in the end.
Hated By The Press
One of the trademark elements of Tobey Maguire's Spider-Man movies is his relationship with the press, specifically with The Daily Bugle, run by the Spider-Man-hating publisher J. Jonah Jameson, as portrayed by J.K. Simmons. Jameson made it his mission to create public hatred for the Wallcrawler, labeling him a "menace" rather than a hero.
Though most of Jameson's juvenile jabs at Spider-Man rolled right off his back, they certainly didn't help when it came to the court of public opinion. Despite the numerous heroic acts that Spider-Man did on behalf of the city, many citizens of New York still viewed him negatively, thanks to Jameson's tirades, making the superhero's job even harder than it already was.
Stabbed By The Green Goblin
No Way Home saw the reemergence of several classic Spider-Man characters, including the return of one of Tobey's greatest villains, the Green Goblin. In the final battle, Tobey's Peter, Peter 2, stops Peter 1 (Tom Holland) from killing the Green Goblin as recompense for the death of his Aunt May. However, in the heat of the moment, the Goblin stabs Peter 2 from behind.
Though Peter managed to survive the wound he sustained from his old nemesis, citing that he has "been stabbed before," he later reveals to Peter 3 (Andrew Garfield) just how much pain he is in. As an older version of Spider-Man, this injury could even prove to be a career-ending one.
Harry's Fall
Harry Osborn and Peter Parker have always had a friendly rivalry in the comics, which is something that the films translated beautifully, as Harry slowly evolves into villainy. Over the course of the last two films, Peter is forced to watch, powerless as his friend grows bitter and angry toward the man whom he believes took his father from him, Spider-Man.
Worse than watching Harry's moral fall is that Peter knew he could stop it. At any time, he could have alleviated his friend's hatred toward him by revealing that Norman had been the Green Goblin. Instead, he chose to honor Norman's final wish and preserve his friend's memory of his father, absorbing all the hatred for himself.
Giving Up On Spider-Man
The events of Spider-Man 2 saw Peter Parker struggling to balance his personal life with his life as Spider-Man. After deciding that the latter weighed too heavily on the former, Peter declares that he is "Spider-Man no more" and gives up the mantle.
Though Peter would eventually learn the importance of sacrifice in order to be a hero, it took months for him to eventually restore his identity as Spider-Man. In this time, he struggled with letting innocents get hurt without intervening, growing somewhat more callous than he had once been, almost forgetting the responsibility that came along with his incredible powers.
Norman's Final Wish
After suffering the blow that would result in his death, Norman Osborn implored Peter to "not tell Harry" about his stint as the Green Goblin. Peter would adhere to the request of the dying Osborn but suffered dire consequences as a result.
Because Peter honored Norman's wish, his life would gradually be torn apart by the secrets he kept. Harry gradually grew closer and closer to what had consumed his father, hating Spider-Man for taking Norman from him. By the time Harry realized the truth, he was already too caught up in rage to think rationally.
Harry's Death
Harry Osborn and Peter Parker had a complicated relationship throughout the trilogy, which lead to the occasional superpowered sparring match between the two former friends. They found themselves united in the end, however, taking on the team of Sandman and Venom. Unfortunately for them, their new friendship was short-lived, with Harry being run through by his own glider.
The loss of Peter's best friend is tragic by itself, but even more so considering just how close Harry and Peter had been to renewing the ways things used to be. After all the years of hatred, backstabbing, and lying, they were inches away from being friends once more--only for Harry to die in Peter's arms.
Bonding With The Symbiote
Though initially presented as a positive, Peter Parker's bonding with the Venom symbiote would only spell disaster for his personal life. After hosting the alien lifeform, Peter's personality began to change, he was prone to mood swings and even lashed out at Mary Jane. Finally, in order to preserve his own life, Peter rejected the symbiote.
The Venom symbiote almost did what no other Spider-Man villain had ever been able to do: corrupt Peter Parker. Though Tobey's Peter learned a very valuable lesson from this encounter, it might be time for Venom to once more plague the life of a different Peter Parker, perhaps as the villain in the MCU's next Spider-Man trilogy.
Uncle Ben's Death
The turning point in every Spider-Man's life is when they hold their dying relative in their arms, knowing that their death is on their hands. For Tobey's Spider-Man, it was his Uncle Ben, who was shot on the street by a carjacker after refusing to give up his vehicle.
This was one moment that Peter would never truly recover from, mostly because he knew that the man who did it was the same man he had selfishly allowed to escape earlier that evening. From that point onward, every criminal Peter caught, every supervillain he defeated, every person he saved, was all his way of atoning for the death of his uncle.