Since the '70s, there have only been five actors who have played the legendary Marvel character, Spider-Man, in a live-action production. Since the iconic first Spider-Man, Nicholas Hammond played the character in the original CBS series and TV films, other than an infamous Japanese Spider-Man played by Kōsuke Kayama, the world would have to wait more than two decades before the character was ever seen on screen again in a live-action film.
When it happened, that first film was accompanied by a buzz around the world due to the character's immense global popularity. With the legendary Sam Raimi directing, early indications showed that the likes of Leonardo DiCaprio were approached for the coveted role.
While Leo turned it down, he did recommend his good friend, Tobey Maguire, for the role. Maguire famously did get the part and has since become an iconic part of the superhero cinematic world. The three films he starred in grossed billions and firmly brought the classic character back to mainstream audiences.
Tobey Maguire's Spider-Man is still often hailed as the best of all. This was largely why audiences everywhere were gushing when he made a surprise appearance in MCU's Spider-Man: No Way Home. Seeing Maguire in the suit again stirred up a ton of nostalgia for his version of the famous hero. In honor of that, here's a look back at Tobey Maguire's best moments as Spider-Man.
10 The Bite
The first Tobey Maguire Spider-Man film was released back in 2002 amid worldwide excitement. With all the advances in CGI since the last time Spider-Man had been seen on film, there was a ton of anticipation to finally see the character swinging from buildings the way the comics had always imagined. However, since the first film was essentially an origin story, we got to watch how he becomes Spider-Man.
The now iconic scene was an all-important one since it stuck to the comics and portrayed the moment Peter Parker is bitten by a radioactive spider. That scene came amid some great ones of Peter being his nerdy self, awkward and yearning for some closeness with Mary Jane. When the moment arrives, it was amazing, since it signaled to everyone that Spider-Man had finally been reborn on film for the first time in over two decades.
9 Testing His Powers
Not long after he's bitten by the spider, Peter Parker learns that something strange is happening to him. In a great scene, he's in an alley when it suddenly dawns on him that the bite may be responsible for all the changes. Almost on instinct, he realizes he can climb walls. This naturally causes a burst of euphoria, and he's soon testing his powers out in any way he can. Before we know it, he's throwing himself off buildings, before the poignant moment when he first figures out the iconic hand gesture that releases his webs for the first time.
8 Kiss With Gwen Stacy
Spider-Man 3 fit in some iconic tropes from the Spider-Man comic universe. While the first two films drew heavily on the relationship between Peter Parker and MJ, the third film introduced another legendary love interest of Spider-Man from the comics. Gwen Stacy may not be MJ, however, she's often been his love interest in many of them, and his number-one girl in some universes too. She was first played on screen by Bryce Dallas Howard, who was stunning in the film.
Her effervescent smile, platinum blonde hair, and large sparkly eyes made for a perfect depiction of the popular character. In this version, Spider-Man's popularity causes him to grow cocky and, in a moment where he immerses himself too deeply into the identity, he repeats his famous kiss with MJ on Gwen Stacy after dropping in beside her at a Spidey appreciation event. While the moment held significance for fans of Gwen Stacy, needless to say, MJ was not happy at all that he did this — and who could blame her?
7 Black Suit Spider-Man
Later in the third film after losing his powers, Spider-Man inadvertently allows Venom's infamous symbiote to bond with him. Without realizing what's happened to him, all he knows is how good it all feels. Swinging around in the dark, the pallid light is a great allegory since this classic storyline from the comics is building up to the infamous black-suited Spider-Man.
The moment he swings into view, and we get a glimpse of the black suit for the first time is amazing. Not only does the new suit look supremely cool, but it also signals that the dark side of Spider-Man is about to be unleashed on film for the first time ever. As this beautifully shot picture from a deleted scene reflects, this moment ultimately starts a battle for Peter Parker's soul as either a hero or a villain.
6 Evil Dances
After Spider-Man gives in to the power of the symbiote, what follows is an unforgettable montage where he unleashes his evil side. Between unashamedly flirting with women, standing up for himself at the Bugle, and getting a new hairdo, Peter later goes for a stroll and winds up dancing his way through Manhattan.
This leads to him embracing an all-new look as Peter Parker too as he dons a dark suit before he performs a hilarious dance, though not everyone liked it. Ultimately, it leads him to another famous dance where he does his utmost to make MJ jealous by dancing with Gwen Stacy. At the end of all this, he loses both women, though this sets up the story brilliantly for his redemption by the end of the film.
5 With Great Power
Since Sam Raimi and Tobey Maguire's first Spider-Man film together featured his origin story, there's one seminal moment in it that defines Spider-Man's entire history as a comic book hero. In this famous scene, Peter Parker has already discovered his powers and is grappling with how to control them, and his ever-changing moods. Uncle Ben, played by Cliff Robertson, tries to get him to understand an important lesson.
While Peter remains mildly belligerent to his advice, Uncle Ben drops the iconic line straight out of the comics as he tells Peter, "Remember, with great power, comes great responsibility." Of course, Peter never understood then, but those words would later haunt him after Uncle Ben dies, but also singularly define the legendary hero he becomes too.
4 Stopping the Train
Spider-Man's immense strength, agility, and the courage he shows in taking on virtually any dangerous situation often leads people to forget just how young he is. Tobey Maguire's Peter Parker was still a 17-year-old high school senior when he was first bitten by the spider. In Spider-Man 2, this fact is brought to the fore when Dr. Octopus unleashes a runaway train that Spidey has to stop.
To stop it, he shows the kind of resilience and selfless courage that makes Spider-Man one of the most beloved heroes of all time. In a moment of desperation, initially unable to stop the train, he sends out a myriad of webs on either side of it and uses them to slow the momentum of the train, while he literally hangs out the front of it and, letting the full force of the train bear into him as he pulls one the webs with all his might to stop it.
While he's successful, it takes all of his strength and renders him unconscious. In a touching moment, the passengers carry him inside, and seeing his face for the first time, they remark in surprise, "He's just a kid." This made for one iconic scene since it showed not just how strong Spider-Man actually is, but also just how much often rests on his young shoulders as a hero.
3 First Glimpse
After going through the trauma of losing Uncle Ben, Peter is initially distraught and has no idea what to do with his powers. However, at the right moment, Uncle Ben's famous words come back to him, and finally realizes his purpose. This leads him to rework his costume, ending up with the classic look in his famous red and blue suit. The scene ends with a close-up shot of Spider-Man in his iconic suit for the first time.
It's a huge moment for the character and the cinema world itself since it heralds the first time the legendary superhero was finally seen on film again. This also kick-starts a new era for the character, one that would grow to encompass a ton of other live-action film appearances and animated films, with two other actors who would go on to play him before all three ultimately reunite in Spider-Man: No Way Home.
2 Return of the Legend
That breathless moment which sees all three of the modern-era Spider-Man actors come together sent the world into a frenzy. A stroke of genius by the MCU, Spider-Man: No Way Home ultimately found a way not just to unite all three Spider-Mans, but also a way to open the door to the possibility of keeping the other franchises going too.
While it's Andrew Garfield's Spider-Man who makes an appearance first, this only heightens the excitement for Tobey Maguire's entrance. When he does walk through the portal and into the MCU, the moment is a goosebump-inducing feast for comic followers and fans of the Tobey Maguire Spider-Man trilogy.
1 That Kiss With MJ
It's now become the stuff of legends. With the perfect backdrop of rain falling around them, Spider-Man saves Mary Jane again and takes down a group of creeps trying to attack her in a dark alley. In his rush to save her, he doesn't have time to put on his mask and luckily fights in the shadows where she can't see who he is.
After knocking out her attackers, she tries to get to him, but he disappears around a corner. She looks around for him, and he suddenly drops beside her while hanging upside down from a web. They're face to face she asks, "Do I get to thank you this time?" She starts to pull off his mask, but he hesitates.
MJ has the courtesy of only pulling his mask halfway down, respecting his need for anonymity. As the pair lock lips for the first time, it makes for cinema gold; this beautifully shot scene carries all the poignancy of the two characters' long history as lovers in the comic books with it.
To top off this magical moment that made comic fans everywhere swoon with joy, as MJ puts his mask back on, he slings away, and she's left beaming up at the rain. She's blissfully unaware that the kiss meant so much more to him than it did to her since Peter Parker has always been in love with MJ.