Spider-Man is one of those characters who’s been played a few times now by actors in high-profile live-action movies, so that can make picking the “best” Peter Parker/Spider-Man actor difficult or, at the very least, potentially divisive. It’s not like Superman, where the answer is pretty clearly Christopher Reeve (sorry, Henry), but it might be a little easier than picking the best Batman actor, because there have been ever more high-profile actors who've played that character in live-action. With Peter Parker/Spider-Man, then, the three big ones are Tobey Maguire, who played him in a trilogy between 2002 and 2007, Andrew Garfield, who starred in two Amazing Spider-Man movies in the 2010s, and Tom Holland, who had three solo films as Spider-Man in the MCU (the third of that bunch also featured Maguire and Garfield in supporting roles).
It’s easy to be fondest of Tobey Maguire’s portrayal, though. He brought an awkward charm and endearing everyday quality to both Peter Parker and Spider-Man, and, yes, nostalgia might also play a part in his films being particularly well-loved, despite some of their flaws. What follows is a rundown of each time Maguire played the character (four in total), ranking those films and Maguire’s contributions to them, starting with the somewhat flawed, and ending with one all-time great superhero movie he starred/shone in.
4 'Spider-Man 3' (2007)
Directed by Sam Raimi
It’s possible to feel a little torn about Spider-Man 3, as it’s a movie of highs and lows (not in an Akira Kurosawa way, though). This was Sam Raimi’s final Spider-Man movie with Tobey Maguire, and the last time the latter played the hero for about a decade and a half. In an attempt to go bigger than what came before, Spider-Man 3 does kind of over-extend itself, making its titular hero clash with numerous villains in the one movie, which has the impact of dulling the potential of certain characters. Venom, in particular, gets used pretty haphazardly, but at least Spider-Man 3 is better than some of his solo movies that started coming out about a decade later.
Yet, within the realm of flawed Sony Marvel movies, Spider-Man 3 cannot be considered one of the worst, because parts of it are a blast. There’s some amazing comedy here that seemingly wasn’t appreciated as intentional camp back in 2007, but has found new appreciators as the years have gone on. There are some truly meme-worthy scenes and lines found throughout Spider-Man 3; perhaps even more than there were in the first two Raimi + Maguire collaborations, and such moments make the film easy enough to sit through. There is still a slightly frustrated feeling one might feel when watching Spider-Man 3, aware that there are good moments found alongside some shakier ones. It’s an overall pretty good movie that, if handled a little more carefully, could’ve been pretty great, but it’s still a sign that Tobey Maguire had a good run with his Spider-Man movies if something this decent (more or less) is his relative worst.
A strange black entity from another world bonds with Peter Parker and causes inner turmoil as he contends with new villains, temptations, and revenge.
Release Date May 1, 2007
Runtime 139
3 'Spider-Man: No Way Home' (2021)
Directed by Jon Watts
Image via Sony Pictures Releasing
Thanks to some multiverse-related chaos, Spider-Man: No Way Home ends up giving you three Spider-Men for the price of one. That’s not nearly as many Spider-People as you get in either Into the Spider-Verse or Across the Spider-Verse, but it’s the quality rather than the quantity that counts here, because those extra Spider-Men are played by Tobey Maguire and Andrew Garfield, reprising their roles and sharing the screen with Tom Holland. It is still Holland’s movie, and probably the best Spider-Man film he’s been in to date. It would also quite easily count as the best Spider-Man movie Garfield has starred in (his two solo outings didn’t give him as much to work with as he deserved, but he was good).
So, it’s a testament to the best Tobey Maguire Spider-Man flicks that No Way Home isn't his best. He is one of the best parts of it, given the film gets off to a slightly rocky start but really finds its footing once the first act is over… and Maguire + Garfield do take a while to show up, with their inclusion treated like a twist (one that’s probably not surprising to many viewers nowadays, though). It’s worth it, in the end, to see the trio of 21st-century live-action Spider-Man actors together, and for the fact it brings back a handful of iconic foes (plus their actors) for the Spider-Men to battle. No Way Home can be messy, is perhaps a tiny bit overstuffed, and lacks a certain visual spark/style the Raimi movies have, but all the good here does inevitably outweigh most of the not-so-good.
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Spider-Man: No Way Home
With Spider-Man's identity now revealed, Peter asks Doctor Strange for help. When a spell goes wrong, dangerous foes from other worlds start to appear, forcing Peter to discover what it truly means to be Spider-Man.
You can’t point to Spider-Man as the first big-budget superhero movie to be a mammoth critical and commercial success, given movies like Superman (1978), Batman (1989), and X-Men (2000) pre-dated it, but it certainly contributed to elevating the superhero genre overall. Since Spider-Man’s release in 2002, there have been too many large-scale – and largely successful – comic book films to count, which can render this particular movie a little quaint in hindsight. But therein lies its charm, too. This is a simple and easily approachable movie that isn't afraid of being both sincere and a little goofy. There’s a difficult tonal balance to walk, but Spider-Man does it surprisingly well, even if its sequel – released two years later – did it even better.
Spider-Man is an origin story for Peter Parker/Spider-Man, going over some story beats that are familiar by now, but probably felt fresh for a good many viewers in 2002 who weren’t familiar with comics. Tobey Maguire and the other actors here might not be super convincing as teenagers, but Maguire does bring a youthful vulnerability to Peter Parker, and his willingness to commit wholeheartedly to both the funny and sad scenes here does make the character more compelling. Peter has his flaws and struggles, as well as his heroic qualities, and Maguire proved able to handle all aspects of the character. When the next film gave him even better material to work with, he shone even brighter, somehow. Speaking of…
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Spider-Man
After being bitten by a genetically-modified spider, a shy teenager gains spider-like abilities that he uses to fight injustice as a masked superhero and face a vengeful enemy.
Release Date May 3, 2002
Runtime 121 minutes
1 'Spider-Man 2' (2004)
Directed by Sam Raimi
Image via Sony Pictures Entertainment
Proving even funnier, more action-packed, and generally more emotional than Spider-Man (2002), Spider-Man 2 feels like a pretty much perfect sequel. It goes bigger when it needs to, but never overdoes it. The action is more exciting, but as a continuation of Peter Parker’s story, it arguably gets more introspective and personal. It gets to the heart of what being Spider-Man at a difficult point in life (young adulthood) might realistically feel like. In ways both small and monumental, Peter Parker is challenged, with the world trying to beat him down again and again, forcing him to confront the choices he's made and whether he can continue being the masked hero New York City needs.
That might make Spider-Man 2 sound gritty and intense, but it’s also just as bombastic and wacky a comic book movie as Spider-Man and Spider-Man 3 can get. It combines silliness and sincerity in such a wholly involving way, feeling like a labor of love when it comes to the way it’s written, directed, put together, and acted. Maguire is also at his best here, and Peter Parker’s dilemmas and struggles have scarcely been so involving and dramatic – again, both in large and small ways. Spider-Man 2 is certainly one of the best movies of its decade, and could well be an all-time great superhero/blockbuster movie, too. It’s a classic, and few movies of its kind come close to touching its greatness.
Image via Sony Pictures Releasing
Image via Sony Pictures Releasing 
Image via Sony Pictures Releasing 
Image via Sony Pictures Entertainment 
English (US) ·