For many of us, Sam Raimi’s Spider-Man trilogy will always be what we use to compare more contemporary Spider-Man films. Those films were awesome but not always because they were done well. The most important thing is that they were memorable, but so were the Spider-Man films that came afterwards, just in different ways. Just look at Amazing Spider-Man (directed by Marc Webb), which gave us a world and characters that better appealed to younger audience members, because it didn’t use horror film elements, though it definitely would have worked with a villain like the Lizard. Mad scientist turns into a cold-blooded creature? That beast was basically written for horror films.
Then we have Spider-Man: Homecoming (directed by Jon Watts), which targeted an even younger demographic. Some people praised the film for being the best one ever, partly because it finally placed the titular hero in the same world as other beloved superheroes, and partly because of the talents of the film’s cast. That’s what we’re focusing on for this list: the cast of each Spider-Man film. We have to! We’ve got three Peter Parkers, three Aunt Mays and of course, two Uncle Bens trying to tell us something about power and responsibility being great.
24. TOPHER GRACE AS VENOM
In last place is Topher Grace as the journalist-turned-alien-monster, Venom. The first few trailers for Spider-Man 3 teased Venom heavily and it got fans excited. What we got was a less-than-satisfactory adaptation of a classic member of Spidey’s rogues’ gallery. That’s mostly the fault of director Sam Raimi, who admitted that he hated the character.
Topher Grace did his best as Eddie Brock in Spider-Man 3. For example, he didn’t go over-the-top in conveying the frustration and anger Brock felt toward Peter Parker, he just wasn’t believable as a psychotic alien monster. He didn’t seem to change much after getting the suit. At one point, he tells Peter, “I like being bad… it makes me happy!” But does it? His behavior didn’t seem too different from before. You’d think all that power would make someone a little more excited. Venom was memorable because he was a classic villain, Eddie Brock as a character in that film was not.
23. JAMIE FOXX AS ELECTRO
Electro isn’t an easy character to adapt. For example, no matter how you do it, his origin story is always going to be ridiculous in some respect, whether it’s because he was in a freak lightning accident or because he fell in a vat of electric eels, as he did in Amazing Spider-Man 2.
Jamie Foxx seems to run with it and while it might initially seem over-the-top, Foxx is able to get us to really sympathize with Max Dillon. His portrayal of Electro, however, quickly turned from decent human being to typical super-powered villain to being a villain’s super-powered sidekick and Foxx’s on screen talents weren’t able to save the character from somehow fading into the background when we think back to that film.
22. BRYCE DALLAS HOWARD AS GWEN STACY
This was the first film adaptation of the character, so there were a few expectations, none of which were met when Spider-Man 3 premiered. Gwen Stacy in that film, spends a couple of minutes dating Peter Parker (if you can even call it that) and the disappears for the rest of the film after she discovers that he was just trying to hurt MJ.
There wasn’t a lot for Bryce Dallas Howard to work with in that role, so it’s no surprise that Gwen Stacy in that film wasn’t all that memorable. She’s perky and superficial but that’s just about it. Howard plays Gwen Stacy as she would other film roles, which works to an extent. She’s not exactly anyone’s favorite character in Spider-Man 3, though, so it’s no surprise that as Gwen Stacy, Bryce Dallas Howard ranks last in the list of two.
21. DANE DEHAAN AS HARRY OSBORN
The characters of the Amazing Spider-Man films were written to appeal to a younger audience, so it’s no surprise that this adaptation of Harry Osborn was younger than what we were used to. Dehaan acted like it and surprisingly, it actually fit quite well with the plot and the character when he was plain old Harry.
He was reckless, cruel, angry and pretty much everything you’d expect a high school aged multimillionaire to be if he were infected with a mind-warping serum. It worked until he actually became the Green Goblin. Then it all fell apart. Maybe it was the character design or just because Dehaan didn’t seem to know how to pull it off. Whatever it was, Dehaan’s portrayal of the Green Goblin just wasn’t believable; in fact, it was downright cartoonish. Sire, it was also memorable, but for all the wrong reasons.
20. JAMES CROMWELL AS CAPTAIN GEORGE STACY
We’re introduced to the police captain George Stacy in Spider-Man 3 but we’re not given much more than a couple of scenes to really see what his character is all about. We know he’s Gwen Stacy’s father but only because of that one brief moment where Eddie Brock tells Captain Stacy, “I’m dating your daughter” at a totally appropriate time with a totally appropriate calmness.
James Cromwell is excellent enough as a police captain but as Gwen’s father… well, he’s not as good. Obviously, there’s only one scene in which he could show fatherly concern, but in it, Cromwell doesn’t. There’s no special sense of urgency and he reacts in the same manner as he would if she were anyone else. George Stacy played a significant role in Spidey’s life in the comics; thankfully, we got an adaptation more akin to the source material later on.
19. MARISA TOMEI AS AUNT MAY
Spider-Man: Homecoming did a lot of things differently. For the first time ever, we were given a middle-aged Aunt May, a concept which felt strange to many who may have forgotten that she’s Peter Parker’s aunt and not his grandmother, despite her appearance in the comics.
Marisa Tomei played a character that just seemed to fit nicely with Peter Parker. If she raised him, he definitely would be as fun and witty as he is. Tomei shows the right amount of concern and exhaustion when appropriate, but she just doesn’t seem like Peter Parker’s aunt. She’s charismatic and stern enough but her character seems to be caught somewhere between close friend and snappy older sister. That’s why, compared to other Aunt Mays, Marisa Tomei ranks lowest.
18. DYLAN BAKER AS CURT CONNORS
Curt Connors is just a college professor in his appearances in the Sam Raimi’s Spider-Man films, and that’s exactly how Dylan Baker plays it. He’s a caring teacher who pushes his students and generally seems like a nice guy; the kind of guy you’d never suspect of one day turning into a scaly, green reptile, which would have happened in the cancelled fourth film.
Dylan Baker portrays Curt Connors as one of the most grounded characters in that film series, so in regards to credibility, Baker does a fantastic job. It’s too bad that fourth film never happened — we would have really liked to see him act out Connors’ transformation into that monster; we’re sure he would have been brilliant if Baker’s dramatic track record is any indication.
17. ROSEMARY HARRIS AS AUNT MAY
For some of us, Rosemary Harris will always be Aunt May. Even though she seemed more like Peter’s grandmother than his aunt, she turned out to be everything comic book fans hoped she would be. Aunt May is one of the most important figures in Peter Parker’s life; she’s his moral guide and one of few influences that keep Peter grounded as Spider-Man.
Rosemary Harris was able to encompass all the essential qualities of Aunt May, able to convey a sense of strength and experience in all the scenes in which she’s imparting wisdom. That strength is clearer in more emotional scenes such as that in Spider-Man 2 when Peter reveals his part in Uncle Ben’s death. There’s a quiet rage and sense of betrayal in her expression, which is just brilliant and adds to her credibility and memorability, especially since she has quite a few scenes. Most of these, of course, are just Aunt May giving long speeches about heroes and marriage proposals.
16. CLIFF ROBERTSON AS UNCLE BEN
Uncle Ben is undeniably one of the most important characters in the Spider-Man mythos. After all, it’s him who gives Peter that character-defining piece of wisdom: with great power, comes great responsibility. You need someone who can play the part of a father-like figure with enough strength and compassion to be believable as the one who basically guided Peter Parker to become the man he is.
Cliff Robertson plays that part beautifully, despite only appearing in the Spider-Man films for a few minutes. He’s able to convey enough inner strength and compassion to be credible as the kind of guy who would try to talk a mugger out of making a mistake, rather than running away as he did in Spider-Man 3. He was also able to pull off that line in the car and make it memorable as a piece of advice without going overboard and having the line rubbed in our faces.
15. SALLY FIELD AS AUNT MAY
The adaptation of Aunt May we got in Amazing Spider-Man 2 seems more realistic than most. There are several reasons for that: first, she’s not too old and not too young like other live-action Aunt Mays. More importantly, she’s able to show more concern and exhaustion from Peter’s ever-changing lifestyle and personality.
Sally Field ticks all the boxes for a believable portrayal of Aunt May. She’s able to convey clear concern for Peter when he comes home beaten up; she’s upset that he doesn’t open up to her and all that frustration seems to come from a genuine place. We can feel and understand it; even those of us who don’t have a nephew with a secret identity and amazing spider-like abilities. She’s even able to make Aunt May’s relationship with Uncle Ben seem real and relatable, which isn’t something we’ve seen before. She’s able to really work with everything she’s given on screen and it helps to set her apart from other portrayals of that same all important Spider-Man character.
14. EMMA STONE AS GWEN STACY
To be fair, Gwen Stacy was a main character in the Amazing Spider-Man films, so Emma Stone had a lot more to work with than her predecessor. This version of Gwen Stacy was smart and witty like Parker, and Stone was able to make that seem pretty real. This added to the chemistry between Gwen Stacy and Peter Parker, something that evidently spilled into the actors’ personal lives, so we’re pretty sure a lot of that was genuine.
Stone clearly had fun with the character, which added to the lighthearted moments of the Amazing Spider-Man films, but she knew when and how to bring more emotion and depth to the screen, which made scenes such as Gwen Stacy’s death touching and memorable. Whoever plays Gwen Stacy next has some large shoes to fill.
13. RHYS IFANS AS CURT CONNORS
Ifans is at something of an advantage, seeing as how his role as the main antagonist, Curt Connors, had a lot more focus in Amazing Spider-Man than Dylan Baker did in his respective films. Ifans distinguishes himself as Curt Connors by not conforming to the typical portrayals of film scientists who are often meek and slightly awkward. His portrayal of Curt Connors seems to have something dark in him long before he ever becomes the Lizard.
It makes sense with his character since he’s a scientist working for Oscorp, pressured into finding a cure for a dying Norman Osborn. Ifans is then able to easily transition from dedicated scientist to mutant reptile and when he starts searching for ways to turn everyone into a giant lizard, that change isn’t so jarring — the mental and emotional instability, not the transmogrification. That’s pretty jarring.
12. MARTIN SHEEN AS UNCLE BEN
The dynamic between Peter and his uncle in Amazing Spider-Man differs quite a bit from what we’re used to seeing. It’s not a perfect relationship where Uncle Ben is a mentor who never loses his patience and Peter always listens and never disagrees; it’s more realistic. They argue and they disagree, much more so than the two characters did in Sam Raimi’s film.
Martin Sheen is able to make us believe that Uncle Ben is his own person, not just a mentor figure in Peter Parker’s life. He cares for his wife, he worried about Aunt May when she had to walk home alone and he gets frustrated with Peter when he acts irresponsibly. Martin Sheen is able to convey all the complexities that make up a credible character: someone who cares about Peter, one who isn’t quite a father-figure but is trying to be. When he came to his inevitable end, you had to shed a tear, at least on the inside.
11. KIRSTEN DUNST AS MARY-JANE WATSON
When you think of Mary-Jane Watson, chances are you’re going to think of Kirsten Dunst as MJ from Sam Raimi’s Spider-Man trilogy. Okay, maybe that’s just because that’s been the only adaptation of MJ we’ve had in the past two decades, but still… you can’t deny that, at least for the first two films, Dunst does a great job at playing that redheaded girl next door.
She’s not as happy-go-lucky as her comic book counterpart but that’s a good thing, since that wouldn’t really mesh well with her co-star’s portrayal of Spider-Man. Dunst’s version of MJ is a lot more down-to-earth and relatable. She’s chasing her dreams and wading through the muck to support it, which is exhausting and she shows it, which is why she works so well in those films and why we rooted for her and Peter to work.
10. THOMAS HADEN CHURCH AS SANDMAN
Here’s an example of how great acting can blunt the effects of poor writing. Despite having incredible sand powers, Flint Marko doesn’t seem like a power-hungry, violent criminal. He seems as though he’s genuinely just desperate to save his daughter from illness and from the humble life she’s trapped in.
You can see it in his expression, even when he’s in the middle of a fight, Church doesn’t show much anger, if at all. There’s just desperation in his eyes. He doesn’t want to fight, but he does because he’s been backed into a corner. We can see him as more of a dedicated father than as a criminal who unnecessarily robs ATMs, armored bank trucks and terrorizes New York in the form of a gigantic sand cloud.
9. TOBEY MAGUIRE AS PETER PARKER
He was the first live-action Peter Parker for a lot of us and to this day, there are many who would agree that Tobey Maguire’s portrayal is still the best. He may not have been as witty or even as powerful as other iterations of the character but he grew on us with his humility and dedication to his responsibility.
In fact, that charm to his character made us like him and the Spider-Man films so much that we forgave a lot of things, like that time the symbiote made him strut cockily along the streets of New York, threatening the good people with awkward dance moves and that awful haircut. The symbiote was truly a creature to be feared. We’re not going to hide the fact that nostalgia plays a huge part in why we love Maguire as Peter Parker, which is why, even though we love him and he’s a terrific actor, we have to rank him last among the other Spider-Men.
8. JAMES FRANCO AS HARRY OSBORN
It’s difficult to take James Franco that seriously as an actor, what with the kind of films we see him in nowadays. Back in the Spider-Man trilogy, though, he showed some real dramatic promise. Harry Osborn in the old Spider-Man trilogy was understandably complex and it came through in Franco’s performance.
It’s great to see a Harry Osborn that can play the part of a mature businessman as well as the young guy still trying to find his way out of his father’s shadow. James Franco conveys the obsessiveness, rage and insanity that goes with the character quite believably, which is what really sets him apart from most adaptations and portrayals of Harry, including that of Dane Dehaan who seems far too childish in comparison.
7. ALFRED MOLINA AS DOC OCK
Doc Ock in Spider-Man 2, had an origin that remained relatively faithful to the comic book source material and the role, with all its emotional weight, could not have been in better hands. Alfred Molina has a way of turning Otto Octavius is a really likeable scientist. More charismatic than Curt Connors and more pleasant than Norman Osborn, audiences were drawn to his character, which made his transformation into Doctor Octopus that much more tragic.
The perfect example of Molina’s fantastic acting skills is that scene in which he mourns the loss of his wife and his life’s work in an abandoned warehouse. He slowly realizes that his mind is being influenced by the tentacles and he gradually surrenders to them after a brief and futile argument. That scene showcases what was some of the best acting in a superhero film back then.
6. DENIS LEARY AS GEORGE STACY
Denis Leary is a talented actor. That’s clear to see even if he doesn’t show all that much emotional range in his portrayal of Captain George Stacy. He doesn’t need to because that’s all in character. Leary is able to convey everything he needs to. Unlike the character his predecessor, Cromwell, was given, Stacy in Amazing Spider-Man is a dedicated father and as well as a city cop. He’s not more of one than he is the other.
Leary can pull off lighthearted, like he did when Captain Stacy went to offer his daughter hot chocolate. He’s also able to hold his own in more serious moments, such as his death scene and it never seems out of character. It gives the character depth and we can see that, even though the film never quite focuses on him as a character.
5. ANDREW GARFIELD AS PETER PARKER
Tobey Maguire lacked a certain confidence as Spider-Man, even after his character had left high school. While Andrew Garfield is playing a much younger Spidey in Amazing Spider-Man, he shows the kind of confidence and wit you’d expect from the wall-crawler and yet somehow manages to maintain that nerdy, awkward quality that makes Peter Parker so much more accessible to the audience.
You have to give Garfield credit for pulling all that off without letting his accent slip, at least not in any noticeable way. He brings a lot of emotion to the role, genuine struggle and self-doubt like we’ve never seen before, certainly not in Sam Raimi’s adaptation. That’s why Garfield is just slightly better as a Peter Parker than Maguire, though still not the best Spider-Man we’ve had.
4. MICHAEL KEATON AS THE VULTURE
This was Michael Keaton’s first role as a supervillain and he absolutely nailed it. Somehow it seems that he was able to use his experience playing more heroic characters to make Adrian Toomes seem like so much more than just your typical hateful, world-threatening supervillain. Looking at how the character was written, we could interpret the Vulture as just being someone who’s mad at the world and wants to destroy it, but Keaton’s performance makes it so much more than that.
Keaton is able to make us really understand the Vulture as someone who isn’t rich and isn’t powerful at first, he’s just a guy trying to look out for the people around him. If anything, his performance is so compelling, it kind of makes us hate characters like Tony Stark a little bit. Rich guy in a flying suit, thinking he’s above it all… kind of makes you want to don a vulture suit comprised of alien technology, doesn’t it?
3. WILLEM DAFOE AS GREEN GOBLIN
Maybe a part of the reason Dehaan’s version of Green Goblin didn’t work for us is because the first Green Goblin many of us saw was done so well. Willem Dafoe has it all: the evil grin, the terrifying cackle, the ability to converse with his own reflection and make that reflection seem like a completely different person. It’s hard to compete with that.
Willem Dafoe will always be Norman Obsorn and the Green Goblin. You could watch those films and say that he was a little over-the-top at times but remember: so is the character. He made it work for him and didn’t shy away from exaggerating the more evil qualities and expressions of the character. That’s actually why he was so entertaining and so captivating to watch.
2. TOM HOLLAND AS PETER PARKER
To date, the best Peter Parker we’ve seen on film is none other than Tom Holland, who most recently played him in Spider-Man: Homecoming after his MCU debut in Captain America: Civil War. Like Andrew Garfield, Holland is an Englishman putting on an accent and he does it exceedingly well. What really separates him from both Garfield and Maguire is that Holland is able to convey a different kind of strength.
The MCU Spider-Man doesn’t seem powerful purely because of the strength of his muscles, it’s the willpower to keep going and face his responsibilities. That is something that has not been shown in a Spider-Man before, though not for lack of trying. Holland is just better at playing the average kid forced to grow through the power he holds. If that’s not enough for you, you should know that he can do a bunch of those flips on his own. This guy is Spider-Man.
1. J.K SIMMONS AS J JONAH JAMESON
Come on. Who did you think would be number one? When you think back to Sam Raimi’s Spider-Man trilogy, J Jonah Jameson is the character that stands out the most. When you were looking forward to the Amazing Spider-Man films or Spider-Man: Homecoming, you were probably wondering about whether or not they were going to cast J.J and if that actor would be able to top what J.K Simmons did.
He had the look and he had the personality. He was loud, cartoonish, angry and perfect as the Daily Bugle editor-in-chief. In fact, fans loved him so much that there have been petitions for Simmons to reprise the role of Jameson in the MCU, something that Simmons himself has expressed an openness to. Admit it. You’re a little excited to hear that. That’s why J.K Simmons as Jameson is our number one.
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