While it was predated by Blade and X-Men, Sam Raimi’s Spider-Man is the movie that solidified the comic book genre as viable blockbuster fodder and laid out the familiar formula for a superhero origin story. Raimi’s first sequel, Spider-Man 2, has been praised as the perfect comic book movie, and while Spider-Man 3 was criticized for its overstuffed plot, the trilogy as a whole ranks among the best of all time.
Tobey Maguire’s definitive on-screen portrayal of Peter Parker faced off against some of the greatest supervillains in movie history – like Doc Ock and the Green Goblin – and some of the worst, like Venom and the “New Goblin.”
Venom
Producer Avi Arad has taken the blame for forcing Raimi to include Venom in Spider-Man 3. The threequel was stuffed with one villain too many, and since the New Goblin was teased throughout the trilogy and the Sandman is Uncle Ben’s true killer, Venom is the most unnecessary one. Topher Grace plays Eddie Brock as a rival photographer gunning for Peter’s job.
Most of the Raimi trilogy’s villains have a sympathetic motivation and a redeemable quality, but Eddie is just a reprehensible jerk. He doctors photos to make Spidey look bad just so he can usurp Peter as the Bugle’s go-to shutterbug, and when he bonds with the malicious Venom symbiote, it feels eerily right. Tom Hardy has since won over fans with a delightfully eccentric take on the character in the Venom solo movies.
New Goblin
James Franco’s Harry Osborn was first introduced as Peter’s best friend, but the character became defined by his hatred of Spider-Man after he caught Spidey dropping off his father’s corpse at the end of the first movie. At the end of the second movie, Harry saw his best friend’s face under the mask and stumbled across his dad’s Green Goblin technology – teasing his transformation into a villain in the third movie. Dubbed the “New Goblin,” Harry swoops down on the glider and attacks Peter early on in Spider-Man 3, then suffers a bad enough bump on the head to completely forget about his vengeful quest against Spidey and treat Peter like a pal again.
This amnesia subplot feels more like a soap opera scraping the bottom of the barrel for storylines than a superhero blockbuster trilogy bringing its central hero-villain dynamic to a head. Harry redeems himself in the finale as he returns to help Peter and makes the ultimate sacrifice to save him, but it doesn’t make up for the soapy amnesia storyline.
Sandman
Played by Thomas Haden Church, the Sandman is revealed to be Uncle Ben’s true killer in Spider-Man 3. The guy that Peter let go was just Flint Marko’s partner-in-crime. While he was squabbling with Ben for a getaway vehicle, Flint’s gun went off and Ben passed away. Despite this reveal, Raimi managed to get audiences to feel for Marko.
He’s an escaped convict, but his sympathetic motivation makes him endearing. Everything he does is for his daughter – he only steals money to pay for her cancer treatments. The power to manipulate sand is pretty silly, but drowning in sand is a horrifying fate and his initial transformation scene is heartbreaking. He keeps trying to pick up a locket containing his daughter’s picture, but it keeps slipping through his sandy fingers.
Green Goblin
Willem Dafoe’s turn as Norman Osborn in the Spider-Man trilogy is authentically creepy. The actor nails the unsettling Jekyll-and-Hyde dynamic between the frightened Norman and his murderous “darker half” – especially when he talks to that darker half in the mirror. Norman is hoisted by his own petard at the end of the first Spider-Man movie, but he continues to haunt Harry throughout the rest of the trilogy. In many ways, he’s the “big bad” of the whole series. His unbridled evil brings out Spidey’s unbridled heroism.
Being the estranged father of Peter Parker’s best friend, the Green Goblin established the trilogy’s trend of Spidey’s villains coincidentally sharing a personal connection with Peter. Dafoe’s performance in the role is typically incredible, but this take on the Goblin is let down by his silly Power Rangers-style mask (which was mercifully shattered within a few minutes of his recent return in Spider-Man: No Way Home).
Doctor Octopus
Alfred Molina’s turn as Doctor Octopus in Spider-Man 2 is still regularly included alongside Heath Ledger’s Joker and Michael B. Jordan’s Killmonger on lists of the greatest supervillain performances of all time. Molina’s performance offers the perfect blend of classical villainy and genuine pathos. He perfectly captures the familiar baddie from the comics while putting his own fresh spin on the character’s humanity.
The actor has a lot of fun with the role of a mad scientist whose robotic arms turn him into a monster, but still digs deep enough to play Dr. Otto Octavius as a human being with real emotions. Molina hams it up when he’s robbing a bank in a trenchcoat and his mechanical limbs are throwing bags of gold at Spider-Man, but brings real dramatic nuance to scenes like Otto’s final sacrifice.