One of the most important things with the making of a superhero movie is to cast the right actor to play the hero – especially if the hero is as iconic as Superman or Batman or, indeed, Spider-Man – but casting the villain is almost as important. They need an authentically menacing presence, the ability to bring nuance to a mustache-twirling archetype, and all the qualities that define the character on the page.

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In various incarnations of the Spider-Man franchise, such perfect actors as Willem Dafoe and Alfred Molina have been cast to round out Spidey’s rogues’ gallery (but they weren’t always the first choice).

Norman Osborn / The Green Goblin

Perfectly Cast: Willem Dafoe

Willem Dafoe as Norman Osborn sharpening a knife in Spider-Man

As a physical presence in life, as a specter in death, and as an interdimensional traveler in the multiverse, Willem Dafoe has given a handful of genuinely creepy performances as the Green Goblin across two decades. This version of the Goblin is let down by his silly mask, but that mask was mercifully smashed to pieces within minutes of Dafoe’s return to the role in No Way Home.

Despite the mask, Dafoe always gave a beautifully unsettling performance as Norman Osborn. He nails the Jekyll-and-Hyde dichotomy of Norman and his “darker half” – particularly when he shares haunting conversations with that darker half in the mirror.

Almost Cast: Nicolas Cage

Nicolas Cage wearing fangs in Vampire's Kiss

Nobody could’ve been more perfectly cast as the Goblin than Dafoe, but Nicolas Cage was in talks for the role early in development. To sweeten the pot, Stan Lee told Entertainment Weekly, “He’d be a great Green Goblin.”

Cage is a noted superhero fan and he’d previously been up for the ultimate comic book role, Superman, in a Tim Burton movie that ended up being scrapped. The actor turned down the Goblin role due to his busy schedule, allowing Dafoe to be cast.

Dr. Curt Connors / The Lizard

Perfectly Cast: Rhys Ifans

Dr Curt Connors experimenting in his lab in The Amazing Spider-Man

Five years after the end of Sam Raimi’s Spider-Man trilogy, Sony hired Marc Webb to direct a reboot repeating the character’s origin story with a darker, edgier, Batman Begins-inspired tone. The Amazing Spider-Man introduced Andrew Garfield as Peter Parker opposite Rhys Ifans as his mentor-turned-enemy, Dr. Curt Connors, better known as the Lizard.

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Ifans’ Connors is a delightfully eccentric academic. The Amazing Spider-Man’s script gave the actor thin, one-dimensional material to work with, but he made the most of it.

Almost Cast: Christoph Waltz

Christoph Waltz as Col Hans Landa in Inglourious Basterds

According to MTV, before Ifans was cast as The Amazing Spider-Man’s reptilian baddie, Tarantino regular Christoph Waltz was considered for the role.

This is hardly surprising, since Waltz is one of Hollywood’s go-to actors for villains. He played James Bond’s arch-nemesis Blofeld opposite Daniel Craig’s 007 and won an Oscar for his sinister star-making turn as one of cinema’s most iconic baddies, Col. Hans Landa.

Adrian Toomes / The Vulture

Perfectly Cast: Michael Keaton

Adrian Toomes in Spider-Man: Homecoming; his head turned to the face backseat of his car

Michael Keaton had already played a winged superhero (in the Batman movies) and a washed-up actor famous for playing a winged superhero (in Birdman) before playing a winged supervillain in Spider-Man: Homecoming. Adrian Toomes offers a dark counterpoint to Peter Parker’s other father figure, Tony Stark.

Toomes is a working-class guy like Peter, but his economic frustrations have driven him to a life of crime. Keaton does a great job of balancing Toomes’ blue-collar relatability with his disturbing sinister edge (particularly when he threatens a teenager with murder).

Almost Cast: Mark Hamill

Luke Skywalker draws his lightsaber in The Last Jedi

The Twitter account of Rotten Tomatoes posted a clip of an interview with Mark Hamill in which he revealed that he was almost cast as the Vulture. When Keaton was first offered the role, he had to turn it down due to scheduling conflicts with The Founder.

During this interim, Hamill was interested in taking the role of the Vulture, but a scheduling change with The Founder allowed Keaton to play the part after all.

Eddie Brock / Venom

Perfectly Cast: Tom Hardy

Tom Hardy as Eddie Brock encased in Venom in Let There Be Carnage

Topher Grace had been terribly miscast as Eddie Brock in Spider-Man 3 – according to CinemaBlend, even he thought so – but Sony ended up finding the perfect actor in Tom Hardy.

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The Venom spin-off shouldn’t have been as big of a hit as it was, especially after the Spider-Man 3 controversies, but Hardy won over audiences with his delightfully eccentric take on the character.

Almost Cast: Dolph Lundgren

Gunner (Dolph Lundgren) hiding behind wall with gun in The Expendables

According to WhatCulture, David S. Goyer wrote a Venom movie for Dolph Lundgren in 1997. Lundgren had played a different bloodthirsty Marvel antihero, the Punisher, back in 1989.

While Goyer’s Venom movie never materialized, he later worked on a bunch of other comic book adaptations, including Man of Steel and the Blade and Dark Knight trilogies.

Dr. Otto Octavius / Doctor Octopus

Perfectly Cast: Alfred Molina

Doctor Octopus standing on a building in Spider-Man 2

Alfred Molina’s reprisal of the role of Doctor Octopus in No Way Home solidified what a perfect casting choice he was in Spider-Man 2. Molina plays into Doc Ock’s classical villainy when he’s under the influence of his mechanical limbs, but he also brings real pathos to a remorseful Otto after he breaks the spell and goes back to his old self.

In Spider-Man 2 and more recently in No Way Home, Molina shared great on-screen chemistry with Tobey Maguire as both a father figure to Peter and a mustache-twirling villain to Spidey.

Almost Cast: Christopher Walken

Christopher Walken with the gold watch in Pulp Fiction

It’s impossible to imagine anybody besides Molina playing Doc Ock – so much so that Kevin Feige would rather bend the spacetime continuum to bring him back than recast the part – but he wasn’t Raimi’s only choice for the role.

Around the time of Spider-Man 2’s production, Molina told TV Guide, “Sam Raimi saw a whole bunch of us character actors. It was me, Ed Harris, Chris Cooper, and Christopher Walken.”

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