Are These Spider-Man’s Greatest Enemies?

***Potential Spider-Man: Far from Home spoilers ahead***

In some ways, a superhero is only as worthwhile as their rogues’ gallery – and Spider-Man has one of the best bunches of bad guys going in the Marvel canon. Having blitzed through six prior live-action Spidey films across three universes since the early 2000s, the franchise has exposed us to a significant number of New York’s most nefarious over the years, some more successfully than others.

Despite entering the fray more than a decade after Sam Raimi’s original Spider-Man hit cinemas, Jake Gyllenhaal’s Quentin Beck, a.k.a. Mysterio, promises to be one of the most intriguing villains yet, gracing our screens in the franchise’s latest instalment, Spider-Man: Far from Home.

With Beck claiming to be a hero from another universe, the trailers set up the character as someone of noble intentions, ostensibly able to fill the void left by Tony Stark’s demise in Avengers: Endgame. Knowing what we do about Mysterio’s comic book origins, however, it’s safe to presume that at least part of his story isn’t quite on the level – we’re leaning towards the multiverse being real, his heroism less so – and watching Gyllenhaal play with those layers promises to be one of Far from Home’s most entertaining prospects.

In any case, he’s got his work cut out for him to earn his place among the pantheon of cinematic aspiring Spider-slayers, a motley bunch of Big Bads who run the gamut from mild irritants to legitimate threats/would-be despots. Behold!

6. ALEKSEI SYTSEVICH/RHINO (PAUL GIAMATTI), MAX DILLON/ELECTRO (JAMIE FOXX) AND HARRY OSBORN/GREEN GOBLIN (DANE DEHAAN)

THE AMAZING SPIDER-MAN 2 (2014)

It shouldn’t be too surprising that arguably the most forgettable Spider-Man movie contains the series’ most forgettable suite of villains.

From Dane DeHaan’s questionable Green Goblin and Jamie Foxx’s scenery-devouring turn as Electro, to Paul Giamatti’s brief cameo as Rhino, it remains evident even now that the real crime here was the attempt to cram in as many characters as possible, at the expense of the narrative.

5. HARRY OSBORN/NEW GOBLIN (JAMES FRANCO), FLINT MARKO/SANDMAN (THOMAS HADEN CHURCH) AND EDDIE BROCK/VENOM (TOPHER GRACE)

SPIDER-MAN 3 (2007)

While the ASM2 Green Goblin is a living nightmare in all regards, it’s still a rung up from James Franco’s extreme-snowboarder look when he takes over the Goblin mantle from his deceased father as New Goblin in Spider-Man 3.

So, why should Franco’s Harry Osborn get to enjoy a higher place on this list than the version that killed Peter Parker’s love interest? Well, primarily, it’s because his co-antagonists are individually more entertaining than Rhino and Electro combined, which is enough to spare this particular trio the wooden spoon of Spider-Man villainy, but only just.

Still, like ASM2, Spider-Man 3 suffers from major overcrowding. Topher Grace’s Venom scans as little more than a hastily thrown-in afterthought  – because he was – and the symbiote storyline comes off as deserving much more screen time to be done proper justice (enter Tom Hardy).

Meanwhile, Thomas Haden Church’s Sandman is given an excruciatingly jammed-in backstory that both tries to paint him as a complex figure and directly ties him to the death of Uncle Ben for some reason. It’s meant to humanise the villain, but, in our humble opinion, this movie’s predecessor pulled this off substantially better.

4. CURT CONNORS/THE LIZARD (RHYS IFANS)

THE AMAZING SPIDER-MAN (2012)

In the spirit of complete honesty, this author must admit that there is pretty much a mental blank slate where any memory should be of Ifans’ turn as the beleaguered Dr. Connors in 2012’s first series reboot, The Amazing Spider-Man. Was he good? Was he better than Dylan Baker, who got to play the non-super-powered Connors in Raimi’s franchise? Did he adequately juggle the character’s duality and pathos with the innately silly premise of being a giant, talking lizard in a lab coat?

Who knows. Absolutely nothing about this film is jumping out right now – its first half was basically just a retread of Raimi’s flicks, which is why it falls at the top of the bottom of this list. The Lizard couldn’t have been as questionable as the villains we’ve talked about so far, but evidently also has absolutely nothing on the top three.

3. NORMAN OSBORN/GREEN GOBLIN (WILLEM DAFOE)

SPIDER-MAN (2002)

Spider-Man’s greatest nemesis of all was memorably first brought to life on the big-screen by career crazy-man Willem Dafoe, who infused his inimitable brand of wide-eyed wildness into his take on Norman Osborn’s great unravelling. Although Dafoe’s performance was great, his costume – which obscured a good deal of said performance – was polarising.

Spider-Man landed at a time when comic-book movies, wounded by the damage wrought by Joel Schumacher’s hyper-kitsch Batman films, were still pretty embarrassed about being comic book movies. It’s why we got the all-black-clad X-Men in their early films (in fairness, a look also heavily influenced by their uniforms in Grant Morrison and Frank Quitely’s New X-Men comics run), and it’s why we got the armored-up, frozen-faced terror of the 2002 Green Goblin, which somewhat muted Dafoe’s expressive performance.

It could have been so much worse (or better, depending on how you feel about nightmarish animatronic masks), though. So at least we’ve got that going for us.

2. ADRIAN TOOMES/THE VULTURE (MICHAEL KEATON)

SPIDER-MAN: HOMECOMING (2017)

Even if Michael Keaton’s put-upon everyman Adrian Toomes had no other lines at all, his bone-chilling read of, “Good ol’ Spider-Man,” to Tom Holland’s Peter Parker – the subtext being that Toomes, himself moonlighting as the tech-stealing criminal known as the Vulture, knows that Peter and the pesky hero are one in the same – would earn him an upper-echelon placing on this list. The menacing, murderous glint in the eye. The creeping smile. The complete absence of kindness behind it all. It is a masterclass in layered villainy.

Outside of that pivotal scene, so commanding is Keaton as Toomes that it’s easy to forget that Homecoming technically has the most stacked movie rogues’ line-up of all: alongside the Vulture, two different versions of the Shocker appear in this film, as well as unnamed or otherwise not-fully-realised versions of the Prowler, Tinkerer, Darter and Scorpion.

Somehow, though, Homecoming handles these characters in a winking way that never makes it feel overstuffed. Instead, there’s plenty of room for Keaton to showcase Toomes’ depth as his criminal motivation slides from vengeful desperation to self-assured devilishness, and it’s an absolute blast to watch.

1. OTTO OCTAVIUS/DOCTOR OCTOPUS (ALFRED MOLINA)

SPIDER-MAN 2 (2004)

It might be hard to believe these superhero-saturated days, but Spider-Man 2 was once the benchmark for comic-book movies. And a big part of that was Alfred Molina’s nuanced – well, relatively speaking – outing as the tragic, tyrannical Dr. Otto Octavius.

Sure, the role (and Molina’s performance thereof) is still layered thick with cheese, and, like Toomes, Octavius is presented as something of a reluctant antagonist, someone who only lends himself to wicked deeds because he believes that’s the way the world has pushed him. But what sets Otto apart from the rest of this sinister society – what makes him the most superior Spider-Man villain – is his unprecedented success in his schemes, especially because he’s not really a bad guy at heart.

Otto’s archetypal ‘one bad day’ takes him from a failed experiment and the death of his wife, to the That’s So Raimi shlock-horror of his mechanical tentacles making him murder an entire team of surgeons, kidnap an old woman and do battle with Tobey Maguire atop a moving train. And that’s all before he resoundingly defeats Spider-Man, delivers his beaten body to James Franco, and sets in motion the destruction of the entire city before a last-minute change of heart (well, change of mind, more accurately) sends him on the express line to redemption via one last grand self-sacrifice.

Was he under the influence of unhinged killbots who drove him to his crimes? Sure, but you also get the sense that Otto would be capable of his actions even without the tentacles. He was already a mean, jealous guy; his arms’ AI simply give him the proverbial push he needed to follow his underlying urges over the edge. Simply put, Molina’s Doc Ock is as complex a character as any of Spider-Man’s best bad guys, and a shining exemplar of effective yet sympathetic evil at a level none of his peers have managed to match. Well, so far, anyway – let’s see what you’ve got, Mysterio.

Spider-Man: Far from Home is in cinemas July 1.