Spider-Man has one of the most colorful rogues’ gallery in comics, but which movie villains made graceful leaps to the screen, and which came across as a big gooey mess?

9Photo: Sony Pictures

Your hero is only as good as your villain. That conventional bit of Hollywood wisdom has been disproved by many a superhero movie in the last decade. Nevertheless, there’s still something exciting about a comic book movie villain who does work. The kind that offers a performance as big and exciting as anything the do-gooders get up to.

And in the realm of superhero movies, few characters have had a stronger roster of such baddies than the Spider-Man movies. Despite existing across three continuities, and three vastly different interpretations of the Web-Head, popularity for the best of Spidey’s rogues can last for years—or even decades—after their first appearance. Just look at the unbridled anticipation about Alfred Molina returning to the role of Doctor Octopus for proof.

Yet with so many foxes in the Spidey henhouse, the question becomes who is the best Spider-Man movie villain—as well as who are the ones that never fully measured up? Well, we’ve taken a poll of the Den of Geek staff in order to provide a definitive answer on who is the best villain to ever get caught in Spidey’s web.

11. Rhino (Paul Giamatti)

It seems faintly cruel to include a villain who was only ever meant to be a throwaway gag (and fodder for the trailers). But then “cruel” might also describe what a respected actor like Paul Giamatti was doing to the Russian accent in his brief and woefully misjudged appearance in The Amazing Spider-Man 2.

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Riffing on the Ultimate Spider-Man comics’ version of the Rhino, wherein Aleksei Sytsevich is turned into a man entombed in a giant body of robotic armor, Giamatti’s Rhino feels like a leftover from the Joel Schumacher era of superhero movies where every scene was played 568 times too big, and there was no such thing as good dialogue. Truthfully, this interpretation of the Rhino character is awful, but I’m sure the paycheck was nice. – David Crow 

10. The Green Goblin (Dane DeHaan)

In the confusing, jumbled mess that is The Amazing Spider-Man 2, perhaps no character–well, with the exception of Paul Giamatti’s Rhino–is given shabbier treatment than Harry Osborn. Played by Dane DeHaan, a moody actor at best and a comatose one at his worst, Harry speeds through an arc in perhaps 15 minutes of screen time that previously took James Franco three movies to complete.

DeHaan’s Osborn begins his journey by coming home after a decade away at boarding school to be at the deathbed of his father Norman (Chris Cooper). He then ends the movie buzzing around on a glider as a grinning psychopath mutated by an injection of magic spider-blood. His “sort of Green Goblin” seems unnecessarily jammed into the movie thanks to Avi Arad and Matt Tolmach’s obsession with creating an instant Spider-verse, and as a result the character–this is supposed to be Peter Parker’s best friend!–makes no impression whatsoever. Plus his costume and makeup suck, and that’s in a movie featuring Jamie Foxx’s Electro get-up. Another reason we’re grateful this particular version of the franchise collapsed. – Don Kaye

9. Electro (Jamie Foxx)

Another winner from The Amazing Spider-Man 2, Jamie Foxx’s twitchy and shallow interpretation of Max Dillon, aka Electro, also felt like it was out of a Schumacher Batman movie. More specifically, it’s a direct knockoff at the screenplay level of Jim Carrey’s Riddler in Batman Forever (1995). But whereas that Batman movie was intended to be camp, Foxx is playing a nebbish loser who relies on all the visual shorthand of an SNL sketch—he has a comb over and two-inch thick glasses while singing happy birthday to himself—in a movie where Andrew Garfield’s Spidey is supposed to be mopey and lovelorn, and whose girlfriend is then murdered in front of his eyes at the end of the picture.

The tonal dissonance between these elements verge on outright disaster, but even in more seasoned directorial hands, it’s hard to imagine Foxx’s Electro going much higher on the list. As originally conceived, he’s a walking set of clichés who is then turned into a neon-blue eyesore. Some of the digital effects of Spider-Man dodging manmade lightning are fun, but they’re little more than a diverting light show before Foxx comes back onscreen to mug beneath a pound of CG makeup.  – DC 

8. The Lizard (Rhys Ifans)

Spider-Man fans were thrilled to see Dylan Baker cast as Dr. Curt Connors in Sam Raimi’s Spider-Man trilogy, complete with missing arm but reimagined as a professor and semi-mentor for Tobey Maguire’s Peter Parker. Alas, Baker never got his shot at transforming into his scaly alter-ego The Lizard. So it fell to Rhys Ifans to pick up the mantle for The Amazing Spider-Man (2012). The results were mixed.

The character’s origins are somewhat rejiggered for this iteration, although some of the basic details of his transformation and motivation remain pretty much the same as in the comics. The problem is that when Ifans turns into the Lizard, the design of the CG-generated creature is bland and unmemorable–no walking crocodile in a lab coat here, which sounds silly when you say it but at least stood out in the comic book.

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Instead he loses all visual individuality and appears like any other CG creature from 10-15 years ago. The idea of somehow tying Peter’s father and Connors together in some kind of past conspiracy also indicates how small this particular version of Spidey’s story is. Ifans does his best, but the lousy visuals and overly complicated plot work against him, as does the character losing his sympathetic backstory of a wife and child to go back to, which is the linchpin of Peter working to save him in the comics. – DK

7. The New Goblin (James Franco)

If you set that silly “New” moniker aside—clearly a byproduct of Sony and toymakers wanting a brand name other than the “Green Goblin” on their next line of action figures—one could make the argument James Franco’s Harry Goblin is better than you remember. Despite being saddled with an unfortunate “amnesia” subplot in Spider-Man 3, Franco’s Harry is one of the best aspects of that film (and, personally, I’d argue its best villain).

With two movies’ worth of backstory and motivation to build from, Harry comes out of the gate running in the threequel, instigating what is still the best aerial fight sequence in any Spider-Man movie to date thanks to Sam Raimi’s gifted knack for balletic action sequences (and finally having the budget and technology to do it right with a Goblin character).

More than just a nifty fight sequence though, Harry’s villainy feels like cathartic payoff to a rivalry that began passive aggressively in the first film when two buddies fell in love with the same girl; it then escalated as Harry’s domineering father drove them apart first as a mentoring presence and then as a ghost haunting their relationship. All of which is satisfyingly explored on the road to a brutal throwdown. And along the way, Harry’s mind games are so cruel, so classically Osborn, that they live up to Franco’s pie eating meme below:

6. Venom (Topher Grace)

Topher Grace’s Venom gets a bad rap. Yes, he was garishly shoehorned into Spider-Man 3 by producer Avi Arad, and director Raimi treated the character like a superfluous afterthought as result. Nonetheless, Grace’s interpretation of Venom is more conceptually interesting than most.

By making Eddie Brock into a narcissistic doppelgänger of Peter Parker, Raimi and screenwriter Alvin Sargent came at the concept of an “evil Spider-Man” more smoothly than the comics—where Eddie is a bodybuilder-sized investigative journalist neither Peter nor Spider-Man had ever met before he begins stalking the Parkers. Also by jettisoning the “lethal enforcer” business, which never really worked on the page or arguably in the Tom Hardy movies either, the filmmakers approached Venom as a shadowy reflection of what Spider-Man could become without Uncle Ben and Aunt May’s upbringing and moral values.

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Frankly, that’s far more interesting than a Venom who likes eating the brains of chickens, in our opinion. Plus, the birth of Venom scene and his physical brutality made him a cool-looking, if exceedingly underdeveloped, villain. – DC 

5. Sandman (Thomas Haden Church)

This classic Spider-Man nemesis (whose comic book debut came in The Amazing Spider-Man #4 in 1963) had the misfortune to appear in one of the weakest of the wallcrawler’s movies, 2007’s Spider-Man 3. It’s a shame because Thomas Haden Church, coming off his acclaimed performance in 2004’s Sideways, does a great job in the role, bringing sympathy and humanity to the character of Flint Marko, who accidentally becomes a shapeshifting supervillain when he falls into a particle accelerator.

We could do without the retconning which makes Marko an accomplice in the death of Uncle Ben, but that’s modern cinematic universe worldbuilding for you. The big problem here is that Marko is wedged into a movie that already includes two other bad guys–James Franco’s Harry Osborn/New Goblin and Topher Grace’s Eddie Brock/Venom–while also introducing Bryce Dallas Howard as Gwen Stacy.

We’ll always wonder how Sandman might have fared in a symbiote-free Spider-Man 3, because even in this cluttered film he stands out as visually dynamic with his comic-accurate outfight and dazzling fight sequences. Marko–or at least a CG version–is also set to appear in Spider-Man: No Way Home, so perhaps we haven’t seen the last of this enduring Spider-villain just yet. – DK

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4. Vulture (Michael Keaton)

Michael Keaton as a winged avenger of the night? Well, it worked the first time, right? (And twice if you count Birdman!) That was the near universal feeling in the press when Keaton’s casting as Adrian Toomes was announced. What caught folks by surprise, however, is how well Vulture worked as an actual character.

On the page, Vulture has generally been one of Spidey’s sillier foes. But on screen, Marvel Studios turned him into a blue collar working stiff who had a morally gray and incredibly sympathetic motivation for becoming a flying corporate raider. It also creates a nice contrast between his murky adult values and Peter’s youthful idealism, giving Keaton a lot to play with in the best scenes of the film—both of which  involve Keaton jabbing with Tom Holland’s hero in the back of a car and later a warehouse.

Honestly, if Vulture’s action scenes were just a little more dynamic, and his beef wasn’t entirely with an off-screen Tony Stark, we imagine old Adrian could’ve ended up higher on this list. – DC  

3. Mysterio (Jake Gylllenhaal)

The Spider-Man movies overall have been hit and miss with the villains’ costumes—we’re looking at you, Electro and Rhino—but Spidey’s two big villains so far in the MCU, Vulture and Mysterio, have been pretty spot-on in their cinematic debuts. Mysterio’s outfit in particular has always been a favorite of ours, fishbowl helmet and all, so we’re glad to see it reproduced accurately as Quentin Beck makes his first cinematic appearance in Spider-Man: Far from Home.

It also helps that Beck/Mysterio is portrayed by Jake Gyllenhaal, one of the finest actors of his generation, who brings plenty of gravitas and nuance to the role. Mysterio’s origins are updated from special effects artist and illusionist to creator of high-tech holograms, and while some fans rue the decision to make him a former Stark Industries employee (so much of Spider-Man’s MCU storyline so far has revolved around the late Mr. Stark), it does make sense in the context of the larger narrative running through all Marvel Studios movies. Plus, even though it turns out to be a ruse, he does introduce the concept of the multiverse into the MCU for the first time—paving the way for plenty of shenanigans to come. – DK

2. The Green Goblin (Willem Dafoe)

You know you’re dealing with an amazing actor when he can make a performance come through that outfit. Yes, yes, there are many jokes that can (and have been) made about the metallic getup Willem Dafoe wears. It really does look like something out of ‘80s daytime television in Japan. But when it’s Dafoe behind the mask, none of that matters.

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One of the best character actors of his generation (and maybe a few more before and since), Dafoe incredulously brings gravitas and weight to a role that was clearly conceived at a time when the ‘90s Batman movies were still fresh on folks’ mind. Dafoe effortlessly slips by those hazards though, creating a character who seems relatively layered. There is genuine compassion and affection in his scenes with his on-screen son, Harry (Franco), and Peter (Maguire), but also implicit toxicity and nastiness bubbling beneath the surface at all times. And I’m not just referring to the Goblin. The lecherous sneer Norman barely hides from Mary Jane Watson (Kirsten Dunst) obviously rested on those lips before the green meanie schtick.

No one would mistake this characterization for great art, but Dafoe is able to rally all these elements into a fuller picture, allowing him to chew scenery like he’s a puppy in a rubber ball factory. One might even wonder if there’s a take of the Goblin gnawing on Osborn upholstery in one deleted scene. Either way, he still got to give Peter the most brutal and physically imposing beatdown this franchise has ever seen. – DC 

1. Doctor Octopus (Alfred Molina)

There are many reasons why Dr. Otto Octavius has persisted as Spider-Man’s greatest villain (according to a 2014 poll) in both the comics and the movies. For one thing, he has one of the coolest costumes around with those cyborg arms, and the backstory of how those mechanisms got fused to his body is classic (he first debuted in the comics in The Amazing Spider-Man #3, in July 1963). But more importantly, Otto and Peter Parker share many similar traits—shyness, scientific brilliance, social awkwardness—and it’s been suggested throughout their history together that Peter could have become like Doc Ock had he not chosen a more righteous path.

Alfred Molina portrayed Doc Ock in Spider-Man 2 (2004), and one of the reasons why that film is still considered one of the greatest superhero movies of all time is his towering, complex performance. Molina’s comics-accurate Doc Ock is a tormented anti-hero more than a villain on-screen, one driven by grief, madness, and pride for his dastardly deeds. But he’s still capable of humanity and ultimately redemption.

Visually, there is still arguably no finer fight between superhero and villain than when Molina’s Doc Ock dryly challenges Spidey to a stunning duel atop a speeding elevated train, which which i as thrilling because of Molina’s underplayed demeanor as Sam Raimi’s gift for blocking dynamic action.We’re glad to see him show up in the MCU with Spider-Man: No Way Home, and he’s truly a villain we were sad to see meet his end in his original appearance. – DK