Spider-Man 2, considered by many important critics such as myself to be one of the best superhero movies ever made, released in theaters 16 years ago this week. The early 2000s hype train that was the Spider-Man film franchise was in full swing at that point, and it did not diminish three years later when Spider-Man 3 hit theaters and concluded the trilogy, earning nearly $1 billion in ticket sales despite being an incredibly stupid movie.

Since Spider-Man 2’s release in June of 2004, the franchise has seen 5 movies and two full-fledged reboots, which is nuts when you think about it. In that time, we’ve seen enough Spider-Man villains on the big screen to field a two-on-two volleyball tournament. To celebrate the anniversary of the wall-crawler’s best live-action outing, I’ve ranked every single live-action Spider-Man movie villain from lamest to most bodacious.

17. Alistair Smythe (The Amazing Spider-Man 2)

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Image via Sony

Alistair Smythe is a mad scientist responsible for creating an army of robots called Spider Slayers, resulting in some of the worst Spider-Man comics of the 1990s. Appropriately, the character appears in The Amazing Spider-Man 2, easily the worst Spider-Man movie of literally any decade. Smythe is played by B.J. Novak and reinterpreted as Electro’s shitty boss at Oscorp, where he does not build a single Spider Slayer. I can’t decide if that’s a good thing or a bad thing.

16. New Goblin (Spider-Man 3)

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Image via Sony Pictures Releasing

As disappointing as Spider-Man 3 was, easily the most disappointing aspect was the payoff to Harry Osborne’s three-film arc. Harry should’ve been the sole villain of this outing, which was clearly the ending that the first two films were building up to, but every aspect of his character gets so bungled that director Sam Raimi had to literally give him amnesia in the first 20 minutes to totally reset him and make room for some sweaty-ass storyline about the Sandman. That said, the portion of the film in which Harry regains his memory and exacts his revenge on Peter is the best part of the film, punctuated by an indelibly smug James Franco chowing down on a piece of pie.

15. The Lizard (The Amazing Spider-Man)

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Image via Sony Pictures Releasing

The Lizard is a villain that has deep personal connections to Peter Parker in every interpretation of the character, but he also looks like an absolute asshole. Seriously, he looks like the GEICO gecko got bit by Telly Savalas and transformed into a mascot for a minor league baseball team. It’s impossible to take The Amazing Spider-Man’s version of the Lizard seriously, so I refuse to try. He looks like I should bonk his head with a rubber mallet at a carnival for some prize tickets. He looks like the Minions made a blood sacrifice to the Florida Gators. He looks like the G.I. Joe action figure your grandmother bought you by mistake. He’s the cinematic equivalent of a screen-accurate costume of Walter Matthau’s character from JFK – an impressive example of a colossal waste of time. I want to slap him every time he appears onscreen because his presence is offensive to me.

14. Sandman (Spider-Man 3)

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Image via Sony Pictures Releasing

Boy, Sandman should’ve been way cooler than this. Another one of Spidey’s oldest villains, small-time thug Flint Marko tumbles into some kind of 1960s science bullshit and gains the power of sand, allowing him to change his body shape and size at will. He’s basically the T-1000, if the T-1000 was made entirely of dirty playground sediment. Thomas Haden Church came right off of his Oscar nom into Spider-Man 3 and gets thoroughly wasted in a convoluted storyline that retroactively makes him Uncle Ben’s killer, except it was an accident you guys, he was only trying to get money for his sick daughter, who is afflicted with Chronic Plot Device. Sandman could be a visually interesting character, but really all we get to see him do is transform into a gigantic sand hulk that apparently costs him the power of speech, because he just grunts monosyllabically as he very slowly tries to crush the webslinger. At the end, Sandman shares a good cry with Peter before turning to sand and floating away on the wind like Mary Poppins. I won’t mince words here, folks - it is extremely whack.

13. The Tinkerer (Spider-Man: Homecoming)

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Image via Sony Pictures Releasing

The Tinkerer is a sort of “blink and you miss it” entry, because you’d probably never realize he’s in Spider-Man: Homecoming unless you paid close attention to the end credits and have an encyclopedic index of the alter-egos of C-list Spidey villains. Phineas Mason (played by Orange is the New Black’s Michael Chernus) is a member of Adrian Toomes’ crew, appropriately tinkering with all the stolen alien equipment to develop bitchin’ new tech. The Tinkerer isn’t a particularly great villain, but Homecoming’s interpretation of him is an interesting and organic way to work him into a believable storyline in the MCU. I honestly wouldn’t mind seeing Mason come back in a future film alongside Toomes and the Shocker (hopefully in that Sinister Six film Sony has been trying to pull off since 2014).

12. Shocker (Spider-Man: Homecoming)

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The Shocker is technically played by two different actors in Spider-Man: HomecomingLogan Marshall Green AKA Tom Hardy’s life model decoy, and Bokeem Woodbine. That said, Woodbine actually plays Herman Shultz, who is the Shocker in the Spider-Man comics. Shocker isn’t that exciting of a villain, but Woodbine is always watchable, and he has a decent fight scene in which he uses his force gauntlets to bash the webslinger into a few school buses. To be brutally honest, this is the best version of the character we’re likely to get, and it’s pretty darn good.

11. Electro (The Amazing Spider-Man 2)

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Image via Sony

A true exercise in wasting both a great character and a great actor, Jamie Foxx played a baffling reimaging of Electro, one of Spider-Man’s oldest villains, in The Amazing Spider-Man 2. Granted, you absolutely couldn’t have portrayed Electro exactly as he appears in the comic, because he looks like a giant sunflower dressed like an alternate on the Jamaican bobsled team from Cool Runnings, but I’m certain the answer was not to turn him into Dr. Manhattan with a Bluetooth earpiece fused to his cranium. That said, Foxx’s hairpiece as Electro’s alter-ego, the nerdy Max Dillion, deserves its own spinoff film.

10. Rhino (The Amazing Spider-Man 2)

Paul Giamatti as The Rhino in The Amazing Spider-Man 2
Image via Sony/Columbia Pictures

Rhino is a muscle-bound goon trapped in an indestructible bodysuit inexplicably designed to make him look like a man-rhino, so the decision to cast Paul Giamatti in this role was nothing short of bold artistic vision. The Oscar-nominated actor briefly appears as a lowlife Russian gangster who is granted a gigantic mechanical rhino zord at the end of The Amazing Spider-Man 2, and honestly, it’s about as good a cinematic interpretation of this character as we’re ever going to get. And Giamatti with a barb wire skull tattoo is pretty flippin’ great.

9. Green Goblin (Harry Obsorne/The Amazing Spider-Man 2)

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Image via Sony

No less than the third version of the Green Goblin we’ve seen so far, I am prepared to Fight Online™ over the fact that Dane DeHaan’s performance as Harry Osborne is far superior to James Franco’s. While The Amazing Spider-Man 2 is far from a good movie, the storyline it explores with Harry gives him considerable pathos and an understandable hatred for Peter, a friend that refuses to give Harry his delicious blood to possibly develop a cure for Harry’s untreatable illness. Also, as much as I hated seeing Emma Stone’s Gwen Stacy get tossed in the fridge, the tiny nerd inside of me did a respectful somersault at seeing The Amazing Spider-Man issue #121 brought to life. DeHaan plays a good villain, and I wish we would’ve got to see him return for another film.

8. Venom (Spider-Man 3)

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Image via Sony

Topher Grace’s portrayal of Venom is still a point of controversy among Spider-Man fans, because geeks never get tired of talking about how much they hate their favorite things. And while I acknowledge that Spider-Man 3’s interpretation of the character is a far cry from how he appears in the comics, I actually really enjoy Grace’s performance. He’s a smug, sleezy version of Peter, and the two get caught in a game of oneupsmanship trying to dick each other over. Of course, once he gets the alien suit, it kind of falls apart – in one of the film’s most absurd scenes, Venom is just randomly swinging around New York City until he literally bumps into Sandman and devises a hasty team-up. And the “otherworldly” shriek he emits is, to put it gently, fucking stupid. But I like the visual design of the character when the costume peels back to reveal Grace’s face – the way the tendrils pull at his skin looks agonizingly painful, a concept that pairs well with his wild-eyed frenzy and literal shark teeth. Spider-Man 3 just had too many characters, so Venom gets relegated to a brief action scene in the final 20 minutes.

7. The Mugger (Spider-Man)

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Image via Sony

The anonymous mugger has been played by two different actors (Michael Papajohn and Leif Gantvoort), but the character remains consistent in that he blasts dear sweet Uncle Ben out of this universe after Peter declines to apprehend him during a robbery. The mugger serves the same narrative function as the man who killed Bruce Wayne’s parents – an avatar of random crime, which can be inflicted upon anyone at any moment. But the mugger is a bit more personal in that, unlike young Bruce Wayne, Peter actually has the power to intervene and chooses not to for selfish reasons. So Peter’s quest for revenge isn’t against any single person, or even against the concept of violence itself, but rather against himself. It’s pretty brutal, you guys, so I feel like this nameless dude with no superpowers deserves a high spot on this list.

6. Flash Thompson (Spider-Man)

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Image via Sony Pictures Releasing

Peter’s high school bully eventually becomes his friend in the comics, but because none of the Spider-Man films will let him grow up, he’s doomed to be forever picked on by Flash Thompson. Joe Manganiello played the character with swole menace in Spider-Man, while Chris Zylka is more of a pretty-boy athlete in The Amazing Spider-Man who constantly harasses Peter. But the best version of Flash so far, in my humble and correct opinion, is Tony Revolori in Spider-Man: Homecoming and Spider-Man: Far From Home. In these movies, Flash is an asshole nerd with wealthy parents. Flash has never been a villain of any consequence, so turning him into a comic relief character that perpetually needles Peter was one of the new films’ best decisions.

5. Green Goblin (Spider-Man)

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Image via Sony

Listen, when I heard that Willem Dafoe had been cast to play the Green Goblin in Sam Raimi’s Spider-Man, I shit no less than one thousand bricks. It’s as perfect a casting choice as Jack Nicholson was to play the Joker. And Dafoe absolutely kills it, so hard in fact that Raimi managed to find a way to include him in both sequels despite the fact that his character is killed off by a rocket spear to the balls at the end of the first film. However, Dafoe’s Green Goblin costume looks like something a Mighty Morphin’ Power Rangers production designer would’ve lost their jobs over. His mask has little eyeholes that flip open whenever he has to deliver a dialogue-heavy scene, and it is the most utterly ridiculous thing in any superhero movie, including all of Arnold Schwarzenegger’s ice puns.

4. Mysterio (Spider-Man: Far from Home)

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Image via Sony Pictures

Jake Gyllenhaal transformed Mysterio, a punchline villain from Spider-Man’s rogues gallery, into one of the most fun bad guys I’ve ever seen in a superhero movie. Conceptually, Mysterio’s gimmick is pretty cool – he uses special effects technology to manipulate the world around him and drop people into nightmare scenarios that leave them questioning reality. And we get to see his bullgoose chicanery in Far From Home’s best sequence, in which Mysterio bounces Spider-Man through a series of ghoulish imagery before ultimately tricking him into walking in front of a train. Plus, Gyllenhaal totally camps it up as the control-freak villain, a former Stark Industries employee who was fired for being… well, a Jake Gyllenhaal character. And his long con to trick Peter into handing over control of a Stark orbital weapons system is such a fun reveal that I don’t mind how exposition-heavy the scene is. Mysterio freaking rules, and Sony had better bring his fishbowl head back for a Sinister Six movie.

3. Vulture (Spider-Man: Homecoming)

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Image via Sony Pictures Releasing

Weirdly, Vulture is one of my least favorite Spider-Man characters, but Michael Keaton’s portrayal of the villain absolutely rips. Keaton plays Adrian Toomes as a blue-collar guy who gets screwed over by Tony Stark (a recurring theme in both of the MCU Spider-Man movies) and decides to start reverse-engineering stolen S.H.I.E.L.D. tech to avoid bankruptcy and keep his crew employed. He’s a guy that is absolutely breaking the law, but you can’t really say that he’s definitely in the wrong. Of course, he is selling advanced weaponry to some pretty dubious characters, and he’s totally willing to murder teenaged Peter Parker in order to stay in business and out of prison. Also, Vulture proves to be a surprisingly formidable foe for Spider-Man, and their fight scenes are both visually exciting and extremely tense, particularly the one in which Vulture simply drops Peter into a lake where he almost drowns. Keaton’s brief post-credits scene, and his teased appearance in the upcoming Spiderverse film Morbius, gives me high hopes of seeing him return for a Sinister Six movie, which would slap harder than anything that has ever slapped before.

2. Doctor Octopus (Spider-Man 2)

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Image via Sony

When I walked out of the theater after seeing Spider-Man 2 for the first time way back in 2004, I remember saying to my friends, “They are never going to top Doc Ock.” And in my mind, that’s still the case. Alfred Molina’s take on the classic villain turns Doctor Octopus into a tragic character with whom the audience totally sympathizes, and also he looks rad as shit. Every action sequence between him and Spider-Man is a top-shelf slobberknocker, with those crazy ass arms raining all kinds of horseshit down on the webslinger, including an elevated train. And when he punches out at the end of the movie, you’re genuinely sad to see him go. Ock has one of the best arcs of any Spider-Man film, he’s a visual treat, and he’s played by certified delightful human Alfred Molina. The only bummer is that he doesn’t sport the character’s traditional math club bowl cut.

1. J. Jonah Jameson (Spider-Man 1, 2, 3 and Far from Home)

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Before you say, “But J. Jonah Jameson isn’t a villain!”, I want to you to clamp your ignorant lips and think about it for a second. Who is the only character in any Spider-Man film that has an irrational hatred of the webslinger? Who relentlessly tries to smear the wall-crawler’s name based on zero evidence of wrongdoing? If Spider-Man had thwarted 9/11 attacks, J. Jonah Jameson would’ve accused him of being in on it. Jameson is arguably Spidey’s greatest nemesis, because he’s also Peter Parker’s employer. So, Peter has no choice but to contribute to Jameson’s endless Spider-bashing if he wants to pay his light bill. It’s a cruel trap from which he will never escape, and it inflicts endless psychological torture. J. Jonah Jameson should live in a Dracula castle on top of an inaccessible mountain for the amount of villainy he’s inflicted on Spider-Man.