Spider-Man is such a layered, interesting hero. On one hand, there is this really smart and kind kid who just wants to be normal, but he also feels a duty to help people and live up to his responsibilities. On the other hand, there’s this awkward teen who wisecracks and is often made the butt of the joke simply because he’s the youngest (or the most naive) person in the room.

Peter Parker became an inventor and superhero at a young age, and no matter how often older heroes bust his chops, he’s proven his mettle time and time again as one of the most capable Marvel characters that has ever lived.

That doesn’t mean that he never has his dark moments, though. From being cloned to nearly destroyed to killed altogether, Spidey has been outsmarted by many different villains over the years. The hero can’t always win, and mistakes are often necessary for learning to take place– even for people with superhuman powers. The villains also make stories more interesting and push our heroes to go the extra mile to become someone they may have never thought possible.

Whether through superhero mistakes, sheer dumb luck, brute strength or crafty cunning, villains just get the upper hand sometimes.

Here are 16 Villains Who Outsmarted Peter Parker.

16. Venom

Venom Spider Man: 16 Villains Who Outsmarted Peter Parker

Aside from Norman Osborn, Venom is the most commonly known, fan-favorite Spidey villain. Remember in The Spectacular Spider-Man when Venom said, “From now on, we’re poison to Peter Parker and Spider-Man! WE’RE VENOM“? Yeah, he meant that. His own name means a venom for Spider-Man.

Several different people have been hosts to the alien Symbiote over the years, but Eddie Brock is the most well-known (aside from Parker himself, who was an unwitting host for a brief time, earning him Venom’s wrath and call for revenge). Since Brock, a reporter, hated Spider-Man almost as much as Venom, it was easy for him to work with the Symbiote inside him.

Venom has been able to block Spider-Man’s spider senses to the point of bullying him and nearly killing him, showing him into the path of a subway train and kidnapping him, holding him captive with webbing. In one reality, Venom takes over Parker’s body, becomes Poison and uses his symbiote offspring to control the corpse of Gwen Stacy… Gross.

15. Kingpin

Ultimate Spider Man being funny with Kingpin Spider Man: 16 Villains Who Outsmarted Peter Parker

Yes, the Kingpin is most commonly associated with Daredevil, but just as Spidey is known to cross over with most big Marvel titles, so are Marvel villains. In fact, Kingpin’s first appearance was in Amazing Spider-Man #50.

Wilson Fisk has bested Spider-Man on multiple occasions, once buying Spider-Man’s name in order to “own” him and his brand. He even managed to trick the police into thinking that Spider-Man was working for him in order to make the web-slinger a target for law enforcement.

Fisk has transferred Spidey’s life force into his own dying son, Richard, put a hit out on Spider-Man and his family… Suffice to say, he has been one of the most cunning foes that Peter Parker has ever faced.

14. Shathra

shathra spiderman Spider Man: 16 Villains Who Outsmarted Peter Parker

Spider-Man doesn’t come up against many villainous women, but when he does, they sometimes take him to the cleaners. Case in point: Shathra, the insectoid who wanted to make Spider-Man into a hearty snack for her bug babies.

Appearing in 17 issues altogether, Shathra encountered Parker on the astral plane, where she thought he’d make a tasty to-go meal. She then impersonated not only a human, but Spider-Man’s lover on the news in order to root him out.

Shathra nearly got away with her plan and paralyzed Peter with her venom, but Ezekiel saved his life and helped trap the insectoid at the Spider Temple in Africa. There, Shathra experienced a taste of her own medicine and was swarmed by a plethora of hungry spiders and consumed. Had it not been for Ezekiel, Peter would have been the one to experience such a fate.

13. Chameleon

Chameleon Spider Man: 16 Villains Who Outsmarted Peter Parker

Dmitri Smerdyakov, a master of disguise, is not only adept at dressing like other people, but mimicking their mannerisms and voices as well. His moniker, the Chameleon, is a spot-on description for his abilities, and with his masterful spy skills, it’s no wonder that he’s also been able to outsmart Spider-Man on occasion.

Not only was he able to discover Spider-Man’s true identity from the late Harry Osborn’s notes, but he also managed to trick Spidey into believing that his parents were still alive with the use of android look-alikes.

Another time, he impersonated Parker and attempted to rape Mary Jane. She beat him off with a bat but the incident was still quite disturbing. The Chameleon’s mental instability has led to him impersonating several villains over the years as well.

12. Morlun

spidey morlun Spider Man: 16 Villains Who Outsmarted Peter Parker

Spidey may make use of animal powers on a daily basis, but so do some of the villains that he comes up against. Take Morlun, the Inheritor whose blood contains DNA from every organism that ever was, for example. This advantage made him virtually unstoppable, resulting in an hours-long battle with Spider-Man during which he never even tired.

While he lost that battle when Parker injected himself with radiation, Morlun eventually did win against Spider-Man, not only brutally killing him but yanking out his eye and eating it in the process!

]Luckily Peter came back to life and as Morlun approached his hospital bed, Peter truly embraced the spider side within himself and attacked him with razor teeth and arm stingers. The Inheritor was killed when Parker met his grisly deed with one of his own and bit his neck.

11. Professor Spencer Smythe

Spider Slayers1 Spider Man: 16 Villains Who Outsmarted Peter Parker

J. Jonah Jameson has attempted to unmask Spider-Man and suss out just how Peter Parker can get so many perfect pictures many times. Once he hired Professor Smythe, the creator of the Spider-Slayers, to take Peter out. Like most of Jameson’s schemes, this one backfired and Smythe outsmarted both Jameson and Peter, shackling them both to a bomb. Of course, Smythe dies of radiation poisoning before he can watch them both die, giving them hours to figure out how to disarm the bomb.

Spider-Man ultimately does freeze the bomb and save both their lives, but Jameson immediately launches into an ungrateful, hateful tirade about how Spidey must’ve been in on it the entire time instead of thanking him after begging him to save his miserable life. Later Smythe’s son Alistaire sought revenge for his father and murdered Jameson’s wife Marla in an attempt to kill Jonah. This led to Peter’s pledge to have no more civilian deaths on his watch.

10. The Jackal

Jackal in Marvel Comics Spider Man: 16 Villains Who Outsmarted Peter Parker

Since The Amazing Spider-Man #129, Dr. Miles Warren, also known as The Jackal, has been a nefarious presence in the comics. Warren, an accomplished scientist, taught at Empire State University where he met both Peter Parker and Gwen Stacy, with whom he fell in love.

Somehow he convinced himself that Spider-Man was to blame for Stacy’s death, and around the same time he cracked, developing another personality as The Jackal. Most of his plans to take out Spidey failed, but not for lack of trying. He even attempted to get The Punisher involved at one point.

The Jackal managed to outsmart Parker by hiring the Grizzly to help trap him and lure him into changing into Spider-Man in front of Warren, confirming what he had previously suspected about Peter’s identity.

9. Black Cat

Black Cat in Marvel Comics Spider Man: 16 Villains Who Outsmarted Peter Parker

“How has Felicia Hardy outsmarted Spider-Man?” you may ask. Black Cat may have a thing for Spidey but she’s still a villain, and she’s outsmarted Peter several times.

She’s slipped away from him on multiple occasions and faked her death, not once but twice, to fool him. She also tricked him another time by pretending to be mentally unstable and obsessed with him so he would leave her in a mental institution where she could easily break out again.

Hardy has also outsmarted Spider-Man in order to work alongside him to fight crime, which turned out to be not so much because she wanted to be a superhero as well, but because she just wanted to be with him. When offered to become an official superhero with the Avengers, she declined.

8. Scorpion

Mac Gargan aka Scorpion Spider Man: 16 Villains Who Outsmarted Peter Parker

One of the classic villains of the Spider-Man saga, Mac Gargan, AKA Scorpion, made his first appearance in The Amazing Spider-Man #19. He started out as a private investigator. J. Jonah Jameson hired him to follow Peter Parker around and find out how he always manages to snag photos of Spider-Man when no one else can. Yes, he hired someone to follow someone he was also paying because that’s the Jameson way.

He wasn’t able to outsmart Spidey right away, but once he became the subject of an experiment with the Scorpion tail (again, at Jameson’s request because the man has no scruples), he then defeated Parker twice. The scorpion is the natural predator of the spider, after all. Going insane and becoming a super villain in the process was the price he paid to do it.

7. Morbius

Morbius beating Spider Man Spider Man: 16 Villains Who Outsmarted Peter Parker

Yes, a vampire has outsmarted Spider-Man. If you were a bloodsucker, wouldn’t you want the best radioactive spider blood that villainy can steal?

Before he became the hero of his own story, Morbius was among some of the most famous rogues of Spider-Man’s history. In fact, he debuted in The Amazing Spider-Man #101 right after the Comics Code Authority finally lifted its ban on supernatural creatures.

Morbius isn’t supernatural, though– he’s a product of a biochemical reaction, not a lamia bite. Still, he does crave blood, and he did manage to outsmart Spidey long enough to get a sample of his super spider DNA to taste.

Unlike most of the villains in this list, Morbius ended up sealing an alliance with Spider-Man and going on to become an antihero in his own right, saving She-Hulk, working with Doctor Strange, and earning himself a leading role in his own comic, Morbius the Living Vampire.

6. Kraven The Hunter

Kraven the Hunter Spider Man: 16 Villains Who Outsmarted Peter Parker

Sometimes you get a villain who kills you to prove a point just before killing himself. Okay, that’s not typical, but that’s what we got with Kraven.

In the story “Kraven’s Last Hunt,” Kraven not only outsmarts Spider-Man, but he also kills and buries him before impersonating him to prove that he’s a better hero. Peter wakes up two weeks later, once the effects of Kraven’s tranquilizers wear off, but Kraven is satisfied that he’s bested Spider-Man. He commits suicide, finally at peace knowing that he was able to not only best Spider-Man, but also catch a criminal (Vermin) that Spider-Man had trouble capturing himself.

It’s considered one of the very best Spider-Man stories ever written, complete with awesome art and twists.

5. Mysterio

Quentin Beck aka Mysterio Spider Man: 16 Villains Who Outsmarted Peter Parker

He’s not the coolest-looking villain of all time, but he sure knows how to cause chaos. Mysterio has been used as the alias of several different villains, but the most notable and well-known incarnation of the baddie is Quentin Beck.

Voted IGN’s 85th Greatest Comic Book Villain of All Time, Mysterio has been around since The Amazing Spider-Man #13. The special effects expert has framed Spidey, almost tricked him into unmasking himself, and kidnapped May Parker. Although he has outwitted Parker on several occasions, unlike the next few villains, Mysterio never really succeeded in completely beating Spider-Man.

Spider-Man is not the only hero who has been outsmarted by Mysterio. The villain has deceived plenty of other superheroes, from the X-Men to Daredevil. The Old Man Logan story alone is enough to send every Marvel reader out for Mysterio’s blood.

4. Mephisto

Spider Man Peter Parker Mephisto One More Day Spider Man: 16 Villains Who Outsmarted Peter Parker

When the demon Mephisto outsmarted Spider-Man, fans were ready to riot. In Earth-616’s “One More Day,” Mephisto offered to save Aunt May’s life in exchange for Spider-Man’s… marriage.

It was a stupid idea in the first place (what demon makes that kind of deal?) and most people, whether they were MJ fans or not, did not like the quick, deus ex machina type ending of Spidey and Mary Jane’s marriage. J. Michael Straczynski and Joe Quesada came up with the idea, and Quesada admitted that the team was simply looking for a way to end their marriage to keep Spider-Man going for another 30 years… because apparently superheroes can’t function when they are married?

Mephisto may have outsmarted Parker by nullifying an entire section of his story with a demonic contract, but plenty of fans ‘ship Spidey and MJ to this day.

3. Doctor Octopus

Doctor Octopus from Marvel Comics Spider Man: 16 Villains Who Outsmarted Peter Parker

Otto Octavius is the villain who grew up bullied, abused by his father and controlled by his seemingly loving mother. Once his mother made him end his relationship with his girlfriend and died during an argument with her son, the brilliant doctor became cruel. When he accidentally fused himself to his mechanical appendages, he also transformed into a nearly unstoppable super villain.

It’s no wonder that Doc Ock was able to outsmart Spider-Man on multiple occasions; he is a nuclear physicist, after all. He’s held Aunt May hostage, organized the Sinister Six, tricked Spider-Man into helping him carry out his own plans, and even tried to marry May.

Fans couldn’t help but celebrate when Spider-Man took on Octavius with a beatdown so bad (after Doctor Octopus left Black Cat nearly for dead) that he developed arachnophobia as a result!

2. Vulture

Vulture Adrian Toomes Spider Man cancer rain Spider Man: 16 Villains Who Outsmarted Peter Parker

Adrian Toomes, also known as The Vulture, was the second villain that Spider-Man ever came up against. Created by Stan Lee and Steve Ditko in 1963, The Vulture appeared in the second issue of The Amazing Spider-Man as a down on his luck ex-business partner of an embezzler. He turned to a life of crime by using his homemade flight harness, which also gives him super strength.

The Vulture has outsmarted Spider-Man on several occasions. He has stolen Spidey’s youth, locked him in a water tank, convinced him to remove his shooters in the easiest way possible (threatening to fly away!), and has simply defeated Parker on several occasions.

While other versions of The Vulture have also taken on Spidey (Blackie Drago, Clifton Shallot, Jimmy Natale), it’s Toomes who will always be known as the one who bested him most often.

1. Green Goblin/Norman Osborn

spidey green goblin Spider Man: 16 Villains Who Outsmarted Peter Parker

The foe who has outsmarted Spidey on multiple occasions, who robbed him of his love and who ultimately betrayed his trust more than anyone is none other than the Green Goblin, AKA Norman Osborn, the father of his best friend, Harry Osborn.

Green Goblin’s superior intellect and insanity make him a double threat, and he is responsible for many tragedies in Peter’s life. The terrible Clone Saga of the 1990s? That was Osborn’s fault. Gwen Stacy’s death? He did that, too. He also fathered Stacy’s children in a one-night stand, adding insult to injury. Who could be so callous as to kill the mother of their own children? Green Goblin.

Harry Osborn hasn’t been the only Green Goblin to outsmart Spider-Man. Harry Osborn, Bart Hamilton, and Phil Urich have all taken on the mantle, but Norman has been and always will be the most well-known incarnation.

Are there any other supervillains who outsmarted Spider-Man? Let us know in the comments!

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