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"You fool! Here in the sky we’re in my element! I’ll shake you off — and be rid of you for good!” So says the Vulture in his first encounter with the Amazing Spider-Man way back in the May of 1963. Played by in the upcoming movie Spider-Man: Homecoming, this super-intelligent airborne villain will certainly give ’s Spider-Man a run for his money. On in the comics, he's even beaten our hero on several occasions! Together, the Vulture and Spidey have given us some of the most thrilling, devastating, hilarious and, ahem, hawkward battles in comic book history; here are their key battles.

First Appearances

The Vulture plots in his first appearance. [Credit: Marvel Comics]
The Vulture plots in his first appearance. [Credit: Marvel Comics]

Vulture first appeared in The Amazing Spider-Man #2, way back in 1963. After originally using his magnetic flight harness and wings to try and wrestle his company back from his conniving business partner Gregory Bestman, Adrian Toomes developed a taste for the thrill of petty crime — thus, Vulture was born. As his airborne attacks became more and more successful, his confidence grew, and he even publicly disclosed the location of his next robbery; big mistake!

A young and desperate Peter Parker recognized that taking and selling photos of this thief was an opportunity to help support his financially vulnerable Aunt May. Donning his Spider-Man costume, Peter surprised the fleeing Vulture by disabling his wings with a magnetic-inversion device that he had invented.

Naturally, Toomes didn’t take kindly to being beaten by a wisecracking upstart; although he'd been captured, he managed to escape from prison just 5 issues later. He confronted Spider-Man, this time with a souped-up suit, and managed to land a few blows on the wallcrawler. But a sprained arm can’t keep Spider-Man down, and he successfully captured the Vulture once again by webbing up his wings. Whilst it was back to prison for old Adrian, this wasn’t the last that we would hear of him.

Rise of the Sinister Six

A year after his comic book debut, Toomes returned in The Amazing Spider-Man Annual #1. After breaking out of prison (again), Toomes joined up with several of Spidey’s other villains — Doctor Octopus, Sandman, Mysterio, Electro, and Kraven the Hunter — to exact revenge upon the wall-crawler by forming a group called the Sinister Six.

The Vulture played a crucial part in the proceedings, relaying to J Jonah Jameson that they had (unknowingly and conveniently) kidnapped Peter Parker's loved ones: Betty Brant and Aunt May. Though Spider-Man's powers were intermittently fading and returning, he still managed to defeat the sorry bunch, due to the fact they all fought Spidey individually, since they all wanted the honor of killing the wallcrawler. Who could've predicted a bunch of criminals wouldn't play well together?!

The Vulture is one of the most prominent founding members of this famous team, and he is one of the few villains to have featured in nearly all of its iterations, which has since included the likes of Venom and the Hobgoblin. Sony were once planning to bring a Sinister Six film to the big screen; these plans have since been shelved, but with Mysterio and Kraven the Hunter projects now in development, Sinister Six could be back on the table.

Identity Theft

Drago gets the goods from Toomes [Credit: Marvel Comics]
Drago gets the goods from Toomes [Credit: Marvel Comics]

As Falcon learned in , people are quick to scoff at “bird costumes” — but it's dangerous to underestimate them. The same goes for the Vulture’s hardware; after all, it allows quick getaways, enhances the wearer’s strength, and has plenty of weapons concealed beneath its razor-tipped feathers.

Inmate Raniero “Blackie” Drago recognized the benefits of the Vulture identity, and whilst in prison, he engineered a (seemingly) fatal accident for Adrian Toomes, and convinced him to give up the location of his second suit. Escaping from prison (which is apparently extremely easy in the Marvel Universe), Drago assumed the guise of the Vulture. Drago had some early success, managing to overpower (an admittedly weakened) Spider-Man, but he was ultimately brought to justice by Kraven the Hunter and Spidey in Amazing Spider-Man #49. Certainly, Drago failed to make the same impression as Toomes, and he didn’t use the suit to its full potential.

When Toomes realized what had happened and heard of Drago's middling exploits, he became enraged, recovered from his attack, and escaped (him too?!) to repair his tarnished reputation. Clashing with Drago, Toomes fought Spider-Man and Drago and defeated both of them, but Toomes was forced to flee and lick his wounds when his equipment was damaged in a second fight with Spider-Man in Amazing Spider-Man #64.

Whilst Drago swore he would never become the Vulture again, he did appear in a prison cell in Marvel Knights: Spider-Man, a comic run which also included the original Vulture. Incidentally, Drago is not the only other person to assume the identity of the Vulture without Toomes’s blessing...

Crimelord and Cancer

A young-ified Vulture! [Credit: Marvel Comics]
A young-ified Vulture! [Credit: Marvel Comics]

The '80s and '90s were crazy times for in general, and Spider-Man is a notable example of this wackiness (see: the entire Clone Saga). During this time, Toomes became involved in a gang run by his nephew Malachi, but he began to suffer from ill health. He struck up a friendship Aunt May’s partner, the paraplegic Nathan Lubensky, and the conflict between Spider-Man and ol' Vulchy became a little bit more personal.

Not knowing who Toomes really was, Nathan did a Robin Williams and urged Adrian to seize the day. Taking the advice to heart, Vulture returned to his bad habits in a newly reformed Sinister Six. Yet he didn't know that May was courting Nathan. As such, when Toomes tried to take May hostage, the shock caused Nathan to suffer a terminal heart attack. Toomes later attempted to make amends with Aunt May after discovering that he’d contracted cancer from the materials that powered his suit. Instead, he suffered a severe beating from an understandably very protective Spider-Man. And Toomes's misfortune didn’t stop there!

After inadvertently coming into contact with an android which was part of Norman Osborn’s manipulations, he absorbed its life force, causing his cancer to be cured and his youth to be restored — complete with a very '90s hairdo, I might add. However, his rejuvenation didn’t last too long, and Toomes was forcibly re-aged thanks to a dying, super-powered man named David Kalen in Spectacular Spider-Man #18.

Incidentally, Toomes was also shown to have this youth-sucking power in the popular Spider-Man Animated Series of the 1990s. He utilized this technology against Spider-Man, yet in doing so, he contracted Spider-Man's mutation disease which turned him into a massive spider. Crazy times indeed....

A Gauntlet and a Grandson

Vulture flying in for the kill! [Credit: Marvel Comics]
Vulture flying in for the kill! [Credit: Marvel Comics]

Sometime after his brush with vigilantism (Spider-Man: Get Kraven), the Vulture was really put through the wringer in Mark Millar’s Marvel Knights: Spider-Man limited series — but then again, which character wasn't? Before he appeared in the story, Toomes had reconnected with his family, becoming very attached to his grandson, so he was devastated when he learned that his beloved relative has leukemia. To fund his grandson's treatment, Toomes returned to crime in a new red and black costume. Alongside Electro, he swindled millions of dollars from Daredevil super villain, the Owl.

Meanwhile, a stressed-out Spider-Man was searching for Aunt May and her kidnapper. The Owl managed to goad Spidey into attacking Electro and Vultur, who managed to beat the Spider-Man so thoroughly that he was landed in hospital. Toomes attacked the ward and tried to finish the wall-crawler off, but he was prevented from doing so due to the timely and brutal intervention of Spidey's ex, the Black Cat.

Black Cat returned the Vulture to the Owl, and after being tortured by the crime-boss's sadistic goons, Toomes later appeared alongside Electro et al as part of Norman Osborn’s Sinister Twelve. Wearing a helmet to mask the disfigurements inflicted upon him, luck did not favor our feathered friend once again — he was subdued, with his other team members, by the Avengers. Poor Vulchy just couldn't catch a break!

The Superior Spider-Man

Vulture and Spidey most recently clashed in the pages of the Superior Spider-Man series, but both characters were very different from their classic iterations. Vulture was a fully fledged crime boss with a new, notably Gothic aesthetic, and now used children to commit his crimes. Spider-Man, on the other hand, was now a reformed Doctor Octopus in Peter Parker's body. Octavius took particular umbrage with Toomes's use of kids due to his own abusive childhood, and viciously put an end to the fight.

The Vulture later appeared when Alistair Smythe took over The Raft, as one of the inmates who were retrofitted to assist Smythe escape. However, like Smythe's plans, Toomes's uprising was swiftly foiled (yet again!) by the Superior Spider-Man.

Toomes has suffered so much pain and indignation at Spidey's hands over the years, but continues to try and best our wall-crawling hero. In many ways, Adrian Toomes is the ying to Spider-Man's yang; his age contrasts Parker's youth, he's a curmudgeon where Peter is enthusiastic, and spiteful where Spidey is compassionate. And though both are defined by their intelligence and reliance on technology, his flight also contrasts with Spidey's wall-crawling.

As such, the Vulture's silver screen debut is long overdue; he was meant to feature in Sam Raimi's Spider-Man 4 and in The Amazing Spider-Man series, but neither of these materialized. Therefore, we can't wait to see what the great Michael Keaton does with the character in !

Which Vulture story is your favorite? Head to the comments and let us know!

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