Imagine wings.

The millions of people who watched the first trailer for July’s Spider-Man re-reboot, Spider-Man: Homecoming, have seen a certain character have his Susan Lucci moment. Spidey’s latest onscreen foe is an airborne jerk who goes by the nom de guerre the Vulture. Played by the dependably movie-improving Michael Keaton, the baddie will join Green Goblin, Doctor Octopus, and Venom as big-screen antagonists for the wall-crawler. It’s natural that the Vulture would be on the short list of villains to showcase in a Spider-Man flick — he’s been around since 1963, making his debut in Amazing Spider-Man No. 2, and he’s been a chronic terror ever since, swooping into hundreds of issues of various Spider-Man series. But his spot at the top of the B tier of the Spider-Man’s rogues gallery isn’t the only reason his appearance in a film is a long time coming. Rather, Keaton’s casting is the fourth known attempt to get the Vulture into a movie — and, suffice it to say, the only one to play out successfully. This is what happened to the other three.

Spider-Man 3

Once the initial run of Tobey Maguire Spider-Man movies had already used up Doc Ock and the Goblin in the first two installments, Vulture was understandably floated as an option for 2007’s Spider-Man 3. According to that movie’s producer Grant Curtis, director Sam Raimi and his brother and co-writer, Ivan, cooked up a story treatment that would have teamed Vulture up with another classic Spider-fiend, Sandman (who did end up in Spider-Man 3, played by Thomas Haden Church). The idea was to present a kind of villainous duality: “Whereas Sandman is dangerous yet conflicted and misunderstood, the Vulture is dangerous, opportunistic, and cunning,” Curtis wrote in his book, The Spider-Man Chronicles. “Sandman keeps his emotions in check; the Vulture wears his on his wings.”

The pitch: Tobey Maguire’s Spider-Man would throw Vulture in jail, leaving the latter to stew in his hatred and cook up a plot for revenge; Sandman would become his cellmate and they’d team up to bust out and wreak havoc; in the end, Spidey would offer a truce to Vulture, who would refuse and die during their big fight, thus “illustrating to Peter the ramifications of a heart hardened by an inability to forgive.” The Vulture character is traditionally portrayed in the comics as an older man, and (according to Curtis) the producers came close to casting Ben Kingsley in the role. The crew even built a model for the character’s wings and did a demonstration in which a stuntman was flown around them at 30 mph. However, the Raimis eventually decided to use Venom in the place of Vulture and Curtis recalls that, on March 15 of 2005, the avian menace was removed from the script.



Spider-Man 4

Hope sprang anew when Sam Raimi began work on a fourth Spider-film near the turn of the decade. According to Movieline (in a scoop obtained by our own Kyle Buchanan, in a previous job), as of 2009 Sony was looking to hire John Malkovich to play the Vulture and Anne Hathaway to play Spidey’s frenemy-flame Felicia Hardy. Felicia is usually portrayed as possessing the criminal alter ego Black Cat, but the movie reportedly would have pulled a fast one on geeks and featured her turning into someone called the Vulturess (which is not a thing in the comics). But the sinister soaring never occurred, as creative differences between Raimi and Sony scuttled the whole film in 2010.

Drew Goddard’s Sinister Six Movie

The Vulture had a third shot at the spotlight a few years later. In 2012, Sony rebooted the franchise with The Amazing Spider-Man, helmed by a new director (Marc Webb) and starring a new actor (Andrew Garfield). It shared no continuity with the previous films, and was a solid box-office performer, leading the studio to make a sequel. Even before it premiered, there were already plans to make a Drew Goddard–directed spinoff about longtime supervillain clique the Sinister Six — of which Vulture was a founding member in the comic books. Once again, though, the character was grounded — this time by disappointing returns on 2014’s The Amazing Spider-Man 2.

Following the lukewarm response to that film, Sony engaged in negotiations with Marvel Entertainment, which had long coveted the Spider-Man film rights that its comics division had long ago sold off. The two firms reached a deal and aimed to reboot Spidey once again, this time as a character situated in the enormously lucrative Marvel Cinematic Universe. Plans for Sinister Six were postponed indefinitely to make room for this new approach. And yet, against all odds, this past July brought redemption for the always-the-bridesmaid villain, when Marvel Studios chief Kevin Feige told a packed San Diego Comic-Con panel that Vulture would be the antagonist of Homecoming. At long last, the curmudgeonly weirdo with the mechanical wings will take cinematic flight.