Despite his place as one of Spider-Man's oldest and most enduring foes, the Vulture has long been an ugly duckling, at least as far as Hollywood is concerned.
Introduced in 1963, in The Amazing Spider-Man #2, Adrian Toomes isn't exactly the picture of the archetypal supervillain. Originally depicted as a bald, aging man with mechanical wings and a bit of a paunch, the Vulture has menaced the wall-crawler for decades, repeatedly upping his game, and upgrading his technology.
However, until Spider-Man: Homecoming, it appeared as if the classic Marvel villain was never going to catch a break on the big screen. Until Michael Keaton was cast in the role of Adrian Toomes in director Jon Watts' franchise reboot, the Vulture's cinematic history was one of near-misses, where mainstream fame hovered just within his reach before being yanked away.
To commemorate the Vulture's big moment, we look back at the past decade of the winged criminal almost appearing in films.
Spider-Man 3 (2007)
Immediately following the release of Spider-Man 2 in 2004, director Sam Raimi and his brother, and frequent collaborator, Ivan Raimi began work on the story treatment for its sequel, in which they wanted to explore Peter Parker's flaws, and the theme of forgiveness. In its earliest form, the script was to bring back Harry Osborn (James Franco) as the new Green Goblin, and introduce two new villains: the Sandman, who made it into the final product (as played by Thomas Haden Church), and the Vulture, who didn't.
Raimi and the producers of Spider-Man 3 actually met with Oscar winner Ben Kingsley for the role in February 2005, and came away so impressed that they were prepared to begin work on the design for Adrian Toomes' costume. "He spoke with passion and purpose while expounding upon his approach if called to play the classic Marvel villain," producer Grant Curtis recalled in his 2007 book The Spider-Man Chronicles: The Art and Making of Spider-Man 3. "His posture was intimidating, his stare mesmerizing."
However, less than a week after that meeting, "the casting process ground to a halt." "The script was undergoing major changes, and one of these was the replacement of Vulture with Venom," Curtis wrote. "The villain swap soon became official and the Vulture's wings were packed away, along with the opportunity to work with Sir Ben Kingsley, to make way for Venom's fangs."
It's been widely reported that franchise producer Avi Arad, the founder of Marvel Studios, pushed for the inclusion of Venom in the film. Whatever the case, Topher Grace (That '70s Show) was cast as Venom's human host Eddie Brock -- ''My first reaction was, This is probably a really bad idea," the actor told Entertainment Weekly in 2007, noting he looked nothing like the comic character -- and the Vulture was history, at least for the time being.
Spider-Man 4 (abandoned)
Despite mixed reviews, Spider-Man 3 was a commercial success, leading Sony to announce a sequel, which promised another opportunity for Sam Raimi and Adrian Toomes. "I was very unhappy with Spider-Man 3, and I wanted to make Spider-Man 4 to end on a very high note, the best Spider-Man of them all," the director told Vulture (no relation) in 2013.
A report surfaced in early December 2009 that John Malkovich was in negotiations to play the Vulture, while Anne Hathaway was circling the role of Black Cat in the planned 2011 sequel. That was at least partly confirmed a month later by Malkovich himself during an interview with an Italian sports program. However, on the same day the actor's comments began to circulate on English-language, Sony announced it had abandoned plans for Spider-Man 4, and would instead reboot the franchise with what would become 2012's The Amazing Spider-Man.
In the 2013 interview, Raimi characterized the split with Sony as the "most amicable and undramatic of breakups." "It was simply that we had a deadline and I couldn’t get the story to work on a level that I wanted it to work," he recalled, adding, "I said to Sony, 'I don’t want to make a movie that is less than great, so I think we shouldn’t make this picture. Go ahead with your reboot, which you’ve been planning anyway.'” And, yes, Hathaway was lined up to play Black Cat.
Storyboards released by artist Jeffrey Henderson provide some idea of what the Vulture might have looked like in Spider-Man 4 (a lot like his original Marvel Comics depictions), and reveal that Mysterio was to play a role in the film. "It would’ve been one absolutely kick ass movie," Henderson wrote on his website. "Seriously. We were working on some crazy- cool stuff, because everyone, from top to bottom, felt that Spidey 3 was a bit of a ‘missed opportunity,' and we all really wanted to help Sam take SM4 to another level so he could end the series on a high note."
Sinister Six (originally targeted for 2016)
More than three years before Sony revealed its current plans for a cinematic universe beginning with Venom and Silver & Black (starring Silver Sable and Black Cat), the studio announced a "franchise brain trust" that would develop The Amazing Spider-Man 3 and spinoffs starring Venom and the villainous Sinister Six.
The latter, targeted for release in November 2016, was teased in 2014's The Amazing Spider-Man 2, which teased the mechanical tentacles and wings of Doctor Octopus and the Vulture in trailers, and signaled their arrival, along with the Green Goblin, the Rhino, Kraven the Hunter and either Chameleon or Mysterio in the film's end credits. (Doc Ock, the Vulture, Kraven, Sandman, Mysterio and Electro, who was introduced in The Amazing Spider-Man 2, formed the original Sinister Six, as shown in 1964's The Amazing Spider-Man Annual #1.)
However, that was before Sony and Marvel Studios announced a deal in February 2015 to co-produce another Spider-Man franchise reboot, leading to the introduction of Tom Holland as Peter Parker in 2016's Captain America: Civil War and the release this week of Spider-Man: Homecoming. While that deal resulted in the Vulture finally arriving on the big screen, with Michael Keaton in the role of Adrian Toomes, it leaves Sony's plans for Sinister Six a looming question.
Writer/director Drew Goddard, who has likened the film's script to The Dirty Dozen, held out hope in 2015 that Sinister Six could still see the light of day. “I intentionally wanted a movie that didn’t have to worry about mythology and continuity,” he explained. “It was important to me to make a movie that could stand on its own. So the good news is, it slots in very well to any plan anybody ever wants. We just need to let a couple years go by, I think.”
The Vulture gets his moment in the cinematic spotlight with the debut this weekend of director Jon Watts' Spider-Man: Homecoming, which stars Toom Holland, Michael Keaton, Zendaya, Donald Glover, Jacob Batalon, Laura Harrier, Tony Revolori, Tyne Daly, Bokeem Woodbine, Marisa Tomei and Robert Downey Jr.