According to some newly uncovered information, it looks like Sony was once looking to hire Angelina Jolie for Sam Raimi’s Spider-Man 4—the ill-fated sequel that never happened.
As most fans know, Jolie recently joined the MCU with the Phase 4 film Eternals, where she brought to life Thena. The actress even got lucky and wasn’t kidnapped by a Celestial at the end of the movie like half her friends, setting her up for some more Marvel stories down the line.
While she hasn’t been officially confirmed to return in a future project, fans know it’s a matter of when, not if.
What if Sony Pictures had grabbed the actress first and thrown her into the world of Tobey Maguire’s Spidey over a decade ago? Such a move could have caused a far different career trajectory in Jolie’s life, even outside of the comic book movie genre.
But in that hypothetical timeline, who would Jolie have played?
Angelina Jolie Could've Played Villain In Spider-Man 4
The Direct received early access to Sean O’Connell's new Spider-Man-centric book, With Great Power. Within it, O'Connell uncovered some fascinating new information for what a fourth Sam Raimi Spider-Man movie could have looked like—which included having Vulture be the big bad and Angelina Jolie potentially being brought on board as well.
Vulture's death wouldn't have ended the movie, however. The Spider-Man 4 filmmakers were planning for Adrian Toomes' daughter to take over his mantle after that, becoming the fearsome Vultress—an original character who isn't in the comics. As for who the studio had in mind during the canceled sequel's 2009 development, it was none other than Angelina Jolie, as her name was reportedly "attached to this pivotal role for a short amount of time" during Spider-Man 4's development.
Jolie's character wouldn't have just been putting on a supervillain suit. In a proposed B-plot for the movie, she would have also been "an accomplished executive representing a venture capital firm that was trying to buy the Daily Bugle."
As for Adrian Toomes himself, Sam Raimi was aiming to modernize him from how he usually is portrayed in the comics. Some of this was reflected in the villain's costume, such as how the feathers on his wings were "designed to flip out like razor-sharp blades."
The director also wanted a scene for the character that lived up to the horror of Doc Ock's big hospital scene. Here, it would have been in the form of a fight scene in a library, where goons were sent to take down the Vulture—needless to say, it didn't go well.
Storyboard artist Jeffrey Henderson noted that the villain would have gotten his trademark name "because when he was done, he didn't leave anything but bones behind:"
“He was essentially a guy that did as a lot of ugly stuff for the government, did a lot of ugly stuff as a private contractor… I thought a clever thing to do would be to say that part of the reason they called him The Vulture was because when he was done, he didn’t leave anything but bones behind.”
So who might have played the antagonist? The studio seemed to want John Malkovich to be its Vulture—add that to all of the above details, and fans would have had a much different take on him compared to Michael Keaton's portrayal in Spider-Man: Homecoming.
One of the big scenes for Vulture would have taken place on top of the t-shaped Citicorp Center on Lexington Avenue in Midtown Manhattan.
Henderson explained how "Vulture [would have] almost kill[ed] Spider-Man," but a last-ditch move by Peter would have sent the big bad to his death:
“They were going to have a big brawl-for-it-all, where Vulture almost kills Spider-Man. And then Spider-Man at the last minute—he’s really wounded, he’s bleeding really badly, he’s in real trouble—Peter finally, almost as a reaction, forces The Vulture off. When he does, it snaps some of the stuff from the wings, so he ends up just tumbling into the ether, off the top of the Citicorp building. That’s what does him in.”
Before his demise, an action scene would have been set in the New York City subway tunnels. That underground battle would eventually emerge from the tunnels and shoot up into the skies.
Another character who could have appeared in Tobey Maguire's fourth outing was Felicia Hardy, aka Black Cat. Had everything gone according to plan, Anne Hathaway could have been the actress to bring the infamous thief to life.
The movie would have also had fun in the opening of the story by showing a montage of Maguire's Spider-Man at the top of his game, taking down villains such as "The Shocker" and "The Stilt-Man:"
“We were going to open the movie with this montage of all the villains we knew that Sam would never be able to use in Spider-Man movies… because Peter, now that MJ [Mary Jane] has gone, he has finally made peace, and he loves being Spider-Man. He’s actually enjoying it. So we were going to try to do The Shocker, Mysterio, The Stilt Man, and that kind of stuff.”
While the movie never came to be, if a fourth Spider-Man film had happened, Henderson revealed that the director wanted to return to the tone and texture of the 1960s and early 1970s comics.
He then revealed that Raimi "wanted to do [Spider-Man 4] his own way... [without] compromise:"
“If [Sam Raimi] was going to do a ‘last’ Spider-Man movie, he wanted to go out on a high note. He wanted to do it his way. No compromise. No last minute [orders to] ‘change this, change that,’... that was the studio’s pitch to bring him back, and unfortunately, I just don’t think it worked out that way.”
The Direct was provided with a review copy of With Great Power for coverage. The book, which covers everything a fan should know about Spider-Man on the big screen, is now available to purchase online.
What Jolie's Alternate Marvel Timeline Looks Like
In some alternate timeline, Angelina Jolie’s Vultress could have been amongst the returning villains in Spider-Man: No Way Home. But what would the domino effect have been if she did have that role?
If the movie itself was good, it might have led to Maguire’s Spider-Man returning for even more films. This could have staved off its Amazing reboot, severely lowering the chances of Garfield getting a chance under the suit.
Worst case scenario? A Spider-Man 4 success could have led to Tom Holland’s webhead never being created; maybe it's best things worked out as they did.
As for when Jolie's MCU character will next be seen, that remains a big question mark. It seems a sequel to her 2021 film will happen at some point, but in the meantime, everyone is left waiting for the announcement to drop.
At the latest, Jolie will almost certainly play some sort of role in Avengers: The Kang Dynasty—that group, in general, is too big to simply ignore due to subpar reception.