Competing with Marvel and DC’s respective catalogs of hundreds of franchise-ready characters, Sony has the rights to dozens of comic book properties all revolving around the same superhero. Fortunately for them, that superhero happens to be arguably the most popular in the world: Spider-Man. And the studio knows this, and that’s why it keeps playing that card.

In the space of just over a decade and a half (2002-2018), Sony gave audiences six different Spider-Men on the big screen, and it’s building its own Spider-Man-centered cinematic universe. But as is with every major franchise, not every decision made behind the scenes went the way some hoped it would go – specifically, the casting choices. Here are 10 actors who were almost cast in Spider-Man movies.

10 Hugh Jackman As Wolverine In Spider-Man (2002)

When Sam Raimi’s first Spider-Man movie was in development, Hugh Jackman was contacted about making a cameo appearance as Wolverine. He wanted to do it, and even flew out to New York to shoot his scene.

X-Men was made by Fox and Spider-Man was being made by Sony, but this was back before studios held their comic book properties to ransom, so there wasn’t much of a legal issue. The reason the cameo fell through is that the Spider-Man producers couldn’t get a hold of Jackman’s Wolverine costume.

9 Scarlett Johansson As Gwen Stacy In Spider-Man 3

Before Bryce Dallas Howard was cast to play Gwen Stacy in Spider-Man 3, the producers considered Scarlett Johansson and Elisha Cuthbert for the role. Johansson would go on to play Black Widow alongside a different Spidey in the MCU.

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Howard, a redhead, was cast to play a blonde character. Ironically, when Kirsten Dunst was cast as Mary Jane, she was a blonde cast as a redhead.

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8 Christoph Waltz As Curt Connors In The Amazing Spider-Man

After Sam Raimi’s Spider-Man trilogy established a relationship between Dr. Curt Connors and Peter Parker, building toward the introduction of the Lizard in the ultimately cancelled Spider-Man 4, Sony carried through that plot thread when they rebooted the franchise with The Amazing Spider-Man.

Although they ended up casting Rhys Ifans in the role, both Christoph Waltz and Michael Fassbender were considered during the reboot’s pre-production process.

7 Kate Hudson As Mary Jane Watson In The Raimi Trilogy

Prior to Kirsten Dunst’s casting in the role of Mary Jane Watson in the Spider-Man trilogy, the producers approached Kate Hudson and offered her the part. However, she turned it down as she’d already committed to starring in The Four Feathers.

Elizabeth Banks also auditioned for the role of Mary Jane, and ended up being cast as J. Jonah Jameson’s assistant Betty Brant.

6 Michael B. Jordan As Harry Osborn In The Amazing Spider-Man 2

In one of The Amazing Spider-Man 2’s many rehashed storylines, Harry Osborn becomes the Hobgoblin. The character ended up being played by Dane DeHaan, but Michael B. Jordan initially auditioned for the role. Strangely enough, Andrew Garfield had initially recommended Jordan to play a male version of Mary Jane.

Jordan went on to star in two Marvel blockbusters, one great (Black Panther, in which he played the humanized villain Killmonger) and one dreadful (the 2015 Fantastic Four reboot, in which he played Johnny Storm).

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5 Robert De Niro As Doctor Octopus In Spider-Man 2

Alfred Molina ended up being the perfect choice to play Dr. Otto Octavius in Spider-Man 2, bringing a real humanity to what could’ve been a ridiculous villain.

Before Molina was cast, though, the producers considered Robert De Niro, Ed Harris, Sam Neill, and Chris Cooper – the latter of whom would end up playing Norman Osborn in The Amazing Spider-Man 2 – for the sequel’s main villain.

4 Christopher Lloyd As J. Jonah Jameson In The Raimi Trilogy

J.K. Simmons ended up being such a perfect choice for the role of Daily Bugle editor J. Jonah Jameson that the producers of the MCU didn’t even both recasting the role and just recruited Simmons again for Spider-Man: Far From Home’s mid-credits stinger.

Before Simmons was cast in the Raimi trilogy, the producers considered Back to the Future’s Christopher Lloyd and Full Metal Jacket’s R. Lee Ermey for the role.

3 Emma Roberts As Gwen Stacy In The Amazing Spider-Man Movies

One of the ways that The Amazing Spider-Man movies set themselves apart from Sam Raimi’s movies was making Gwen Stacy the primary love interest as opposed to Mary Jane Watson.

When casting was underway for the reboot, the producers considered Emma Roberts, Teresa Palmer, Mia Wasikowska, Mary Elizabeth Winstead, and Lily Collins.

2 Billy Crudup As Norman Osborn In The Raimi Trilogy

Billy Crudup was cast to play Norman Osborn in Sam Raimi’s initial Spider-Man movie, but he dropped out after the filming schedule clashed with that of Almost Famous and he also came to think that he was too young to convincingly play James Franco’s father (he’s only ten years older than him).

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Before Willem Dafoe was cast, the producers offered the role to John Travolta, Mel Gibson, Robert De Niro, Nicolas Cage (who later voiced Spider-Man Noir in Spider-Man: Into the Spider-Verse), and John Malkovich (who would later be cast to play the Vulture in Raimi’s Spider-Man 4, which was ultimately canned).

1 Tobey Maguire As Peter B. Parker In Spider-Man: Into The Spider-Verse

Although the older interdimensional Peter Parker ended up being played by Jake Johnson in Spider-Man: Into the Spider-Verse, the producers considered casting Tobey Maguire to reprise his role from the Raimi trilogy.

However, they changed their minds because they didn’t want Maguire’s presence to overshadow the movie being Miles Morales’ journey. It’s unclear if the producers would’ve also tried to get Kirsten Dunst to play Mary Jane if they went with Maguire, but that would seem like a no-brainer.

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