In an unexpected twist to making movies about villains, Sony announced that they cast Dakota Johnson as Madame Web. She is usually a secondary character to Spider-Man, so this is a very intriguing choice to continue growing the SSU (Sony’s Spider-Man Universe). Though it hasn't been confirmed, she will likely be playing the Cassandra Webb iteration.
There is very little information available at this time beyond Johnson’s casting, so theories and questions abound over how Madame Web will connect with Venom, Morbius, and/or Kraven the Hunter. As such the possibilities are ripe for various characters to appear – whether as the primary antagonist, secondary figures, or cameos.
Spider-Woman (Jessica Drew)
Jessica Drew’s Spider-Woman is one of the most iconic members of the Spider-Army, yet she hasn’t appeared in a movie. Although, Issa Rae is set to voice the character in Spider-Man: Across the Spider-Verse, Part One, she could also appear in live-action, perhaps in Madame Web.
Jessica has unique abilities and a complex backstory – being a brainwashed Hydra spy – that sets her apart from Spider-Man and the other Spider-Women. Furthermore, it is hypothesized that Olivia Wilde is actually developing a Spider-Woman film as part of the SSU, so perhaps Jessica Drew could cameo in Madame Web or vice versa.
Kraven The Hunter
Aaron Taylor-Johnson will star as Sergei Kravinoff, the titular character in Kraven the Hunter, coming out in January 2023. Kraven and Madame Webb (Cassandra Webb) have an intricate history with his daughter, Ana, actually killing Cassandra. This sort of relationship could be explored between these two films and the future of the SSU.
In fact, due to the timing of Dakota Johnson’s casting announcement – and it being the only news coming out of Sony about projects beyond Kraven the Hunter – it could be surmised that she might make an appearance in it, perhaps as a post-credits stinger. Therefore, Kraven would also be the villain most likely to return in Madame Web.
Spider-Woman (Julia Carpenter)
A character and specifically the Spider-Woman with the strongest connection to Madame Web is Julia Carpenter, who literally took over for Cassandra Webb. Upon her death, Webb passed on her powers of precognition to Carpenter, though at the loss of her physical sight.
Interestingly, Cassandra is an elderly character and Johnson is not – though there could be a storyline to address this – so there is a possibility that she could actually be playing Julia Carpenter instead of Cassandra Webb. Nevertheless, it would be very surprising to not see Julia in some way in Madame Web, maybe even in a Spider-Woman role.
Gregory Herd
One of the most important storylines related to Cassandra Webb is the Gathering of Five. The lynchpin to this group is Norman Osbourn aka the Green Goblin as he seeks more and more power through particularly arcane methods. However, following Spider-Man: No Way Home, it is unlikely that this character would be utilized for future films, therefore opening up the opportunity for another gathering member, Gregory Herd.
Gregory Herd is sometimes called Override or Shadrac and could take on the role of villain in Madame Web. Interestingly, Cassandra Web is also a gathering member and during the ritual, she is restored to youth – so there is an established connection between these characters.
Spider-Woman (Mattie Franklin)
Another member of the Gathering of Five, Mattie Franklin is a possible option to appear in some way in Madame Web. She eventually becomes the fourth Spider-Woman after the gather since she actually gains the powers that Norman Osbourne wanted. She and Madame Web do work together at times with Web serving as the “person in the chair.”
If the Gathering of Five storyline were to be adapted or utilized in any way, Mattie Franklin could very well feature. However, of all the Spider-Women, she is the least likely to appear simply based on popularity or relevancy. Depending on how this film sets up future projects, though, Mattie Franklin could still play an important role.
Chameleon
Another classic Spider-Man villain is coming to the silver screen in Kraven the Hunter with The White Lotus actor, Fred Hechinger cast as Dimitri Smerdyakov aka Chameleon. Of course, the two characters are related in the Marvel comics – literally, they are half-brothers. While this relationship will likely be addressed and explored in Kraven the Hunter, Chameleon could also be set up to be a bigger feature in future films.
Perhaps, Chameleon could even be the big bad to Madame Web. His abilities to impersonate nearly anyone would make a very intriguing hurdle to overcome for Madame Web, and any other heroes she might be joined by.
Silk
Cindy Moon aka Silk has already appeared in live-action, actually as part of the MCU in Spider-Man: Homecoming played by Tifanny Espensen – nevertheless, she could still make an appearance in Madame Web. She has become a popular Asian-American superhero in Marvel comics since her creation in 2014.
In fact, Sony is supposedly developing a tv show for Amazon Prime Video in which Silk would appear as the titular protagonist. Therefore, it would not be surprising for them to tease her or even introduce her in some way in Madame Web. In particular, she is unique as part of the Spider-Army because some of her abilities and awareness rival and even surpass Peter Parker’s Spider-Man.
Jackpot
Sony has many different projects in the works beyond Madame Web including one around Sara Ehret aka Jackpot. She is a relatively unknown character to the masses, only being introduced in 2007, yet they see potential in the leading role of her own film. Arrow and Legends of Tomorrow writer Marc Guggenheim was hired to pen the script – though no other information has been made available.
It would be important to introduce this character to audiences for any potential project. As such, Sara Ehret – whether she has acquired her abilities and taken up the helm as Jackpot or not – could play a role in Madame Web.
Jackal
One of few members of Spider-Man’s iconic rogues gallery that has yet to appear in a film, live-action or not, is Miles Warren aka the Jackal. He has played an important role in Spider-Man’s history by cloning Peter Parker and creating Ben Reilly and Kaine Parker, the Scarlet Spiders.
Jackal is undoubtedly a genius and talented, but he is driven mad so he could make an intriguing villain or adversary for Madame Web in her film. Perhaps, the cloning story could be applied in some way to Madame Web – it would give Dakota Johnson plenty of opportunities to play different characters.
Ezekiel Sims
Ezekiel Sims, simply called Ezekiel, was a supporting character to Spider-Man during a limited period in the early 2000s. He does have powers similar to Spider-Man and even tried to be a hero himself in his youth, but now in his 50’s, he is a different person. Ezekiel has a strange connection to the more mystical and ritualistic sides to things that could play a role in the SSU’s future.
He could bring an interesting element to Madame Web, though because his role in the comics is minimal it would likely be the same in the movie. Nevertheless, it is more possible that he could appear in the upcoming Silk-centered series as their history is entwined and complex.