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Will ‘Spider-Man: No Way Home’ (Re)introduce the Sinister Six?

With the Sinister Six possibly set to make their movie debut, let’s recap how the supervillain crew came to be

Marvel/Sony/Ringer illustration

The most anticipated Marvel release since Avengers: Endgame arrives on Friday, as Spider-Man: No Way Home makes its way to theaters around the world. The film’s first teaser broke the record for the most-viewed movie trailer in 24 hours when it was released in early September, shattering the previous mark, held by Endgame, with a staggering 355.5 million views across all online platforms in its first day. In many ways, No Way Home serves as the webhead’s own Endgame crossover, combining characters from almost 20 years of live-action Spider-Man movies as they come together for the conclusion of Tom Holland’s (first?) trilogy in the role of Marvel’s most popular superhero.

While Sony and Marvel Studios have remained silent about whether or not Holland will be joined by the other Spider-Men of the past, the marketing push behind No Way Home has revolved around the movie’s lineup of villains—and there are a lot of them. From Willem Dafoe’s Green Goblin to Jamie Foxx’s Electro, many of Spider-Man’s greatest foes dating back to Tobey Maguire’s Spider-Man trilogy in the 2000s are returning to the big screen in this massive multiversal spectacle. With five of them already revealed by No Way Home’s two trailers, it appears as if the infamous group of Spider-Man villains known as the Sinister Six could be arriving at last. The hype fueled by that potential team-up and a groundswell of Spidey nostalgia has put the movie in position to bolster the box office with a COVID-era-record opening weekend haul. So ahead of the film’s release, let’s examine the Sinister Six’s origins in the comics, recap Sony and Marvel’s past attempts at bringing them to life, and take a look at the five confirmed villains who are being resurrected for the grand finale of Peter Parker’s three-part coming-of-age story in the MCU.

Introducing: The Sinister Six

The Sinister Six wasn’t the first team of supervillains to assemble in comic books when it first appeared in 1964, but it’s become one of the most popular in the many years since, even as its roster has been refreshed or expanded time and time again. A group composed of Spider-Man’s enemies was conceived by Stan Lee and Steve Ditko when they were putting together the first edition of The Amazing Spider-Man Annual, a special 72-page issue that carried the promise of being “Spidey’s biggest, longest, greatest battle” to date.

The original Sinister Six was formed by Doctor Octopus and featured Electro, Mysterio, Sandman, Vulture, and Kraven the Hunter alongside him. While each had failed to defeat Spider-Man individually in previous stories, Doc Ock believed that with all of their sinister forces combined, they could finally beat him. (Of course, their first plan ends up being to fight him individually, one after the other, instead of all at once, so they end up just losing again anyway. Call it a trial run.) In most instances, the Sinister Six’s schemes fail because the bad guys just can’t seem to get along, as each of them wants the glory of beating their mutual enemy to themselves. However, the second time they joined forces, in 1990’s “Return of the Sinister Six” story line, the six set their differences aside and fought Spidey simultaneously. Naturally, he thwarted them anyway, but the teamwork was a breakthrough in supervillainhood.

The Sinister Six forms for the first time in The Amazing Spider-Man Annual no. 1
Marvel Comics
Spider-Man faces the Sinister Six together in The Amazing Spider-Man no. 338

In the years following the Sinister Six’s debut, the team has cycled in new villains as former members either died or departed. Classic Spidey villains like Venom, Lizard, and Scorpion have all joined the group at some point; with over half a century’s worth of comics since Amazing Spider-Man Annual no. 1 was published, pretty much every one of Spider-Man’s nemeses has been a part of the team at one point or another. One iteration of the group even doubled itself in size, when Norman Osborn rebranded them as the Sinister Twelve. (I’ve gotta say, the group name just doesn’t feel right without the alliteration. Good thing there has also been a Sinister Seven and a Sinister Sixty.)

To date, there have been well over a dozen variations of the Sinister Six in the comics, including the most recent version, which arrived in a 2021 story line called “Sinister War.” With Doc Ock leading the group in the majority of its efforts against Spider-Man over the years, the Sinister Six have nearly succeeded thanks to some of the mad scientist’s wildest plans, such as when he managed to convince the entire world that he could solve global warming just so he could almost burn it to a crisp instead in 2012’s popular “Ends of the Earth” story arc. Even though Spider-Man always saves the day, the Sinister Six just keep coming back, with many more incarnations of the team appearing in animated shows, video games, and other forms of Spidey-centric media.

The Sinister Six in the Movies and Beyond

The desire to square Spider-Man off against a group of his greatest enemies has extended from the comics to the big screen and beyond. In 2007, Spider-Man 3 shifted away from the previous films’ narrative strategy of focusing on a lone villain—which had led to a pair of iconic performances in Dafoe’s Green Goblin and Alfred Molina’s Doc Ock—and increased its number of bad guys to three. (Well, four if we’re including the jazzed-up Bully Maguire.) But by the end of the movie, Spider-Man 3 really had only two villains, Sandman (Thomas Haden Church) and Venom (Topher Grace), as James Franco’s Harry Osborn dropped his beef with his oldest friend to fight alongside him in the climactic final battle.

Seven years later, 2014’s The Amazing Spider-Man 2 followed suit, with three villains for Andrew Garfield’s Spider-Man to face: the extremely blue Electro (Foxx), Rhino (Paul Giamatti, playing an unhinged Russian mobster), and yet another Green Goblin (Dane DeHaan). The film was met with mixed reviews from critics, like Spider-Man 3 before it, but The Amazing Spider-Man 2 didn’t achieve the same degree of financial success that the final movie in Sam Raimi’s trilogy did. Sony had originally made plans for further sequels and spinoffs in Garfield’s Spider-Man series, including the studio’s first real attempt at a movie centered on the Sinister Six, but none of them ever made it through the production process.

The prospective Sinister Six film was slated for a fall 2016 release, with filmmaker Drew Goddard (The Cabin in the Woods, Bad Times at the El Royale) attached to write and direct. But by May 2016, the MCU had already reintroduced Spider-Man in Captain America: Civil War, and Garfield’s web-slinging days were over. “I don’t know how close it got, but I definitely had a few meetings, and it was really exciting,” Garfield told Collider earlier this year while talking about the canceled Spidey spinoff. “I’ve got to say, because I love Drew so much, and I love Cabin in the Woods, and the other stuff that he’s made. … Maybe one day he’ll get to do it, but it would’ve been cool.”

The first time that an iteration of the Sinister Six appeared on the big screen in earnest arrived with the Oscar-winning Spider-Man: Into the Spider-Verse in 2018, with many of the villains’ character designs drawing inspiration from the Ultimate Marvel comics universe in which Miles Morales’s Spider-Man was introduced. This was, by far, the best attempt by any Spider-Man movie to incorporate multiple villains into a story, perhaps in part due to the narrative choice to focus on only two of them—Kingpin, an already well-established and popular Marvel villain, and Miles’s uncle, who’s revealed to be the villain known as the Prowler.

Beyond the movies and the comics, the Sinister Six have appeared all over the vast Spider-Man multimedia-verse. From the critically acclaimed Marvel’s Spider-Man game from Insomniac Games to the chaotic Broadway musical Spider-Man: Turn off the Dark, the Sinister Six are a constant source of material for stories about the beloved superhero. (I can’t say that I ever saw the canceled Broadway show, which was notorious for its injury-inducing stunts and its bloated production costs, but I am fascinated by the original Sinister Six villain they introduced and named after a popular brand of hot chocolate.) No Way Home may be the first successful attempt at bringing the supervillain team into a live-action movie, but it certainly won’t be the last.

No Way Home’s Sinister … Five?

While No Way Home’s first teaser highlighted the returns of Dafoe’s Green Goblin and Molina’s Doc Ock, the second trailer confirmed that at least three more Spider-Man villains were set to appear with their original actors reprising their roles—Spider-Man 3’s Sandman, along with Electro and Lizard (Rhys Ifans) from Garfield’s Amazing Spider-Man series. Together, they all share the common threads of knowing Spider-Man’s secret identity and, with the exceptions of Sandman and Lizard, the fate of dying while fighting against him.

Green Goblin, Doc Ock, and Sandman are all returning more than a decade after the conclusion of Maguire’s Spider-Man trilogy, in which they were all introduced. In 2002’s Spider-Man we met Norman Osborn, whose evil alter ego Green Goblin is a fan favorite among Spidey villains and still stands as Spider-Man’s greatest onscreen nemesis despite being the first one to ever appear almost 20 years ago. That’s in large part due to Dafoe’s incredible performance as the Oscorp scientist and CEO, whose dangerous experiments provide him with enhanced strength, as well as a murderous alternate personality that feeds off his darkest desires. At the end of Spider-Man, Osborn dies when he impales himself on his own glider while trying to kill Spider-Man—an incident that eats away at his son Harry until he follows in his father’s footsteps as the next Green Goblin.

Next to be introduced (in Spider-Man 2) was Molina’s Dr. Otto Octavius, another gifted scientist whose ambitious experiments transform him into a monster. Attempting to create a source of energy that could provide the power of the sun in the palm of his hand, Octavius becomes bonded to the four artificially intelligent mechanical tentacles he uses as handling equipment for the device after he’s unable to contain it during a demonstration. In his final moments in the film, though, Doc Ock (sort of) finds redemption, as he drowns himself in the Hudson River along with the second failed version of his energy source when it threatens to destroy New York City.

Finally, Spider-Man 3 retroactively introduced Uncle Ben’s true killer, a man named Flint Marko. Marko is a small-time criminal who steals money to support the treatments of his sick daughter, at least until he stumbles into a particle physics test facility that fuses his molecules with a pit of sand. (This is, by far, the most absurd Spider-Man origin story, which says a lot when the competition includes radioactive spider bites and freakin’ Topher Grace getting jumped by some black, alien goop after praying to God for the death of Peter Parker.) After fighting with Spider-Man a few times, Sandman escapes at the end of the movie when Peter empathizes with him for trying to help his daughter and forgives him for killing Uncle Ben.

Along with the trio of villains from Maguire’s trilogy, No Way Home is bringing back a pair of bad guys from Garfield’s less successful Spidey series. Like Osborn and Octavius before him, Dr. Curt Connors is a brilliant scientist whose overambitious experiments go awry. In The Amazing Spider-Man, Connors worked alongside Peter’s father in the field of cross-species genetics, always striving toward a breakthrough that could regenerate his missing arm. Of course, his attempt to splice his DNA with a lizard transforms him into a violent hybrid of man and … lizard. (In retrospect, this seems pretty predictable.) By the end of the movie, he’s trying to turn everyone else in the city into a lizard like him, which would have finally validated some persistent conspiracy theories.

Lastly, in The Amazing Spider-Man 2, Foxx’s Max Dillon is an awkward, unsuspecting electrical engineer working at Oscorp until an accident electrocutes him and sends him falling into a vat of genetically engineered electric eels, turning him into electricity incarnate. (OK, I retract my previous statement about Sandman—this is probably the most absurd Spider-Man origin story.) Electro later teams up with this series’ version of Harry Osborn and Green Goblin as they attempt to take down Spider-Man and Oscorp, but he dies when Peter and Gwen Stacy manage to overload him with more electricity than his body can handle. Foxx’s character was disliked by critics and fans alike, but he’s receiving a major glow-up in No Way Home that effectively provides a fresh start for the formerly blue-tinted villain.

In the past, the most flawed live-action Spider-Man films have been the ones that overstuff their stories with too many villains to develop within the time constraints of a single movie. Yet No Way Home is looking to succeed where its predecessors have failed by weaving in the backstories of five characters from five previous Spidey films in Sony and Marvel’s first attempt at bringing the Sinister Six to life outside of the animated Into the Spider-Verse. The sixth and final mystery villain is still up in the air ahead of the film’s release on Friday, but after months of chaotic ramp-up to No Way Home that featured constant casting rumors and a series of unfortunate Sony leaks, the wait to see whether someone will win the Sinister Sixth Man (or Woman) Award is about to be over.