We all have our favorite Spider-Man villain, but what about our favorite stories involving villains associated with another superhero or team? Why should Captain American or the X-Men get all the fun fighting the likes of the Red Skull or Magneto? This list celebrates the very best stories involving Spider-Man taking on a villain best associated with another hero. 

At #6 is Amazing Spider-Man #237 with a plot by Roger Stern, script by Bill Mantlo and art by Bob Hall:

Through the first four spots on this list thus far, I’ve talk about Spider-Man going toe-to-toe with some of Marvel’s biggest evil-doing heavyweights like Doctor Doom, Red Skull and Juggernaut. So naturally this story, against one of the Marvel Universe’s biggest losers, ends up perhaps being the most emotionally poignant of the list. 

“High and Mighty!” is yet another entry that superstar writer Roger Stern can take credit for, though he does get a scripting assist from Bill Mantlo (with Bob Hall filling in for John Romita Jr. on pencils). In retrospect, one might look at the creative team shuffling on Amazing Spider-Man #237 and assume that it’s just a throwaway fill-in issue that arrived in one of the most storied runs in ASM history. And those people would be wrong.

As evidenced in the cult favorite series of a few years back, Superior Foes of Spider-Man, good, high-quality stories could still be told using the back catalogue of Marvel’s extensive and illustrious list of rogues. The trick, as it is in almost any kind of writing, is to make the audience care about your characters even if it’s someone as unsuccessful as Wilbur Day, aka the Stilt-Man, a villain first introduced in the pages of Daredevil who quickly evolved into a punchline.

Day is a meek scientist who creates a suit with hydraulic legs/stilts for himself a means to commit crimes. He has never been successful, though there was this one time where he had one of Marvel’s flagship heroes on the ropes before Daredevil arrived to save the day. That hero, naturally, was Spider-Man.

A big reason why ASM #237 works so well with its narrative is that Stern and Mantlo call back to this early Silver Age tale (Daredevil #27) where Stilt-Man is actually successful in “defeating” Spider-Man. Stern/Mantlo don’t actually ask their audience to read this issue, but they use the older plot to build new motivation for Wilbur. And because of this through line, it’s very easy for the reader to then care for Wilbur’s plight and plans. 

ASM #237 opens with a Wilbur Day who has been beaten down by the weight of his own failures. He has a new and improved suit that he cobbled together with some technology, but he contemplates what the point of it all is, since he’s such a loser. However, he suddenly (and conveniently) remembers his one major success — that time he beat Spider-Man. And that’s when he concocts a plot to beat Spider-Man again, because, sure, lighting can strike twice, right? 

The comic proceeds to give us a lot of backstory on Day — maybe too much given the flow of the issue’s nrration. But it’s forgivable because it all feeds into making the reader sympathize with the villain, which in turn gets paid off with another excellent Stern twist-ending. 

Peter’s initial confrontation with Wilbur comes on the New York City subway where both characters are in plain clothes. Peter’s Spider Sense is going off as he moves closer to Day, but he disregards the warning after seeing such a mousy-looking individual in front of him. 

Beyond being funny, the scene also lays the groundwork for Spider-Man’s possible failure in a rematch against Stilt-Man. Spidey certainly has his moments of ego, but he rarely underestimates an opponent and the fact that he’s so nonchalant about this man he sees on the subway sells the idea that with Spider-Man’s guard down, anything is possible.

When Spider-Man and Stilt-Man inevitably confront each other in costume, Spidey looks to have a handle on things. He even manages to counter a spray of the villain’s knockout gas, the same gas that floored Spider-Man when the two met in Daredevil #27 (Spider-Man comments that he’s not about to fall for the same stunt twice). It looks like Stilt-Man’s dreams of redemption and grandeur are over when Spider-Man does the most Spider-Man thing ever: he pushes Wilbur out of the way of a laser blast and takes the brunt of the hit himself. 

As Spider-Man lies unconscious on the ground, Wilbur Day is presented with his own Uncle Ben moment. He could squash Spider-Man like a … ahem … bug, or he could do the noble thing and rescue him from certain death inside the laboratory where the two were fighting. It’s a wonderful moral dilemma for a character that until this issue, truly lacked the depth in personality to pull off such a decision. Does Stilt-Man establish himself as one of Marvel’s chief rogues or does he accept that in killing Spidey he’s living a lie in thinking of himself as being victorious, and thus makes a more noble choice instead.

Considering Peter hadn’t been “killed” by an enemy until years later (first Morlun, then Doc Ock), of course we all can guess what Stilt-Man decided. And it would have been really something for Marvel to kill off one of its flagship heroes at the hands of a guy that most people thought was a total joke. But that’s why Stern and Mantlo are such great storytellers here. They took a total loser like Stilt-Man and put him a story with stakes. You were going to feel for both he and Spider-Man regardless of what his final decision was going to be.

As Stilt-Man deposits Spidey on the sidewalk in front of a couple of cops, he tells him that they’re now both even. When the cops inquire what he meant by that, Spidey realizes that by saving Wilbur’s life, Wilbury was essentially obligated to save his. That certainly sounds like a logical conclusion, but that’s only because Spider-Man, someone of great character and nobility, says it. In reality, Stilt-Man, a villain, has no moral obligation to repay someone who saved his life. But Wilbur Day, the man, did.