Every time I reach the end of Roger Stern and John Romita’s Spider-Man/Black Cat storyline in Amazing Spider-Man #226-227, I find myself feeling a bit melancholy. These comics are certainly not bawl your eyes out sad like ASM #121 or ASM #400, but Stern’s script so effectively taps into the pathos of the doomed Spider-Man and Black Cat relationship, that the storyline lands like a punch to the gut all the same. In short, this is one of the most depressing Spider-Man stories I have ever read – and I mean that with the highest amount of praise.

Over the span of just two issues, Stern and Romita Jr. take the reader on a very emotionally complex journey that hits both the highs and lows of what it means to be Spider-Man. I cannot say enough, just how wonderfully constructed Stern’s script is – its build from Felicia’s oft-putting escape from a mental hospital (complete with her tying up and verbally abusing a heavy set nurse), to the potential happy ending that is teased at the end of ASM #226, to the final image of Cat falling into the water below, presumably killing her (but obviously not).

Stern packs so much character work and standard superhero action in the arc, while maintaining a steady pace that never spins out of control. These comics represent a “journey” in every sense of the word. In retrospect, I’m a bit shocked that the storyline doesn’t get tossed around more often as one of the all time “best” Spider-Man arcs. Perhaps it gets lost in the shuffle of all of the other amazing Stern/JRJR stories from there epic run together in the early 1980s.

Rather than spooning layer after layer of superlatives on top of this storyline, I should probably give you a bit more detail as to what is so terrific about it. For one, using the foundation that is laid by Marv Wolfman and Keith Pollard in Black Cat’s earliest stories, Stern and JRJR take dramatic strides with the character to the point that I care about her and her potential romance with Spider-Man.

In her first appearance, Felicia is flirty and mysterious, but still comes across as a fairly one-dimensional criminal who just happens to hold the power of “sex” over the likes of moralist like Spider-Man. We never got a sense as to why Spider-Man would suddenly fall for someone like the Black Cat outside of the fact that she looks good in her costume, nor were readers given any reason to root for the two of them to get together.

In ASM #226, Stern gives us the characterization that was missing during the Wolfman run. The reader sees that Felicia’s life of crime has treated her well financially – and in great contrast to Peter’s subpar living conditions that he can barely afford despite the fact that he’s one of the New York City’s greatest superheroes. But as some wise philosophers from England once said, money can’t buy you love. Cat realizes there’s something missing from her life that she’s not going to be able to fill from another heist. When she goes out to run a mundane errand like laundry and gets hit on by some random guy, she realizes that for all of his moralizing and do-gooding, Spider-Man and his love is what she needs.

The sequence marks a more realistic and well explained turn of character for Felicia. There are now motivations backing her actions, and these motivations add legitimacy to her proposal to “go straight” if it means she and Spider-Man can get involved with each other romantically.

In another logical character turn, Spider-Man is justifiably skeptical of Felicia’s advances, but also senses the sincerity of her offer. Of all of the character in the Marvel Universe, Spider-Man is certainly someone who could identity with being miscast and mislabeled by other people as a menace or a crook. Cat is still unwilling to meet Spidey all the way and “turn herself in” for the sake of their relationship. And her justifications for that are well-reasoned – what good is being in a relationship with Spider-Man if you’re going to be rotting in a jail cell somewhere?

What follows next in the remainder of the storyline is this back and forth dance where these two characters keep trying to compromise and meet in the middle somewhere only to find that there is no actual middle ground to be reached. Spider-Man appeals to one of the few friends in a position of authority that he has in police Captain Jean DeWolff to grant Black Cat some semblance of authority (a request that is meet with rightful cynicism and incredulity from Jean), while Felicia finds a life of crime is harder to quit than she realized and instead offers Spider-Man an opportunity to live like a King and Queen together, robbing from the rich and giving to themselves.

And that is where the tragedy of this relationship inherently lies. Spider-Man and Black Cat are like Romeo and Juliet without the family drama. Instead of it being Capulets and Montagues, it’s morality vs. amorality. It is power and responsibility vs. if it feels good, do it. These worldviews are far too different and irreconcilable, and both of these characters know it. Yet, they continue to soldier on with their idealistic plan until it all spirals out of control.

ASM #227 ends with one of the saddest chase scenes you’ll ever get in comics. A hobbled Spidey awkwardly runs after Felicia, trying to convince her to turn herself in and go to prison. Felicia evades Spider-Man like he’s a monster from a horror movie, understanding that no amount of charm or sex appeal will reverse the inevitable course of events. Spidey does eventually catch up to her and webs her up, but she chooses to roll into the water and assumedly die, rather than go to prison.

If that ending isn’t tragic enough, Stern rubs more salt in the wound by introducing a twist straight out of an O’Henry story. DeWolff arrive at the scene with signed papers from the district attorney that would have granted Felicia amnesty. After Spidey explains what just happened, Jean notes that if she had only reached Spider-Man and Black Cat sooner, her apparent death could have been avoided.

So a middle ground for Spidey and Black Cat could have been reached after all. Maybe they weren’t as star-crossed as they initially seemed.

Just devastating stuff from Stern.

Despite the fact that I did enjoy a lot of the storylines that followed that showed Spidey and Felicia officially together, if the tale of these two lovers did indeed end with ASM #227, I would have been completely satisfied because of how Stern crafted this story. I would confidently say it stands at the very top of any Spider-Man/Black Cat storyline list and is probably one of the better Spidey/romance stories to ever be published.