One problem with stories in serial fiction is that any genre is repetition, as writers and artists tell stories that were done before, and usually better. This often happens when writers worry too much about keeping everything intact for the long term. However, it is possible to go to extremes with stories that work into the short term, but may harm the series in the long run.
A while back, I made a list of the top 15 Spider-Man characters: Flash Thompson, Sandman, Harry Osborn, Kraven the Hunter, Roderick Kingsley/ The Hobgoblin, The Alien Costume/ Venom, Mary Jane, Norman Osborn, Aunt May, Doctor Octopus, The Kingpin, The Punisher, Curt Connors/ The Lizard, J Jonah Jameson and (of course) Peter Parker. JM DeMatteis, widely and appropriately considered one of the best Spider-Man writers, wrote defining arcs for three of those characters. The Gift, with Aunt May, was ranked the twelfth best Spider-Man story by CBR readers. The Harry Osborn saga was #10. Fearful Symmetry, with Kraven, was rated the best Spider-Man story of all time. And each of those tales ended with a death of the spotlighted character.
Web of Death, a Clone Saga-era crossover DeMatteis co-wrote with Tom Defalco, also ended with a new villain killing off Doctor Octopus. So DeMatteis’s death count arguably rises to four great Spider-Man characters. As the writer of Amazing Spider-Man at the time, DeMatteis was involved in many of the big decisions of the Clone Saga. While there was a lot of editorial interference, the creative teams agreed that they wanted three monumental things happen at the same time: Aunt May’s death, Mary Jane’s pregnancy, and the revelation that the Peter Parker in the books was the clone. Each of those decisions was undone, and the four characters Dematteis killed off have returned.
In an interview with the Crawl Space podcast, DeMatteis said that he was sure at the time that his big decisions would eventually be reversed. This seems somewhat irresponsible. It was especially wrong of DeMatteis to kill off Harry Osborn and Aunt May, considering what they brought to the series. When writers bring stories with borrowed characters to a close, that often sucks for the later writers and readers in a serial medium. They have to choose between telling their own stories, or cleaning up after their predecessors.
Some of his biggest fans suggest that Dematteis took risks. The recommendation is that other writers should follow in his lead. So they’re on the side of the Commitment to Change in the Illusion of Change debate. It’s worth noting that with four more Spider-Man writers like DeMatteis, we probably wouldn’t have any of the best Spider-Man supporting cast members or villains left.
Those who applaud JMD’s bravery often suggest that writers have a choice between telling good stories and being mindful of the future. I hate bad stories, but inconsequential bad stories tend to be forgotten pretty quickly. The most hated stories tend to be be consequential. The runs of Dan Slott and Roger Stern demonstrate that writers can still tell good stories while remembering that they’re borrowing the characters from their successors.
I also wouldn’t say that his scripts were particularly brave. These were mostly conventional crowd-pleasers from a guy who knew his craft, and was acknowledged to be a good writer. The odds were pretty likely that the issues would be well-received, even if the long-term consequences were bad.
The stories in which May and Harry were killed were well told and respectful. But it was still cheap, unimaginative and selfish. The hero’s maternal figure tells him that she’s proud of him. And that she knows more about him than she thought. It’s kinda hard to screw up that one. Likewise the cliche of the likable villain sacrificing himself to save the lead.
Incidentally, resurrecting May and Harry weren’t unimaginative crowd-pleasers, largely because the resurrections of supporting characters killed in well-received stories aren’t something fans ask for. Even if the characters brought something interesting to the series.
An odd thing here is that I’m criticizing stories that I would also recommend. I think any Spider-Man fans should seek collections of Kraven’s Last Hunt, as well as the back issues of his Spectacular Spider-Man run with Sal Buscema, and Amazing Spider-Man #400. J.M. DeMatteis is a talented writer. And the Spider-Man comics have brought out the best in his work. But it’s difficult for a writer of his talents to screw up with that type of crowd-pleasing set-up. Many other writers have accomplished that with the same trope. Stan Lee had done it a few times, including in the Spider-Man comics.
While talent and skill is important, any writer who can’t get a similar reaction from Aunt May’s death or Harry Osborn’s death is probably not fit to write the major Spider-Man comics. One problem with the JMD approach is that while a talented writer should be able to get good material when killing off characters as if it were a movie instead of a serial, a poor writer or a careless one on a deadline can screw it up, which will be problematic for a story that has repercussions for years to come.
It does seem to me that stories in which a notable character dies are more likely to be acclaimed. In the Spider-Man comics, there’s Amazing Fantasy #15, the Death of Bennet Brant, the Death of Frederick Foswell, the Death of Captain Stacy, the Deaths of Norman Osborn & Gwen Stacy, the supposed Death of Black Cat in Amazing Spider-Man #227, the Death of the Tarantula, the Death of Jean Dewolfe, the Death of Ned Leeds. Kraven’s Last Hunt and a few others.
You could contrast DeMatteis with Gerry Conway, who killed off two of the most important Spider-Man characters in the course of one story. When Conway killed off Norman Osborn, he replaced him with a new villain (the Harry Osborn Green Goblin). He also ended the story of Gwen’s death with a moment between Peter and MJ. In his case, he was opening new doors while closing others. On the other hand, JMD mostly closed doors. He brought stories that had been ongoing for decades to an end, but didn’t offer anything new as an alternative.
DeMatteis wrote an excellent back-up story for Amazing Spider-Man #700. He has said that he’s not interesting in returning to the comics on a regular basis, although he would love to write a spinoff with Ben Reilly. That’s welcome news to fans of the character, who have been clamoring for his return for some time. An irony is that one reason Ben Reilly is unlikely to be brought back is that there have been too many deaths and resurrections. If JMD hadn’t unnecessarily killed off Harry and May, retcons explaining how the deaths of two supporting characters were faked would not have been necessary. Fans might not be as cynical whenever a character was in danger, which means that it would be easier to make the case for resurrecting Reilly.
DeMatteis’s best-received story is the one which involves the least significant of the characters he killed off. Kraven the Hunter probably would not be considered one of the series’s best characters if it were not for Fearful Symmetry. DeMatteis followed up on that story in the Soul of the Hunter one-shot, two battles with Vermin in his first Spectacular Spider-Man run, a retelling of Spider-Man’s first encounter with the Hunter in the 1996 Sensational Spider-Man annual, a Chameleon arc in his second Spectacular Spider-Man run and the introduction of Kraven’s most successful son in a subsequent storyline. His take on the villain was so definitive that there was some anger at the return of the villain during the Brand New Day era.
I didn’t mind Grim Hunt’s resurrection of Kraven the Hunter, as it left the character in a much different place than where he was at the beginning of KLH. Nor did I mind that it contradicted Soul of the Hunter, although that’s largely because I didn’t think that story was all that great. I’d give it a “B” while Grim Hunt would be an A- or an A.
The characters seemed to be resurrected in reverse order. Kraven was killed off in 1987 and returned in 2010. Harry Osborn was killed off in May was killed off in 1994 and returned in 2007. Aunt May’s departure was the briefest. Her death was in 1995 and her return (with the revelation that the woman who died was an actress in the employ of Norman Osborn) came in 1998.
Harry Osborn was a fixture of the book during the Brand New Day era. While he’s currently away from the book, future writers have the option of being able to use the character. That isn’t possible when characters are indiscriminately killed off.
There is the argument that Spider-Man needs more ghosts. Although there’s also a point when ghosts are excessive and redundant. Harry was already a legacy character. Even as a ghost, he was tied to Norman. And you’re not going to have a new supervillain using stuff they found in Aunt May’s lair. Plus, Peter already has Uncle Ben as the family ghost. Aunt May worked better in a different role.
What Would Spidey Do? 
Conway was pretty bloodthirsty as well but it’s forgotten. He said in interviews that he never expected the comics industry to truck along for more than a few more years which may be why he also killed Doc Ock, Miles Warren, Hammerhead and the original Mysterio (that one was off panel). Granted those deaths weren’t as grand as the JMD deaths detailed here.
Strongly disagree; DeMatteis chose to write stories likely to be impressive or at least memorable but that’s no guarantee they would have been well-received, especially as many fans resent change. DeMatteis wrote them without seeming predictable or forced and it’s the fault of later writers for either not coming up with good enough new characters or undoing the deaths.