Marvel’s Peter Parker, or the Friendly Neighborhood Spider-Man, remains one of the comics’ most entertaining characters. His charming humor and gripping stories explore what can make even the most ordinary individuals heroes. However, despite the cheerful nature of Spider-Man, Marvel’s resident webslinger isn’t without his flaws. With Peter Parker about to encounter the infamous Venom Symbiote in Marvel's Spider-Man 2, fans of the webhead may want to learn just what other nasty things Spider-Man has done in his career.

Some stories in the comics have pushed Spider-Man to the edge, making Peter Parker commit acts that may even make readers question his morals. Readers who want to get to know Peter Parker on a deeper level may want to explore the worst of his actions, especially regarding the reasons why he resorted to these choices.

8 Refusing To Stop A Thief

Spider-Man discovers Uncle Ben's killer

When Peter Parker obtains his powers in 1962's Amazing Fantasy #15, his desire to get back at his bully Flash Thompson is a reasonable response as a teenager. However, when he ignores the reports of a thief in the area, Peter gets a wake-up call when Uncle Ben dies in his arms because of that same runaway. Although one can't expect Peter to know what is "good" at his age, readers can hope that Peter becomes the hero he needed when he was bullied.

RELATED: Spider-Man: Alternate Versions Of The Webslinger That Need Their Own Game

Uncle Ben's death eventually gave Peter a desire to save others with the great responsibility his powers had bestowed upon him. Still, it’s reasonable to say Peter could at least have known better than to think some lowly thief is beneath him.

7 Almost Killing Kingpin

Spider-Man almost kills Kingpin

When Tony Stark convinced Spider-Man to unmask himself in support of the Superhuman Registration Act, this event in Marvel’s Civil War comics puts Peter Parker and his entire family in danger. This is exactly what happens when an imprisoned Kingpin orders a hit on Peter’s family, which critically injures Aunt May. In retaliation, Peter Parker dons a black costume and goes to prison, where he mocks Kingpin’s lack of powers and beats him within an inch of his life, threatening to kill him and anyone else who messes with his family.

Fans may hold Peter to a higher standard, and at the same time, demand he make a statement for going too far. Peter openly mocking Kingpin and beating him almost to death may have been irresponsible for someone with great power. However, not killing Kingpin out of a moral objection may also endanger more families.

6 Trapping A Dying Robot Master In A VR Loop

Spider-Man and Mendel Stromm

Originally the scientist who developed the Green Goblin Serum, Mendel Stromm was embittered when Norman Osborn stole his supposed fortune. After failing to assassinate Osborn, Stromm obtains a robotic body and uses the name Robot Master in his attempts to kill the businessman. Spider-Man eventually becomes Stromm's enemy when the webhead thwarts another assassination attempt on the Green Goblin.

When one of his last attempts to kill Osborn involved transferring his consciousness to a computer, Mendel began trying to take over his mind. Mendel asks Spider-Man to end his life before the computer takes over entirely, but Spider-Man decides to lock him in a virtual reality loop instead. While SHIELD finally finds Mendel’s comatose mind years later, one could surmise it wasn’t Spider-Man’s call to decide to go against Mendel's wishes. Had SHIELD not found him, Mendel would have been trapped in an endless loop - a fate perhaps worse than death.

5 Kissing His Dead Ex’s Daughter

Sarah Stacy kisses Peter Parker

One of the many ways Marvel messed with Peter Parker’s life goes way back to 2005’s Sins Remembered. This storyline reveals that Norman Osborn had assaulted Gwen Stacy before her death, resulting in the birth of twins Sarah and Gabriel. Mary Jane eventually reveals that she knew of the twins’ origins all along, courtesy of Gwen, who made her promise not to tell Peter.

RELATED: Spider-Man: Locations Outside NYC The Games Should Explore

When Sarah comes to Peter for aid to find a missing and estranged Gabriel, a misunderstanding leads to Sarah kissing Peter in front of a shocked Mary Jane. Despite the unintentional nature of the kiss, the implied sexual tension between Peter and Sarah does not rid Peter of suspicious vibes. Not only that, the twins having Norman’s enhanced blood aged them much faster, meaning despite Sarah’s appearance and mindset as an adult, she is still probably physically five to nine years old.

4 Committing Manslaughter

Spider-Man hits Charlie

The 1980s Spider-Man Versus Wolverine team-up takes a dark turn when happy-go-lucky Spider-Man finds himself at odds with the always-wary Wolverine. In the story, the separate investigations of Spider-Man and Wolverine lead them both to the culprit: Charlemagne, a former KGB operative who was also Wolverine's former comrade and potential ex-fling. Although at first only a case involving assassinated ex-KGB operatives, the stakes get personal for Spider-Man when Ned Leeds is killed while they chase this story.

When Charlie asks Wolverine to kill her before the KGB can, Spider-Man arrives and misunderstands the situation. In a conflict between Wolverine and the webhead, Spider-Man accidentally punches Charlie. While a metahuman like Wolverine could tank the punch, Charlie’s regular physique couldn’t handle the hit, dying on the spot.

3 Actual Murder

Spider-Man deals the killing blow to Massacre

When a dying Doctor Octopus switches minds with Peter Parker, the latter asks the villain to continue his legacy, and Doc Ock pledges to become a “Superior” Spider-Man. In the events of 2013's The Superior Spider-Man, Dock Ock ponders the cyclical nature of superheroes and villains, deciding to outright kill the captured minor villain Massacre after the latter's killing spree. What makes this situation rather horrifying is that Massacre had claimed to feel a “spark” of emotion before he was killed.

RELATED: Spider-Man: Best Marvel Cameos In Spider-Man Games

Moreover, when it’s revealed that an aspect of Peter’s consciousness was left in his mind all along, one could wonder how much of Doc Ock was influenced when he decided to pull the trigger. A more horrific iteration of this exists in Spder-Man 8351, where he abandons his family to protect them from danger as he and Wolverine become black-ops assassins.

2 Making Peace With Venom

Spider-Man fights Venom

Back in Amazing Spider-Man #375, a confrontation between Spider-Man and Venom had the rivals promise not to meddle in each other’s affairs. From Spider-Man’s perspective, this finally means Venom leaves him and his family alone. And from the perspective of Marvel’s editorial team, this allows them to use Venom’s growing popularity and begin making him an antihero.

Though this publishing decision made Venom a more popular character today, his journey as an antihero meant leaving a trail of bodies in his wake. Unfortunately for fans of Spider-Man, the webhead’s selfish choice of wanting Venom to leave him alone put the lives of Venom’s victims in Peter’s hands.

1 Dealing With The Devil

One More Day

In what many Marvel fans consider the pinnacle of editorial messing with Spider-Man, 2007’s One More Day became the justification for putting Peter in the unfortunate shoes of an awkward hero that will never grow up. The events of this comic have Peter Parker and Mary Jane agreeing to have Mephisto save Aunt May’s life from a stray bullet. The cost? The entirety of their marriage "didn't happen," their unborn child will disappear, and Peter and Mary Jane won't ever be a thing.

On top of the ridiculous "impossibility" that the likes of Doctor Doom, Doctor Strange, and even the High Evolutionary can't save Aunt May, it's irresponsible for Peter to not consider how this deal will tamper with the lives of everyone involved with him and Mary Jane. Not to mention, Aunt May's passing will finally help her reunite with Uncle Ben. And Peter seems to forget the vastness of magic in the Marvel Universe can help him get in touch with Aunt May, anyway. After all, Doctor Doom did manage to fight Mephisto to get his mother's soul - why can't Peter?

Marvel's Spider-Man 2 is slated for an October 2023 release as a PlayStation 5 exclusive.

MORE: Spider-Man: Best Marvel Cameos In Spider-Man Games