To some, Spider-Man is the greatest superhero of all-time. And even if you don't agree with that statement, there's no disputing that ol' Web-head is at least in the conversation when it comes to the greatest heroes to ever grace the pages of a comic book.
Since debuting back in 1962's now-iconic Amazing Fantasy #15, Peter Parker has spent the subsequent decades being one of the most fascinating and relatable comic book characters, with his everyday problems, balancing act of various real-world situations, and humour and vulnerability all being elements that have consistently made Spider-Man stand out from the pack of all-powerful god-like figures and stoic geniuses.
For readers, Spider-Man is simply their hero. But while the famed creation of Stan Lee and Steve Ditko usually manages to do the right thing and save the day regardless of what the odds are, it's not always been plain sailing for Spidey. In fact, there have been an alarming number of times where Spider-Man has made some horrendous decisions or done some completely F'd up things.
With that in mind, then, here are nine of the most messed up things that Spider-Man has ever done.
9. Attempting To Kill Sin-Eater AND Fighting Daredevil - The Death Of Jean DeWolff
From Peter David and Rich Buckler, The Death of Jean DeWolff came in the middle of a rough few years for Spider-Man. Story-wise, the mid-late eighties were great for Spider-Man, but those same years absolutely sucked if you were Spider-Man.
To give some context, Jean was a police captain who Spidey had become close with in the years prior to David and Buckley's 1985 tale. As you may have guessed by the title, the arc of The Death of Jean DeWolff saw the, well, death of Jean DeWolff.
While their relationship wasn't quite as tethered together as Batman and Jim Gordon, Jean had been set up to become the Gordon-lite to our beloved wall-crawler. So, when Spider-Man found out that DeWolff had been killed, it was a huge shocker both for Peter Parker and for readers.
The mysterious Sin-Eater would be the person behind this murder, and even more alarming for Spidey was the fact that Sin-Eater had now set his sights on Betty Brant. After Betty had managed to keep this villain at arm's length momentarily, Web-head swung in to save the day and put a stop to Sin-Eater.
Where the surprising and messed up element of this comes into play, though, is that Spider-Man doesn't just take Sin-Eater down in the way that all good heroes take down their rogues gallery. No, instead Spidey beats Sin-Eater into unconsciousness and then keeps on pounding down on his knocked-out foe.
To make matters worse, Daredevil has to step in to stop Spider-Man from killing Sin-Eater - and then Spider-Man and Horn-head end up coming to blows over all of this!