Spider-Man has always been known as the bubbly, light-hearted, friendly neighborhood hero, but what makes the character so relatable, other than his charm and inner nerdiness is the emotional story arcs he goes through. Spider-Man has now been around for over 50 years, so there’s no surprise that among the thousands of comics featuring the web-slinger, there have been some downer moments.
In Avengers: Endgame, Tom Holland gave us a glimpse of what a heart-broken and scared Peter Parker looks like, but the comics have given us some equally or perhaps even more gutwrenching moments. Whether that be through loss and grief, or love and family, or everything in between, Spidey has been through a lot.
10 Spectacular Spider-Man #107-110: The Death Of Jean DeWolff (by Peter David & Rich Buckler)
Jean DeWolff was introduced to fans as a police detective who had a particular disliking towards our very own web-slinger Spider-Man. Over time, however, the pair developed a lovely friendship and became very close allies. This, however, came to an extremely sad ending, after her ex-lover Stan Carter, aka Sin-Eater, killed Jean.
To make it even sadder, after her death, Spidey finds a collection of photographs of the two of them, that she kept for herself. It proved just how much she really cared about him, which must have been heart-breaking for Peter.
9 Spectacular Spider-Man #200: The Death Of Harry Osborn (By J.M. DeMatteis & Sal Buscema)
The next comic on the list is another death, this time with one of Peter’s best friends, Harry Osborn. After suffering from his identity and battling with his other self, the Green Goblin, Harry once again becomes the Green Goblin and embarks on one final battle against Spider-Man.
The death became even more emotional when moments before, Spider-Man was about to die too, Harry came back to his senses and saved his life and spent the final seconds of his life apologizing to his best friend for everything he had done to him over the years.
8 The Amazing Spider-Man #248: The Kid Who Collects Spider-Man (by Roger Stern & John Romita Jr.)
Very rarely does a comic book break and warm a reader’s heart at the same time, but the ‘Kid Who Collects Spider-Man’ storyline definitely does just that. The story follows a young boy called Timmy Hammond, who happens to be a huge Spider-Man fan, and gets to live out his dream of meeting the hero himself.
After showing him all his Spidey memorabilia, Peter opens up to the boy about power and responsibility, and what it really means to be a hero. It’s in this speech that fans are reminded of all the pain he’s been through over the years. Then in the final stinger, it’s revealed that this really was Timmy’s final wish as we realize he’s staying at the Slocum Brewer Cancer Facility.
7 The Amazing Spider-Man #121: The Night Gwen Stacy Died (by Gerry Conway & Gil Kane)
As later revamped in The Amazing Spider-Man 2 movie featuring Andrew Garfield and Emma Stone, this comic book is one of the most famous of them all and defined the rest of Spidey’s life. Losing someone you love is devastating, and despite all his efforts, Peter just couldn’t save Gwen.
After getting kidnapped by the Green Goblin, Gwen is thrown off the Brooklyn Bridge, and in a moment that will stick with fans for years, Peter tries to save her and catch her with his webbing, only for the sudden jolt to cause whiplash and snap her neck. The grief-stricken hero then delivers one of the saddest lines ever seen in a comic book that is sure to leave anyone in tears.
6 The Spectacular Spider-Man #6: My Dinner With Jonah (By Chip Zdarsky & Michael Walsh)
Daily Bugle presenter J. Jonah Jameson has a somewhat unstable relationship with both Spider-Man and Peter Parker, but it’s precisely this that made this comic book surprisingly tragic.
Spidey agrees to a special one-hour interview with Jonah in exchange for some intel on his enemies. It started off as an intense back and forth debate and ended with an emotional talk where Jonah reveals that his agenda against Spidey is because he feels like he has nothing else left in his life and doesn’t what to let the people who he’s lost down. No one would have expected that from him.
5 Ultimate Spider-Man #160: The Death Of Spider-Man (by Brian Michael Bendis & Mark Bagley)
Any superhero death is an extremely sad moment, but in the Ultimate Universe, watching Peter Parker die after an all-out fight with Norman Osborn was one of the hardest to take. The main reason it hit so hard was the fact that his family and loved ones were all right there with him.
MJ was holding him, Aunt May was watching from behind, as were his friends Gwen Stacy and Johnny Storm. Because the Ultimate Universe is a lot darker as well, this was the last time fans ever saw this version of Spidey.
4 Spider-Man: Reign (By Kaare Andrews & Jose Villarrubia)
This isolated and unique storyline was full of action and incredibly sad moments, as the future version of Peter, 30 years into the future, in fact, struggled to come to terms with the death of Mary Jane Watson-Parker.
Obsessed by hallucinations and haunted by his demons, Spidey was having an extremely hard time, so when his former enemies team up to form the newly named ‘Sinner Six,’ an old, heart-broken Peter must use all his inner strength to overcome them and the new brutal police force, The Reign.
3 The Amazing Spider-Man: Dead No More: The Clone Conspiracy (by Dan Slott, Christos Gage, & Jim Cheung)
Over the years, plenty of characters have had some pretty impactful and emotional deaths in the Spider-Man comics. We’ve already mentioned the deaths of Gwen Stacy, Harry Osborn, and even Peter Parker himself, but The Clone Conspiracy takes this to a whole other level.
In this limited series, all the characters that readers have seen pass away in the past are revived as clones, only to tragically die due to a problem with the cloning process. So even though people have already been through the pain of watching them die, fans have to relive this all again in one massive swoop.
2 Friendly Neighbourhood Spider-Man Annual #1: Leah (By Peter David & Ronan Cliquet)
In just six pages, Marvel manages to tell one of the most emotional stories they have ever told. Leah is a homeless girl, who also loves Spidey, and sleeps in a cardboard box covered in pictures of the web-slinger.
The comic follows her dreams as she imagines going on cool adventures with Spidey, but when she doesn’t wake up, fans really feel the gut punch. It’s a beautifully told story about a young girl spending her final moments in her imagination, and definitely leaves you in tears.
1 Spider-Man: Life Story (by Chip Zdarsky & Mark Bagley)
Spider-Man’s comic book history spans almost sixty years, so it’s no surprise that he has been through a lot of different things. Some happy moments, like getting married and having kids, and some sad ones like losing his best friend and family. All these moments however are retold in this beautiful comic.
Fitting in key events from his past, from each decade, Spider-Man: Life Story takes fans on a rollercoaster of emotions as we explore his action-packed life one more time as a story from beginning to end.
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