
Since first appearing in 1962, Spider-Man has become Marvel’s most recognizable and beloved superhero. Fans connect with his youth, incredible powers, memorable villains, and witty sense of humor. It’s no surprise that the web-slinging hero of New York City was adapted for the screen relatively early on. Spider-Man continues to be incredibly popular, and his place in the Marvel Cinematic Universe has solidified his status as one of the world’s most popular superheroes.
Look, I’ve been a Spider-Man fan forever, and while there’s tons of fun, it’s also a really sad story. It’s amazing how much loss and tragedy has shaped Peter Parker into the hero he is. Honestly, some of the deaths in the live-action movies are just devastating. They really stick with you and explain why he does what he does. I wanted to put together a list of the most heartbreaking ones – the ones that truly left me reeling and, I think, really define his journey.
Doctor Octopus
‘Spider-Man 2’ (2004)

Sony Pictures
Everyone was excited for Spider-Man 2, the follow-up to the 2002 hit, and it didn’t disappoint. In this film, Spider-Man (Tobey Maguire) has to save New York City from a new enemy: Doctor Octopus (Alfred Molina), a brilliant scientist who’s gone rogue. Many superhero fans consider Spider-Man 2 to be the best superhero sequel of all time.
I’ll admit, I rarely feel anything when a villain goes down, but Doc Ock’s death actually got to me. It’s a really tragic story – he started as a brilliant scientist, Dr. Otto Octavius, but a failed experiment cost him his wife and his sanity, turning him into Doctor Octopus. What’s so heartbreaking is that by the end, Spider-Man manages to free him from the robotic arms controlling him, and he realizes what he’s become, horrified by his actions. It wasn’t really him causing all that chaos, it was the technology. And then, in a final act of redemption, he sacrifices himself to destroy his own dangerous creations. It was a genuinely moving moment.
Uncle Ben
‘The Amazing Spider-Man’ (2012)

Sony Pictures Releasing
Following the disappointing reception of Spider-Man 3, the Spider-Man franchise was relaunched with The Amazing Spider-Man. Starring Andrew Garfield and a new supporting cast, the film offered a reimagining of Spider-Man’s beginnings, with a new romance and a different villain. While The Amazing Spider-Man didn’t quite reach the heights of the 2002 film, some viewers feel it’s underrated.
Everyone familiar with the Spider-Man story already knows how Uncle Ben dies, thanks to the 2002 film. The Amazing Spider-Man attempted to rework this tragic event, showing Uncle Ben (Martin Sheen) and Peter in a new situation that ultimately leads to the same outcome: Uncle Ben is shot and killed by a burglar—a burglar Spider-Man had the power to stop. While it’s heartbreaking to see Uncle Ben die and Peter grieve, the scene doesn’t feel as powerful because it’s a story we’ve witnessed before.
George Stacy
‘The Amazing Spider-Man’ (2012)

Sony Pictures Releasing
In the reboot of The Amazing Spider-Man, Denis Leary plays Captain George Stacy, the father of Spider-Man’s girlfriend. As an NYPD captain, he leads the effort to stop Spider-Man, believing him to be a dangerous vigilante. By the end of the film, Captain Stacy discovers Spider-Man is actually his daughter’s boyfriend. They briefly work together to defeat the villain, the Lizard (Rhys Ifans), but Captain Stacy tragically dies in the process.
In his final moments, he asks Peter to stay away from his daughter to protect her – a promise Peter sadly breaks. This is another heartbreaking event for Andrew Garfield’s Spider-Man. In the comics, Captain Stacy’s death is a pivotal moment, drastically changing public perception of Spider-Man. However, the movie version doesn’t feel as impactful as a later tragedy in the sequel.
Harry Osborn
‘Spider-Man 3’ (2007)

Sony Pictures Releasing
I was so excited for Spider-Man 3! The first two movies were amazing, and everyone was buzzing about finally seeing Venom (Topher Grace) on the big screen. Plus, they were bringing back the Green Goblin (James Franco) and introducing Sandman (Thomas Haden Church)! It felt like they were trying to do too much, though. Peter Parker was battling all these villains and dealing with his own personal struggles, and honestly, it just didn’t quite work. It really didn’t live up to the expectations, and it’s tough to watch knowing how great the first two were – it’s definitely a weaker film in Sam Raimi’s career.
From the very beginning, Harry Osborn (played by James Franco) was Peter Parker’s closest friend. However, their friendship fell apart when Harry discovered Peter was Spider-Man, and he wrongly believed Spider-Man had caused his father, Norman’s, death. Driven by a desire for revenge, Harry became the new Green Goblin and Spider-Man’s enemy. Later, the two managed to repair their friendship and fought alongside each other against Venom and Sandman, but tragically, Harry was killed during the battle, causing another devastating loss for Peter Parker.
Gwen Stacy
‘The Amazing Spider-Man 2’ (2014)

Sony Pictures Releasing
In The Amazing Spider-Man 2, Spider-Man is back, this time battling two new enemies: Electro, played by Jamie Foxx, and a reimagined Green Goblin, played by Dane DeHaan. While many know Mary Jane Watson as Spider-Man’s famous love interest, Gwen Stacy (Emma Stone) was actually his first love in the comic books. The Amazing Spider-Man movies explore their relationship, showing both its exciting start and its heartbreaking end.
The movie’s climax recreates a heartbreaking moment from the comics: the Green Goblin throws Gwen Stacy from a great height. Spider-Man tries desperately to save her, but fails. Gwen’s death is one of the most devastating moments in Spider-Man’s history. It’s especially tragic because Peter broke his promise to Gwen’s father—his promise to stay away from her to protect her. That decision ultimately led to her death, making the loss even more painful.
Uncle Aaron (Prowler)
‘Into the Spider-Verse’ (2018)

Sony Pictures Releasing
I was so excited when Into the Spider-Verse came out because it finally brought Miles Morales to the big screen! As a comic fan, I already loved him – a fresh take on Spider-Man with a totally different story. And honestly, even though he’s a superhero, it didn’t shield him from hardship. Miles’ uncle, Aaron Davis, played by Mahershala Ali, was a huge influence on him. He really encouraged Miles to be himself and express his creativity, which was the opposite of what his dad wanted. That’s why when something did happen to Aaron, it hit Miles – and me, as a viewer – so incredibly hard. It was a really powerful moment.
The story takes a heartbreaking turn when it’s revealed that Miles’s uncle, Aaron, is actually the Prowler, a villain working for the notorious Kingpin – widely considered one of the greatest animated villains ever created. Aaron discovers Miles is Spider-Man and bravely defies Kingpin’s orders to kill him, which leads to him being fatally shot. Miles is forced to watch his uncle, a significant and cherished figure in his life, die – a deeply upsetting moment for both him and viewers.
Aunt May
‘Spider-Man: No Way Home’ (2021)

Marvel Studios
Over the past two decades, moviegoers have enjoyed three different actors playing Spider-Man: Tobey Maguire in the first trilogy, Andrew Garfield in a rebooted series, and now Tom Holland as part of the Marvel Cinematic Universe. The film Spider-Man: No Way Home uniquely combined all three Spider-Men in one movie, made possible by Doctor Strange and the multiverse. The film also featured familiar villains from past Spider-Man movies, with the original actors returning to their roles.
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Tom Holland’s Spider-Man movies don’t bother with the familiar origin story – we already know how he got his powers. We generally assume Peter Parker had an Uncle Ben who died, just like in other versions. But No Way Home throws a surprising curveball: instead of Uncle Ben, it’s Aunt May who fulfills that tragic role for this Spider-Man.
In the film, the Green Goblin (Willem Dafoe) kills her, causing Spider-Man (Tom Holland) to experience a profound loss for the first time. While Uncle Ben’s death has been shown before, Aunt May’s passing is particularly impactful. She’s been a steady and significant figure in Peter’s life, and her longer role in the Marvel Cinematic Universe makes her death even more heartbreaking.
Uncle Ben
‘Spider-Man’ (2002)

Sony Pictures Releasing
In 2002, Spider-Man was a massive hit and dominated Hollywood. Even today, it remains a fantastic superhero movie thanks to its impressive visual effects, strong cast, and compelling story. The film covers all the essential background of Marvel’s most famous character, including the heartbreaking event that shaped him. Peter Parker (Tobey Maguire) shares a close bond with his Uncle Ben (Cliff Robertson). However, a disagreement causes them to part ways, unknowingly for the last time.
Peter returned to their meeting place hours later and found Uncle Ben lying on the sidewalk, seriously wounded by a gunshot. Uncle Ben weakly called out Peter’s name twice before passing away. The tragedy was compounded by the fact that the same burglar Peter had previously let go was responsible for the shooting. This devastating loss was a turning point in Peter Parker’s life, the event that inspired him to become Spider-Man and cemented the meaning of Uncle Ben’s famous words: “With great power comes great responsibility.”
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2026-02-12 20:06