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7 Most Heartbreaking Moments in Stranger Things

7 Most Heartbreaking Moments in Stranger Things

For four (going on five) seasons, Stranger Things has given us plenty of moments filled with nostalgia, thrilling action, and heartwarming relationships. Amidst all the ’80s throwbacks and pop culture homage, the show is consistently good at tugging at the heartstrings without veering too far off melodrama land. You can chalk it up to the writing, which understands its characters and what drives their actions at any given time, and the performances by the cast, so stellar across the board, despite most of them being young kids when they started out. It's finally time to break down the most heartbreaking Stranger Things moments.

Every season, we get a standout moment that defines the show’s love for its characters – moments that show their humanity, selflessness, and love for one another, moments that break our hearts and make us shed tears for these fictional Hawkins residents. Now that the series is reaching its ultimate conclusion, we’re looking back at the 7 times the show did its best. 

 

7. Bob’s Death (Season 2)

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In season 2, Sean Astin made his debut on the show as Joyce (Winona Ryder)’s kind new boyfriend Bob. The character represents a welcome stabilizing presence in Casa Byers, who is severely lacking a dependable father figure. Meanwhile, the casting of Astin – who shot to fame in The Goonies – ups the 1980s nostalgia quotient. And it’s not even random, since season 2 took a lot of inspiration from that movie’s hidden tunnel and treasure-hunting plot. 

It didn’t take long for Bob to integrate with the rest of the cast, with him being involved in the kids’ investigation – endearing him to Will and Jonathan Byers, two kids long traumatized by their absent father. And so, when he got fatally attacked by the Demodog at the end of the series, it was a great loss both to the Byers family and us audiences, who’ve been rooting for Will, Jonathan, and Joyce to have a happy home after all they’ve been through. 

 

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6. Billy Sacrificing Himself (Season 3)

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Since season 2, Billy (Dacre Montgomery) has been the show’s most menacing antagonist. From bullying the kids to tormenting his stepsister, Max (Sadie Sink), he’s easily one of the most hated characters in the entire show. 

Season 3 has Billy under the control of the Mind Flayer, turning him from a high school bully to a killing monster. However, in a testament to the show’s masterful writing, we eventually get a glimpse of Billy’s tortured childhood via Eleven (Millie Bobby Brown)’s vision. The revelation helps us understand where all of Billy’s anger came from and sympathize with the abandoned child underneath the cruel facade, showing that it’s always the hurt people who hurt people. With his last shred of humanity rediscovered, Billy eventually makes the ultimate sacrifice to protect El from the Mind Flayer’s attack – giving him his final redemption. And so, we grieve for an abused child who never gets to correct his wrongs in life, but hopefully finds peace in death.

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5. Hopper’s Letter to Eleven (Season 3)

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All season long, we watch El and Hopper's (David Harbour) father-daughter dynamic strain as El pushes for more freedom. Both of them have been through so much before meeting each other, histories that complicate their bond even though we can see they do love each other underneath all the snarls and scoldings. Having lost a daughter once, it’s no wonder Hopper gets extra protective around El – something the latter couldn’t understand with her still limited social skills. And so, Hop can only show his care by actions, including sacrificing himself to destroy the Russians’ secret plant, therefore aiding El and co in the most dire time. 

But what truly gets you is the quiet denouement later on, when a grieving El belatedly reads Hop’s letter to her. Right then, she finally understands the depth of Hopper’s feelings, making for a bittersweet moment that leaves her with regret and longing. Who knew the line “keep the door open three inches” could reduce grown men to tears?

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4. Eddie’s Death (Season 4)

Another season of Stranger Things always means the arrival of a beloved new character. Season 2 had Max, season 3 had Robin (Maya Hawke), and season 4 had Eddie (Joseph Quinn). With his metalhead curls, D&D obsession, and winsome persona, Eddie became an immediate fan favorite and the kids’ new big brother figure, especially to Dustin (Gaten Matarazzo).

Though he’s brought into the whole Upside Down business by accident, Eddie tunes right in almost immediately and plays a pivotal part in the final battle against Vecna – going out in the best way possible, rockin’ out to Metallica before sacrificing himself for his friends. His farewell scene with Dustin never fails to turn on the waterworks, but it’s the fact that he’s blamed for Vecna’s destruction later on that makes his death especially hurtful. 

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3. Will’s Declaration for Mike (Season 4)

Will (Noah Schnapp) is inarguably the most suffering character in the whole Stranger Things cast. He’s been through a lot since season 1: kidnapped by the Demogorgons, possessed by the Mind Flayer, and just when things seem normal again, he realizes that his friends have outgrown the things he missed out on. And that doesn’t count the big secret he’s keeping on his own: his budding romantic feelings for Mike. 

Since season 3, Will is grappling with his homosexuality, something that would spell doom for a small-town teenager back in the 80s, and his complicated feelings toward Mike and El, both people he cares about and envies. His silent struggle culminates in a car conversation with Mike, where he pours his heart out to Mike, pretending it’s about El. 

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2. Max’s Running Up The Hill Escape (Season 4)

Depressed following Billy’s death, Max becomes the target of Vecna’s terror in season 4. Her bouts of depression make her vulnerable to Vecna, who ends up trapping her in his mental hellscape. And this is when Max, inches away from death, hears her friends calling out to her with the aid of her favorite Kate Bush song “Running Up The Hill” and realizes there is hope.

The tense scene of Max literally running toward the light has become the most resonating scene in the series’ history – an apt depiction of everyone who’s ever dealt with debilitating depression, as well as the power of friendships (and music) as a healing force. 

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1. Max’s “Death” and Resurrection (Season 4)

… And that’s why the latter scene, when Vecna actually captures Max when she goes back to fight him, hurts doubly. Here’s a girl who’s been through so much, escapes it, only to fall victim again in gruesome fashion. As if the image of Max – blinded and bloodied – pleading for her life is not enough, we have Lucas (Caleb McLaughlin) bawling his eyes out helplessly as Max dies in his arms. If it weren’t for El saving Max’s life later on, it would go down as the most traumatizing scene in the history of TV shows. 

 

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