The Marvel Cinematic Universe may be best known for its epic battles, quippy one-liners, and sprawling story arcs, but none of that would mean much if it couldn't also get its audience emotionally invested in its immense cast of characters. Perhaps one of Marvel's greatest successes has been the way it has humanized every significant player on its impressive roster, from a talking tree with a three-word vocabulary to an entitled billionaire with a god complex. While we love seeing our favorite heroes win, it's in hardship that they become the most relatable, showing us that underneath all of the tremendous superpowers and advanced training, they're still people who grieve, doubt, regret, and worry, just like us.

Although most MCU fans likely don't flock to theaters (or, more recently, the TVs in their living rooms) to see the latest superhero adventure hoping for a good, cathartic cry, plenty of the films that make up the first three phases of the MCU include their fair share of heartbreak. As a matter of fact, there are so many gut-wrenching moments in the MCU that wrangling this list down to a manageable size meant leaving some pretty poignant events off entirely (my apologies to Yondu and the Ancient One).

Additionally, I tried to vary the types of sadness represented here, from grief to broken friendships and missed opportunities, so that it was more than just a laundry list of deaths. You'll also notice several pretty huge moments had to be consolidated into single entries in order to keep Infinity War and Endgame from utterly dominating the list (as it is, they still get several entries apiece).

With all that said, while we all have some specific moments that tend to make us a little (or a lot) verklempt, these stand out as the cream of the emotionally devastating crop. Behold, the saddest MCU moments thus far.

"I had a date." - Captain America: The First Avenger

Captain America: The First Avenger Ending Chris Evans
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The MCU has included many love stories over the course of its long run, but perhaps its sweetest — and most tragic — was introduced early on, when scrappy, scrawny army recruit Steve Rogers (Chris Evans) met British agent Peggy Carter (Hayley Atwell) in Captain America: The First Avenger. Like several of the MCU's strongest relationships, the attraction between Peggy and Steve was a slow burn, yet the romantic tension between them set off sparks bright enough to light up the night sky. Unfortunately, before the two could go on their first date (in which Peggy promised to teach Steve to dance), he found himself piloting a damaged plane loaded with weapons of mass destruction, and was forced to crash it in the Arctic to keep the weapons from detonating and killing millions.

Steve and Peggy kept talking on the plane's radio right up until the moment Steve went into the ice, planning the date they both knew would never happen. 70 years later, Steve was recovered from the ice by S.H.I.E.L.D., perfectly preserved in the same condition he was in back in 1945, although the rest of the world had moved on. After learning from Nick Fury (Samuel L. Jackson) what has happened to him, a bewildered Steve looks around Times Square, profound sadness etched on his face as he says softly, "I had a date."

For the rest of his time in the MCU, even as Steve works to make a new life for himself in his new century, there is always an undercurrent of regret about the life he never got to live, and the love he never got to have. Now more than ever, we all know the disappointment of missing out on opportunities and events that we were really looking forward to; imagine missing out on an entire lifetime.

Loki reacts to Frigga's death - Thor: The Dark World

Loki Thor the Dark World Tom Hiddleston
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While it's definitely sad, Frigga (Rene Russo) wasn't really a significant enough presence in the MCU for her death to register as one of its saddest moments, save for one thing — the reaction of her son, Loki (Tom Hiddleston). When Thor: The Dark World begins, Loki is imprisoned on Asgard for the crimes he committed during the events of Thor and The Avengers, which means he's not really involved when Malekith (Christopher Eccleston) shows up on his family's doorstep searching for the Aether, and murders Frigga in the process. Afterward, Thor (Chris Hemsworth) and Odin (Anthony Hopkins) don't even bother to tell Loki about his mother in person; they send an unnamed guard to deliver the devastating news.

Adding insult to injury, Loki isn't informed about his mother's death until after her funeral, meaning that he doesn't get to bid her farewell, and is instead left to grieve alone inside his cell. It is only later, when Thor wants something from him, that Thor goes to visit his brother, and Loki drops his glamour to reveal the extent of his mourning: he's destroyed the furnishings in his cell and cut up his feet, and his normally polished appearance is now rumpled and disheveled. He tries to ask Thor about the circumstances of Frigga's death, but Thor isn't interested in talking about their mother, leaving Loki to continue to stew in his questions. While Loki is one of the MCU's more morally ambiguous characters, there's never any doubt that he loved his mother, and that she loved him, making the way he is forced to deal with her death seem particularly cruel.

"I'm not going to fight you." - Captain America: The Winter Soldier

Captain America the Winter Soldier
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Steve Rogers has two great love stories within the MCU -- his eventual wife, Peggy Carter, and his lifelong best friend, Bucky Barnes (Sebastian Stan). Growing up, the bigger, stronger Bucky always served as Steve's defender, shielding him from bullies and believing in him even when no one else did. After Steve took the super soldier serum and became Captain America, their roles were reversed, with Steve saving Bucky when he was taken as a prisoner of war. Steve thought he lost Bucky for good when he fell from a moving train in 1945, so he's shocked when his oldest and dearest friend shows up again in 2014 as the Winter Soldier, a Hydra assassin.

Of course, after Hydra's brainwashing, Bucky has no memory of his friendship with Steve, but the same cannot be said for Steve, who is heartbroken to see what has been done to his best friend. During the climactic scene of Captain America: The Winter Soldier, Bucky prepares to fight Steve to the death, but Steve can't bring himself to fight back, dropping his shield and telling Bucky, "I'm not going to fight you. You're my friend."

"You're my mission," Bucky retorts, then screams the words again as he pummels Steve into a bloody mess. "Then finish it," Steve wheezes in response. "Because I'm with you to the end of the line."

Even though we know that's not actually the end of the line for Steve -- and is actually the beginning of Bucky's journey back to the good guys -- it's a truly heart-wrenching moment to see the heroic and kind-hearted Steve get nearly killed by the person he cares about more than anyone in the world.

"I didn't ask to get made!" - Guardians of the Galaxy

Guardians of the Galaxy Rocket Raccoon
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For the most part, Guardians of the Galaxy serves as the wacky comic relief of the MCU, and its kooky cast of misfits are hardly the ones who immediately come to mind when thinking of the franchise's most hard-hitting emotional beats. Yet when Peter Quill (Chris Pratt) attempts to pacify Rocket (Bradley Cooper) after breaking up a fight between him and Drax (Dave Bautista), Rocket delivers one of the most earnest and tragic speeches in the MCU, giving us a glimpse at the immense pain and insecurity simmering underneath Rocket's prickly exterior.

"He thinks I'm some stupid thing!" Rocket yells after Quill tries to placate him by telling him that Drax wasn't making fun of him. "He does! Well I didn't ask to get made! I didn't ask to be torn apart and put back together over and over and turned into some little monster!" When Quill tries to claim that no one is calling him a monster, Rocket shoots back, his voice breaking, "He called me vermin! [Gamora] called me rodent!"

The hurt in Rocket's voice is palpable, and informs everything we understand about Rocket from that moment forward. While at first he comes off as a cavalier loner who doesn't care about anyone but himself and Groot (Vin Diesel), this moment is where we realize that Rocket's personality has been shaped by a long history of abuse, and that he is still carrying the deep scars of intense trauma.

The death of Quicksilver - Avengers: Age of Ultron

Avengers: Age of Ultron Elizabeth Olsen Aaron Taylor-Johnson
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Before Avengers: Age of Ultron, the biggest casualty of the MCU was side character Phil Coulson (Clark Gregg) in The Avengers, and the years-long trend of Earth's Mightiest Heroes being able to come away from every flight with their numbers intact left them with a feeling of invulnerability. That all ended with Age of Ultron, which introduced superpowered twins Pietro (Aaron Taylor-Johnson) and Wanda Maximoff (Elizabeth Olsen), otherwise known as Quicksilver and Scarlet Witch.

Although the pair began the film as antagonists, their consciences eventually moved them to switch sides, teaming up with the Avengers to take down Ultron and his army of robots. They seemed to fit right in with the quippy, flashy style of the Avengers, and it seemed as though they would both be permanent additions to the roster. But that impression was short-lived, with Pietro sacrificing himself toward the end of the film in order to save Clint Barton (Jeremy Renner) and a civilian child.

Although the death of Pietro was already sad, the way it's always sad to lose a fun, promising character to an act of noble self-sacrifice, it was made exponentially more effective by the reaction of Wanda. Despite being nowhere near her brother when he died, Wanda somehow felt his death, either through her powers or through their twin connection, or both. She fell to her knees, screaming in grief, and let out an energy wave that incinerated the foes that surrounded her. Even if the audience wasn't invested in Quicksilver, it's hard not to be moved by such a strong reaction from his sister.

Captain America vs. Iron Man - Captain America: Civil War

Chris Evans and Robert Downey Jr. in Captain America: Civil War
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Steve Rogers and Tony Stark (Robert Downey Jr.) were never the closest friends within the MCU, functioning more as friendly co-workers than best buds, but it still felt like a punch to the gut when they went for each other's throats at the end of Captain America: Civil War. Up until that point, they'd been having what amounted to an intellectual disagreement, superhero-style, with Tony being in favor of the government-backed Sokovia Accords, and Steve being opposed. Sure, they had a massively destructive fight at a German airport, but at the end of the day, they all still seemed to like and care about one another.

But at the end of the film, after Tony learns that Bucky killed his parents and that Steve still wants to protect him, things get ugly. And although Steve seems to still frame their conflict in terms of his loyalty to Bucky, Tony views it as the loss of a friend, making it clear to Steve that he feels hurt and betrayed. When the two fight, it's no longer the playful, entertaining combat of the airport, but one in which they're actually trying to do serious damage. Watching two of the MCU's most iconic and endearing heroes viciously tear into each other is hard to watch, and at the end, when Steve walks away, leaving Tony lying beaten on the ground, it feels like we've all lost.

"I just wanted a sister." - Guardians of the Galaxy Vol. 2

Guardians of the Galaxy 2 Nebula
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Nebula (Karen Gillan) is first introduced as one of the secondary antagonists of Guardians of the Galaxy, Gamora's (Zoe Saldana) adopted sister who is sent by Thanos to subdue her after Gamora goes rogue. Nebula continues pursuing her sister in Guardians of the Galaxy Vol. 2, and catches up with her on Ego's (Kurt Russell) planet, where the two take turns trying to smash each other to smithereens before Nebula declares herself the winner. Gamora accuses her of always being obsessed with winning, and Nebula shouts back, "You were the one who wanted to win, and I just wanted a sister!"

As Gamora tries to process what her sister just said, Nebula goes on to explain that as children, it was Gamora's drive to win that caused Thanos to favor her. He continually attempted to improve Nebula via painful mechanical upgrades in order to make her a match for her sister, instilling in Nebula the belief that she was never good enough for the rest of her family, and leaving her with a relentless drive to prove herself. Like several other entries on this list, the exchange is sad not only because of the pain the characters are feeling in the moment, but because of the lifetime of hurt it exposes.

Peter Parker calls for help - Spider-Man: Homecoming

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Although Peter Parker (Tom Holland) was introduced in the MCU fighting alongside the adult heroes in Captain America: Civil War, Spider-Man: Homecoming drives home the reality that despite his great powers, the web-slinger is still just a kid. Nowhere is this more apparent than following Peter's disastrous confrontation with the Vulture (Michael Keaton), which ends when the villain uses drones to drop an entire warehouse on Peter.

After the Vulture leaves Peter for dead, we see Peter trapped beneath tons of rubble, gasping for breath as metal and concrete presses down on him. At first, he tries to get himself out, but quickly gives up, overwhelmed at the enormity of the task. Peter then begins to cry, screaming for help even though he knows no one is likely to hear, and even if they do, there's not much they could do to help. It's the reaction of a kid stuck in an impossible and overwhelming situation who just wants an adult to intervene and make things better, and it's heartbreaking to know that no one is listening. Of course, moments later Peter goes into Spider-Man mode and is ultimately able to free himself, but for those few moments when he's just a trapped child begging for help, it's absolutely gutting to watch.

Erik and N'Jobu reunite - Black Panther

Black Panther Sterling K Brown
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There are a lot of reasons why Black Panther can be an emotionally draining watch, especially in the wake of Chadwick Boseman's tragic passing at the age of only 43. Yet while many of T'Challa's scenes carry tremendous weight both apart from and within the narrative, it is the scenes featuring his rival, Erik Killmonger (Michael B. Jordan), which wind up being the saddest within the context of the film itself.

One of the most resonant Killmonger scenes follows his defeat of T'Challa, when he takes the heart-shaped herb and enters the ancestral plane himself. There, he returns to his childhood home and the scene of his father's murder. Soon, N'Jobu (Sterling K. Brown) shows up too, and Erik reverts back to a child himself in the presence of his father. The two talk about being unwelcome in the place that should be home, and about death being an inevitable part of life. The short but heavy conversation leads to tears from both of them as they wrestle with loss and regret, even as Erik returns to his tougher, adult form. The reunion lasts only a couple minutes, but it is loaded with deep sadness, the intimate grief of a broken family coupled with the broader tragedy of an unjust world.

"Bury me in the ocean." - Black Panther

Black Panther Ending Michael B Jordan
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One of the great triumphs of Black Panther was how, unlike most MCU films, it managed to humanize its villain just as much as its heroes, making his eventual defeat and death feel more like a loss than a victory. Although we spend the film rooting for T'Challa, it's hard not to sympathize with Killmonger's cause, if not his methods. T'Challa seems to agree, and after stabbing his cousin in the stomach during their final battle, he helps him outside to see a Wakandan sunset. There, T'Challa offers to attempt to heal Erik using his advanced technology, but Erik declines, offering these as his poignant final words:

"Bury me in the ocean, with my ancestors that jumped from ships, because they knew death was better than bondage."

T'Challa's reaction to Killmonger's death is not one of celebration, but of grief, as he respectfully kneels beside his cousin's body and crosses his arms over his chest. It's a scene that not only drives home the inherent sadness of the loss of a sympathetic character, but also the profound tragedy of the centuries of racial injustice that led him to taking such extreme measures.

The casualties of Thanos' search for Infinity Stones - Avengers: Infinity War

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While it's the end of Infinity War that immediately comes to mind when considering the film's high body count, the carnage begins in the very first scene, with a truly devastating loss. Following the destruction of Asgard at the end of Thor: Ragnarok, Thanos (Josh Brolin) boards the survivors' ship and kills half of the refugees. He spares Thor and Loki, thinking they can lead him to the Tesseract, and Loki seems as though he may be willing to go along with Thanos' plan -- but then turns on him, attempting to assassinate the Mad Titan. Unfortunately, Loki's attempt is thwarted, and Thanos brutally chokes him to death as a distraught Thor looks on. Before Loki dies, he claims the name "Odinson" for the first time, looking Thor in the eye and showing just how far he's come since his introduction, making his loss that much more devastating.

Later, when Thanos is told he has to give up something he loves in order to acquire the Soul Stone, he brings his daughter, Gamora, to Vormir to act as his sacrifice. Upon realizing what Thanos plans to do, Gamora laughs, thinking that because Thanos doesn't truly love her -- or anyone, for that matter -- that he won't be able to get the stone. To her horror, that doesn't stop Thanos from throwing her off a cliff, killing her. It's an unceremonious end for a vibrant character, made that much worse by the fact that she dies knowing that her "father" was willing to kill her in order to enrich his own power.

"You could never hurt me." - Avengers: Infinity War

Paul Bettany and Elizabeth Olsen in Avengers: Infinity War
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Although Infinity War is filled with fallen heroes, only one is taken out by a fellow Avenger -- and one he loves, to boot. During the final battle, when Vision (Paul Bettany) realizes that the Infinity Stone in his forehead is all that stands between Thanos and unlimited, universe-annihilating power, he asks his girlfriend, Wanda, to destroy the stone, which he knows will kill him in the process. At first, Wanda refuses, but Vision pleads with her, telling her that she won't hurt him, and echoing back her words from earlier in the film: "I just feel you."

Weeping, Wanda unleashes the energy beam that will destroy the stone. Right up until the moment that it shatters, Vision continues to reassure her, whispering, "It's all right. It's all right. I love you."

It's the only time in the MCU that we've seen a hero forced to kill someone they love, and even in a movie that wipes out over half its cast, it stands out. Between Wanda's unbridled grief as she tries to break the stone, and Vision's valiant attempt to make it as easy as possible for her, the moment feels almost unbearably unfair and painful -- made even worse when, moments later, it's revealed that it was all for nothing.

"Mr. Stark, I don't feel so good." - Avengers: Infinity War

avengers-infinity-war-spider-man-death
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Superhero movies have been around for decades, but it wasn't until Infinity War that one had the nerve to end with the deaths of over half of its heroes. Following Thanos' snap after obtaining all of the Infinity Stones, audiences and Avengers alike looked on in confused disbelief as some of the MCU's most popular characters disintegrated before our eyes, including Black Panther, Star-Lord, and Doctor Strange. But probably none of the deaths at the end of Infinity War hurt quite so much as the loss of Peter Parker, whose Spidey-sense gave him a few extra seconds to realize that something was very, very wrong before he started to disappear.

After telling his surrogate father-figure, Tony Stark, that he doesn't feel good, Peter collapses into his arms, crying as he pleads, "I don't want to go," over and over. Tony's shell-shocked reaction, and the stunned silence of the surviving Avengers back on earth, were echoed by everyone watching the film, who had never expected to see the MCU go quite that dark.

"You're so big." - Avengers: Endgame

Avengers Endgame Scott Lang Cassie
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Although one could argue that the reunion between Scott Lang (Paul Rudd) and his daughter Cassie (Emma Fuhrmann) in Avengers: Endgame was more bittersweet than sad, there was something profoundly heartbreaking in watching Scott silently process that he'd missed a huge chunk of Cassie's childhood. The moments leading up to his hug with Cassie are also filled with tension, as Scott frantically searches the memorials of the dead for his daughter's name, but it's not until he has her in his arms that the full impact of what's happened finally hits.

At first, Scott just appears stunned at the sight of his teenage daughter. But when they embrace, and she can't see his face, we can see so much more play out on his face. Along with his relief that she's alive, Scott's face wrinkles with deep grief at what he's missed, and at what he could have lost. But when she looks at him again, he quickly smooths his expression and offers her a brave smile, trying to make the moment easier for her even though we can tell how hard it is for him. "You're so big," he exclaims, pulling a sob-infused laugh from Cassie. It's a tender and ultimately uplifting moment, but there's an undercurrent of sadness that can't be ignored, made all the more effective by the fact that we're not used to seeing Scott play serious scenes, so this one hits hard.

Two original Avengers fall - Avengers: Endgame

Avengers Endgame Vormir Hawkeye Black Widow
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It feels almost disrespectful to combine these two into a single entry, but the truth is that Natasha Romanoff (Scarlett Johansson) and Tony Stark both sacrificed themselves in the same movie, in pursuit of the same goal, so it's fitting to talk about them together. Natasha (a.k.a. Black Widow) met her end on Vormir, on the same cliff where Gamora was sacrificed in Infinity War. But unlike Gamora, who was thrown to her death against her will, Natasha duked it out with her best friend, with each of them fighting to save the other from a rocky end. Ultimately, Natasha prevailed, assuring Clint that it was okay before she fell to the rocks far below, all in the name of obtaining the Soul Stone that would allow them to reverse what Thanos had done.

It's because of Natasha's sacrifice that Bruce Banner (Mark Ruffalo) is able to bring back everyone that was killed at the end of Infinity War, and that Tony is ultimately able to steal all of the Infinity Stones from Thanos and wipe out his armies, once and for all. After defeating Thanos, Peter Parker, James Rhodes (Don Cheadle), and Tony's wife, Pepper Potts (Gwyneth Paltrow), all gather around the fallen Iron Man, offering him love and support as he gradually fades away. "We're going to be okay," Pepper tells him bravely, referring to herself and their daughter, Morgan. "You can rest now." It's only once Tony is gone that she allows herself to cry.

While only Tony got an on-screen funeral, the losses of both him and Natasha were profoundly felt by long-term fans who had followed these characters for years. They're by far the most significant deaths in the MCU to date, and will no doubt continue to be felt deeply in future films.