The 14 Most Heartbreaking ‘Grey’s Anatomy’ Episodes To Watch If You Want To Ugly-Cry

ABC/Byron Cohen

Grey's Anatomy is a show that often seems made for the sole purpose of making you weep. And I'm not talking about a single tear shed quietly during a somber moment — I'm talking about actual crying that requires tissues and at least three glasses of wine. Throughout its lengthy history, the most heartbreaking episodes of Grey's Anatomy have emotionally devastated viewers more than they've been prepared for.

Fans of the show have been blessed with some of the most romantic and heartwarming content ever aired on television, but they've also seen death, destruction, and heartbreak in equal, if not more plentiful, measures. Grey Sloan Memorial Hospital can be a place where dreams come true and where lasting relationships are built, and it can also be the place where hope comes to die. It's the luck of the draw on any given episode which of these you'll encounter, so you'd better be ready for whatever's coming down the pike.

But if you're in the mood for a good cry, and to spend your afternoon bundled in a blanket, reliving all the ways Grey's Anatomy creator Shonda Rhimes has hurt us over these past 14 seasons, buckle up and take a peek at some of the most difficult episodes you can cry through.

1. "Losing My Religion" — Season 2, Episode 27

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Denny Duquette and Izzy Stephens were going to get married, and probably live a long and happy life together, but in true Grey's fashion, that is ripped away at the most distressing of times. Izzy goes through so much to save Denny, who has a bad heart — even though she probably should've been fired for half of it — and it ends up being all for nothing.

2. "Didn't We Almost Have It All?" — Season 3, Episode 25

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Cristina Yang was such a cold, hardened badass on the surface that it made her few moments of weakness even more staggering. In this episode, she's left at the altar by Burke, which is sad enough on its own. But then, right before she begs Meredith to rip her out of the wedding dress that seems to be suffocating her, she says, "I'm free." Her subsequent sobs seem to both mourn the loss of Burke and celebrate the relief of being unburdened from a marriage she might not have wanted too much to begin with.

3. "Now Or Never" — Season 5 Episode 24

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If this episode doesn't shoot straight to the top of your mind when thinking about the most heart-wrenching episodes of Grey's Anatomy, then it's very possible you have no soul. After half the episode features Grey Sloan doctors attempting to figure out the identity of the mystery patient who's been hit by a bus, viewers and surgeons both realize who it is in one swift kick to the gut. It's George, sweetheart of both America and the hospital, and he ultimately meets his demise as the episode draws to a close.

4. "Death and All His Friends" — Season 6, Episode 24

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The hospital shooter episode of Grey's Anatomy was probably one of the most jarring hours of television ever aired. It is unexpectedly bloody, and takes the lives of several doctors. Not only do viewers see Cristina operate at gunpoint on Derek after he is shot, but they also see Bailey desperately trying and failing to save the life of Percy, who's also taken a bullet.

5. "That's Me Trying" — Season 7, Episode 7

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The arc of Richard's first wife, Adele, is one of the series' most poignant and realistic, but it's often overlooked in favor of flashier, more shocking storylines. But this episode, as Adele is in the throes of Alzheimer's disease and begging Richard not to dismiss her as a burden, really will rip your heart out.

6. "Dark Was The Night" — Season 8, Episode 9

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Teddy and Henry are the most underrated couple in all of Grey's, and frankly, I will not stand for it. The two initially got married because Teddy had fantastic insurance and Henry was struggling to pay for the treatments that were keeping him alive, but the love that comes after is anything but a ruse. They are finally living a happy, domestic life, and suddenly his health takes a turn for the worst. Even more twisted is the fact that Cristina, Teddy's prodigy, is unknowingly operating on Henry when he dies, and they have to lie to Teddy about his condition so as not to compromise a surgery of her own. She doesn't find out until near the end of the next episode that her husband is dead.

7. "Flight" — Season 8, Episode 24

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In this Season 8 finale, Grey's Anatomy takes the catastrophe to a whole other level. Meredith, Derek, Lexie, Mark, Arizona and their plane's pilot crash in the middle of the wilderness, and the chaos that ensues cost some of them dearly. In perhaps the most heartbreaking moment, Mark stays by Lexie's side and holds her hand as she nears her final breaths, telling her that he loves her and that she's going to make it through. If only.

8. "Going, Going, Gone" — Season 9, Episode 1

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Shonda Rhimes has been responsible for a lot of trauma in my life, but this one takes the cake. After Mark Sloan seems perfectly perky following the plane crash that took Lexie's life and Arizona's leg, he abruptly falls into a coma from which he never awakes. Callie, Derek and the rest of the hospital are wrecked, and it is made worse by the fact that flashbacks of Mark are peppered throughout the episode. Honestly, how dare they?

9. "Things We Said Today" — Season 9, Episode 10

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Never forget that Richard Webber shows up to Miranda Bailey's wedding just after losing his wife, because he knows he has to be there to support her. This shot of Richard crying, silently mourning the love of his life at a time when no one is there to comfort him, will forever be one of the most difficult moments of Grey's Anatomy.

10. "All I Could Do Was Cry" — Season 11, Episode 11

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April and Jackson knew that something troubling was happening with April's pregnancy a few episodes before she was actually set to give birth, but that didn't soften the blow of this hour. The couple makes the decision to have the baby and cherish it for the very little time they'll have, even though they know it won't survive long. Jackson tries to embrace God in a last-ditch effort to help April, the other doctors light candles in the chapel, and they are eventually able to say a proper, devastating goodbye to little Samuel.

11. "How To Save A Life" — Season 11, Episode 21

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Even if you're not a rabid Derek fan like much of the fanbase, you'll still be in pieces after this episode. The avoidable death, the monologue outlining how the doctors at a foreign hospital were failing him, Meredith's reaction — all of it swirls together in a blur of an episode, and viewers are suddenly left without one of the longtime staples of the show.

12. "'Be Still, My Soul" — Season 13, Episode 18

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Maggie's character and her trauma really come through in this episode, as she struggles to let go of her dying mother. The two share a somber final scene as Maggie paints her mother's nails, finally accepting that there isn't much else to be done, and her mother tells her what she hopes for the rest of her life.

The moment when Maggie realizes she's gone after getting up to open a window and returning to the bed will truly rip your heart out, and it's made even more heartbreaking when she continues to paint her mother's nails in silence.

13. "One Day Like This" — Season 14, Episode 17

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In this episode from the most recent season of the show, April is helping to treat Rabbi Eli, a wise and holy man who gives her exactly what she needs in that moment. April's still grappling with her relationship with God, and what Eli gives her with his final breaths is chilling. She gives him companionship and allows him to fulfill his purpose — helping people — right up to his end, and he gives her the kick she needs to see good in the world again.

14. "Cold As Ice" — Season 14, Episode 23

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As April lies unconscious on what might be her deathbed, Jackson sits beside her bed and says that he knows she's still in there. He cries and tells her that he believes in her, and believes she can come back. He then turns his words to God — one that Jackson has traditionally not even believed in — and promises to do anything if April is saved. Again, how did they not end up together?

This is certainly not even close to an exhaustive list of heartbreaking Grey's episodes — I could fill a book with moments from throughout the show's run that will have you dissolving into a puddle of tears — but these stand out from the pack in terms of sheer sadness and shock. Luckily, the show isn't all doom and gloom, though it can sure seem like that sometimes. Grey's Anatomy uses its characters' pitfalls to show just how hard they can bounce back, no matter how much pain they (and the viewers) endure along the way.