Look, Gandalf makes me cry a lot. Probably more than anyone else in the legendarium, and that’s saying something. Plus, I’m just a person who cries a lot, so while some of these I’ve only cried about once, or even just in spirit, some of them I’ve cried about every damn time. There’s no order to these, though a few of them are definitely grouped together for a reason, and I’m sure I’ll, at least, be a crying mess by the end of this, so get your tissues ready!

I mean, duh. Has anyone ever not cried when Gandalf falls with the Balrog? Everything is primed for it–we think he’s just done something wonderful, and then the whip comes back up, Frodo is screaming, Aragorn looks absolutely dumbfounded, the music starts getting all sorrowful, and it’s just the worst. This could, of course, also be one of my favorite Gandalf is a badass moments, but yeah, it gets me every time when he falls. I still remember just absolutely sobbing in the theater, and my dad leaning over to be like, “Have you read the second book yet?” YEAH DAD BUT IT’S STILL SAD.

This is more post-battle that makes me cry. Gandalf has gone through so much, way more than we even see in the trilogy, and the fact that he has to go up against a Balrog is bad enough, but then that he also has to die fighting it? It’s heartbreaking. No one deserves the pain that Gandalf goes through, least of all him, and I hate so much that he falls fighting a Balrog after all he’s already witnessed and managed to survive.

Art by Marta
Look, every time I think about this piece of art, I just burst into tears because it’s not fair! All Gandalf, when he was still Olórin, ever wanted was to live peacefully with Lady Nienna, to tend to her magic and the world around her, to live within the quiet circle of her beauty & glory. And yet, he needs to be sent to Middle-earth because no one else is capable enough to do the job that the Istari need to do, and it’s just the worst.

Not to mention then he has to do it all over again?? I call bullshit. I mean, sure, the only worst thing I can imagine happening is Gandalf not coming back to continue to help everyone, but it absolutely breaks my heart that he has to leave the peaceful land of the Valar again. It’s bullshit, I tell you.

Art by Alexandra
And, of course, I cry every time he finally gets to go home. In my head, baby!Olórin is slowly surfacing in Gandalf just like LADY NIENNA I’LL BE RIGHT THERE DON’T WORRY! His face of utter peace in the Grey Havens is more of a relief grey because finally, after not only everything we’ve seen during the War of the Ring, but all the trauma and chaos of the Second Age, finally, Gandalf gets to shed his worldly troubles and go back home.

I know it’s coming every time, but as soon as Helm’s Deep starts to feel hopeless, I’ve got this bubble of emotion just rising up in me, and by the time this scene finally hits, my dad and I are practically screaming, “Look for coming on the fifth day, at dawn, look to the east!” We’re such nerds, and I love it, and I will never not weep with pure excitement every time I see Gandalf crest that hill.

I think, honestly, this one is more of a music moment for me, but also, just seeing Gandalf’s incredibly powerful goodness piercing through Sauron’s shadow as he rides out to save the men from Osgiliath is beautiful. Because that is, at the end of the day, what Gandalf’s magic is. Just as Sauron’s storm is a manifestation of his darkness, the light pouring out of Gandalf’s staff, that makes even the Nazgûl turn away, is a manifestation of his good heart, and that just gets to me.

Art by Valerio Buonfantino
Perhaps one of the worst evils in the world is discovering your best friend is not who they say they are, and realizing that you no longer want them in your life. Friendship breakups are the hardest thing in the world to experience, and I feel for Gandalf so much when he finally sees the truth of Saruman. Because honestly? Saruman is probably Gandalf’s oldest friend, and dearest in a lot of ways, and having to come to terms with the fact that his best friend is no longer someone he can trust–that’s got to hurt in the worst sort of way.

Art by sydsir
Another kind of horrible friend thing for Gandalf would definitely be discovering that Bilbo probably has the ring. Sure, he doesn’t actually confirm that until it’s in Frodo’s hands, but there’s this niggling doubt for several long years where Gandalf knows that’s what’s happened, even if it hasn’t confirmed it, and I can’t imagine what that must feel like for him, to know that he dragged Bilbo into this mess he’d created in trying to not allow Sauron to have an allegiance with Smaug, and now the worst thing in the world has come to the least-deserving person. Gandalf was trying to turn the tides of an eventual war, and, in doing so, he unknowingly put one of his oldest friends in terrible danger, and that must have just broken his heart.

And, finally, following the same kind of path, I think Gandalf probably comes to the realization that he’s sending Frodo to his potential death several times over the course of the trilogy, but this one must be the worst. Frodo is so trusting, and still so innocent here, even if the ring has begun to weigh on him, and he’s always going to look to Gandalf first. And, knowing that, and knowing all that’s to come, must be a burden in and of itself for Gandalf. Because he knows that this task must be done if they’re all going to survive, but what he wouldn’t give for it not to be done by this sweet little hobbit that he loves so dearly.
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