I don’t really find stuff sad because my heart is pretty much made out of bricks but the anime adaptation of “CLANNAD After Story” was the only anime that made me tear up. Nagisa and Ushio’s deaths scenes was the saddest shit ever.
Kanon, CLANNAD, Rewrite…
I have to go with CLANNAD.
Kanon was beautiful in my opinion, and underrated. Every route made me question things about our everyday stuff, the things we take for granted. Kanon made me realize to love the people/things we take for granted, cause sooner or later, you’d loose it. Not to mention how beautiful every route was.
Rewrite was beautiful as well. The fight scenes didn’t help my emotions much, but I found the route’s just horrifying to watch. Shizuru’s route, Kotori’s, Akane’s, etc. I found Rewrite routes to just be beautiful, showing the struggle, and strength of each heroine.
And CLANNAD. CLANNAD was beautiful to me. Every route helped the storyline, even if it wasn’t relevant, you should still tell that it helped the storyline because of what appeared. The routes had to do with family too, which I find beautiful, other than the Katsuki thing, and Kappei. CLANNAD made me feel “Feels” in each and every route.
Now for the others
Air - Well, it was confusing and had too much symbolism for me. I also thought that the routes were irrelevant to to story. Even if they might have been relevant.
Planetarian - Who doesn’t love Yumemi ? I found the storyline as beautiful, but sadly, I found myself bored reading the first half of the story since it had to do more with fixing Gena and looking at stars.
Tomoyo After - I agree with Takafumi. It did teach you how important life was, enjoying life to the fullest. I gotta say though, the music in it was just beautiful. I think it was better than CLANNAD music in my opinion.
Little Busters! - Eh. I found Haruka’s, Yuiko’s, and Refrain the only routes worth reading. Most of the stories didn’t help the plot much.
Little Busters! - EX. I liked, the same routes again, since it was modified, and Saya’s and Kanata’s as an add on. I think their routes were good, expanding more into the plot/route.
Kud Wafter - Haven’t read it. Seems boring, not a fan of Kud’s interest and backstory.
Rewrite Harvest Festa - Not sad. Seems more like a happy add on for a fan disc.
Angel Beats! - It is sad, the overall plot, but I don’t think anyone wants to know all the SSS member’s backgrounds. You’ll loose interest pretty fast if you decide to explore all the back stories. But it did have a good message, for portions of it.
Harmonia - Haven’t played it. The plot seems nice though. Not to mention the ED 
Charlotte - Eh. I won’t say too much until all the episodes come out. So far though, it seems like it’ll be very sad, considering if you look at the back stories.
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I’d have to with air. Misuzu is just so innocent, yet at the same time she tries so hard demonstrating her strong spirit and soul, but even so she passes away. Her death impacted me more than any other key character
@Kotarou I agree that Kanon is one of the most beautiful key stories and is overflowing with deep messages, however it was never really excruciatingly sad. Shiori’s route was pretty sad, and Makato’s almost made me tear up but overall I woudn’t say it was as sad as Air or Clannad
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Well, I guess, but I found the routes as sad. Considering some routes even related to people. Other than Makoto’s since, yeah.
I’d have to go with Little Busters! although that might not quite be fair, because Little Busters! and Planetarian are the only Key VN’s I’ve read (the rest I’ve just seen the anime). I’m expecting CLANNAD to take the ‘saddest’ slot after I read it when SP’s translation comes out.
But yeah, Haruka’s route, and the end of Refrain though…
That feel when you look at the poll results and planetarian is the only one that ISN’T capitalized…
But anyways I voted Clannad because I watched the anime first and the field scene just hit me so hard. I can’t explain all that much on why but that was the only time I cried and I can’t cry to anything else. I feel like Little busters would have been sadder if I played the vn before the anime but since I watched the anime and knew the secret of the world and all that stuff it just didn’t hit me as hard.
Yeah, Key are a bit weird with titles…
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Oh wait really? I thought it was OP’s mistake
I don’t make mistakes.
Especially not when it comes to planetarium.
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I voted for Air
Which is weird, because Air is the only Key work that didn’t make me cry.
I mean, Air has some dark twisted stuff happening to the characters which I find quite tragic. And the ending isn’t happy, unlike the rest. It just didn’t make me emotional like the other Key works did.
As far as most emotional, I’d definitely say Clannad, then Angel Beats!. But AB! is sadder than Clannad.
Planetarian is also sad but not very emotion-inducing (for me, anyway…).
Little Busters! has lots of sadness but turns out happy… It didn’t make me super emotional though, which I am blaming the anime for.
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I have to go with CLANNAD.
CLANNAD taught me so much about life. How we should appreciate the things we have because not everyone has it. It taught me to not have regrets. Regrets are something that you cannot change, but something that you can overcome. CLANNAD taught me to have hope for the future, how with everyone struggling, we’re here today, living in this beautiful world.
CLANNAD for sure, has one of the best writings and quotes. One of the most beautiful things I’ve ever read. Every route was filled with despair, and the execution of the routes itself made me bawl.
One other news, who voted for Harmonia ? 
Rewrite is my favorite Key VN but I have to go with Little Busters, it still hits me whenever I remember it, I can’t wait to replay the steam ver
CLANNAD and Little Busters are both generally more heartwarming than sad - there are intensely sad moments in both but generally those are resolved in a manner that is almost entirely positive with no bittersweetness to be encountered.
IMO it’s between Planetarian and Tomoyo After, and I think Planetarian edges out Tomoyo After by just a bit. There was almost never a hopeful moment in Planetarian - its a setting of absolute despair and its ending doesn’t do anything to make that feeling any better. Little Busters was the hardest hitting to me, but the saddest? Not by a long shot.
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It was a pretty hard decision, seriously. Key works are ALL sad.
I decided to exclude those that seemed the least likely to be the saddest. Well, I can’t judge those I haven’t read already so to me, it’s neither Kud Wafter nor Harmonia. Was Charlotte even sad? Oh right, there is the deaths of Ayumi and that long haired guy who’s always drenched whoes name I forgot but it’s not like deaths are inexistent in other Key works… Planetarian was sad but the only sad part was Yumemi getting broken so I can’t say that it’s the saddest. So, definitly not Planetarian or Charlotte. Kanon was sad… kinda… So was Air but… I can’t get myself to call either of these two the saddest. They are the only Key works that didn’t even make me feel like crying. Rewrite was pretty sad (Uuuu… Sakuyaaaaa, Esakaaaaa, Kotarouuuu) but it felt like the “sad” part wasn’t… important? Nah, it was definitly important but when Rewrite is mentionned, the sad parts just don’t come to me first and I need to particularly remember them to feel like crying… All I can say is that it didn’t feel like the saddest of them. Angel Beats has a pretty sad story but I only watched the anime which didn’t feel all that sad. I expect that the VNs would be WAY more sad but I have yet to read them. Tomoyo After was pretty sad but calling it the saddest wouldn’t feel right to me so I’ll just exclude it.
And so… That leaves me with two VERY hard choices: Clannad and Little Busters. They were both really sad and the closest to make a tear fall from my eyes (I’m not the type to cry because of a story). However, I’ll go with Clannad. Why? Refrain in Little Busters was definitly the saddest route of all Key. However, except for Haruka’s and Kurugaya’s routes (I haven’t read EX so I don’t know about the EX routes), the heroines’ routes weren’t sad, at least, they wouldn’t compare to Clannad’s routes that were almost all equally sad and heartbreaking. So, yeah, Clannad’s the saddest for me.
…How many times have I written the word sad I wonder… I’m too lazy to count.
This topic is heavily subjective, so I’m voting for AIR. The exact memories of it aren’t too recent in my mind, but I remember suffering a long, deep period of sadness when reading it. Maybe, for me, it wasn’t the best Key story. It was also so symbolic that completely understanding the basic themes beneath the entire story is almost impossible without external help. However, for me, reading AIR has been the saddest experience with a Key work. Two main causes of it:
-Nostalgia: The entire VN was soaked by nostalgia. Maybe because of the location, maybe because of the music (that relaxing guitar song that sounded sometimes still has a place in my heart) or maybe because of the MC’s attitude, but almost at every time, when reading AIR, I had the same feeling that you had when remembering a happy summer, in your childhood, which was better than the one you’re currently living.
-Sad stories: without getting into much detail, it felt like reaching something similar to a relatively happy ending was a miracle, both in the heroine routes and the common ones.
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After some consideration I’ve changed my vote to planetarian. Of all of the Key VN’s I’ve read, they have sad parts but the fact that planetarian has an ending so devoid of love is too powerful. The Junker tries to hold onto hope by literally holding onto Yumemi’s memories but there is no guarantee he will ever be able to use them. There’s a tiny sliver of hope but planetarian’s ending is, overall, negative. Clannad and Little Busters! made me cry way more than planetarian did (partially due to length) but for both I was smiling by the end.
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Even though clannad is my personal favorite, the one which made me cry is little busters. The story was already so sad was combined with the sad soundtrack it felt like someone was chopping onions beside me.
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Personally, the saddest would be Air, followed by Kanon, Planetarian and then Clannad. My favorite is Little Busters! because while it didn’t bring as much sadness to me it did shake my emotions more and made me cry like a baby.
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Personally, I would say that Kanon or CLANNAD have the saddest stories, but I still voted for CLANNAD in the poll above because it is the only series so far that actually made me cry while watching.
Remembers (CLANNAD spoilers) Nagisa and Ushio dying
Narrative voice : And so formed the Pacific Ocean…
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Little Busters has the most votes? Why is that?
