Aatrox - 10/10; Aatrox is very frequently miserable over his existence, but the line between sad and angry is blurred, and he fluctuates between both. He also wants to kill everything. Oof.
Ahri - 5/10; Ahri has lots of regret, but she's doing her best not to make so many messes. It gets hard sometimes, but I think she can do it.
Akali - 2/10; Akali is more bratty than sad, but she does get upset sometimes at her former friends and the overall state of Ionia.
Alistar - 2/10; Alistar is definitely more angry than sad over what happened in his past, but there's a tinge of remorse there as well.
Amumu - 12/10; the saddest boy. He needs a hug.
Anivia - 4/10; Anivia is the "motherly" sad type: less sad over what happens to her as much as what happens to the people she cares about. A lot of shit is happening.
Annie - 3/10 (6/10); a little girl with dead parents and only a teddy bear for company is pretty sad. Annie is just too young to fully process what happened.
Ashe - 5/10; Ashe has had some dark things happen to her, but she channels her sadness into determination rather than wallowing in it.
Aurelion Sol - 4/10; he wouldn't admit it, but Aurelion's only joy is creating and observing his creations. He doesn't like the way things are going.
Azir - 0/10; any regret Azir may have had has been replaced with motivation to restore Shurima to its former glory.
Bard - ?/10; it's Bard, who can say? I don't think he's "sad" so much as "befuddled with everyone's stupidity".
Blitzcrank - 0/10 (2/10); Blitzcrank is a robot, so he technically shouldn't be sad. However, since he's a helpful boy, he has some sad hours in him as well.
Brand - 0/10 (7/10); oof, a mess. Brand isn't called "the Burning Vengeance" for nothing, but Kegan definitely counts as a sad boy.
Braum - 1/10; just a dash of sadness for Braum, but it's more out of compassion than anything else.
Caitlyn - 0/10 (2/10); Caitlyn has some regrets, but she puts up a façade of kinkiness and formality to hide it.
Camille - 1/10; Camille won't admit a thing, but she's just too old not to have had bad things happen. She doesn't dwell on them.
Cassiopeia - 7/10; Cassiopeia goes from murderous to miserable pretty easily, but she's been slowly getting used to her new form. Probably still cries herself to sleep.
Cho'Gath - -10/10; Voidborn don't feel sadness. Cho'Gath probably loves it, because he's a bastard.
Corki - 0/10; just a flying meme, really.
Darius - 5/10; Darius is a regretful lad, but he tries his hardest to control his emotions. It's a combination of "Men don't cry," and "No daughters, only soldiers."
Diana - 7/10; sad, angry celestial vessel with unrequited emotions. Diana feels pretty shitty most of the time.
Dr. Mundo - 0/10; can he even feel sadness? Does he know what it is? These are the questions that keep you up at night.
Draven - 0/10; what reason would Draven have to feel sad? His life is pretty swell as it is.
Ekko - 5/10; sad boy with dead friends. There's more to Ekko's technology than genius: he wants to turn back time for a reason.
Elise - -10/10; Elise is an evil bitch.
Evelynn - 2/10; ironically for ~~such a whore~~ a demon, Evelynn's existence is pretty depressing. She doesn't like sad people, and she definitely wants to be alive. She gets no sympathy from me, though.
Ezreal - 2/10; meh. Ezreal isn't a sad boy (but I'm sure he'll cry when Lux rejects him). There's also that thing about his parents...
Fiddlesticks - 0/10 (8/10); Fiddlesticks had a sucky life and a suckier death. However, he's a bit of a birdbrain now, and sadness is beyond him.
Fiora - 3/10; Fiora puts up a stern face, but it's clear that the burdens of nobility are weighing heavy on her. Luckily (for her), she's also a stuck-up bitch.
Fizz - 1/10; annoying little shit. He did watch a civilization disappear, though.
Galio - 5/10; Galio can go between "bright and heroic" to "melancholy and existential" fairly easily, but he prefers not to project his uncertainties onto other people.
Gangplank - 2/10; Gangplank did a lot of bad things to get to where he is, and I think he may even regret some of them. Breaking up with Illaoi has taught him something important.
Garen - 4/10; it's not all sunshine and rainbows for the Crownguards. Garen does his best not to let it show, but he has quite a lot of concerns about certain things.
Gnar - 0/10; not mature enough to feel sad.
Gragas - 0/10; too drunk to feel sad. May catch up with him later.
Graves - 7/10; prison isn't a nice place to be stuck in. It only gets worse when your "best friend" betrays you. Graves is a man with lots of regret.
Hecarim - 0/10; Hecarim is too stupid and bloodthirsty to feel sad (~~unless he betrayed Kalista out of some twisted love?~~).
Heimerdinger - 0/10; emotional reactions are an obstacle in the way of technological progress.
Illaoi - 1/10; Illaoi might get a little bit sad sometimes. A _very_ small bit.
Irelia - 6/10; oof, girl's went through a lot. Getting thrust into a position of leadership and being forced to fight in war at her age was definitely not good for her mental health.
Ivern - 1/10; just the tiniest tinge of melancholy for his old, barbarian self. Otherwise, Ivern is really positive.
Janna - 4/10; Janna is like Anivia, and human emotions and belief can impact her. She really does want to help as best as she can.
Jarvan IV - 3/10; heavy is the head that wears the crown. Jarvan has some issues regarding his friends, family and countrymen. He luckily has a girlfriend to help him get through it.
Jax - 5/10; Jax tries not to let it get to him with his boisterous attitude. The loss of his people says "no".
Jayce - 1/10; he's a jerk, but he means well. Not very sad, though.
Jhin - 5/10; his entire life is sad, and he may even recognize it on some level. However, he can't do anything about it.
Jinx - 0/10 (6/10); Jinx is a mess, but her mental state has deteriorated too much for her to be able to acknowledge it.
Kai'Sa - 5/10; trauma and more trauma, but Kai'Sa is the kind of person not to let it get to her. She's been doing fairly well so far.
Kalista - 8/10; Kalista could use a hug, she went through a lot. Of course, she very rarely gets to remember her former self.
Karma - 3/10; depends on the incarnation. Karma is good at not letting her sadness get the better of her. Must be the meditation.
Karthus - -10/10; Even when he was still human, Karthus was weirdly fine with all the starvation and dying. As a lich, he probably can't feel sadness. But damn if his songs aren't depressing (~~and beautiful~~).
Kassadin - 7/10; daddy misses his little girl. He's going his best, but no one is made of iron (except Mordekaiser, but he's an asshole).
Katarina - 4/10; Katarina has daddy issues (maybe Kassadin should adopt her?). It doesn't help that she's a mess when it comes to romance.
Kayle - 4/10; I know what you are beneath your armor, Kayle: bothered by regret and doubt far more than you'd like to admit. You even miss your sister, don't you? You can't deny your humanity forever.
Kayn - 0/10 (7/10); child soldier, Darkin wielder, ~~gay~~, and a disaster all around. Kayn has "lots of feelings". Rhaast is having the time of his fucking life, though.
Kennen - 0/10; electric furball is trying to emulate Shen. I'm not sure how well it's working out for him.
Kha'Zix - 0/10: Voidborn don't feel sadness. Again.
Kindred - 2/10; Lamb is melancholy and Wolf is a mood swinger, but they aren't really sad. They have each other, after all.
Kled - -10/10; it's Kled.
Kog'Maw - 0/10; Voidborn don't feel sadness. _Again._
LeBlanc - ?/10; it's LeBlanc, so who knows? I think she may have actually forgotten how to be anything other than manipulative (~~and turned on by men who are smart like she is~~). On the other hand, who knows what regrets she's hiding...
Lee Sin - 1/10; Lee Sin doesn't seem to think dragons should feel sad. He looks pretty stable to me ~~when he's not setting himself on fire~~.
Leona - 4/10; homosexuality strikes again. You wouldn't think the Sun, of all celestial objects, could feel down. Well, you'd be wrong.
Lissandra - 1/10; crippled, old, and still not over her existentialist friends. Lissandra has regrets, but getting through to them is a challenge.
Lucian - 7/10; Lucian's wife is dead. Did you know?
Lulu - ?/10; it's Lulu.
Lux - 6/10; oh boy. Lux has problems, that we know. She tries not to show them, but sometimes it's pretty hard (thanks, Sylas).
Malphite - 0/10; another helpful boy. He just wants to protect you. He even likes the Voidborn.
Malzahar - 0/10 (10/10); too insane to be sad, too suicidally depressed not to be. That's rough, buddy.
Maokai - 7/10; Maokai is a very sad and very angry tree. Considering what happened to his home, which was once a paradise on earth, I can't blame him.
Master Yi - 5/10; Yi is both the last practitioner of Wuju and an Ionian, which puts him in a rough spot. Being Wukong's tutor doesn't help. ~~I also couldn't bother to read his short story again.~~
Miss Fortune - 6/10; Sarah is made of trauma and revenge, which means that ~~she's sexy~~ she's a moody woman a lot of the time.
Mordekaiser - -10/10; Mordekaiser is an evil bastard.
Morgana - 8/10; Morgana... should tone it down a little. Listening to sad songs at 4 AM isn't a good idea. And stop tearing those pictures of Kayle.
Nami - 2/10; Nami is struggling to both help her people and the world against the Void. However, I think she's more stressed than sad.
Nasus - 6/10; Nasus is an old and tired dog. He should get a pat on the head, but instead, he has to deal with Xerath and Renekton.
Nautilus - 0/10; Nautilus once had a sad backstory. Now, he has tentacles. This is one of those rare cases where I'll say that it's not an improvement.
Neeko - 3/10; Neeko has regrets, of course; last of the Oovi Kat, and all that. She's too airheaded to let it bother her, though. ~~Being a lesbian doesn't help.~~
Nidalee - 2/10; Nidalee acts confident and proud, but growing up in the jungle isn't a healthy experience for a girl.
Nocturne - 0/10; being Nocturne is suffering (literally). On the other hand, he's a spiritual entity that subsists on fear. "Sadness" here translates more to "utter hatred for all forms of life".
Nunu & Willump - 3/10; Nunu is too young to really be sad, and Willump is too old to let things bother him too much. However, since they're searching for Nunu's mother...
Olaf - 0/10; Olaf wants to die. He's also bored.
Orianna - 0/10 (5/10); Orianna is similar to Blitzcrank, but her existence is more melancholy. She did have a biological father (which Blitzcrank lacked), but she will have to ask herself difficult questions in the future.
Ornn - 4/10; grumble, grumble. Ornn is grumpy and prefers to be alone, but that's just because he's scared of losing things he cares about again.
Pantheon - ?/10; I honestly don't know what the concept of war would be sad about. Itself? What it does to the world?
Poppy - 0/10; Poppy is meant to be a comedic character; compared to her old self, her story isn't nearly as dark. However, her wandering and lack of self-awareness has a tragic quality to it.
Pyke - 0/10; Pyke is too insane to be sad. Any sadness he may have felt has been turned into a desire for revenge.
Qiyana - 0/10; Qiyana is too arrogant and ambitious to be sad.
Quinn - 5/10; Quinn went through tragedy before, and I don't think she's gotten over it. Her attitude is a cover for her feelings.
Rakan - 1/10; it's Rakan.
Rammus - ?/10: ?
Rek'Sai - 0/10; Voidborn don't feel sadness. **_Again._**
Renekton - 0/10 (7/10); Renekton is too insane to be sad. On the other hand, being trapped with Xerath for millennia guarantees that the devil tried to exploit all of his vulnerabilities. Renekton is not good right now.
Rengar - 1/10; Rengar's youth was unfortunate, but he's since managed to recover from it. A little bit of his past clings to him still.
Riven - 7/10; Riven was quite literally suicidal, but she's slowly getting over it. These things take time.
Rumble - 0/10; Rumble is too quirky for sadness (and too much of a machine fetishist).
Ryze - 6/10; an old man with lots of regret. Ryze's life is shaped by disaster and his inability to prevent it. He's trying his best, but he's just too tired of it all.
Sejuani - 4/10; Freljordian traditionalism is difficult, even if Sejuani is strong. Her relationship with Ashe didn't end so well, and her life isn't going in a good direction.
Shaco - ?/10; ?
Shen - 0/10 (2/10); balance must be maintained. There is no time for regret. ~~Unfortunately for Shen, he's still human.~~
Shyvana - 3/10; Shyvana stuggles with uncertainty over her mixed heritage, her place in the world, and likely her relationship with Jarvan. ~~Getting rid of her dad wasn't a smart choice.~~
Singed - -10/10; Singed doesn't give a shit. It's kind of inspiring, actually.
Sion - 0/10 (6/10); a lumbering, undead behemoth shouldn't feel sadness. Except, of course, when you reanimate him using blood magic. Sion's mind is a mess.
Sivir - 1/10; Sivir is greedy above all else. I don't blame her, but I don't think sadness pays well (unless you're a poet).
Skarner - 7/10; Skarner's quite miserable; having your people harvested for magical crystals tends to do that. It'd be easier if he were a regular scorpion.
Sona - 2/10; Sona seems very emotional (she is a musician, after all), but if she's feeling sadness, she's not telling.
Soraka - 6/10; like Anivia and Janna, except a little more. Soraka has likely spent the most time mingling with humans, and felt the most of their pain. She's trying to be a positive mom.
Swain - 1/10; Swain knows he has to make sacrifices. His human weaknesses are there, but he keeps them in check.
Sylas - 5/10; Sylas is bitter, but more angry than sad. He's channeling his contempt in a destructive way, lashing out at the world for its cruelty.
Syndra - 8/10; Morgana, except angrier, and far less well-intentioned. Syndra is an emotional disaster.
Tahm Kench - -10/10; despair tastes truly wonderful. A connoisseur of human suffering would never pass it up.
Taliyah - 3/10; Taliyah is about as emotional as a girl her age can be. Her life hasn't exactly been the best, but she's dealing with it.
Talon - ?/10; Talon was a street urchin, but he hides his emotions. Probably not the most positive guy around.
Taric - 3/10; Taric loves life. He protects life. He just doesn't cry over it. Then again, he doesn't have the brightest past.
Teemo - ?/10; mysterious, as ever.
Thresh - -10/10; Thresh enjoys his newfound godhood. To say that he doesn't delight in mortal pain would be a filthy lie at best and an insult to his malevolence at worst.
Tristana - 0/10; Tristana really likes to shoot things. She also pretends to be stern.
Trundle - 0/10; Trundle is an asshole.
Tryndamere - 3/10; Tryndamere has his doubts about himself. Having his whole tribe massacred by an avatar of mass slaughter wasn't the most pleasant experience. Ashe is helping him cope.
Twisted Fate - 5/10; Fate tries to pass himself off as a man of no consequence. He fails, as evidenced by Graves.
Twitch - 0/10; Twitch is too stupid to be sad.
Udyr - 5/10; dad is having some trouble handling himself. Spirit walking is exhausting business, you know. Let it not be said he's not trying.
Urgot - 0/10; no more regrets; burn the world down. The strong will survive. The weak will go up in flames.
Varus - 7/10; Valmar and Kai have issues, to put it lightly. Varus is no better, despite his inhumanity.
Vayne - -10/10; Vayne took a tumble off the cliff of despair and into the ocean of psychopathy. ~~Damn, she's hot.~~
Veigar - 9/10; enough trauma and emotional twisting to plunge the world into an eternal darkness ruled by the one and only true master of wickedness.
Vel'Koz - ?/10; Voidborn don't feel sadness- actually, Vel'Koz is just so alien he'd make even Cho'Gath go "What the heck?" He's cool like that.
Vi - 5/10; Vi puts on a brave face (noticing a trend with the roster yet?), but her past still haunts her. Good thing her girlfriend is there to comfort her.
Viktor - 7/10; emotional reactions are an obstacle in the way of technological progress. Except Viktor can't put his behind himself.
Vladimir - -10/10 (10/10); Vladimir is just a disaster creature. What with his dark, tragic backstory and psychological problems, he feels... everything, always. Depends on the mood.
Volibear - 0/10; it's "mr. sir _the_ Volibear" to you. He'll bite your face off.
Warwick - 7/10; Warwick is a furry mess. He can't remember what he did, but he knows that, no matter how hard he tries, he can't make up for his wrongdoings. Another sad dad.
Wukong - 1/10; too much of a prankster for sadness.
Xayah - 2/10; angry and sour. Don't let her tell you otherwise; edgelords can be sad.
Xerath - -10/10; Xerath, you magnificent bastard. You managed to turn your bitterness into omnipotence. Honestly, I'm jealous.
Xin Zhao - 2/10; Xin is not that sad, he just has some misgivings about his standing in Demacia.
Yasuo - 7/10; depressed ronin. He's slowly getting better. Maybe shave and get a haircut?
Yorick - 10/10; Yorick is old, tired, and so lonely he thinks his shovel is ample company. At least he doesn't want to murder the world like Aatrox, so he's got that going for him.
Yuumi - 1/10; she's a cat. She also has a missing owner.
Zac - 2/10; Zac is a blob. He's a helpful blob, but copying emotions might be a little weird for him.
Zed - 7/10; this is the man who made Kayn into what he is. He killed his master, betrayed his best friend, was put through hell by Jhin, and has turned into a mass murderer. At least he's not gay, right?
Ziggs - 0/10; explosions distract Ziggs from the meaninglessness of everyday Yordle existence.
Zilean - 7/10; Zilean is Ryze, except older. This means that he's had even more time to fester in his bitterness. Unlike Ryze, he has also seen one possible future. It doesn't look good.
Zoe - ?/10; Change tried sadness once. Got bored of it.
Zyra - 0/10; humans are yummy. Flowers aren't sad.