I felt it... everywhere. Everywhere. I still feel it! I just want this to be over!
In a series where the protagonists are teen outcasts and single parents beset by bullies, government organizations and supernatural terrors, you can expect your pity-gland to get the workout of its life.
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The Woobie
The Party
- Eleven, given her harsh beginnings as a human guinea pig locked up in a secret laboratory for the first 12 years of her life. You'd be hard-pressed to find a viewer who doesn't want to give her a hug and that is without getting into the events of the series.
- In Season 2 she is rescued by Hopper but has to live in a cabin away from society out of fear of the government capturing her again all while dealing with a disgruntled and frustrated Hopper whose parenting skills are not exactly perfect despite wanting to see Mike and the others again, then when she sneaks out and risks being discovered she sees Mike with Max and mistakes this interaction for being replaced in the group. After getting into a fight with Hopper, Eleven then decides to go and find her birth mother, only to discover what Brenner did to her and that she has a "sister" in the form of Kali/Eight. Upon finding her however she learns that she not only is a delinquent and criminal but she has a far more violent methods in getting back at the people who hurt him, causing Eleven to be disillusioned by Kali and head back to Hawkins.
- Season 3 is not kind to her either. Eleven's relationship with Mike becomes damaged due to Hopper's manipulations, she is constantly pursued by the Mind Flayer and its thralls out of revenge for closing the gate and supposedly loses her powers and new father Hopper when they stop the Soviets and the Mind Flayer's plans, leading to her moving away with Joyce and her family to get away from all of Hawkins' bad vibes.
- Season 4 has shown to have made things worse. She struggles to make friends, is targeted by bullies and still mourns for Hopper all while lying to her boyfriend that she's having a good time in California. She then hits her bully Angela with a roller-skate out of revenge for embarrassing her in front of Mike, not only bringing up past trauma from her time in the lab but almost ends up in juvi for her actions. In her breakdown in front of Mike, she shows that her self-esteem is crushingly low, believing everyone, even her boyfriend who she has to hell and back with three times already, sees her as a monster deep down. Then she learns that her friends are in trouble and agrees to let Owens re-awaken her powers, only to discover that the presumed dead Brenner is alive and that the method to regaining her powers involves reliving one of the worst days of her life where she apparently killed all of the other children within the lab.
- Mike. He's a Woobie even in season 1, constantly being bullied both physically and mentally by Troy. Throughout season 2, he's been through so many stressful and horrific experiences that it's hard not to feel sorry for him. When Mike talks about the first time he met Will at kindergarten, he is practically devastated. Not to mention the fact that he is going through the grieving process regarding Eleven and is stuck in the denial phase. Luckily for him, Eleven does end up coming back, however by the end of Season 3 she has to move away, separating them once again, though this time they have the capability of having a Long-Distance Relationship.
- Will Byers, given his nightmarish time spent in the Upside-Down during the first season, which has given him legitimate PTSD. And then he falls victim to Demonic Possession in the second season. The general consensus is that this poor boy needs a vacation. Joyce, Jonathan, Mike, Dustin, and Lucas were all devastated to some degree by Will's disappearance and subsequent illnesses. Especially Joyce, as she's nearly (if not obviously) driven to madness by it.
- He gets a more realistic case of this in Season 3, as his friends would all rather get girlfriends and hang out at the mall instead of hanging together at home playing D & D. Will desperately tries to liven things up with his latest campaign, but Mike angrily tells him that keeping this up is childish and isolating. Mike even goes as far as to bring up Will's lack of interest in getting a girlfriend, which can feel really harsh if you're one of those people who reckons Will is gay, or just considering Will is frequently bullied for being seen as such. It also comes off as Will trying so hard to still keep things as they were despite them growing up and feeling left behind as his friends all focus on themselves than their group (not helped that Will is probably clinging onto their D & D games as the only times he felt happy with his best friends considering the amount of trauma caused by his own life and the PTSD of the Upside Down).
- Season 4 confirming that Will is gay and in love with Mike adds a whole new flavor of suffering and retroactively makes Will's situation in the first three seasons even worse. Will not only had to endure other characters' digs at his perceived sexuality and comments about him being a "freak", he had to realize at some point that they were right, while also watching his best friend and crush date his adoptive sister and struggling with the very real possibility that Mike learning the truth could destroy their friendship.
- Max Mayfield. She comes from a troubled home life where she lives with a sadistic older stepbrother. She's rough around the edges, but she's still a good person who wants to make friends and is treated rather coldly. While Lucas is consistently nice to her, Mike is rude and crass towards to her for no other reason except the feared belief she's replacing El. And when she finally meets El, the latter coldly shrugs her off out of jealousy.
- Season 3 makes it worse when she still loves Billy despite his shitty behavior towards her and is borderline shaken and left devastated when he dies saving not just the whole world, but her.
- Season 4 then outright shows that she has developed PTSD from Billy's death and though her abusive step-father is gone, her mother has to work two jobs to make due with bills and has become an alcoholic as a coping mechanism. She ends up pushing her friends and boyfriend Lucas away and becomes Vecna's next target, which tragically leads to her getting killed (in front of her boyfriend!). And while El saves her physically, she's at best comatose or braindead at worse. Over all, poor girl.
The Teenagers
- Jonathan in season 1. In the midst of an already difficult adolescence, he's forced to arrange a funeral for his little brother because his mother appears to slowly be going completely insane. At one point, he has to purchase Will's casket immediately after fighting with his mom in public to keep it together and shooing away several nosy onlookers and looks completely overwhelmed and lost.
- Nancy in season 2. She is racked with guilt over her role in the death of Barbara and can't even tell her parents or begin to make amends because of the Government Coverup. This starts to go away once Jonathan joins forces and she begins to get the ability to act on her issues.
- In Season 3 Nancy learns the hard way that her gender and lack of experience are a massive hindrance when it comes to working in a white-collar business. Even when she displays more passion and skill at journalism than her superiors, all she gets in return is nasty gaslighting.
- Steve from Season 2 onward: While Steve tries to be a respectful and loving boyfriend after his Heel–Face Turn with Season 1, it's not enough: Nancy breaks up with him during the second season due to her own struggle with Barb's death and developing feelings for Jonathan. While he takes it with stride (and even takes Dustin under his belt), it's obvious he's emotionally broken from it. Season 3 makes it worse where he struggles to adapt to the real world after failing to get into all the schools he applied to, leaving him to work at a mall. And that's before he's brutally tortured by Soviet operatives. Also, he falls for his co-worker Robin and confesses his feelings to her, but she turns him down because she's a lesbian. Like with Season 2, he takes it with stride, but it's hard not to hug the poor reformed bully when he's trying so hard to be a good person.
- Robin Buckley, introduced in Season 3. Her snarky attitude and dismissiveness towards Steve is gradually revealed to be a case of Sour Outside, Sad Inside; she spent her high school years an outcast looked down upon by popular people like Steve, and mentions being treated badly by her peers. While captured under Starcourt, she's also tortured, albeit nowhere near as badly as Steve. Then, when Steve reveals he's developed feelings for her, she turns him down because she's a lesbian. As she does, she worries this might repulse Steve from even wanting to be her friend and mentions it makes her feel freakish. Thankfully, Steve is a good guy and remains a loyal friend, but considering this is rural, Reagan-era Indiana, things probably aren't going to be easy for the poor girl.
- Chrissy Cunningham from season 4. Though she looks to be a perfect and happy girl with a loving boyfriend and bright future, Chrissy is emotionally abused by her mother for not meeting her standards of being a proper lady and is implied to have developed an eating disorder as a result, which causes her to do drugs to relieve her pain. She becomes tormented by Vecna with nightmarish visions until he makes her his first victim, brutally killing her in Eddie's home.
- Eddie Munson quickly becomes an example of this in season 4. He is branded a freak and outcast simply for liking heavy metal and being the leader of a Dungeons & Dragons club, which during the 80s was mistakenly seen as linked to Satanic or Occult practices before quickly being pinned as the prime suspect behind all of Vecna's killings, including Chrissy who was at his home when she was killed. Eddie has no choice but to hide as the whole town excluding the Party see him as a pariah while also having to deal with Jason and his friends hunting him down. In the end of it all, Eddie chooses to sacrifice himself to buy the others more time and tearfully telling Dustin to watch over the next misfits that join the Hellfire club.
The Adults
- Joyce Byers. She's mentioned to have had anxiety issues prior to the series, and her divorce with her Jerkass husband is said to be especially messy. Then she loses her son Will in the first season and is made to think he's dead due to the Hawkins Lab's machinations, going so far as to have to attend a funeral for him while completely in denial. She goes through intense psychological distress in her efforts to find Will, arguing with her older son, Jonathan, and being forced to face all manner of horrific monsters from the Upside-Down, as well as traumatic visions of her son trapped in her walls. She then has to go to the Upside-Down herself to try to rescue him.
- This only gets worse in Season 2, when Will is possessed and she has to put him through intense pain to try and free him, face off against corrupt doctors and hidden conspiracies, and lose Bob, her new boyfriend and chance at happiness, quite horribly as he is mauled by Demodogs in front of her while all she can do is scream.
- Then in Season 3, this loss has left her with clear PTSD that both makes her consider moving out of Hawkins and prevents her from being able to pursue a romantic relationship with Hopper, which causes him to act quite harshly towards her. They eventually make up at the end of the season...just in time for Hopper to be caught in front of the gate during a fight, which Joyce herself has to close, apparently killing him in the process. No wonder the poor, kindhearted woman seems broken by the end scenes.
- Terry Ives; Arguably the most tragic character, who didn't even face a gruesome death! After going through a near-fatal childbirth, her baby daughter (Eleven/ Jane) is taken from her (which she witnesses but nobody believes). Then she finds her daughter in the rainbow room many years later, but just as she is about to save her daughter, Dr. Brenner and his men capture her and strap her down to a table, where they silence her by electrocuting her (setting it to the highest level-450), which then leaves her brain dead, with nothing but the worst, painful memories of her life. The tie-in novel Suspicious Minds reveals that her parents died when she was young, was regularly subjected to painful experiments by Brenner and her boyfriend Andrew was killed in the Vietnam War as part of Brenner's manipulation.
- Hopper all the way: While he is a very blunt and snarky man, you can argue his entire jaded view of life was caused by the death of his daughter to cancer and his eventual divorce with his wife. Season 2 also pushed him into this when raising Eleven but keeping her protected for most of the events leading up to Season 2 caused tension between the two of them. Add more onto implied feelings for Joyce and then comforting her when Bob dies, it's hard not to hug him.
- Season 3 has him being a super Papa Wolf to Eleven, trying to start a relationship with Joyce only to be snubbed (accidentally) and just when it seems the two are going to be a thing, he's either killed due to the Russians' experiment of opening the Upside-Down again or he's kept prisoner in Soviet Russia by the end of it.
- Season 4 shows he is now in a Soviet prison, tortured for information and being prepared to be fed to a Demogorgon and after attempting to stage a plan to escape with a corrupt guard, the plan goes south when the middleman Yuri decides to double-cross them. It gets to the point where he seemingly gives up and confides with Enzo that he sees himself as a curse that kills everyone he loves, and now is heartbroken that his plan will most likely get Joyce killed.
- As of Season 3, Karen Wheeler. We see how frustrated she is with her role in the home and her marriage to a man who earns a lot of money but has no sense of appreciation for what she does and what the family goes through. She seems to seek solace in a glass of wine and romance novels while her kids get older and are less dependent on her. She only seems to liven up when Billy, a boy who is around the same age as her daughter, flirts with her and she even goes so far as to consider cheating on her husband until she realizes she could destroy her family. and when Nancy confides in her misogynistic workplace, Karen pretty much reveals that she used to be ambitious and wanted to make her mark on the world but after being beaten down because of her gender and perceived intelligence, she gave up to be a stay at home mom whose only focuses on how her house looks and how pretty she is, all for a husband who doesn't notice.
- Victor Creel arguably rivals Terry Ives in terms of how tragic of a life they had. As a former captain in the army, he ordered a strike which led to the death of a baby which has haunted him even to this very day. He moves into a brand new house with his wife and children, only to be targeted by what appears to be a demon, revealed to be Vecna, who kills his wife and daughter and nearly kills his son. Victor is then deemed insane by Hawkins and pinned as the killer to which he attempts to commit suicide to join his family, only to be stopped by the orderlies at the asylum he was condemned to. It's no wonder this man claims to still be in hell but if that wasn't enough, it's revealed that his wife and daughter weren't killed by a demon, but his own son who developed psychic powers and resented his family and humanity in general.
Jerkass Woobie
- Jason Carver has some Jerkass moments and his blind pursuit of Eddie and the Hellfire Club is definitely not okay but he does warrant some sympathy. Jason subverts the Jerk Jock trope by genuinely loving his girlfriend Chrissy, even adamantly stating that she would never do drugs or get into trouble, and becomes heartbroken when he discovers she was killed. Through a combination of grief and fearmongering propaganda, he becomes convinced that Eddie and by extension the Hellfire Club are a cult who invoke the powers of Satan to commit these killings and ignorantly spreads the seeds of anarchy in a misguided attempt to get justice for his girlfriend. Then he witnesses Patrick, his friend, being brutally murdered right in front of him. And after all that, he unintentionally causes Max to be killed by Vecna, leading to the Gates to open, and getting himself killed in the process as well.
- Billy is an Ax-Crazy, sadistic bully to his step-sister and her friends (as well as Steve)... and then you find out his father is even worse to him, violently bullying him and calling him derogatory names. And then you find out that he grew up watching his father abuse his beloved mother, resulting in a traumatic divorce and Billy being cut off from her. There's no way he could have turned out as anything but the bastard he is. Being used by the Mind Flayer couldn't have been pleasant for him either.
