Note: Spoilers for the anime will be unmarked. You Have Been Warned.
Iron Woobie
- Kakashi Hatake is one of Konoha's strongest ninja, but is plagued inside by the death of his father and the deaths of his Sensei and best friends, Rin Nohara and Obito Uchiha, particularly after he promised Obito he'd protect Rin to the end. It got so bad that the Third Hokage assigned Kakashi away from the ANBU corps and towards teaching so he would be able to rediscover his kindness. Despite his pain, Kakashi is a consummate professional who soldiers on throughout.
- Jiraiya, who was never able to win the heart of the love of his life (until just before he died, and even then he never found out she returned his feelings), who lost his best friend to evil, and lives with immense guilt for failing to save the lives of his student Minato the Fourth Hokage and his teacher Hiruzen the Third Hokage. Jiraiya even says happiness is something he isn't meant for and that his life has been a series of failures. Nevertheless, Jiraiya never stops fighting for his home, and has made it his life's mission to find a lasting peace in the Shinobi world. The man never, ever, ever breaks down or stops soldiering on.
Jerkass Woobie
- Neji is introduced looking down on his teammate, Lee, and hating Hinata enough to Breaking Speech her about her inferiority and trying to kill her. It is later revealed that he believes that his father was killed for the main branch when he was young, and he can be punished at any time, potentially fatally, if the Main Branch members activate the Cursed Seal on his head. Once he learns the truth, he overcomes his previous belief that You Can't Fight Fate, which results in him working to improve his relations with the main family and getting along with Lee when he isn't acting too eccentrically.
- Kimimaro nearly claimed the life of Naruto, Rock Lee, and Gaara, and was willing to kill his teammates if they disobeyed him. However, considering that he suffered from a terrible illness, was kept isolated by his clan before Orochimaru came along, and that Orochimaru happily sent him to die along with Kabuto, it's hard not to feel sorry for him.
- Sora in the Fire Temple Filler arc, who is incredibly rude to most people, but has a dark past and an even darker present, as the host of much of the Nine-Tailed Fox's chakra.
- Itachi Uchiha. He doomed himself to a life of being hated by his only remaining family, who he truly loved all along, along with the stigma of being a missing-nin AND part of an evil organisation, all while hating violence and combat. He was ordered to kill his family in order to prevent another war from breaking out, but he spared Sasuke. His actions were partly motivated by love for Sasuke, but he put on a cold emotionless front, acting like he just wanted to kill Sasuke and take his eyes (which wasn't true, of course); but one cannot deny that his methods of helping Sasuke (Mind Raping him twice) were a bit extreme. In short, you hate him for some of his actions, but once you learn the reason, you also want to hug him. That or kick him in the balls because of how big a mess he ended up making of things in spite of how much you might pity him.
- Karin. She used to be one of the most hated characters in the manga and she was a bit of a jerk before she started to genuinely care for her other teammates, and then her being so badly hurt by Sasuke and her warning Sakura about Sasuke intending to kill her made her turn into a Jerk Ass Woobie for a good fraction of the fandom. Still, die-hard SasuSaku fans remain firmly in their Die for Our Ship position. The fact that she actually got over Sasuke after all he did to her has also helped pull her out of the Scrappy pile. Unfortunately, as of Chapter 627 she was placed back into the Scrappy pile after when Karin reunited with Sasuke, she immediately forgave Sasuke for trying to murder her, despite realizing that Sasuke despised her and vowing to move on and resuming her one sided fangirl-ish crush on him.
- The Nine-Tailed Fox. You'd never believe it, but after the asskicking that it endured, to have its power taken from it and locked away again is very depressing. It openly expresses its bitterness over humans imprisoning it and using it as a power source for decades and not even acknowledging him as a person and not a thing, something even Naruto's mother Kushina is guilty of. This sentiment is starting to be recognized by the fandom. Even Naruto feels sorry for it, and apologizes for trapping it in its prison again.
- Utakata, the Jinchūriki of the Six-Tailed Slug. He is quite aloof toward Hotaru and tries to rid himself of her at every opportunity, but this is largely the result of him being a fugitive for killing his master when he tried to extract his Tailed Beast, an experience that left him quite bitter and unwilling to trust others. And just when he comes to terms with this, Pain captures him and extracts the Six-Tails, killing him.
- Kabuto has become one. He had a deep existential crisis after Orochimaru's death (Naruto inspired him to continue) and he is shown thinking that all he wanted was for someone to notice him. He just wanted to be acknowledged. Still doesn't excuse his monstrous moral event horizon crossing moments though.
- Even before that he was one considering how horrible his life was. Meeting Orochimaru was actually the best thing that ever happened to him.
- In the pilot, Naruto is even more of a brat than at his worst in Canon, having no friends or social skills. He traps another youkai boy in a hole for bad-mouthing him, although it edges on revenge when the boy goes from insincerely claiming to be Naruto's friend to trying to blackmail him in a matter of seconds. And yet, when he's framed for murdering Takeshi, his horror and grief over the death of the man he was starting to befriend is heartwrenching. You also have to wonder what he went through when he is almost completely unable to understand why Kuroda would be willing to trust him enough to go to prison in his place.
- Sakura Haruno in Part I, yeah, she constantly beats up Naruto, and broke her friendship with Ino, but she was picked on because of her gigantic forehead and most of her attempts on hitting on Sasuke end in failure.
- She got it even worse in Part II, yes she is the same girl that clings to Sasuke despite him constantly acting like a jerk and tried to kill her twice, make a painfully fake love confession to Naruto as well as suffering from a bad case of Aesop Amnesia at times, but no matter how much she tried to train to keep up with them, she is looked down upon by fans and other ninjas simply because compared to Kakashi, Naruto, Sasuke, and eventually other characters such as Hinata and Shikamaru, she is completely neglected by the author to the point that could not catch up with them.
- Beyond blatant things like that, the way the narrative treats Sakura is actually really sad, all things considered. First, she's put on Team 7 with basically no regard for how an average girl from a civilian family will be affected by being on a team with a jinchuriki and a traumatized massacre survivor, then Team 7 is assigned a sensei who barely interacts with her and is never seen teaching her one on one despite how blatantly she needs to be trained for improvement, then on her first real mission she's repeatedly brushed off in battle and told to just stand there and guard Tazuna while the others fight (bonus: Naruto and Sasuke completely ignore her while freeing Kakashi from Zabuza), then during the Forest of Death she's pit up against a Legendary Sannin and shortly after she's pit up against three Sound-nin who are way out of her league while she's physically exhausted and sleep deprived from taking care of Naruto and Sasuke, then she finally gets a relatively fair fight with Ino but despite the fact that she should logically have an advantage since Ino is primarily a long range fighter and while it's Played for Laughs, Sakura is clearly physically strong enough to punch somebody's lights out, the match ends in a draw as essentially a cop out, then Kishimoto sidelines her until Part II after faking like he's going to finally begin developing her and let her start to catch up to her teammates, then she gets to show us how far she's come up against a member of the Akatsuki finally proving that yes, she is both competent and strong, and then she's sidelined for the rest of the series because she's a medic.
- Hiashi's jerkass tendencies can be at least partly explained by watching the Caged Bird Seal tear his family apart, the fact that his eldest daughter Hinata was nearly kidnapped when she was only three years old, setting in motion a chain of events leading to his brother's death, which he was helpless to prevent, the fact that his nephew nearly killed Hinata, and the strong implication that his wife is dead. To drive the point home further, when Neji died on him and Hinata, Hiashi felt crushed in that he failed his brother again.
Stoic Woobie
- Konan is probably the biggest example in the series, which is certainly saying something. A war orphan forced to eke out a living with her childhood friends Yahiko and Nagato, she would form Akatsuki alongside them in hopes of bringing peace to their country, she gets captured by Hanzo who forces Yahiko (whom she's heavily implied to have romantic feelings for) to commit suicide to save her. Afterward, she has to watch as Tobi corrupts Nagato and the Akatsuki into a terrorist organization, resulting in the former murdering their mentor. Nagato would then give his life to bring back those he killed in his assault on the Hidden Leaf village, meaning that she's lost the final person tied to her past. And just as she herself pulls a Heel–Face Turn, Tobi kills her when she makes a futile attempt to protect Nagato's body. But you'll find it hard to tell what she's been through given that she rarely loses that stoic expression.
The Woobie
- Rock Lee was bullied since his early childhood for being unable to use ninjutsu and genjutsu and called a "failure", his crush on Sakura is never reciprocated, and he ends up almost permanently crippled by his match against Gaara while trying to prove himself to his rival/teammate Neji. Years later, he ends up losing said teammate, tearfully promising to his dead body to hold onto his feelings.
- To sum it up better, he is unable to perform anything other than martial abilities, has been training night and day since a young age and continues doing so rigorously even when his arm and leg are crushed by Gaara. Because of how powerful he's become due to that training, he is one of the characters who suffer from the Worf Effect the most in this series. How dead-set is he on proving himself as a ninja? Tsunade tells him that she can try to restore the use of his arm and leg through surgery, but that it's basically a coin-flip as to whether he'll survive. He responds that if she can't bring herself to go through with this operation, he'll kill himself anyways. And he does so while grinning ear-to-ear.
- Hinata Hyuga was abused by her harsh father and the rest of her family from childhood, and she lost her rightful position as heiress to the Hyuga clan because they mistook her kind, gentle nature for weakness. Her cousin Neji, who was supposed to protect her with his life, grew up to hate her for nine years, and he ends up brutally attacking her (both physically and verbally), to the point of almost killing her, in the Chunin Exams preliminaries. Her familial shame resulted in a huge inferiority complex and crippling shyness, which tragically persisted up until she met Naruto when they were children.
