- The Digimon franchise has at least one in every adaptation:
- Gatomon (aka Tailmon) had it rough since her birth: separated from the others while still an egg and spending most of her youth alone, she was eventually taken under the wing of Myotismon, whose name is synonymous with Bad Boss. She spent a lot of time being beaten and tortured simply for her 'defiant eyes.' She eventually leaves Myotismon, but there's a high price: her only close friend, Wizardmon, is killed by Myotismon for turning as well.
- Gabumon from the first Digimon Adventure also qualifies to some extent. When he was talking with Matt in one episode, he admitted that he had no friends before he met him. Imagine a nice, warm-hearted Digimon like Gabumon alone, sad and friendless. The fact that he already makes Puppy-Dog Eyes frequently is enough to score him woobie points. Also, Tai tends to tease Gabumon about his pelt quite a bit, though he thankfully stopped eventually. Poor guy.
- Another character that fits this trope perfectly is Ken from Digimon Adventure 02. His eventual rise and redemption are all the better for the hell that the second half of the series puts him through.
- Digimon Tamers: 10-year-old Jeri Katou, originally the Plucky Comic Relief/Love Interest, is one of the only humans to have her Digimon permanently destroyed, by watching him be impaled and eaten by Beelzemon. Whom she still spares from death because she doesn't want more people to die in front of her AND for Takato/Giulmon/Gallantmon to go off the deep end. She is then kidnapped by a modern day Eldritch Abomination, and psychically tortured for several weeks so her angst and unhappiness fuels up said monstrocity. YEOWCH.
- Ruki Makino/Rika Nonaka, also from Digimon Tamers, is a lesser one once you explore her character. Abandonment issues from her Father walking out on her mother, her Mom's a good person but is more interested in her career and oblivious to her needs in the beginning, thus leading her to pushing people away until it's almost too late.
- Kouichi Kimura from Digimon Frontier is as good an example as every other Sixth Ranger in the series. The last thing his dying grandmother tells him is that he has a twin brother, whom he's never met. He goes looking for said brother and can't get to courage to go talk to him. When he finally does work up the courage, he misses the elevator and falls down the stairs, ending up either unconscious or dead (it's never really explained) Either way, his soul is separated from his body and he winds up in the Digital World, where he is brainwashed into the Evil Twin (or maybe not) and made to fight his brother and his brother's new-found friends until he's brought to his senses by The Power of Friendship.
- Ikuto, from Digimon Savers, also is given some of the woobie treatment. First, his foster mother is killed right in front of him. Then his friend, Gotsumon, deems him a traitor (because he's human) and tries to kill him. Next, he meets his real father, who wants no part of him at first as he might bring back some serious emotional issues his mother suffered from. Once he does meet his mother, she's arrested. Then an entire fleet of digimon, headed by Gotsumon, declares war on Earth unless he's turned over to be executed. After that, his foster father is killed right in front of him, and suffers quite a bit while it happens. Hell, that's not even taking in his whole identity complex either.
- There's also Touma from Savers. First, his mom was hit by a truck and died on their way to a festival, so he was sent to live with his rich Austrian father. Touma's dad is a good guy, but spineless, so he did nothing when Touma's grandmother basically refused to acknowledge him either for being half-Japanese or illegitimate. Then, we find out he has a younger sister who's very ill, and that the reason he's been working himself so hard that he's a licensed doctor at age 14 is to cure her. And that's not to mention the Fake Defector bit he pulled, which involved him nearly killing Ikuto and Yatagaramon, and indirectly killing Agumon.
- Like its predecessors, Digimon Universe Applimonsters also has its Sixth Ranger, Yuujin and Offmon pair to fill this role for the series. They already used to deal with self-esteem issues for a long time, thus having trouble at forgiving themselves. They finally get better after being each other's buddy. Until the written destiny shows them that they're not meant to be good and happy. In the last arc, the Big Bad exploites their bond to trigger the world destruction for him. Despite being fully innocent, both still blame themselves for hurting the people they care. Both end up taking the path of tearjerking Heroic Sacrifice, in order to beat the Big Bad and let everyone else alive. Though Offmon somehow survives at the end, Yuujin doesn't.
Woobie / Digimon