BoJack strangely overlaps this with the jerkass and regular variety. Yes, he's certainly a jerk whose shortcomings are partly the cause of his constant downfalls. But his punishments are so harsh and with such long-term consequences that it's increasingly hard to see his flaws as the only thing keeping him down with his environment, upbringing and constant misunderstandings making him a worse perso—ehmm, horseman than he truly is. Yet, time and time again the only thing that keeps him going is the vague hope that things will eventually get better and he'll make a turnaround and as such refuses to give up, even when the world gives him enough reasons to do so.
Herb Kazzaz spent the majority of his younger years climbing through Hollywoo in order to carve a niche in television history. Starting as a standup comedian, there he met BoJack Horseman, young actor who also had dreams of fame and together they became best friends (although from his part, it's possible he always wanted to be something more). As their mutual friend, Charlotte, left and both rose to stardom with their vehicle Horsin' Around, Herb fell into an exhausting rut of directing prima donna assholes, including his best friend, with whom he was slowly drifting apart. The stress reached its breaking point and lead him to being exposed when he has a sexual encounter in a public bathroom to vent out some steam. Everyone with their backs turned on him, Herb's dismissal came from the passivity of his friend BoJack due to his continued friendship with him threatening the show and his job. Swinging between self-pity, actual work and suffering from cancer, he still refuses for life to stoke him down easily which still doesn't stop him from showing a few cracks during BoJack's later visit: first passively-aggressively remarking upon his condition and his betrayal in bitter tone and then lashing out in a furious, sad and resigned tone to BoJack about how little he cared for him after being fired. Ultimately, after a possible recovery, he ends up dying in an unrelated accident, his hopes of publishing his passion novel and leave his mark crushed postmortem due to his horrid talent at writing.
BoJack is a cynical and lazy alcoholic, but his story of childhood neglect/abuse and incurable guilt at the hands of losing his best friend to show business make him a flawed and sympathetic person. He reveals in season 2 that all he wants is to be happy, and that even doing his dream project will only help him cope. We see in season 2 how, even though he wants more than anything to better himself, his toxic personality will inevitably push away his loved ones. Depending on how sympathetic you are to him after "Escape From L.A.", the rest of it will make you want to reach through the screen and give the poor guy a hug. And from that episode onward it only gets much worse for him.
Diane Nguyen, none other. She can have enough sympathy points to earn her reputation as a normal type of Woobie; yet that makes no less inexcusable when she goes off the deep end and takes advantage of people who've been nothing but benevolent: her boyfriend (later husband) Mr. Peanutbutter is often dissed by her when he stands in the way and Princess Carolyn and BoJack could tell some really great stories about the levels of ungratefulness and entitlement she can show at her worst when pushing her ideological agenda. Still, Diane has suffered through a ghastly childhood, a constant sense of inferiority, need for approval and the reminder that her search for a meaningful purpose is futile with all her achievements destined to be forgotten in due time. Not to say that when she grasps she has made a mistake, she's usually the one who feels it the harshest.
Princess Carolyn is a cunning, scheming, ruthless feline agent for whom backstabbing, faint praises and even sweetened poison is every day routine, with no taboos, morality and people being safe from her manipulative hand at handling movie deals, be it friend (BoJack, Todd, Lora, Diane), client (BoJack, Mr. Peanutbutter, J.D. Salinger) or even foe (Vanessa Gekko, Rutabaga, BoJack); this practical way makes her the best at her job and has robbed her of her youth, idealism and ability to function outside the cog machine of Hollywoo. In spite of that, she often tries to reach out to other people, mostly viable romantic partners who rarely hold her back and constantly take advantage of her. Topping it off, PC has often reached out beyond her duty to help her clients in any way she can, a trait sorely missing in most Hollywoo agents. Not that it has helped her much or caused her nothing but trouble which as she sadly comments might be the form she prefers it.
BoJack's mother, Beatrice, was a terrible mother, yet season four manages to give her a hell of a Freudian Excuse that makes it hard not to feel sorry for her. Her brother died in WWII; her mother couldn't handle the grief, and her father had her mother lobotomized because he couldn't handle her emotions. She then gets Scarlet fever and is forced to destroy her favorite doll as a result. Her father later tried to get her to marry someone for his own financial gain, but she instead wound up marrying BoJack's dad after accidentally becoming pregnant. However, their marriage soon fell apart in part because of his inability to make money through his writing, which left her cold and resentful towards BoJack.
Diane after her traumatic ordeal in Cordovia. She doesn't emote a lot beyond apathy and quiet sadness, but she's clearly shaken by what transpired over there and how little she feels she did about it.
Base-Breaking Character status aside, Ana is revealed to be one, as well as a Jerkass Woobie, through her stories. When she was just a teenager, Ana decided to sneak out to a party only to end up sliding out the highway and nearly drowning. From then on, she decided to work as a lifeguard to overcome her bubbling fear of water. Seeing as she apparently wished to save as many people as possible from drowning, her instructor advised her to not focus on cases in which the victim will do "most of the drowning" instead of avoiding it, as they might cause her to drown as well. Taking that lesson to heart, Ana navigated through life with a hard shell and a darwinistic mindset, only to get more and more isolated in her personal life leading to divorce and not seeing her daughter. It's only sealed in "Stop The Presses" when BoJack follows her to her home after she puts a front of not wanting him to know her personal life and he sees a lonely, normal person underneath the mysterious, emotionless façade she puts.
BoJack's mother, Beatrice, is definitely a JerkAss in her later years; but before that, she was a little girl growing up in the 40s, having to deal with the death of her brother in World War II, a sexist, emotionally distant father, and a traumatized, grieving (later lobotomized) mother.
Princess Carolyn, when not a full-fledged Magnificent Bastard, can also fall in this category whenever love is concerned. She just wants to have a stable relationship and so far she's been rebuffed or manipulated because of it.
Diane herself is this most of the time, when some of her behavior doesn't put her in the Jerkass territory. It's revealed early in the first season that despite appearing well-adjusted, she had just as bad of a childhood as BoJack, with her family and brothers often ganging up against her. Add to that generalized anxiety and constant questioning of self-worth on her part as a sense of futility in every thing she does.
Sarah Lynn. Her Stage Mom forced her into a career as a performer when she only ever wanted to be an architect, it's heavily implied that her stepfather molested her, BoJack's Anti-Advice ended up killing her self-esteem, and once her fame dried up, she spiraled into a years-long intoxicated depression that eventually killed her.
Hell, even Todd, second only to Mr. Peanutbutter in terms of happy-go-lucky characters, gets Woobie moments, most notably in the way BoJack constantly belittles him.
Gina Cazador: A secretly AdorkableBroken Bird whose arc in Season 5 involves her learning to be vulnerable and believe in herself again, only to get hurt in ways that are increasingly painful to watch. BoJack spends the whole season inadvertently toying with her emotions, and in the last two episodes, shes forced to deal with the terrifying psychological consequences of his prescription drug abuse, including him nearly strangling her to death; and the only way she can salvage her lifelong dream of becoming a star is by putting on a fake smile, covering her neck bruises with make-up, and pretending none of it happened. And then once she starts getting gigs again, the trauma from said strangling has made her paranoid about doing any stunts on set, leading her to Freak Out! over something as simple as a dip in a dance without being able to explain why, causing her cast members to dislike her and directors to badmouth her to their colleagues. Ouch.