BoJack Horseman is currently anticipating its sixth season, with several occurrences from season five remaining unresolved. Fans saw the anthropomorphic eponymous character sink to his lowest depths yet, assaulting his girlfriend and co-star Gina Cazador (voiced by Brooklyn Nine-Nine actress Stephanie Beatriz) following a tumultuous drug addiction.

RELATED: 10 Best Quotes From BoJack Horseman

BoJack (Will Arnett) has always tread a shaky line between being a sympathetic protagonist and an irredeemable narcissist. The Netflix animated series portrays a profoundly flawed individual who, despite remaining sympathetic, has committed awful acts. Here are the ten worst things the troubled horse has ever done.

His Terrible Advice To Sarah Lynn

Horsin Around BoJack Horseman

BoJack Horseman's exchanges with the women in his life tend to err towards toxic, as evidenced by his relationship with Sarah Lynn. In the episode "Prickly-Muffin," BoJack gives his young co-star some cruel and bitter advice, urging the precocious child to never stop giving the fans what they want as nobody will ever truly love her.

BoJack projects his insecurities onto other characters frequently. Sarah Lynn's struggle with drug addiction and a subsequent downward spiral can be credited to this dark moment in BoJack's past.

Taking Princess Carolyn For Granted

In season one, BoJack is depicted as having little regard for his girlfriend and agent, Princess Carolyn (Amy Sedaris). Despite PC doing her best from a professional and personal stand-point to fix all of the problems BoJack creates for himself, he repeatedly refuses to commit properly to their relationship and often takes her support for granted.

This co-dependent relationship is a reciprocated condition, however. Princess Carolyn is happiest when solving other character's issues and BoJack's propensity towards instability provides her with a project to work on and a problem to fix.

Kissing Diane

Diane Nguyen (Alison Brie) is one of the few characters in the show who BoJack seems to respect. They share a number of similarities, including being inclined to pessimistic self-reflection. However, Diane has not escaped the poor treatment that BoJack inflicts on those closest to him.

During season one's "The Telescope," Diane accompanies BoJack on a visit to his former friend Herb Kazzaz (Stanley Tucci) when a conflicted BoJack kisses her. Diane immediately rejects him, as she is engaged to Mr. Peanutbutter (Paul F. Tompkins). BoJack doesn't stop there, however, as during the next episode "Horse Majeure" he concocts numerous elaborate schemes to sabotage their wedding.

Betraying Herb

In the same episode as his rejected move on Diane, BoJack attempts to make peace with Horsin' Around colleague Herb Kazzaz, though his past behavior comes back to haunt him. Herb, who now has cancer, refuses to forgive BoJack for abandoning him after he was fired from the show he created.

RELATED: BoJack Horseman's 10 Saddest Moments, Ranked

This is an important moment in BoJack's journey of self-realization. His attempt to reach out to Herb was for his benefit, an effort to obtain closure. When Herb refuses to tell BoJack what he wants to hear, it symbolizes that forgiveness, unlike fame, is not something that can be handed to him.

Sleeping With Emily

Todd Chavez (Aaron Paul) is the moral compass and comedic relief of BoJack. His light-hearted and simplistic optimism is a stark contrast to BoJack's narcissistic nihilism and, despite being his best friend, Todd hasn't escaped the heartbreak BoJack inflicts on those closest to him.

In season three's "Stop The Presses," BoJack sleeps with Todd's ex-girlfriend and best friend Emily (Abbi Jacobson). Although Todd and Emily's relationship was no more due to Todd coming to terms with his asexuality, this represents BoJack's consistent disregard for boundaries and friendship etiquette.

Sabotaging Todd's Rock Opera

BoJack's incessant need to put Todd down is an ironic echo of his mother Beatrice's (Wendie Malick) cruel, disparaging treatment of him during his childhood. Despite everything that happens, Todd maintains an optimistic outlook and a cheerful disposition, something which a deeply troubled BoJack is envious of on a subconscious level.

BoJack's treatment of Todd is harsh, but deep down he needs him. In "Zoes And Zeldas," Todd attempts to make his rock opera a success, to his best friend's chagrin. BoJack purposely distracts Todd with a video game that sabotages his performance, ensuring he remains with BoJack rather than pursuing his ambitions.

Sleeping With Sarah Lynn

During the episode "Prickly-Muffin," a directionless BoJack invites his former co-star to stay with him following her break-up with Andrew Garfield and battle with drug addiction, though ultimately only fuels her self-destructive ways to soothe his guilt-ridden feelings towards her.

In an abhorrent twist, BoJack ends up sleeping with his pseudo-daughter instead of providing her with the paternal love and support she needs.

Strangling Gina

Season five saw BoJack deal with drug addiction after an accident on-set for Philbert, and this triggers a mental breakdown that causes him to assault his co-star and real-life girlfriend, Gina.

RELATED: The 10 Best Guest Stars From BoJack Horseman, Ranked

It is a sad reflection of Hollywood culture, as in "The Stopped Show" Gina expresses to BoJack that she doesn't want him to confess to his actions and be forever dubbed as "the girl that got strangled by BoJack Horseman."

Pursuing Penny

This is one of BoJack's most damning moments and an example of his self-centered actions damaging the people around him. After he flees the set of Secretariat to stay with former friend Charlotte (Olivia Wilde) in New Mexico, an emotionally repressed BoJack almost gives in to the advances of Charlotte's 17-year-old daughter Penny after being rejected by the family's matriarch.

The question as to whether BoJack would have slept with Penny if Charlotte had not intervened is left unanswered, with both the audience and BoJack not knowing the answer.

Causing Sarah Lynn's Death

Sarah Lynn and BoJack Horseman in a motel

In his final act of carelessness with Sarah Lynn's life, BoJack encourages his protege to abandon sobriety in season three's "That's Too Much, Man!" A hurt and hopeless BoJack ropes the troubled former teen star into a reckless drug-fueled binge, which leads to Sarah Lynn dying from an overdose.

Sarah Lynn's story was a tragic tale about Hollywood's darker side and a warning to BoJack that his actions, despite his intentions, have consequences.

NEXT: Tuca And Bertie: 5 Things It Does Better Than BoJack Horseman (& 5 It Does Worse)