12 Saddest Bojack Horseman Episodes

Rather than being based on the sadness of the titular character, as most of the episodes on this list are, Ruthie focuses on the life of Princess Carolyn. Named for PC's great, great, great granddaughter, the episode starts with Ruthie giving her class a speech on her ancestor in the distant future.

She actually starts the episode in a fantastic position, enjoying living with her boyfriend and pregnant with his child, but as Ruthie said, this was a story about one of the worst days of her life. First, she broke her priceless family heirloom necklace, was fired by Courtney Portnoy, was forced to fire Judah after he betrayed her, she devastatingly suffered another miscarriage, and finally found out that the priceless family heirloom was in fact nothing special.

Clearly, the focus is on the miscarriage more than anything, as a life-changing, soul destroying kick while she was down, however the fact that Ruthie existed at all suggested that she would eventually have a child, so the happy ending that was promised always seemed likely.

But this is BoJack Horseman, and happy endings are rare. After breaking down, unable to face telling Ralph the news or even going home, she got drunk and broke up with her boyfriend for suggesting other options of having a baby. The absolute gut punch of this episode is the revelation that Ruthie was never real, but merely a figment of Princess Carolyn's imagination she thought up to make herself feel better.