History TearJerker / BoJackHorseman

* "Out to Sea" compares a day in the life of the separated Diane and Mr. Peanutbutter. Mr. Peanutbutter seems to have it much better than Diane, who is disgraced and ashamed from returning to L.A. with nothing to show for it. Then he quietly sneaks away from his own party to sigh and look up at the stars as he pines for his wife.

** The ending credits replace the usual theme with a miserably beautiful song about not looking back.

* The pen-pal prank video, with teenage Diane shakily complimenting the hobo's beard and then breaking down crying.
** If you look at the hobo, it's clear that he was really uncomfortable doing this, and probably just needed the money.

* The ending of "Say Anything" would've been a triumphant one if the events of "The Telescope" didn't make part of it a ShaggyDogStory and the reveal that [[spoiler:no one remembered or bothered to wish Princess Carolyn a Happy Birthday]].
-->'''Laura the secretary:''' Are you gonna head out soon?
-->'''Princess Carolyn:''' Where else would I go?
** The ending credits replace the usual theme with a miserably beautiful song about not looking back.
* Bojack's [[WrongGenreSavvy misconception that real life operates like a sitcom]] finally blowing up in his face when Herb [[TheReasonYouSuckSpeech calls him out]] on how selfish and petty he is.

* Any time Bojack asks if he's a good person or if people like him.

--> '''Todd:''' As you know, I was hurt, but then I realized that's just how you are, You know? And maybe I just need to stop expecting you to be a good person, so that way, I won't get hurt when you're not.

* Mr. Peanutbutter ends up reading a lot of hate mail directed towards Diane during "Hank After Dark" and goes steadily more depressed because of all the terrible things people are saying about her.

** The ending where it's revealed that the events of the episode cost Kelsey her job, because Turtletaub fired her for disobeying his orders... especially since it was established a few episodes earlier that Kelsey needs a big budget movie success to provide for her daughter and avoiding losing custody to her ex-wife.

*** Even before Charlotte drops the bomb that it's AllJustADream, it's pretty easy to tell that something is up with this too-perfect scenario. The reveal hurts, but the anticipation is ''murder!''
*** The majority of his MushroomSamba counts as well, as it reveals just how [[BrokenBird psychologically broken Bojack really is]], including a flashback to his StageMom pushing him into singing the "Lollipop song" for her friends at the Supper Club, telling him something he later passed down to Sara-Lynn.
--->'''Beatrice''': Nobody gives a damn what you feel! You've got an audience out there, and they want to hear you sing! [[AbusiveParents Now you want your mommy to love you?]] You go out there, and you do the only thing you're good for, which is ''singing the god-damned lollipop song!''

--> '''Bojack:''' Okay, just to be totally clear, [[ItMakesSenseInContext we're shooting each other]] to determine whether we're holding guns or brooms, right? Not because you're still mad about the whole me sabotaging you with the rock opera and your live stream and suchety-such?

* In "The Telescope", we learn that Bojack abandoned his friend Herb after he got kicked off the staff of his sitcom, when all Herb really needed at the time was a friend. To be fair, Bojack was coerced into it by his heartless studio executives[[note]] and Herb initially wanted Bojack to threaten to walk if he got fired[[/note]], but he still carried a lot of guilt over that. Years later, Bojack tries to make amends, but Herb [[RejectedApology doesn't forgive him]] and tells Bojack that he'll have to live the rest of his life without closure, sealing Bojack's status as a JerkassWoobie and giving his relationship with Herb some emotional depth and brokenness.

Despite being advertised as a comedy, the later episodes of Bojack Horseman are anything but.

* Any time Bojack asks if he's a good person or if people like him.

-->'''Bojack''': I guess my question is - do you think it's too late for me? [[RealisticDictionIsUnrealistic I mean am-am-am]] I just doomed to be the person I am? The-the person in that book? It's not too late for me, is it? It's-- it's not too late-- Diane, I need you to tell me that it's not too late. I-I-I need you to tell me that I'm a good person. I know that [[ItsAllAboutMe I can be selfish and narcissistic]] and self-destructive, but [[JerkWithAHeartOfGold underneath all that, deep down, I'm a good person]], and I need you tell me that I'm good, Diane. Tell me, ''please'', Diane. [[AintTooProudToBeg Tell me that I'm good]].

** In the same episode, an intoxicated Todd gently admits that he no longer expects Bojack to ever be a good friend so he can stop being disappointed whenever he doesn't do the right thing.

** During his MushroomSamba, Bojack dreams of a life where he left showbiz, got together with Charlotte, started a family with her and living a simple but fulfilling and happy life. Moreover, he actually ''does'' seem like a good father (unlike his own parents who were horribly [[AbusiveParents abusive]]), and Charlotte is very sweet and Bojack is actually a nice and normal person around her on his own accord. And then Dream!Charlotte seals it when she says how much happier Bojack would have been had he chose this life.

** Charlottes hatred of Bojack by the end of the episode is absolutely heartbreaking, especially remembering the Maine hallucination in "Downer Ending". Consider that Bojack is implied to still love her- and the implications that Bojack [[spoiler: was about to give in to Penny's seduction]] not out of some selfish or disgusting act of no self-control, but rather an attempt by Bojack's subconscious to sabotage his relationship with Charlotte for good.

** Charlottes hatred of Bojack by the end of the episode is absolutely heartbreaking, especially remembering the Maine hallucination in "Downer Ending". Consider that Bojack is implied to still love her- and the implications that Bojack [[spoiler: was about to give in to the seductions of Penny, Charlotte's daughter]] wasn't some selfish or disgusting act of no self-control, but rather an attempt by Bojack's subconscious to sabotage his relationship with Charlotte for good.

** Charlottes hatred of Bojack by the end of the episode is absolutely heartbreaking, especially remembering the Maine hallucination in "Downer Ending". Consider that Bojack is implied to still love her- and the implications that Bojack [[spoiler: attempting to sleep with Penny, Charlottes daughter]] wasn't some selfish or disgusting act of no self-control, but rather an attempt by Bojack's subconscious to sabotage his relationship with Charlotte for good.

** And ''then'' his mother calmly walks into the living room and blames it all on Bojack, telling him that he'd "better grow up to be something great to make up for all the damage [he's] done."

** And the reason he never cries in public is because the one time he tried a cigarette as a kid his mom caught him and [[RadishCure forced him to finish it]] in front of her telling him [[MenDontCry that he should never to cry in front of others, least of all her]].

--->'''Beatrice:''' I'm punishing you for ''being alive''.