Too Much, Horseman: Ranking the Most Depressing "Bojack Horseman" Episodes

Say goodbye to Hollywoo.

Bojack Horseman, the washed-up sitcom star (who is also a horse) voiced by Will Arnett, is outta here.

The second half of his animated show’s sixth and final season lands on Netflix today, wrapping up the often-haunting saga of a narcissistic addict wrestling with the demons of his (horse) past.

Besides dealing with all that, it is also a very silly series set in an alternate universe in which bipedal animals—sometimes with names like Mr. Peanutbutter, embodied by the genius Paul F. Tompkins—live in harmony alongside actual people. (We reiterate: the emotionally-wracked star is a walking, talking horse who wears human clothes.)

No review will ever encapsulate the essence of Bojack Horseman better than this tweet:

Me: I like the funny horse cartoon

Bojack: you inherit your parents' trauma but you will never fully understand it

Me: haha the cops a cat

— please be nice to patrick (@ruff_bluffs) September 10, 2017

As one character says to another in the finale, "I can’t tell if you’re being smart or stupid." Bojack Horseman has always been both.

That was especially true in Season 5, even when we wondered why showrunner Raphael Bob-Waksberg and his writers—including producer Lisa Hanawalt, who defined the visual style—didn’t let a healthy, happy Bojack ride off into the sunset after he forged a bond with his newly-discovered sister Hollyhock (Aparna Nancherla).

Instead, they used the burgeoning #MeToo moment to paint Bojack as a celebrity who hadn’t yet fully reckoned with his abuses of power, and the way in which the women in his life suffered.

It was dark.

This last lap goes to even darker depths, with a couple of sleuthing reporters circling a story that’ll potentially destroy Bojack's career. Viewers already know what they're after: how he was instrumental in the accidental overdose of Sarah Lynn (Kristen Schaal), not to mention the pattern of skeevy behaviour that saw him ruin basically every meaningful relationship he ever held.

It’s grim, murky stuff, setting up Bojack as a Louis C.K. or Kevin Spacey-type and testing the audience to see if they’ll follow him down his new spiral of despair. The series, in its last instalments, even takes us to its most perilous edge of all, questioning whether or not Bojack can—or wants to—be redeemed.

But this is the grey area Bojack Horseman loves to live in, baby. In fact, it was the moral greyness that actually made it great.

To celebrate one of the most interesting, complex and, of course, hilarious shows of the past decade, let’s remember its biggest bummer episodes.

*Spoilers ahead for Seasons 1 – 5 but not for Season 6.*

10. "Ancient History" (Season 5, Episode 9)

More than any other character, a friendship with Hollyhock was Bojack’s best shot at redemption… and he squanders it in this episode. After his anxious sis flushes his painkillers down the drain, Bojack drags her along to a shady drug deal. At the end of the episode, after she makes him promise he’ll get sober, he decides to drive into oncoming traffic just so he can get a prescription for more painkillers. And, just to remind you, this is only the 10th saddest episode of Bojack Horseman.

9. "The Telescope" (Season 1, Episode 8)

The cosmic opening credits to Season 6 focus on Bojack’s frayed relationship with his old friend Herb Kazzaz (Stanley Tucci), and for good reason. In "The Telescope", he tries to mend fences after discovering Herb’s dying of cancer, but Herb isn’t able to forgive Bojack for his past betrayal. Herb later dies, and Bojack carries the trauma across all six seasons (especially S6).

8. "Escape From L.A." (Season 2, Episode 11)

This is the moment we knew Bojack Horseman wasn’t effing around: Bojack’s old friend Charlotte (Olivia Wilde) finds him about to bed her teen daughter Penny (Ilana Glazer). This is when viewers really had to consider who their hero was—what would have happened if Charlotte hadn’t walked in?—and when the show had to decide whether or not this would be his rock bottom. It wasn’t.

7. "Free Churro" (Season 5, Episode 6)

This remarkable, Emmy-nominated bottle episode sees Bojack delivering a rambling eulogy to his cruel, mentally ill mother Beatrice (Wendie Malick). Easily the funniest single episode on this list, it’s still a plaintive reflection on the wreckage wrought by Beatrice, and a reminder that death does not close the lid on lingering past abuse. Arnett was rarely better than he was here.

6. "Stupid Piece of Sh*t" (Season 4, Episode 6)

As Bojack continues to care for his dementia-addled mother (now nursing a "baby" doll), we get to see and hear his innermost thoughts: a scattershot cacophony of self-loathing, emphasised by the frenzied animation. The kicker: learning at the end that Hollyhock may be carrying this family’s self-loathing trait too.

5. "Ruthie" (Season 4, Episode 9)

Bojack had previously explored abortion with Diane (Alison Brie) previously, and this episode sees Princess Carolyn (Amy Sedaris) dealing with miscarriage. That it’s told from the perspective of her never-to-be-born daughter makes it all the more heartbreaking. Also making things worse: Todd (Aaron Paul) is starting a Clown Dentist practice in her apartment. Chilling.

4. "The Showstopper" (Season 5, Episode 11)

Where the makers decide to stretch Bojack’s misdeeds to—potentially—the point of no return. It's hard to watch Bojack choke his girlfriend/co-star Gina (Stephanie Beatriz) in a drug-induced haze while shooting gritty cop drama Philbert. I don’t know if the show ever got more disturbing than this… except for maybe the next three examples.

3. "That’s Too Much, Man" (Season 3, Episode 11)

Was Bojack responsible for Sarah Lynn’s addiction? He certainly helped the former child star off the wagon, and failed to protect her when she needed better parental boundaries as a kid. But even if they were both adults—and both outside of their senses—when she died of a heroin overdose in "That’s Too Much, Man", there’s no excusing his cover-up that follows. The chickens come home to roost in Season 6. However, before that judgment arrives, there’s this ep, where Sarah Lynn’s imagines another, better life, only to lose the only one she was doomed to live.

2. "The View from Halfway Down" (Season 6, Episode 15)

Nope, we’re not gonna say what goes on in this ep. The pic isn't even from "The View from Halfway Down", which is the penultimate instalment of the series. Just take heed: it’s #2 for a reason. Prepare yourself accordingly.

1. "Time’s Arrow" (Season 4, Episode 11)

The best episode Bojack Horseman ever produced, as we finally see the world, and the past, through Beatrice’s increasingly mangled mind. It ends with a simple act of generosity on Bojack’s part, and a returned act of politeness from Beatrice—the only and last kindnesses they’ll share.

Anyway, have a fun weekend!

Bojack Horseman is available to stream on Netflix.

Header Image: Netflix