10 Saddest Supporting Character Deaths in Cowboy Bebop

Every episode of Cowboy Bebop mostly revolves around the escapades of Spike, Jet, Faye, Ed, and even Ein as they travel to various planets in search of wanted criminals whose capture will finally put them in a different tax bracket. Over the course of their travels, fans were introduced to characters that the Bebop crew’s members had been acquainted with not only years before, but people they’d just met that same day.

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What makes this anime so rich is that all of these characters have their own complex desires, and yet a happen ending is rarely around the corner for any of them. There’s no getting around that Cowboy Bebop isn’t for the faint of heart; death commands its narrative, and unfortunately, many of these secondary characters met gruesome ends that in some cases, they just didn’t deserve.

10 Chessmaster Hex

In “Bohemian Rhapsody”, the Bebop crew searched for a man who, after wanting revenge against the Gate Corporation for using his Astral Gate designs without his blessing, set traps in many of these Gates that activated 50 years later. While his evil plot worked without a hitch, Chessmaster Hex had been living in a junkyard for so many decades that he’d gone senile and forgotten all about his past.

As his name suggests, he was only concerned with playing chess in his old age. While nothing stopped Spike and the others from turning him in for the promised bounty, it was admirable that they decided to let him go, allowing him to pass on peacefully after winning a chess match against Ed, his fiercest opponent.

9 Wen

Wen might’ve been an antagonist in “Sympathy for the Devil”, but he was just as much a victim as anybody else.

The Astral Gate accident of 2022 that devastated Earth not only killed his parents, but made him immortal, trapping him in the body of a 12-year-old for half a century. By the episode’s end, he finally got the rest he deserved after being shot with a special bullet that caused all his years to catch up with him at once.

8 Pao Pu-Zi

In “Boogie Woogie Feng Shui”, Jet teamed up with Pao Meifa, the daughter of his former associate Pao Pu-Zi, in a quest locate the sunstone, which Meifa felt was connected to her father’s sudden disappearance. Pu-Zi needed his daughter to find the sunstone so that he could say his final goodbyes, revealing that he was trapped in hyperspace with a waning supply of oxygen aboard his ship.

While it was unfortunate that he was leaving behind a young woman to face such a cruel universe on her own, he would’ve never wound up in such a predicament had he not joined the Blue Snake crime syndicate in the first place.

7 Mad Pierrot

Mad Pierrot definitely needed to be stopped, but it’s worth noting that he was a victim of a society that only cared about money and technological innovation while often putting human decency aside. Experiments were done on Mad Pierrot to make him the perfect killing machine. They were definitely successful, given his impressive track record and the fact that he nearly killed Spike twice.

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Unfortunately, his mind regressed into a childlike state when he was quarantined at a secret facility due to being deemed a failed experiment. This childlike mind became his downfall; when Spike managed to get one hit on him, he went into a wild temper tantrum, putting himself in the path of a parade of giant robot animals where he was crushed flat, begging for his mother.

6 Roco Bonnaro

Roco Bonnaro only resorted to petty crime because he wanted to support his blind sister. Spike saw that he was a good but misdirected kid, and helped him retrieve the Grey Ash plant that could cure his sister’s blindness.

The two later fought through an ambush, but Roco, not paying attention to his surroundings, was shot through the back. While his sister’s eyesight was eventually restored, Roco’s death ensured that his sister would never get to see him with her own eyes.

5 Katerina Solensan

In Cowboy Bebop’s first episode, Spike and Jet were on the hunt for Asimov Solensan, a high-ranking crime syndicate member who fled after betraying his own gang in hopes of starting a new life with his wife, Katerina. Katerina’s dream was to leave the planet of Tijuana and experience a finer life on Mars, and while she knew that she’d need money to lead a new life there, she paid the ultimate price for marrying a crime syndicate member as a means to her end.

This episode set the dark, melancholy tone that would remain for the rest of the series, with Katerina killing her husband as he flew his ship towards a police barricade that blew their ship to smithereens, killing her in the process. While it’s easy to disregard all sympathy for her since she aided her husband in his evil pursuits, many viewers would find it easy to sympathize with someone who just wanted to create a better life for themselves.

4 Shin

While there are countless crime organizations scattered across multiple planets in the world of Cowboy Bebop, perhaps the most dangerous is the Red Dragon Crime Syndicate, which boasts skilled members like Spike and Vicious. Shin was one member who didn’t really want out, but wanted the syndicate to change for the better.

This is why, in the final two episodes of the series, he teamed up with Spike to put a stop to Vicious so that Spike would be the one to control the Red Dragons in his place. Unfortunately, just before he and Spike reached Vicious, Shin was shot and killed, a fate that he would’ve had coming regardless given his profession.

3 Gren

Vicious attempting to kill Spike was just him fulfilling the will of the Red Dragon Crime Syndicate, since Spike did in fact betray the organization by defecting. This can be justifiable for fans wanting to play devil’s advocate. Vicious’s betrayal of Gren, on the other hand, was completely uncalled for. Gren admired Vicious as a soldier, serving alongside him during the Titan War, only to have Vicious testify that he was actually a spy, which essentially derailed Gren’s life.

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Years later, he got the chance to confront Vicious, but like everyone else who had any qualms whatsoever with the Red Dragon assassin, he was mortally wounded as a result of their battle. He died with his ship floating towards Titan, the place that in some ways ruined his life and in others gave him a reason to continue living it.

2 Annie

After Vicious took over the Red Dragon Crime Syndicate, he was determined to kill everyone who had a connection to him, even if they weren’t in the organization themselves. Annie’s former husband and her friend Mao were involved in the syndicate, but both of them had already been killed, and yet Vicious saw that it was fit for her to join them in the afterlife.

Her last moments were pretty heartbreaking; she made a fleeting remark about the cold weather before dying in a dark corner of her own shop, a place that should’ve been her safe haven.

1 Julia

It’s almost ironic that Spike spent so much time searching for Julia only for her to be killed when they finally crossed paths. They could’ve ran away together and put the syndicate behind them. If they’d fled to some abandoned corner of Earth, for example, they would never be bothered for the rest of their days, but Spike remained determined to take Vicious down once and for all.

A firefight against some Red Dragon goons led to Julia being shot and killed, taking her last breaths in Spike’s arms. With her death, it’s no wonder why he ran into the Red Dragon Crime Syndicate’s hideout guns blazing, since with Julia dead, Spike had pretty much died too.

NEXT: Cowboy Bebop: 5 Times It Proved To Be The Best Anime Of Its Decade (& 5 Times It Fell Short)

Next 10 Times Anime Villains Made More Sense Than The Heroes

About The Author Lavell (212 Articles Published)

When he isn’t writing for CBR, Lavell is usually playing videogames, catching up on interesting anime, or writing novels. An English major from the University of Virginia and an active member in New York’s television scene, he enjoys meeting people who care about telling good, tasteful stories. You can follow him on Instagram @yungvelly.

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