Television series
Trigun
Vash the Stampede is a walking disaster with a sixty-billion-dollar bounty and an almost pathological commitment to not killing anyone, ever, no matter how many towns explode around him. Trigun spends its first half as a goofy episodic western with slapstick and gunfights, then quietly reveals the grief and philosophy underneath. It's for anyone who wants a hero whose silliness is armor over something much sadder.
If you liked this
Cowboy Bebop1998
Same era, same jazz-soaked melancholy, same trick of swinging from slapstick to heartbreak inside a single episode. If Vash's tonal whiplash worked on you, this is the show that perfected it.
But Cooler and more noir, with less goofy comedy and a colder, more resigned kind of found family.

Fullmetal Alchemist: Brotherhood2009
A pacifist protagonist wrestling with a monstrous sibling, questions of forgiveness versus vengeance, and huge action set pieces that never lose the moral thread underneath.
But Much longer and plot-heavier, with less of the episodic freedom and standalone-episode charm Trigun has.

Rurouni Kenshin: Meiji Kenkaku Romantan1996no page yet
A reformed killer who has sworn never to draw his sword again, haunted by a past that keeps catching up with him — the samurai version of Vash's vow.
But More earnest and traditionally structured, with far less of Trigun's absurdist comic relief.
The wildcard
Something you would not have found on your own.
Shane1953
Trigun is remixing this exact foundational myth: the reluctant gunfighter whose legend forces bloodshed on him no matter how hard he tries to walk away from it.
A gunslinger who wants to hang up his guns and live peacefully, only to find his reputation drags violence back to him anyway — Vash's entire arc, in black and white, decades before anime existed.
But Slow, stately, and completely earnest, with zero slapstick or cartoon energy to soften the myth-making.

More like this (8)
Samurai Champloo2004
A mismatched trio wandering a violent world, blending genuine laughs with sudden tragedy and a restless, anachronistic energy that feels like Trigun's cousin.
But Feudal Japan swaps guns for swords, so the sci-western flavor and desert-planet mythology are gone.

One Piece1999
A goofy, absurdly overpowered hero hiding real grief, leading a found-family crew, refusing to kill even his worst enemies. Vash energy, just turned up to eleven.
But An enormous, ongoing commitment, and the silliness runs even higher than Trigun's.

Outlaw Star1998no page yet
A contemporaneous space-western with bounty hunters, a scrappy ship crew, and pulpy adventure-of-the-week fun in the same genre lane as Trigun.
But Lighter and more straightforward, without Trigun's philosophical weight or emotional gut-punches.
Baccano!2007no page yet
Immortal gangsters, alchemy, and gunfights told in a gleefully nonlinear structure that mixes pulpy violence with real charm and dark comedy.
But A bigger, more chaotic ensemble cast means less single-character focus than Trigun offers.
Gungrave2003no page yet
A gunslinger anti-hero with a mafia past, wrestling with loyalty and the cost of violence, in a much slower, more brooding register.
But Considerably grimmer and slower-paced, with far less humor to leaven the darkness.
Firefly2002
A live-action space-western crew of outlaws, all banter and loyalty until tragedy hits, with the same lived-in frontier grit Trigun's planet Gunsmoke is built from.
But Cancelled after one season, and the tone is more straightforwardly Western with none of the anime's cartoon exaggeration.

The West1996
Gunsmoke's dusty towns and outlaw legends are pastiche of the American frontier; this documentary shows what that mythology was actually built on top of.
Strip away the myth and look at the real economic brutality and human cost of the frontier iconography Trigun borrows so freely — a genuinely sobering counterweight to all that gunslinger romance.
But Nine-plus hours of narrated documentary history with no characters to follow and no plot to speak of.

The Iron Giant1999
Both ask whether a creature designed to be a weapon can choose not to be one — Trigun asks it frantically, this film asks it softly.
A gentle, immensely powerful being built for destruction chooses restraint and love instead — the same core dilemma as Vash, but rendered tender, simple, and quietly devastating in an animated family film.
But Much shorter, aimed squarely at kids, and sentimental where Trigun is frequently manic, violent, and morally messy.

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Recommended by
Cowboy Bebop, A Fistful of Dollars, Vampire Hunter D: Bloodlust, Cyberpunk: Edgerunners