Dragons and Randomness

Tails is the monk, Tang Sanzang

Amy is Piggy, Zhu Bajie

Knuckles is Sandy, Sha Wujing

And Shadow is the Great Sage, Sun Wukong

This is what happens when Tyrogue in training can't choose a fighting style to lean to, unlike with Hitmons.

Hitrogue is based on a mixed martial art (MMA) fighter: it's obsessed with mastering as many fighting techniques as possible, to the point where it can get too carried away and pick up a fight it can't win. It's generally weaker than regular Hitmons, because instead of being exceptionally good in one style, it's decent in many.

Tired of being too weak, holding grudges against the more skilled Fighting types, Hitrogue ultimately decides that rules, descipline, and the code of honor is not for it, and evolves into Ruffrogue. Based on the illegal fighters, it'll do anything to win a battle no matter the cost. Embracing Tyrogue's initial mischievousness, Ruffrogue is a master of dirty tricks. It's not afraid to hit too hard into all the right places, doesn't care about its opponent's wellbeing, and the concept of mercy is just foreign for it. It doesn't give up, and won't let its foe to give up either, until neither of the two can stand on their feet.

Hitrogue's hairstyle is loosely based on the MMA training helmets, and its outfit is basically shorts and the MMA arms/legs protection. The hardened skin on Ruffrogue's hands are somewhat based on various weapons ruffians put on their knuckles, such as brass knuckles, combined with knuckle calluses that develop after long excessive trainings, and its bright upper tooth is based on a mouthguard! Its ears are also dark and puffy, like how fighters' ears look like after being damaged and broken many times.

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Instead of going the cold cruel way of Glalie and Froslass, Snorunt stays near humans who adore it and takes in their warmth, both literal and figurative.

By either being gifted smoldering charcoals or finding some by itself (or, by a game mechanic, holding the actual Charcoal item), Snorunt evolves into Snorzy ("snoring" rather than "snow" + "cozy"). It hides the pieces of coal under its belly, taking in as much of their heat as possible until they run out of it, and the long furry flaps of skin Snorzy developed help it keep the warmth inside. It's much slower than Snorunt, but instead has great Defense and even greater Special Defense, as nothing can bother this peaceful creature when it's all warm and cozy like this. Children often gather around Snorzy and take a break from playing in snow by hiding their legs under this Pokemon's fur until they're warmed up and ready to play again. And as a little bonus, Snorzy doesn't shiver as much as Snorunt! Only occasionally, when it runs out of hot coals.

Being exposed to a Fire Stone, Snorzy absorbes its fire energy and becomes Snuggloo ("snuggle" + "igloo") who can now generate heat of its own! This kind-hearted Pokemon helps lost children by taking them inside its thick snowy coat and keeping them warm until help arrives. The orange patterns of Snuggloo's coat glow in the dark, as if there was a bonfire burning inside of it, which only helps people to spot it. It enjoys warming up smaller Pokemon too! A single Snuggloo's age can be told by how large in size it is.

Snorzy is inspired by kotatsu, specifically an old-fashioned type powered by burning coals being buried underneath it. And Snuggloo, as already said, is inspired by an igloo and loosely by various Eskimo fur coats. Its patterns glow the same way igloo glows when a fire is lit inside, and the Pokemon itself grows in size overtime the same way igloos do.

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Clamperl that fell victim to the jewelry industry.

Instead of being left to evolve the natural way, Clamperl was caught in a Luxury Ball in order for its pearlescent body to be turned into extra fancy pearl beads, thus becoming Matiara (from "mutiara" and "mati", Indonesian for "pearl" and "death" respectively (thanks to my Indonesian friend Hexx_Vixtar for the idea!), + "tiara"). Its shell was made into a jewelry box, and several Clamperls were sewed together into a single piece. The mysterious powers Clamperl posesses are now centered around Matiara's suffering and longing for the sea, granting it the secondary Ghost type, and its Water-type attacks are now all made of its tears.

Getting more pearls (or Clamperls) into its possession, Matiara evolves similarly to how Clamperl evolves into Huntail or Gorebyss. The sheer concentration of pain and grudge allows Necreel ("necro" + "nacre" + "eel") to float in the air freely, as if it was swimming in the ocean it so longed for. It hunts down humans deliberately, especially seeking out the richest ones in order to take its revenge and claim as many jewelry as possible while it's at it. Necreel is the number one threat for the pearl farms, some of which had to close or relocate their business because of a single Necreel hunting them down.

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I also had this idea for Scyther evolutions with a high sexual demorphism, where the female is much bulkier and wears severed heads of male Scythers as her armor, while the male is now a hollow chitinous shell possessed by a ghost, but I kinda ran out of fuel at this point and ended up not liking the design very much, so... just have it as a bonus :D