Hellish Jay & Skyler are two minor antagonists in Squidbillies. They appear exclusively in the episode "The Tiniest Princess". The orange monster is named "Hellish Jay" while the blue one is named "Skyler".
Hellish Jay, and Skyler are two are large ant-man like monsters that are very similar, and look identical to each other in appearance. The two monsters appear in two different colors which are orange (with small orange spots on his forehead), and blue with both monsters having large rows of teeth. With both monsters having very large noses. Hellish Jay has orange curly shaped eyes with two small pupils, while Skyler has yellow curly eyes with his own two small pupils. Both monsters have growing balls for tails. Hellish Jay's is colored purple, while Skyler's is colored red.
These two are two large monsters of an unknown species, which is claimed to be an ant-man, that can only appear on Halloween night, and both appear to be hostile. Both Monsters are described by Granny with the lack any hair, no skin and "a devilish tight ass". Both monsters have the abilities to roar, or speak English, most notably Skyler. However Hellish Jay usually roars mostly onscreen. Hellish Jay also has his own cellphone, that he holds to call Early with.
They encounter Early, Rusty, Granny, and Sheriff around a campfire on the same night, which the latter was close to Hellish Jay into being into a relationship with him, even having fun smoking cigarettes, holding hands together, going on carnival rides with him, and eating cotton candy, and having sex with him in Sharif's police car. But Sheriff hasn't heard from him since three days have passed, making him cancel a trip to Costa Rica, and Jay got a refund on the tickets, and left a bite mark on Sheriff's body offscreen. Oddly Skyler also shows friendship with the Sheriff, who calls him cool, also he mentions that Lil is scoping him (referring her as a chick), and he feels better if he sucked down some blood shooters (which were body shots) to presumably suck Rusty's blood.
Eventfully, after some chatting, both monsters are killed by Early's shotgun, but return as ghosts, leaving their bodies behind, but after Sheriff dresses up as a baby, as they don't hurt babies, but failed, and Early accidently explodes his own house with dynamite going through Skyler's body, the two monsters end up having sex with each other as Skyler is attracted to Hellish Jay, due to his muscles, making them obviously gay. After this, the Cuyler family, and the Sheriff encounter a third monster, and the two are last seen doing the same thing over, and over again, and both are never seen again.
- "The Tiniest Princess" (Only Appearance for Skyler)
- "Mephistopheles Traveled Below to a Southern State Whose Motto Is 'Wisdom, Justice and Moderation'" (Hellish Jay cameo)
- These two are one of the few characters in the series that have been killed, but return as ghosts.
- Some sources related to the show claimed that these two are called an "ant-man" such as Adult Swim.com's description for their debut episode, despite having no resembling of an ant.
- A reddish Hellish Jay makes a brief cameo in the episode "Mephistopheles Traveled Below to a Southern State Whose Motto Is 'Wisdom, Justice and Moderation'" when Squid Satan is summoned by Reverend and covers the land of Dougal County in flames, he briefly appears coming out of a hole of flames.