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Jimmy Two-Shoes

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 The title character. The happy-go-lucky boy somehow ended up in Miseryville and stayed there. His goal is to spread happiness in Miseryville, much to Lucius' chagrin. Voiced by Cory Doran.

Beezy J. Heinous

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 Jimmy's best friend. Son of Lucius Heinous VII who rules Miseryville. He is bigger than his father but is lazy and he'd rather spend time with his friends. Voiced by Brian Froud.

Heloise

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 A very intelligent young girl and Jimmy's other best friend. She works for Misery Inc. as top inventor in making hazardous products for people in bringing misery. She is sadistic and likes to torment anyone she hates which is pretty much almost everyone. She has a big crush on Jimmy. Voiced by Tabitha St. Germain.

 Heloise: [overhears Jez laughing sarcastically] No one laughs at Jimmy but me!

Cerbee

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 Jimmy's pet monster dog.

Lucius Heinous VII

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 The seventh ruler of Miseryville and in charge of Misery Inc. He is a short, red devil-like creature who is the father of Beezy J. Heinous and is very much unlike his son. He hates Jimmy due to his happy attitude being a foil to his plans. He is dating Jez. Voiced by Sean Cullen.

Samuel "Samy" Garvin

 Lucius's assistant who dreams of stardom and fame. He is timid and often abused by his boss. He used to serve Lucius' father, Lucius Heinous VI, for 87 years. Voiced by Dwayne Hill.

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Jez

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 Lucius's girlfriend who is tall, blue and can change her noses. She is often very picky in her dates with him and threatens to break up with him. She lives in a white mansion and owns a pet dog named Jasmeen who Cerbee, Jimmy's pet, once fell in love with. Voiced by Valerie Buhagliar.

Saffi

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 Beezy's girlfriend who is an orange-skinned, one-eyed creature. She hates statues and destroys any she sees. She usually spouts one-word phrases such as "Yogurt!" and "Smoothy-Smooth!" but occasionally speaks sentences. Voiced by Sunday Muse.

General Molotov

 Head of Lucius' muscle, Molotov is large and in charge...whenever he isn't being bossed around by his wife. He also has a son named Tory, and a baby daughter named Blamo. Speaks in a vaguely Russian accent. Voiced by Dwayne Hill.

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Lucius Heinous VI

 The sixth ruler of Miseryville, Lucius VII's father and Beezy's grandfather. He's even crueler and more evil than his son. He is rather old and is in a wheelchair, with his limbs occasionally falling off. Lucius overthrew and cryogenically froze him many years ago, but he's defrosted every now and then for various reasons. Voiced by Sean Cullen.

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Dr. Ludwig Von Scientist

 A demon evil genius with a German accent who somewhat resembles an owl. He's not employed by Misery Inc. but is Heloise's arch-rival in mad science. Voiced by Dwayne Hill.

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Dorkus

 A tiny, one-eyed demon who's Heloise's lab assistant. He often has invention ideas of his own, but they're not very good. Heloise has numerous clones of him in case he's ever injured or killed, which is often. Voiced by Dwayne Hill.

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Rudolpho and Peep

 A father/son team of con artists who live to swindle the people of Miseryville out of their money. Rudolpho will sell you just about anything, but expect it to have some kids of flaw, while Peep will merely pick your pockets. Rudolpho is voiced by Juan Chiron, and Peep by Christian Potenza.

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