Simon Bar Sinister was the main villain in the Underdog cartoon show. Simon is the wickedest man in the world, and it was his ambition to rule the world, but each time, Underdog defeated him. Voiced by Allen Swift, and based on the voice and looks of Lionel Barrymore, Simon appeared to be only two feet tall.

The "Bar Sinister" in his name was a macaronic reference to a mark from heraldry, in English called a bend sinister; on a shield it was denoted by a line (to those facing the shield) from the top right to the bottom left. (The French equivalent is barre, and is pronounced the same way.) His name could be translated as "Simon, the Bastard" (see baton sinister). Additionally, his name could be a mock or pun on Simon Bar Jonas or Simon bar Kokhba.

In Aramaic, the word bar means "son of". Simon's most famous saying was, "Simon says!" His henchman was Cad Lackey, who, though generally dull-witted, was occasionally capable of pointing out flaws in his boss's plans. Contrary to the mad scientist stereotype, Simon actually paid attention to Cad's suggestions.

In the 2007 live-action film adaptation, he is portrayed by Peter Dinklage. In the movie, Bar Sinister was originally a geneticist for a company in Capitol City, using dogs as test subjects for the betterment of mankind. But after being laughed at by the Mayor after attempting to have his research expanded to law enforcement, Bar Sinister began his work to create a super-power formula to get revenge.

However, the incident resulted in the destruction of his lab that not only scarred his forehead, losing some of his hair, and being limped in his right leg, but created Underdog.

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