The Monarch

The Monarch is the archenemy of the Venture Bros and is one of the world's most powerful supervillains despite his rather comedic lack of sucess: largely down to his arrogance, inability to not get tricked and his over-dramatic nature - all of which are parodies of traditional megalomanical behavior common in supervillains - he is named after the Monarch Butterfly, which he has taken an obsession with a modelled his entire empire around.

History
The Monarch was the child of a wealthy couple who died when their private plane crashed in the New Jersey Pine Barrens. The Monarch was the only one to survive the crash, and spent 3 months living in the forest amongst a colony of Monarch butterflies, who "adopted" him. As he was ignorant of their migration patterns, the butterflies eventually left, and the devastated Monarch hitch-hiked to the city and collected his sizable inheritance. The remainder of his boyhood and teenage years were likely spent in New York, as "The Trial of the Monarch" revealed Monarch's connection with the 1980s New York punk scene. The Monarch apparently left New York to go to college [he, Thaddeus Venture, Werner Underbheit, Pete White, and Mike Sorayama all went to the same college at the same time. Brock Samson attended for one of those years, but was a freshman to the others' senior class levels. In college, he was known as Malcolm and shared a creative writing class with Dr. Venture; apparently, the Monarch devoted all of his assignments to butterflies (which led Venture to initially assume he was a "closet case"). At some point in college, The Monarch made his first attempt to kill Thaddeus, which instead resulted in Underbheit's disfigurement.

After graduating college with a BA in Creative Writing, The Monarch went to work at the Guild of Calamitous Intent as a registered low-level henchman to Sea An-enemy, Helicoptro, and Joseph and his Amazing Technicolor Nightmare Coat, while he waited for his trust fund to come out of escrow. During this time, he also illegally moonlighted as his "Monarch" alter-ego, unsuccessfully arching on a young Dr. Venture. He was working as Shadowman 9 for Phantom Limb when he met his future wife; she had just failed at being a solo super-villain (Lady AuPair), and accepted a Number 2 position working for Phantom Limb, this time as Queen Etheria. Donning one of his "early version" butterfly costumes, he attended a dinner party held by the Guild, and successfully seduced Queen Etheria in his car parked outside; Phantom Limb discovered this, and both Queen Etheria and The Monarch left together.

With the guidance of his new Number 2 (Doctor Girlfriend), The Monarch gave up his henching career, and turned to full-time arching of Doctor Venture. Using The Monarch's vast wealth, they built a giant, floating military base from which to launch his attacks on Dr. Venture. Near the end of the first season, he and Doctor Girlfriend have a falling out over a tell-all book published by the Monarch's henchmen (according to the Monarch, "filled with lies and pictures of also-lies"), which brought to light her salacious past with a variety of other supervillains. She left him and went back to Phantom Limb, who in turn framed the Monarch for murder so that he could have Doctor Girlfriend to himself. The Monarch managed to escape from prison and rebuilt his career, eventually winning back Doctor Girlfriend; The Monarch and Doctor Girlfriend were officially married at the beginning of season 3, whereupon she changed her name to Dr. Mrs. The Monarch.

In return for recognition and leniency from the Guild (and for permission to marry his wife), The Monarch was forced to stop arching Dr. Venture, a fact which he has trouble coming to terms with. Season 3 saw The Monarch sinking ever-lower in depression over not arching Venture: killing all 8 of his "new assignments" from the Guild, nearly ruining his marriage, raiding the Venture compound and having sex with "GUARDO" (a robotic guardian with the face of Dr. Venture), claiming it to be an attempt to give it chlamydia; and finally arching Jonas Venture, Jr. on a trial basis. Thanks to a "family by-laws" loophole found by Dr. Mrs. The Monarch, season 3 ends with a horrific showdown at the Venture compound, where The Monarch donned shooting, flying (but otherwise immovable) armor and faced off against the O.S.I. He ended up killing all of the Hank-and-Dean clone slugs, several O.S.I. troopers, many of his own henchmen, and finally fell to earth in a nauseated bundle, to be picked up by his remaining henchmen and his wife.

In the second episode of Season 4, The Monarch kidnaps Hank & Dean and tries to order Dr Venture to pay a ransom. Hank is immediately rescued by Captain Sunshine, who takes him back to his lair to make him the new Wonder Boy. (The Monarch killed the last Wonder Boy while he and Dr. Girlfriend were broken up.) Dr Venture gets Dean back and then both he and the Monarch track down Captain Sunshine's lair in order to get Hank back. His wife creates for Monarch a solar ray cannon, guessing that Captain Sunshine's powers don't work at night. However, the ray gun empowers Sunshine who then defeats the Monarch. The Monarch, his wife, and 21 head home in a cab. One of them then fires a dart at the cabbie when he inquired about the fare.