Molotov Cocktease (voiced by Mia Barron): a highly-trained assassin, Brock Samson’s sometimes-ally, sometimes-antagonist, and full-time love interest. Years ago, she killed his partner, and he killed her father in revenge and plucked out her left eye (which Brock still disturbingly keeps in a jar as a keepsake of his love for her). Despite their history, she holds Brock in very high regard and doesn’t understand his loyalty or obedience to the Ventures. She is an ex-Soviet agent, now making her living as a mercenary. She shares a somewhat sadomasochistic relationship with Brock, who has referred to her as “the only woman [he has] ever loved.” Unfortunately for him, she wears a chastity belt bearing a Soviet hammer and sickle mentioning that “it is always cold in Siberia” to Brock’s exclamation of “I thought the Cold War was over,” so their relationship can never be consummated. Her name is a pun combining “Molotov cocktail” with “cock tease” (referring primarily to her chastity belt). In some Venture Bros. related artwork, her last name is spelled “Coqtiz,” though “Cocktease” seems to be the official spelling. Her name is also an obvious reference to Bond girls who have improbably provocative names such as Pussy Galore.
Col. Bud Manstrong (voiced by Terrence Fleming): Until recently, with the late Anna Baldovitch, was the leader of the two man crew of the abandoned space station, “Gargantua-1”. He is a very repressed individual who cowers under the will of his inebriated, oversexed mother and his severely hyperconservative attitudes towards sex (taught by his father) brought tremendous strain on the relationship between him and Baldovitch, especially when Brock Samson ended up in the middle of things. After Gargantua-1 crashed on a wanted terrorist, Manstrong is treated as a hero and was offered the vice-presidency, which he turned down in horror upon learning of the president’s indiscretions (strongly satiric of the Clinton-Lewinsky Affair despite that the president resembles Lyndon Johnson physically and George W. Bush vocally). Alternates between immaturity and sheer denial when confronted with sex and anything remotely unpleasant (and often behaving quite stupidly in the process, such as trying to criticize Brock Samson’s bad manners while being attacked by him, or picking a fight with him later despite Brock’s attempt to apologize and make friends).
Watch and Ward (voiced by Christopher McCulloch and Doc Hammer respectively): Two Guild operatives who seem to be part of some form of communications center. They work directly with Sovereign. They frequently engage in petty arguments that are based on actual conversations between the show’s creators. Their names may derive from the Watch and Ward Society.
The Master (voiced by H. Jon Benjamin): a supernatural presence who lives in a black void accessible through a portal in Triana’s closet, he is Dr. Orpheus’s old teacher and mentor to magic. With a much more laid-back personality than Orpheus, he often chides his student for being extremely uptight. However, this attitude seems to be his method of imparting advice to his pupil; he convinces Orpheus to better himself by pointing out his flaws. He has admitted that Orpheus is still his best student and seems to have a fondness for him, frequently letting Orpheus come to him for advice. The Master is a shapeshifter who seems to delight in taking forms that in some way arouse him. In his first appearance, he takes the form of Cerberus, and derived pleasure when one of the heads he doesn’t control performs autofellatio. His next appearance is as the horse rumored to have squashed Catherine the Great; he is seen suspended by a pulley-system preparing to engage in sexual intercourse with a multi-headed doppleganger of Catherine, telling her not to wince. This was meant to be a lesson in “biting off more than you can chew.” Later, he appears as Dr Orpheus’ ex-wife, Tatyana, while constantly bragging about her beauty as well as planning to jump-rope naked in front of a mirror while in her form. The last form he is shown in, and incidentally the only one he does not derive any particular pleasure from, is an older, neurotic, balding version Dean Venture, used as a sort of “worst case scenario” to convince Triana Orpheus to embrace the gift of magic she inherited (which according to him is much more lucrative than art school, which her father was pushing her toward).
Myra Brandish (voiced by Joanna Adler): Hank and Dean’s possible biological mother. According to Brock, she was an American Gladiator under the name PowerKat (though this is possibly only a cover-up story made by Brock to hide her relationship with the family from Hank and Dean). However, she claims to be a former O.S.I. agent who guarded Venture in the same manner as Brock does, except that Myra fell for Dr. Venture and after some aggressive, one-sided flirting on her part, they had a fling, resulting in Hank and Dean. Regardless of her true past, Dr. Venture has admitted to having sex with her. Unfortunately, she went insane and has since become a recurring nuisance for Dr. Venture and Brock; she would periodically break out of the asylum and do something different based on whatever medication she is on, such as burning down the compound. Some evidence does exist to support Myra’s claim to have worked for the O.S.I. In “I Know Why the Caged Bird Kills” she accurately quotes some of the same regulations that Col. Hunter Gathers quoted to Brock during their first meeting. Also, in “Shadowman 9: In the Cradle of Destiny”, the Monarch has a flashback of being beaten up by Myra in the Venture Compound which is identical to Myra’s own recollection of the same incident from “I Know Why the Caged Bird Kills”.
General Manhowers (voiced by Christopher McCulloch): Due to his high military rank, he is one Dr. Venture’s main clients. Has ordered 144 Venturesteins and 100 Oo-rays for military use. Is apparently a General of the Army, though he refers to the Army while wearing a blue Air Force uniform in the pilot episode. This is perhaps due to his somewhat failing mental state, which causes him to go on long tirades about practically nothing. Loves Fruitopia.
Dr. Henry Killinger (voiced by Christopher McCulloch): A cross between the diplomat Henry Kissinger, the magical nanny Mary Poppins, and a stereotypical super villain, he never goes without his “magic murder bag”. The Monarch hires him as a new “number two”, and he implements new reforms into the Cocoon in an attempt to turn around their spectacular failures. He ends up reuniting Dr. Girlfriend with the Monarch, and it is implied that this was his intention all along, as well as the Oni’s failing attempt to reunite Myra Brandish and Dr. Venture. Once finished, he flies away with his umbrella in a similar manner to Poppins. He returns in “Showdown at Cremation Creek (Part II)” for the wedding of the Monarch and Dr. Girlfriend as the minister and flies away again as Phantom Limb attacks the Cocoon, where the ceremony is being performed. Killinger appears again in a larger role in “The Doctor Is Sin”, an episode of season 3, when Dr. Venture faces the possibility of having to sell the Venture Compound, and Killinger shows up to turn the company into an efficient super-science machine. It is speculated that Killinger’s plan all along was to turn Dr. Venture into a super villain, such as reuniting him with an insane Myra and keeping the Monarch away from him. An encounter between Dr. Orpheus and Killinger, wherein Killinger told Orpheus, “Your powers are useless on me, you silly billy,” left Orpheus comatose, hinting that there may be far more to Killinger than meets the eye. In fact, Orpheus later tells The Alchemist, after they -with Brock Samson – broke in to the Venture Compound in order to save Dr. Venture from Killinger, that Killinger is “slightly more magic” than they are. It was mentioned in the commentary for “I Know Why the Caged Bird Kills” that Killinger may actually be the alter-ego of Henry Kissinger in the Venture Universe, but they hadn’t decided yet. However, he is also an extremely efficient at what he does, as when he charged Brock back rent, he also helped Brock with his taxes to show him how he could make more money, spending time with the Venture boys to the point they referred to him affectionately as ‘Uncle’, as well as got Dr. Venture over his fears with his father.
The Sovereign/David Bowie (portrayed by Christopher McCulloch/voiced by James Urbaniak): The mysterious entity who runs the Guild of Calamitous Intent. He mostly communicates only through telescreens which distort his face and voice. He was invited to the Monarch and Dr. Girlfriend’s wedding and gave away the bride. In a nod to his reputation as one of rock music’s greatest chameleons (and possibly referencing the ability of his character in the movie Labyrinth), Bowie has the ability to shape-shift into anything from another human being to a bird or even an inanimate object such as a cigarette or even create his own, seen when he transformed into an older Dr. Venture. Though he runs the Guild, he is not above playing pranks with his abilities, pretending to be Dr. Venture from the future when he greeted him. It’s also revealed that his identity is considered an open secret amongst the Guild.
Dermott Fictel (voiced by Doc Hammer): An obnoxious teenager who first appeared in “The Buddy System”. At the end of “The Buddy System”, he states he met his father, which he claims to be Brock Samson in “Tears of a Sea Cow”. This should not be taken as fact, however as Dermott is a compulsive liar; however Dermot’s mother (shown only briefly in silhouette) supported this contention, while Dermott is also large and blonde like Brock. He saw Fight Club in theaters, having sneaked while his mom thought he was watching a movie starring Elmo. He and his mom live in a trailer park near the Venture Compound. He repeatedly claims to be a world-renowned martial artist, and makes obviously false excuses when asked to demonstrate.
Kiki: Col. Gentleman’s servant and lover, based on a similarly-named youth with whom William S. Burroughs had a relationship while living in Tangiers,[2] and subsequently wrote into his novel Naked Lunch.
S.P.H.I.N.X.
Col. Hunter Gathers (voiced by Christopher McCulloch): Brock’s former mentor from when he was in training for the O.S.I. Gathers has since gone into hiding after having a sex-change operation, taking a job as a dancer at Nightingales, a strip club. He appears to be a reference to Hunter S. Thompson and his name a play on the term Hunter-gatherer (indeed, the character appears to be a sort of criss-cross between Thompson, with the author’s aviator sunglasses and cigarette holder, and Col. Nick Fury.) Other than Brock, Gathers was the only O.S.I. agent who believed the Guild was still in existence in the late eighties, as in “The Invisible Hand of Fate”. Despite being extraordinarily eccentric, he seems to care about his job and defending his country. He also taught Brock the strict rule of never killing women or children, as that differentiated them from the “bad guys”. This is something he used to his advantage when he went rogue from the O.S.I. who then sent Brock to kill him (as Brock doesn’t kill women). He is apparently a member of Molotov Cocktease’s “Black Hearts” assassination guild, as shown in the scene following the end credits of “The Family That Slays Together, Stays Together (Part II)”. However despite the sex-change operation, he still has the same face and voice as before—including perpetual five o’clock shadow. He also stated in “The Invisible Hand of Fate” that he wanted to be born with “big, beautiful tits”, which turns out to be foreshadowing (down to the fact that he has large breasts, but can still grow facial stubble). The sex-change and apparent betrayal of O.S.I. was revealed in the Season 4 opener as an elaborate ruse to infiltrate the Black Hearts, when Gathers and Samson were captured by Sphinx agents, and Gathers revealed himself as an undercover Sphinx officer, complete with revealing the reversal of his sex-change with the statement to Samson’s revelation ‘You don’t know DICK!’, grabbing his groin.
Shore Leave and Mile High: Two former O.S.I. agents fired for violating O.S.I.’s don’t ask, don’t tell policy. They changed their names after converting to Christianity, “curing” their homosexuality. Their appearance and code names seem to be parodies of G.I. Joe characters, especially Shore Leave, who resembles Shipwreck. “Holy Diver” is the title of a song by DIO, which could be the source of his name. “Sky Pilot” is the title of a religious song by The Animals. They use religious combat equipment “beamed” upon them in a way that parodies both Bibleman and The Centurions yet it takes so long the fight is halfway over when they finally finish, and even then, they eschew its use in favor of prayer. Both have joined Hunter Gathers in Sphinx. Holy Diver was actually created during the commentary for Assassinanny 911, when Hammer and Jackson were thinking of names in the style of “The Tick”. However, in the episode Pinstripes & Poltergeists, it is revealed they faked being a couple, as well as their conversion to religious fanatics, for their cover.