The Guild of Calamitous Intent
The Guild of Calamitous Intent is the primary antagonist in the series. It functions as an organization of supervillains, akin to a trade union, offering benefits such as health insurance and establishing rules and conduct standards among its members and their adversaries, primarily superheroes and super-scientists. Serving as a stabilizing force in the world of supervillainy, the Guild prevents unchecked chaos by organizing its members into a cohesive force and restricting their actions to Guild-approved targets, thereby curbing total destruction, murder, and mayhem. Initially led by the enigmatic figure known as "The Sovereign" and the Council of Thirteen, the current iteration of the Guild suggests a refuge for missing or presumed deceased rock stars. In Season 6, most of the Council of 13 is eliminated by The Sovereign to solidify control and confront the supernatural supervillain group, The Investors. Following The Sovereign's accidental demise at the hands of O.S.I., surviving members, including Dr. Mrs. The Monarch, Dr. Phineas Phage, Dr. Z, Red Mantle, and Dragoon, under Dr. Henry Killinger's guidance, form a new Council of 13, with assistance from the surviving Revenge Society members, after Killinger eradicates the Investors to restore balance between O.S.I. and the Guild. Although Killinger declines the Sovereign role, he bestows control of the Guild to the council. Season six introduces the New York branch of the Guild, comprising the organization's most dangerous supervillains. Notably, the original Guild charter does not stipulate a specific number of council members, and members cannot actively engage in arching their enemies.
The current iteration of the Guild was reportedly established around 1959 by Phantom Limb's grandfather. However, its roots extend back to the late Victorian era, when it operated as a heroic organization under the leadership of Colonel Lloyd Venture, Rusty Venture's grandfather. This earlier incarnation was devoted to safeguarding an enigmatic artifact known as the "ORB." A schism within the organization arose over differing views on the ORB's purpose. Fantomas founded the Guild of Calamitous Intent in 1910, advocating for using the ORB to dominate mankind, while Lloyd established the modern version of the OSI, aiming to utilize the ORB for the betterment of humanity.
The Monarch
The Monarch (voiced by Christopher McCulloch): Dr. Venture's self-styled nemesis, whose real name is Malcom Fitzcarraldo. He is obsessed with monarch butterflies, which he claims raised him as a child after he survived the plane wreck that killed his parents. While attending State University, he began arching Dr. Venture, though the reasons remain unrevealed (though possibly due to mocking his affinity for butterflies and suspecting him of being a "closet case"). He later worked for various villains and served as Phantom Limb's Shadowman 9 until becoming The Monarch and winning over Dr. Girlfriend. Despite frequently portraying himself as Dr. Venture's nemesis, their rivalry exists solely in The Monarch's imagination. In reality, Dr. Venture sees him more as a nuisance than a genuine threat, even entrusting his sons to The Monarch's care due to his incompetence. He is also Captain Sunshine's unofficial arch-enemy, demonstrating greater ruthlessness by killing Wonder Boy III and sending the hero his charred corpse. The Monarch eventually lost his arching privileges against Rusty after being discovered as an unsanctioned Guild villain. However, he regained the right to arch Rusty by invoking the Guild's "prior escalation" clause. In season one's finale, he was wrongfully convicted of murder and imprisoned due to framing by Phantom Limb. After escaping in season two, he rebuilds his criminal enterprise, reuniting with Dr. Girlfriend and eventually marrying her. By the third season, they reside in Phantom Limb's former mansion in the gated community of Malice. In season five, The Monarch's Cocoon ship, home, and henchmen are destroyed by Sgt. Hatred, leading him, his wife, and Henchman 21 to relocate to The Monarch's abandoned childhood home in Newark, New Jersey. Losing his cocoon and henchmen substantially lowers his Guild ranking, thereby revoking his rights to fight Dr. Venture. In "Faking Miracles," The Monarch discovers that his father was the Blue Morpho. Assuming his father's hero identity, he and Henchman 21 eliminate New York Guild members harassing Dr. Venture to advance on the waiting list. In season 7, it's hinted that The Monarch's mother had an affair with Jonas Venture, making him Dr. Venture's half-brother, a revelation that shocks him. In the film, Ben reveals that he and Dr. Venture are clones of the original Rusty Venture, with The Monarch having baboon DNA spliced in to counter premature alopecia, though it results in heightened aggression. He was given to Don Fitzcarraldo by Jonas Venture.
Henchman 21
Henchman 21/Gary Fischer [3] , briefly known as S.P.H.I.N.X. Commander and occasionally as the Viceroy (voiced by Doc Hammer): A pop-culture geek who, at the series' outset, serves as a henchman for The Monarch, always alongside his closest friend Henchman 24. He authors "Flight of The Monarch," a tell-all that leads to The Monarch's incarceration. Following Henchman 24's demise, he undergoes intense combat training, emerging with enough strength and martial skill to challenge Brock Samson. Together, he and Samson defeat Monstroso, a common foe. Henchman 21 continues to converse with what he believes is Henchman 24's ghost, though Henchman 24's ghost suggests he may only exist in Henchman 21's mind (a notion both confirmed and refuted in Operation: P.R.O.M.), echoing Rudyard Kipling's "The Man Who Would Be King." In "Operation P.R.O.M.," 21 is invited to join S.P.H.I.N.X., an anti-unlicensed superhero team, where he finds camaraderie and begins to question his loyalty to The Monarch and villainy in general. Ultimately, he realizes villainy isn't his path and resigns from The Monarch's service. In "From the Ladle to the Grave: The Story of Shallow Gravy," a 2011 Venture Brothers special set after "Operation P.R.O.M.," he is interviewed wearing a S.P.H.I.N.X. uniform with his face obscured, going by the name Viceroy. Following "Operation P.R.O.M.," Gary assumes command of S.P.H.I.N.X., though it's short-lived as original S.P.H.I.N.X. members seize control, prompting O.S.I. to disband the organization. Gary resides in the Venture Compound's backyard after Dr. Venture and Sgt. Hatred destroy S.P.H.I.N.X.'s headquarters, mistakenly believing Gary planted bombs there (in reality planted by The Monarch and Dr. Mrs. The Monarch during an infiltration attempt). Later, adopting his "Viceroy" persona, he aids Hank and Dermott in a bank robbery to reach Teddy at Dunwitch Asylum. After assisting Hatred in rescuing Dr. Venture, he leads The Monarch's henchmen in overthrowing the moppets and decides to rejoin The Monarch, not out of loyalty or to the henchman lifestyle, but because The Monarch is his only remaining friend. By Season 7, 21 is The Monarch's sole henchman, aiding him in his role as the new Blue Morpho by eliminating Dr. Venture's enemies, though he struggles with guilt as he has never intentionally killed before. Attempting to stop the killings, he captures several archenemies, but one cannibalizes the others. In the season finale, the Guild offers Gary a chance to become a supervillain and leave The Monarch, but he declines, reaffirming his loyalty to his best friend and his desire to help him settle his grudge.
Henchman 24
Henchman 24 (voiced by Christopher McCulloch): A tall, thin man with a voice reminiscent of comic Ray Romano and described by 21 in the second season's first episode as resembling Jerry Seinfeld with a unibrow. He served as Shadowman 24 for Phantom Limb simultaneously with The Monarch's tenure as Shadowman 9. The Monarch promised to promote him to "number 2" in exchange for a favor, a pledge never fulfilled. Henchman 24's powder blue Nissan Stanza serves as the replacement Monarch Mobile after The Monarch's lair is destroyed, but it's promptly stolen by a fleeing prostitute. The Stanza mysteriously reappears in The Monarch's Cocoon garage, heavily damaged from the Cocoon's crash in the Grand Canyon. The Monarch remembers little about 24 besides his voice, likened to Ray Romano's. Formerly a factory worker, 24 confides in Dean that his ex-girlfriend married his father and he aspired to become a cabinet maker. He perishes in an explosion at the end of the season three finale. Throughout season 4, his skull appears as an object with whom #21 converses as before. In "Pinstripes & Poltergeists," #24 seemingly manifests as a ghost haunting #21 due to lack of alternative options. In "Operation: P.R.O.M.," it's revealed that #24 wasn't a ghost during season 4 but a figment of 21's grief-stricken imagination. 21's acknowledgment of this allows him to come to terms with 24's demise. Though he suspects foul play in 24's death, he accuses Tim Tom and Kevin, enabling The Monarch's henchmen to overthrow them.
Dr. Mrs. The Monarch
Dr. Mrs. The Monarch, née, formerly known as Dr. Sheila Girlfriend (voiced by Doc Hammer): The wife and assistant to The Monarch. Throughout much of her tenure as The Monarch's second-in-command, she donned Jackie Kennedy's iconic short pink jacket and pillbox hat, echoing the former First Lady's style and accent, typical of Long Island. Her humorously deep voice stems from a past smoking addiction, satirizing the former First Lady's lower-than-usual vocal pitch. Following The Sovereign's demise, Dr. Mrs. The Monarch rises to prominence within the Guild, placing strain on her marriage with The Monarch—especially when his authority to arch Dr. Venture is revoked due to his perceived low status in comparison to a Level 10 Protagonist like Venture. The Monarch believes his wife should expedite his ascent to a higher rank, whereas she prioritizes her role within the Guild, adhering strictly to protocol. Unlike her husband, Dr. Mrs. The Monarch often delineates between her villainous persona and her true self, frequently addressing herself by her birth name, Sheila, and maintaining amicable relationships and collaborations with certain protagonists and their allies when necessary.
Tim-Tom and Kevin
Tim-Tom and Kevin (voiced by Christopher McCulloch and Doc Hammer, respectively): Achondroplastic dwarves who previously served as Dr. Girlfriend's assistants during her solo career as Lady Au Pair. Despite their surly, foul-mouthed, and seemingly psychotic behavior—readily engaging in ferocious attacks with their matching stilettos with minimal provocation—they maintain a respectful demeanor toward Dr. Girlfriend. However, in her absence, their demeanor shifts markedly, revealing a more aggressive and unstable disposition. Although typically intimidating towards others, they exhibited fear when confronted and threatened by The Monarch, particularly when his wife was not present—an occurrence that underscored the only instance they displayed vulnerability. Despite their tendency to bully others, they developed a modicum of respect for 21 following his transformation into General 21.
They are presumed to have perished in the destruction of the Cocoon, orchestrated by Sergeant Hatred.
Watch and Ward
Watch and Ward (voiced by Christopher McCulloch and Doc Hammer, respectively): As the communications and operations liaisons for the Guild of Calamitous Intent, Watch and Ward are responsible for interacting with prospective protagonists and antagonists to facilitate appropriate arching assistance. Watch is characterized by a tactical eyepatch covering his left eye and a bald appearance, while Ward sports an eyepatch over his right eye, with hair protruding from beneath his cowl. The duo frequently engage in arguments, often drawing inspiration from real-life conversations between McCulloch and Hammer, such as Ward's irritation when Watch consumes his juice box.
Dr. Henry Killinger
Dr. Henry Killinger (voiced by Christopher McCulloch): A highly skilled businessman and negotiator, Dr. Henry Killinger demonstrates a profound understanding of legal matters, particularly tax law. While he possesses magical abilities, the precise nature and scope of his powers remain ambiguous. Some characters struggle to comprehend him when he speaks due to his complex manner of communication.
Dr. Killinger's notable appearances involve spontaneously offering his services as a strategist, business consultant, and motivational coach to main characters, free of charge, in the episodes "I Know Why The Caged Bird Kills" and "The Doctor Is Sin". In both instances, his intervention leads to a significant improvement in the efficiency of his clients' endeavors. Despite his status as a supervillain capable of ruthlessly dispatching adversaries, Dr. Killinger also exhibits the capacity for forming genuine friendships and performing acts of kindness. He fosters an avuncular relationship with the Venture boys in "The Doctor Is Sin", to the extent that they affectionately refer to him as "Uncle Henry".
The Sovereign
The Sovereign (voiced by Christopher McCulloch, with an impersonation of David Bowie by James Urbaniak): A mysterious figure who leads the Guild of Calamitous Intent, The Sovereign primarily communicates through telescreens, which distort his face and voice. While initially appearing as David Bowie, "O.S.I Love You" reveals that he is a shapeshifter who frequently adopts Bowie's likeness. Whether The Sovereign is the actual David Bowie within the show's universe remains ambiguous.
In "All this and Gargantua-2", The Sovereign orchestrates the murder of most Council of 13 members and engineers an assault on Gargantua-2 as part of a larger plan to eliminate the Investors. He meets his demise while in eagle form, shot down by Headshot.
Force Majeure
Force Majeure: The original sovereign of the Guild of Calamitous Intent, Force Majeure was an elemental villain and the archenemy of Jonas Venture. He met his demise at the hands of the shape-shifter who later assumed the role of The Sovereign. He was married to Madame Majeure and is hinted to be the biological grandfather of the Venture Brothers.
Iggy Pop
Iggy Pop (impersonated by Christopher McCulloch): An American rock musician and one of the Sovereign's henchmen. He possesses the ability to create spheres of energy that explode upon his command, "Pop." Despite betraying the Sovereign in favor of Phantom Limb, he meets his demise at the hands of the Sovereign for his treachery.
Klaus Nomi
Klaus Nomi (impersonated by Christopher McCulloch): A German singer and one of the Sovereign's henchmen. He possesses the ability to sing in a hypersonic voice, and his bowtie can function as a projectile. Despite betraying the Sovereign in favor of Phantom Limb, he meets his demise at the hands of the Sovereign for his treachery.
Eon
Eon: The Sovereign's new bodyguard, bearing a striking resemblance to longtime Bowie collaborator Brian Eno.
Monstroso
Monstroso (voiced by Christopher McCulloch) is both a lawyer with the Mammoth Corporation and a supervillain licensed with the Guild of Calamitous Intent. His size is enormous, with a lap sufficient for Dr. Girlfriend and a brace of four additional revelers. Monstroso is prosperous enough to have employed the bulk of The Monarch's men while he was in prison, no doubt due to his lawyer and supervillain vocations. In "The Silent Partners", Monstroso has the Investors kidnap Billy Quizboy, and it is revealed that he is dying of heart failure and requires a transplant from King Gorilla. Billy was chosen because of his skills, and the Investors would return the favor by forging documents signed by Billy to "officially" give him credentials to be legally recognized as a doctor and "immortality" for his recognized fame as a great surgeon because the surgery is so difficult. Billy completes the transplant, and in the post-credits scene, Monstroso appears to be recovering from his surgery, although he appears to be unaware that he is no longer on his boat but actually at the Sphinx headquarters on the Venture compound. However, in "Operation: P.R.O.M.", Monstroso is rescued by Molotov, and it is revealed that he and Molotov are in a romantic relationship. After the limousine, in which he is being rescued by Molotov, falls off a cliff, Brock finds it in the season 5 premiere and finds Monstroso's "body" was a fake, with no trace of Molotov. He and Molotov are eventually captured by O.S.I. in "O.S.I. Love You", but he is killed by the Investors after he reveals too many guild secrets to Brock.
Torrid
Torrid (voiced by Christopher McCulloch) is the archenemy of the Order of the Triad. He is first assigned as their archenemy in "Fallen Arches" when he kidnaps Triana Orpheus to the Torrid Zone. He possesses fire-based powers. In "Showdown at Cremation Creek", he steals the All-Seeing Orb, prompting The Alchemist and Jefferson Twilight to question the utility of having an archenemy. Torrid's final appearance is when he attempts to open a portal to the Second World, unwittingly getting sucked into it and then summoning an elder god that the Triad are unable to defeat, leaving Orpheus' protege, the Outrider, to save them all.
Truckules
Truckules (voiced by Christopher McCulloch) is a supervillain with themes of both trucks and Hercules. He was formerly Number One for Dr. Mrs. The Monarch, from whom she learned how to hotwire any vehicle. His upper body resembles that of Optimus Prime's, and is so wide that when he attends The Monarch's wedding, he requests two seats.
The Intangible Fancy
The Intangible Fancy (voiced by Christopher McCulloch) is a supervillain with the ability to become intangible. He attends Dr. Venture's yard sale to make a purchase but becomes embroiled in the ensuing fight. Later, he is questioned by the Council of 13 after attempting to smuggle contraband.
The Investors
The Investors (Caecius: voiced by Doc Hammer; Skiron: voiced by John Hodgman; Lips: voiced by T. Ryder Smith) are a mysterious group of supervillains introduced in "Pinstripes & Poltergeists" as members of the Guild aligned with Monstroso. They possess seemingly omnipotent abilities, capable of granting the dreams and wishes of individuals through "contracts," albeit at a steep price. Despite being sought after by both O.S.I. and the reformed S.P.H.I.N.X., they evade capture.
In "O.S.I. Love You," they disguise themselves as O.S.I. Mister level operatives, including Mister Frost (voiced by Christopher McCulloch), Mister Sample (voiced by Dana Snyder), and Mister Yourname (voiced by Brendon Small), the latter of whom has not undergone proper induction. Their goal is to interrogate individuals regarding the whereabouts of Monstroso and Molotov Cocktease. During Brock's interrogation, they kill Monstroso, successfully deceiving General Gathers until the real Mister operatives arrive.
During the opening of Gargantua-2, they aim to "collect" what they offered to JJ Venture by destroying the station. Concurrently, The Sovereign plans to attack the station to eliminate the Investors before they demand their due from him. With assistance from Phantom Limb, they sabotage the station, escape The Sovereign, and confront Dr. Henry Killinger on Meteor Majeure, where they perish in battle.
Augustus St. Cloud
Augustus St. Cloud (voiced by Christopher McCulloch, originally James Urbaniak) is the affluent former rival of Billy from their quiz show days, both being collectors of sci-fi and Rusty Venture memorabilia. He initially appears at Dr. Venture's tag sale, enduring Baron Ünderbheit's attacks due to The Monarch's intervention. Later, he joins the ranks of supervillains, despite not being an official Guild member yet.
After making a substantial donation to the Guild's Widows and Orphans charity, he gains induction into the Guild and the privilege to choose from a pool of archnemeses. He insists on selecting Billy Quizboy, and Watch and Ward comply after another generous donation. St. Cloud's feud with Billy escalates when they must retrieve items he purchased from Dr. Venture to fund the Palaemon Project, uncovering St. Cloud's Asian albino henchman, "Pi Wai." Despite refusing to consume $1 worth of pennies, the exact value Billy outbid St. Cloud in an eBay auction years earlier, Billy triumphs over St. Cloud in a trivia contest once again. He reclaims Venture's hovercraft, essential for handling the Palaemon Project mutants, and H.E.L.P.er, who had been sold to St. Cloud.
St. Cloud is recognized by his short and stout stature, deadpan voice, round dark glasses, and assortment of ginger pageboy-style wigs. His immense wealth and somewhat petulant demeanor lead him to employ monetary persuasion or acquisitions to achieve his objectives.
