List of The Venture Bros. characters

This is a list of main and recurring fictional characters from The Venture Bros., a comic science fiction television series aired on Adult Swim from 2003 to 2018.
Team Venture consists of the central characters in the show; they previously resided in a fortified compound in Colorado Springs which also served as the headquarters for their company, "Venture Industries." Following the destruction of the compound in Season Six and Dr. Venture's inheritance of his brother's fortune, they relocate to the Ventech Tower at Columbus Circle in Manhattan.
Dr. Thaddeus "Rusty" Venture (voiced by James Urbaniak): Dean and Hank's father, head of Venture Industries, and clone-brother of The Monarch. He is a capable scientist and inventor, but his greed, lack of formal education, and insistence on cutting corners result in his attempts at technological innovation failing, causing chaos for him, his family, friends, and sometimes the world at large. Although the money he earns is sufficient to support him and his family, it fails to satisfy his greed and his aspirations to match his father's wealth and success. While he cares for his sons, his father's abusive and negligent parenting influences the way he treats them, sometimes showing as much indifference to them as his father did to him. In Season 7, it is revealed that Dr. Venture is not the original, but rather a clone of the first Rusty Venture, who died in the past.
Brock Fitzgerald Samson (voiced by Patrick Warburton): Born in Omaha, Nebraska, to a single mother, Brock is a hypermasculine one-half Swedish, one-quarter Polish, one-quarter Winnebago "murder machine" who serves as a bodyguard to the Venture family. He attended the same university as Dr. Venture until he was expelled for accidentally killing one of his football team's teammates. Despite holding a license to kill, Brock eschews guns and instead favors a Ka-Bar fighting knife as his signature weapon. He grapples with his role in the world and his purpose, guided by a personal code of ethics concerning innocents and whom he will eliminate if they pose a threat to himself or the Ventures. Brock owns an orange 1969 Dodge Hemi Charger named "Adrianne," frequently seen driving or shirtlessly washing at the Venture compound. Following the explosion of the car carrying Henchman 24, H.E.L.P.eR.'s head was briefly embedded in Brock's chest, leading to 24's death; the head was later removed and replaced with a metal plate.
Henry Allen "Hank" Venture (voiced by Christopher McCulloch): Hank, the elder fraternal twin with blond hair, is a teenage boy and one half of the titular duo. He emerges as the more extroverted and adventurous of the pair, drawn to action and thrill-seeking, often envisioning himself as a vigilante superhero. In season 4, he exhibits increased rebelliousness following Brock's departure, even losing his virginity to an older woman who happens to be his best friend's mother. After briefly affiliating with former Henchman 21's rendition of S.P.H.I.N.X., Hank acquires the power suit of former S.P.H.I.N.X. member The Countess, donning it until it is stolen and destroyed. This incident leads to Hank undergoing physical therapy due to muscle atrophy. In season 6, he opts out of college and takes on a job as a delivery boy at a pizzeria. Additionally, he embarks on a romantic relationship with Sirena Ong, the daughter of his father's current Guild-assigned villain, Wide Wale. In season 7, Hank slips into a coma after discovering Sirena's infidelity with Dean but eventually recovers.
Dean Venture (voiced by Michael Sinterniklaas): As a teenage boy and one half of the eponymous pair, Dean is the younger fraternal twin with red hair. Despite being more timid than Hank, he exhibits signs of greater emotional maturity. Dean garners more favor from their father, who grooms him to succeed as the heir to Venture Industries. Like his brother, Dean has faced death over a dozen times, only to be replaced by an exact clone each time, devoid of memories of his demise. Following a breakup with Triana and the revelation of his clone status, Dean adopts a more emo persona, donning a black "speedsuit" and relocating from his childhood bedroom, displaying reluctance to join family adventures. However, Hank's optimism and familial support pull him out of his emotional slump. In season 6, Dean enrolls at the fictional Stuyvestant University in New York, excelling as a philosophy student and befriending Brown Widow, his roommate. In season 7, he engages in an affair with Hank's girlfriend, Sirena Ong, but later regrets his actions.
H.E.L.P.eR. (voiced by Christopher McCulloch; credited as "Soul-Bot"): H.E.L.P.eR., short for Humanoid Electronic Lab Partner Robot, serves as the Venture family's helper robot, communicating through electronic beeps. Despite his sensitivity, the Ventures often regard him as an old appliance or pet. Throughout their adventures, H.E.L.P.eR. frequently gets smashed to pieces but miraculously appears repaired by the next episode.
Sergeant Hatred, also known as Courtney Robert Haine, is voiced by Brendon Small in season 2 and Christopher McCulloch from season 3 onward. He serves as Brock's former supervisor in the O.S.I., the husband of Native American villainess Princess Tinyfeet, and the Venture family's bodyguard. He is a large, muscular man with a giant red 'H' tattooed on his face, often seen wearing military fatigues. Despite being a convicted child molester for having slept with a 17-year-old, he is liked and respected throughout the supervillain community for his unfailing politeness and generosity; certain episodes also reveal that he knows his sexual attraction to teenagers is wrong, and tries to keep it in check using medication and electroshock therapy. He is known for his caring nature beneath his battle-hardened exterior.
Dermott Fictel (voiced by Doc Hammer): An obnoxious teenager who first appears in "The Buddy System"; he was hinted to be the son of Brock Samson. Dermott is a compulsive liar and frequently interjects wild, and often clearly false, claims about his abilities and past deeds into unrelated conversations. He is Hank's best friend and occasionally visits the Venture compound from the nearby trailer park where he and his "mother" live. In "Everybody Comes to Hank's", Hank sleeps with Nikki Fictel (voiced by Kate McKinnon), whom Dermott knows as his older sister, but is actually his mother. His real father is also revealed to be Rusty, making him Hank and Dean's half-brother. He stays behind when the Venture family moves to New York and later joins the OSI, being accepted as an operative despite his lack of training, thanks to a good word put in for him by Dr. Venture.
Dr. Jonas Venture Jr., also known as J.J. (voiced by James Urbaniak): Dr. Venture's deformed twin, who was absorbed by Rusty in the womb and surgically freed from Rusty's body after being mistaken for a tumor. Although he has the body of an infant, he has an adult appearance and seems to have inherited his father's brilliance. He is scientifically astute, hard-working, attractive to women, and a multi-billionaire CEO of a profitable corporation. However, his worship of his father causes the original Team Venture to dislike him greatly, as he ignores their importance to his father's life, business, and legacy. JJ dies in "All This and Gargantua-2" when he sacrifices himself to prevent his space station, Gargantua-2, from harming people, when it self-destructs due to sabotage from The Investors. In his will, he bequeaths his fortune, the New York City Headquarters, and technology patents to his brother.
Triana Orpheus (voiced by Lisa Hammer): Dr. Orpheus's 17-year-old quasi-goth daughter. She has purple hair and is fairly friendly with the Venture twins. She and Dean become close until they have a major fight and fall out after she chooses to date another boy named Raven over Dean. In season four, it is revealed that she has inherited her father's abilities when she encounters her father's mystical mentor, who purposely took up residence in her closet because of her power.
Pete White (voiced by Christopher McCulloch): An albino computer scientist and co-founder of Conjectural Technologies. He attended college with Venture, Samson, Baron Ünderbheit, and The Monarch, where he hosted a new wave radio show called "The White Room". After earning a doctorate in computer science, White and Billy Quizboy collaborated on a Jeopardy-style game show called "QuizBoys", with Pete as the host and Billy as a contestant. However, they were fired for cheating and rigging the shows in their favor. Despite a brief falling out, Pete eventually reunited with Billy. They took up residence in a trailer near the Venture Compound. Like Venture and Quizboy, White is skilled and knowledgeable in super science and technology but tends to be lazy and half-hearted in his efforts. In season six, after Dr. Venture inherits his brother's company and fortune, Pete and Billy move to New York City with the Venture family. There, they become leading scientists for Dr. Venture, assisting him in inventing breakthrough technology to sell through Ventech.
William Whalen, a.k.a. Master Billy Quizboy (voiced by Doc Hammer): Self-proclaimed "boy genius" Billy Whalen is an adult with a speech impediment and growth hormone deficiency. Despite suffering from hydrocephalus, his intellect remains unaffected. He gained recognition as a contestant on the game show Quizboys, hosted by Pete White. When White cheated on his behalf, they were both disqualified from the show, and Billy's winnings were seized by the SEC. Seeking employment, White and Billy approached Dr. Venture, but were rejected. Later, in a misunderstanding, Billy lost a hand and an eye in a dogfight. Subsequently, he was recruited by Brock Samson and Hunter Gathers, who equipped him with a mechanical hand and camera eye for undercover work. While spying on Professor Hamilton Fantomas, Billy suffered an accident that led to the creation of Phantom Limb and the loss of his left eye once again. Despite lacking formal education, he became a medical doctor, neurogeneticist, and co-founder of Conjectural Technologies. He briefly joined the Order of the Triad after performing brain surgery on the Outrider. In season 5, his old nemesis Augustus St. Cloud became his and White's designated arch-enemy. In Season 6, he and Peter relocate to New York City with the Venture family to assist Dr. Venture in developing breakthrough technology for the Ventech brand.
The Pirate Captain (voiced by Christopher McCulloch): The leader of the "ghost pirates" in "Ghosts of the Sargasso". Following his initial encounter with the Venture family, he took up residence on the X-2 after facing challenges finding employment. When Jonas Jr. acquired the ship, he hired the captain, who has only been addressed as "The Captain" thus far. He lived with Jonas Jr. on Spider Skull Island, assuming roles such as butler, caretaker, and right-hand man. The Captain consistently refers to Jonas as "Chairman". Subsequently, after J.J.'s demise, he becomes an employee of Dr. Venture upon inheriting J.J.'s New York City business.
Bobbi St. Simone (voiced by Jane Lynch): Bobbi St. Simone is the proprietor of a sanctuary for cybernetic animals. In the 1960s, she was an actress in a bikini movie who had an affair with Jonas Venture, who also bestowed upon her invisibility powers. Following the failure of her film, Jonas coerced her to work for the O.S.I. as a mole within The Guild of Calamitous Intent. She later assumed the identity of Madame Majeure after falling in love with and marrying Force Majeure. However, she fled with her daughter Debbie after Force Majeure was murdered by The Sovereign. Bobbi struck a deal with Dr. Venture to transfer her powers to her daughter, implying that this was in exchange for Debbie's eggs, making her Hank and Dean's biological grandmother.
Dr. Byron Orpheus (voiced by Steven Rattazzi): A necromancer who rents a portion of the Venture Compound and is friendly with Dr. Venture. Along with Brock, he is one of the few associates of Dr. Venture who displays competence and morals, although his pomposity tends to detract from his abilities. His speech is filled with overly dramatic phrases, delivered in a theatrically grandiose voice with emphasis on mundane topics, usually accompanied by ominous trumpet-laden music. After witnessing Dr. Venture's various enemies, he develops a fervent desire for a nemesis of his own and is later given the opportunity when the Guild approves his request for one in the season 2 episode "Fallen Arches", holding a series of interviews for the position. He is fiercely protective of Hank and Dean Venture, after being responsible for their "death" at the end of Season 1, only to find out the truth about the boys in Season 2. He is the father of Triana Orpheus, who lived with him on the Venture Compound until she moved in with Orpheus's ex-wife after breaking up with Dean Venture. By season 7, it appears that he and the Order of the Triad move to New York City in order to be closer to The Ventures.
Jefferson Twilight (voiced by Charles Parnell): An old friend of Dr. Orpheus, Jefferson Twilight is a dhampir who fights Blaculas (black vampires) for a living, wielding two swords. He suffers from diabetes and low blood sugar, leading him to crave sugared liquids. His left eye is discolored, functioning as a magical Blacula tracker he calls the "Blood Eye." The episode "What Goes Down Must Come Up" reveals much of his backstory, including that his mother was taken by marauding Blaculas when he was ten and he was a tank commander in the USMC. Initially upset about lacking a magical ability, it is discovered that he has the ability to act as a bridge between worlds, something that once saved his friends.
The Alchemist (voiced by Dana Snyder): Another old friend of Dr. Orpheus, The Alchemist is on a quest for the philosopher's stone and a cure for AIDS. Unlike Twilight and Orpheus, he appears less serious about his endeavors and prefers mixing business with pleasure. However, his true stance on the Triad was revealed in the episode "Showdown at Cremation Creek", where he expressed a commitment to balancing the universe rather than engaging in constant battles against supervillains. He is openly gay and a fan of Jimmy Buffett. He shares a friendship with Hank, seeing similarities between them. Sometimes referred to as "Al," it's unclear if this is his real name or simply a nickname. He harbors a strong dislike for the internet after discovering his former boyfriend's infidelity on MySpace. In "Everybody Comes to Hank's," it's revealed he was previously in a relationship with Shore Leave, but the latter erased his memory of it due to The Alchemist's perceived clinginess. In "OSI Love You," he and Shore Leave share an amorous video chat, suggesting they reconciled.
The Office of Secret Intelligence is a branch of the United States government that handles supervillain activity, both combating groups of supervillains or assisting super scientists and superheroes with their Guild of Calamitous Intent-assigned archenemies. A pastiche of G.I. Joe and S.H.I.E.L.D., in the 1980s they fought against the supervillain organization S.P.H.I.N.X. in the Pyramid Wars, during which the original S.P.H.I.N.X. was defeated. The O.S.I. operates from a hovering base based on the helicarrier and seems to answer to a division known as the Misters who are the go-between with the "Secret President."
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 voiced by Christopher McCulloch (voiced by Marx St. Cloud for the pilot): 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/Gary Fischer, 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 (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, 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 (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 (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 (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 (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 he would frequently appear as David Bowie, when departing, The Sovereign would often change into eagle form and fly away, suggesting that perhaps Bowie possessed magical abilities. However, in "O.S.I. Love You", Monstroso reveals that The Sovereign was in actuality a "down-on-his-luck shapeshifter" who had met the real Bowie in 1972, and had adopted his likeness in public ever since. This detail had been hidden even from high-ranking Guild operatives — after learning of the deception, Watch and Ward are dismayed to realize that their signed albums are worthless forgeries.
In "All this and Gargantua-2", The Sovereign orchestrates the murder of most Council of 13 members and engineers the destruction of Gargantua-2 as part of a larger plan to eliminate the Investors. This greatly alarms the "old guard" of the Guild (i.e. the oldest remaining members of the Council), causing them to contact the O.S.I. in the hopes of stopping him. In exchange for immunity, the Guild members reveal the location of his secret lair; the long-time bitter enemies then team up for an all-out assault. As the Guild and O.S.I. close in on it, The Sovereign activates its self-destruct and flies away. He then meets his demise while in eagle form, having accidentally been shot by Headshot after the boat he is aboard experiences turbulence from the explosion.
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 (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 (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: The Sovereign's new bodyguard, bearing a striking resemblance to longtime Bowie collaborator Brian Eno.
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 (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 (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 (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 (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 (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.
The governing body of the Guild of Calamitous Intent consists of the following known members:
Wide Wale (voiced by Hal Lublin): The leader of the New York branch of the Guild, he is brought in to help shore up support for the Guild and the council after the events of Gargantua-2. He agrees to join only if he is given the arching rights to Dr. Venture. His real name is Chester Ong, and he is the younger brother of Doctor Dugong, a scientist whom The Monarch seemingly killed. As a result of a laboratory accident, he has physical aspects of whales as part of his biology; these traits were inherited by his daughter Sirena. In Season 7, he forbids his daughter from seeing Hank Venture since he doesn't approve of him. He later captures The Monarch and tells him that he plans to kill him out of revenge for his brother's death. He also tasks Hank with killing him, but he refuses, and just when Wide Wale is about to do it, Dr. Mrs. The Monarch and Red Death appear with Dr. Dugong, who grew a new head, allowing him to survive The Monarch's attempt on his life before he went into hiding, provided by the OSI. Wide Wale is then faced with dealing with his daughter and brother, who are angry that he didn't tell them about Dugong. In "The Terminus Mandate," he resigns from his seat on the council, as he is unable to let go of his personal vendettas, though he remains an ally to them.
Red Death (voiced by Clancy Brown): A skinless red supervillain similar to the Red Skull. Despite his terrifying visage and reputation, he is actually a kind and loving husband and father. However, when arching or in times of anger or other elevated emotion, he slips into an evil persona with no hesitation to kill. In Season 7, it is revealed that Red Death was a member of a gang of young Guild villains at the beginning of his career in the 1980s.
A newly formed, independent organization of villains primarily established to counter the Guild of Calamitous Intent. Consequently, several of its members have had negative encounters with the Guild in the past. The society's founder is Phantom Limb, who initially conceived it as his "team" to acquire the ORB for use against the Guild. However, this version of the Revenge Society consisted solely of Phantom Limb himself, along with inanimate objects he believed to be real individuals: a coffee mug named Wisdom, a toaster named Chuck, and a shoe called Lady Nightshade. After escaping Guild custody, Phantom Limb joined forces with Richard Impossible to establish the current Revenge Society. This iteration has swiftly achieved success in the realm of villainy, although they failed to eliminate Dr. Venture twice in "Bright Lights, Dean City." The group has since been effectively disbanded as of "All This and Gargantua-2."
Ünderland is a micronation situated near Michigan. Formerly under the dictatorship of Baron Werner Ünderbheit, the nation enforced mandatory conscription for all men aged 18 and compulsory euthanasia at 40. Notably, Ünderland lacked prisons, with all crimes punishable by death. However, following the events of "Love Bheits," Ünderbheit is ousted, leading to Ünderland's transition to a democratic society.
The Fraternity of Torment stands as one of the few supervillain collectives outside the Guild of Calamitous Intent. Comprising mostly marginalized individuals ostracized by society due to various physical deformities, they frequently clashed with Team Venture during the 1960s. However, Jonas and his team often appeared to taunt and bully them for amusement rather than engage them out of a sense of justice. Although the original group's remnants surface in "Now Museum, Now You Don't", they still maintain a presence in the realm of organized supervillainy alongside the "Peril Partnership".
The Peril Partnership is a supervillain coalition headquartered in Toronto, serving as one of several rival factions to the Guild of Calamitous Intent. Members of this organization can be identified by the letters 'PP' on their attire. In season 7, it is unveiled that the Peril Partnership has infiltrated the Guild. However, this revelation exposes a splinter faction comprising some American members of the Peril Partnership, seeking to instigate a conflict between the Guild and their organization, with the aim of usurping control as the preeminent supervillain consortium.
Originally a terrorist organization that served as the primary adversary of the O.S.I. 20 years ago until its defeat in the Pyramid Wars of 1987. The conflict erupted when S.P.H.I.N.X. seemingly took credit for the Movie Night Massacre on Gargantua-1, resulting in the death of Jonas Venture Sr. and numerous others. However, it was later revealed that the Sovereign had framed S.P.H.I.N.X. using the form of S.P.H.I.N.X. Commander. Disillusioned with the O.S.I.'s bureaucracy, several of its members decided to adopt the S.P.H.I.N.X. identity, along with their surplus equipment, to combat rogue supervillains. By the end of season 4 and the start of season 5, former O.S.I. agents who had joined S.P.H.I.N.X. were reinstated into the O.S.I., leaving Henchman 21 as the sole remaining S.P.H.I.N.X. operative. Gary attempts to recruit new members but inadvertently reunites the original S.P.H.I.N.X. members. Aware that their loyalty chips will soon dissolve, resulting in their demise, they prepare for a final suicide attack against the O.S.I. S.P.H.I.N.X.'s rented headquarters within the Venture compound is destroyed in the season 5 episode "S.P.H.I.N.X. Rising," forcing Gary to reside in the Venture's backyard. The original surviving S.P.H.I.N.X. members are: