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 broadcast on Adult Swim.
Team Venture.
Team Venture comprises the central characters in the show; they formerly lived in a fortified compound in Colorado Springs that doubled as the headquarters for the company, "Venture Industries". After the compound was destroyed in Season Six, and Dr. Venture inherits his brother's fortune, they relocate to the Ventech Tower, located at Columbus Circle in Manhattan.
Dr. Rusty Venture.
Dr. Thaddeus "Rusty" Venture (voiced by James Urbaniak): Dean and Hank's father, head of Venture Industries, and half-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, resulting in chaos for him, his family, friends, and sometimes the world at large. Although the money he earns is enough to support him and his family, it's also not enough to satisfy his greed and his ambitions to be as wealthy and successful as his father. While he cares for his sons, his father's abusive and negligent parenting influences the way he treats them, sometimes being as callous and indifferent to them as his father was to him.
Brock Samson.
Brock Fitzgerald Samson (voiced by Patrick Warburton): A one-half Swedish, one-quarter Polish, one-quarter Winnebago "murder machine" who acts as a bodyguard to the Venture family and attended the same university as Dr. Venture. Although Brock possesses a license to kill, he refuses to use a gun and instead wields a Ka-Bar fighting knife as his signature weapon. He has shown signs of being somewhat conflicted with his place in the world and unsure about his purpose, and has a personal code of ethics regarding innocents and whom he will kill if they are a threat to him and or the Ventures. He owns an orange 1969 Dodge Hemi Charger named "Adrianne", which he is often seen driving or washing at the Venture compound"."
Hank Venture.
Henry Allen "Hank" Venture (voiced by Christopher McCulloch): A teenage boy, one half of the eponymous pair, a fraternal twin with blond hair. He is shown as the more outgoing and daring of the pair, and is more attracted to action and adventure, seeing himself as a vigilante superhero. In season 4, he became even more rebellious when Brock left, even going so far as to lose his virginity to an older woman who turns out to be the mother of his best friend. After briefly joining the former Henchman 21's version of S.P.H.I.N.X., Hank attained the power suit of former S.P.H.I.N.X. member The Countess, which he wore until it was stolen and destroyed, leaving Hank in physical therapy for some time due to his atrophied muscles. In season 6, Hank decides to forgo college and gets a job at a pizzeria as a delivery boy. He also begins a relationship with Sirena Ong, the daughter of his father's current Guild-assigned villain, Wide Wale. In season 7, he falls into a coma after he discovers Sirena cheating on him with Dean, but recovers.
Dean Venture.
Dean Venture (voiced by Michael Sinterniklaas): A teenage boy, one half of the eponymous pair, a fraternal twin with red hair. While timider than Hank, he shows signs of being less emotionally immature than his brother. Dean is more favored and liked than Hank by their father who grooms Dean to succeed him as the heir to Venture Industries. Like his brother, Dean has been killed over a dozen times, but each time he is replaced with an exact clone who has no memory of the death. After being dumped by Triana and discovering he is a clone, Dean became more of an emo, dressing in a black "speedsuit", moving out of his childhood bedroom, and becoming more unwilling to go with his family on adventures. However, Hank snap some out of it by showing optimism and being a part of their family. In season 6, Dean begins attending the fictional Stuyvestant University in New York, where he thrives as a student of philosophy, and finds a friend with Brown Widow, his roommate. In season 7, he has an affair with Hank's girlfriend, Sirena Ong, but regrets doing so.
H.E.L.P.eR..
H.E.L.P.eR. (voiced by "Soul-Bot"): The Venture family's personal helper robot, who communicates via electronic beeps. Though he is very sensitive, the Ventures often treat him like an old appliance or pet. The robot routinely gets smashed to pieces during the course of their adventures but seems to get repaired by the next show.
Sergeant Hatred.
Sergeant Hatred AKA Courtney Robert Haine (voiced by Brendon Small in season 2 and Christopher McCulloch from season 3 onward): Brock's former supervisor in the O.S.I., husband of Native American villainess Princess Tinyfeet, and the Venture family's bodyguard. He is a large man with a giant red 'H' tattooed on his face and wears 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. 
Dermott Fictel.
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. 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.
Venture acquaintances.
Dr. Jonas Venture, Jr..
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 greatly dislike him, 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 and testament, he bequeaths his fortune, the New York City Headquarters, and technology patents to his brother.
Triana Orpheus.
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 boys. She and Dean become close until they have a major fight and falling out after she chooses to date another boy called 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 as a result of her power. 
Pete White.
Pete White (voiced by Christopher McCulloch): An albino computer scientist and co-founder of Conjectural Technologies. He went to college with Venture, Samson, Baron Ünderbheit, and The Monarch where he hosted a new wave radio show called "The White Room". After graduating with a doctorate in computer science, White and Billy Quizboy worked in tandem on a Jeopardy-style game show, called "QuizBoys" in which Pete hosted and Billy participated. After being caught cheating and rigging the shows in their favor, White and Quizboy were fired and left to find new lives. While the two had a short falling out, Pete eventually rejoined Billy. They found refuge in a trailer near the Venture Compound. Like Venture and Quizboy, White tends to be somewhat lazy and half-hearted in his efforts despite him being very well skilled and knowledgeable in superscience and technology. In Season Six after Dr. Venture inherits his brother's company and fortune, he and Billy move to New York City with the Venture family and become one of Dr. Venture's leading scientists, helping him invent breakthrough technology to sell through Ventech.
Billy Quizboy.
William Whalen, a.k.a. Master Billy Quizboy (voiced by Doc Hammer): A self-proclaimed "boy genius," Billy Whalen is actually an adult with a speech impediment and growth hormone deficiency. He suffers from hydrocephalus, although his intellect seems to be unaffected by this condition. He starred as a contestant on the game show Quizboys hosted by Pete White. When White cheated for him, they were both kicked off the show and Billy's winnings were frozen by the SEC. White and Billy approached Dr. Venture looking to work for him but Rusty turned them both away. After this, William accidentally entered Billy into a dog fight, thinking it was an underground quiz match, Billy lost a hand and eye in the mix-up. Billy left White and was recruited by Brock Samson and Hunter Gathers, who provided him with a mechanical hand and camera eye. Brock and Hunter sent Billy undercover to spy on Professor Hamilton Fantomas and dig up dirt on the possible existence of the Guild of Calamitous Intent. Fantomas had Billy help with his experiment, but the experiment went wrong, Fantomas became Phantom Limb and Billy lost his left eye again. After a mind wipe, Brock smuggled Billy out of O.S.I. and left him with White. Despite not having a formal education and training, he became a medical doctor and neurogeneticist and co-founder of Conjectural Technologies. He also briefly joined the Order of the Triad in exchange for his performing brain surgery on the Outrider after claiming he should be paid for his endeavor. In season 5, Billy's old nemesis Augustus St. Cloud became his and White's designated arch-enemy, much to the duo's delight. In Season 6, he and Peter move with The Venture family to New York City to assist Dr. Venture with inventing breakthrough technology to sell under the Ventech brand. 
The Pirate Captain.
The Pirate Captain (voiced by Christopher McCulloch): The leader of the "ghost pirates" in "Ghosts of the Sargasso". After his initial encounter with the Venture family, he began living on the X-2 after having difficulties in finding a job. When Jonas Jr. acquired the ship, he hired the captain. He has not been referred to by any name or nickname other than "The Captain" so far. He resided with Jonas Jr. on Spider Skull Island and fulfilled the duties of a butler, caretaker, and right-hand man. The Captain always refers to Jonas as "Chairman". Later, after J.J.'s death, the Captain becomes an employee of Dr. Venture when he inherits J.J.'s business in New York City.
The Order of the Triad.
Dr. Byron Orpheus.
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 the only associate of Dr. Venture who displays any sort of 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 over a background of 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 Oprheus's ex-wife after she broke 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.
Jefferson Twilight (voiced by Charles Parnell): An old friend of Dr. Orpheus, who fights Blaculas (black vampires) for a living and wields two swords. He suffers from diabetes and low blood sugar, leading him to thirst for sugared liquids. His left eye is discolored as it is 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.
The Alchemist.
The Alchemist (voiced by Dana Snyder): Another old friend of Dr. Orpheus, who is searching for the philosopher's stone as well as a cure for AIDS. Unlike Twilight and Orpheus, it would seem that he is much less serious about his business and would rather mix business with pleasure; however, his true opinion on the Triad was revealed in the episode "Showdown at Cremation Creek", where he stated that he was more into helping the balance of the Universe than running around fighting one Super-Villain. It has been openly acknowledged that he is gay and a fan of Jimmy Buffett. He is also friends with Hank, as he feels the two of them are similar. He is sometimes referred to as "Al", but whether this is his real name or merely short for Alchemist is uncertain. He has an open hatred of the Internet due to finding out his previous boyfriend was cheating on him via MySpace. It is revealed in "Everybody Comes to Hank's" that he was previously in a relationship with Shore Leave, but that the latter erased his memory of it because The Alchemist had become too "clingy." In "OSI Love You", he and Shore Leave have an amorous video chat implying they got back together.
O.S.I..
The Office of Secret Intelligence is a branch of the United States government that handles supervillain activity, both combatting 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."
Archvillains and henchmen.
The Guild of Calamitous Intent.
The Guild of Calamitous Intent are the primary antagonists in the series. They are an organization of supervillains that serves as a trade union for villains, providing benefits such as health insurance and sets the rules and standards of conduct between its members and their enemies who tend to be the superheroes and super-scientists of the world. The Guild acts as a stabilizing influence on the world of super-villainy, as without it they would be unchecked free agents with no rules restricting their behavior. The Guild not only serves to organize the world's supervillains into an organized force, but it also controls and limits the villains from total mass destruction, murder, and mayhem by restricting their attacks to Guild-approved targets. Early in the series, it was led by a mysterious figure known only as "The Sovereign", and a group of villains called the Council of Thirteen. The current incarnation of the Guild is implied to be a haven for missing and/or presumed deceased rock stars. In Season 6, most of the Council of 13 is killed by the Sovereign in order to consolidate his control over the Guild and as part of a plan to defeat the supernatural, supervillain group, The Investors. After The Sovereign is accidentally killed by O.S.I., the remaining survivors of The Sovereign's purges, Dr. Mrs. The Monarch, Dr. Phineas Phage, Dr. Z, Red Mantle, and Dragoon forges a new Council of 13, surviving Revenge Society members with help from Dr. Henry Killinger after he killed the Investors in order to restore the balance between the OSI and the Guild. He declined the role of Sovereign and left control of the Guild to the Council. Season six introduces the New York branch of the Guild, which is made up of the most dangerous supervillains the organization has to offer. It is later revealed that the original Guild charter does not mandate that the Council must have exactly thirteen members, and members of the Council cannot be actively arching their enemies.
The current incarnation of the Guild was apparently founded around 1959 by Phantom Limb's grandfather, but its history can be traced back to the late Victorian era, where it was a heroic organization led by Colonel Lloyd Venture, Rusty Venture's grandfather, dedicated to the protection of an enigmatic sphere known as the "ORB". The Guild then split over how to use the ORB, with Fantomas founding the Guild of Calamitous Intent (who wanted to use the ORB to control mankind) in 1910 while Lloyd founded the modern version of the OSI (who wanted to use the ORB to help mankind).
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 which killed his parents. He attended State University where he began arching Dr. Venture, but for reasons as yet unrevealed (though possible making fun of his love of butterflies and thinking he was a "closet case"). He then began working for a variety of villains, and was employed by Phantom Limb as Shadowman 9, until he became The Monarch and seduced Dr. Girlfriend. Though he frequently describes himself as Dr. Venture's nemesis, their rivalry resides completely in The Monarch's imagination. In reality, Dr. Venture considers him more a nuisance than a genuine threat, and is even fine with leaving his sons in The Monarch's care due to his general incompetence. He is also the unofficial arch-enemy of Captain Sunshine, to whom he is far more ruthless, even brutally killing Wonder Boy III and sending the hero his charred corpse. The Monarch eventually lost his privilege to Arch Rusty after it was discovered that he was not a Guild-sanctioned villain, and upon registering killed five heroes and super-scientists he had been assigned to before being given the job of Arching Rusty's brother, Jonas Jr. until The Monarch uses the Guild clause of "prior escalation" to be able to attack Rusty again. At the end of season one, he was convicted of murder and sentenced to prison after being framed by the Phantom Limb. In the second season, he escapes and begins to rebuild his criminal operation, reuniting with Dr. Girlfriend in the process and eventually marrying her. As of the third season, the two have moved into Phantom Limb's old mansion in a gated community called Malice. In the fifth season of Venture Brothers, there is a photo The Monarch finds while undercover at the Venture compound of him as a toddler playing with Rusty and accompanied by his parents and the Venture family, suggesting The Monarch and Rusty could have been childhood friends. At the end of season 5, his Cocoon ship, his home, and all his henchmen were destroyed by Sgt. Hatred, forcing The Monarch, his wife, and Henchman 21 to move into The Monarch's abandoned childhood home in Newark, New Jersey. He also loses his rights to fight Dr. Venture, as the loss of his cocoon and henchmen lowered his Guild ranking substantially. In the episode "Faking Miracles" The Monarch discovered that his father was the Blue Morpho. The Monarch then took up his father's hero identity and, along with Henchman 21, began killing New York Guild members who were antagonizing Dr. Venture so that he could move up the waiting list. In Season 7, it is implied that The Monarch's mother slept with Jonas Venture to conceive him, as part of a blackmail Jonas was doing to his father, making him the half-brother of Dr. Venture. 
Henchman 21.
Henchman 21/Gary Fisher, briefly S.P.H.I.N.X. Commander and occasionally the Viceroy (voiced by Doc Hammer): A pop-culture geek who at the beginning of the series is a henchman for The Monarch, always seen with his closest friend Henchman 24. He writes "Flight of The Monarch", a tell-all that starts the chain of events ending in The Monarch's incarceration. After the death of Henchman 24, he goes into heavy combat training and emerges with sufficient strength and martial prowess to contend with Brock Samson. He and Samson then work together to defeat Monstroso, a common enemy. Henchman 21 still speaks to what he believes is Henchman 24's ghost, though Henchman 24's ghost suggests that he is only a figment of Henchman 21's imagination (simultaneously confirmed and refuted in ), in echoes of Rudyard Kipling's classic story "The Man Who Would Be King". In "Operation P.R.O.M.", 21 was offered a chance to work with the anti-unlicensed superhero team, S.P.H.I.N.X. He found he enjoyed working "with guys who actually know what they're doing" for once, and began to question his dedication to the ways of The Monarch and evil in general. By the end of the episode, he realizes that being a villain is not for him, and quits the ranks of The Monarch. In "From the Ladle to the Grave: The Story of Shallow Gravy" 2011 Venture Brothers special which takes place after "Operation P.R.O.M," he is interviewed while wearing a S.P.H.I.N.X. uniform with his face censored, and using the Viceroy name. After "Operation P.R.O.M." Gary becomes the commander of S.P.H.I.N.X., which does not last long when the former members of the original S.P.H.I.N.X. take over, forcing the O.S.I. to shut S.P.H.I.N.X. down for good. Gary lives in the backyard of the Venture Compound, as S.P.H.I.N.X.'s headquarters is destroyed by Dr. Venture and Sgt. Hatred when they believe Gary has planted bombs under the Venture Compound, as he can identify them as his own painted the colors of The Monarch, when they were in fact planted by The Monarch and Dr. Mrs. The Monarch in their earlier infiltration attempt. He later helps Hank and Dermott to try to get to Teddy by adopting his "Viceroy" moniker in a bank robbery to get into the Dunwitch Asylum for the Criminally Insane. After attempting to help Hatred retrieve Dr. Venture, he leads The Monarch henchmen in overthrowing the furious moppets and decides to rejoin the ranks of The Monarch, returning not out of loyalty to The Monarch or the henchman lifestyle, but because The Monarch is the only friend he has left. By Season 7, 21 finds himself the only remaining henchman of The Monarch. He assists The Monarch when he becomes the new Blue Morpho by killing off Dr. Venture's archenemies, though he finds himself burdened by guilt for doing so, as he has never intentionally killed someone before. He attempts to end the killing by kidnapping several of the archenemies he would have had to go after and merely holding them captive until The Monarch was made Dr. Venture's official antagonist again, but one of them cannibalizes and kills the others. At the end of Season 7, the Guild offers Gary a chance to become a supervillain and leave The Monarch. He declines, declaring the monarch is his best friend, and he wants to help him with his grudge.
Henchman 24.
Henchman 24, (voiced by Christopher McCulloch): a tall, thin man with voice characteristics resembling comic Ray Romano and was described by 21 in the first episode of the second season as resembling Jerry Seinfeld with a unibrow. He served as Shadowman 24 for Phantom Limb at the same time The Monarch was Shadowman 9. The Monarch promised to make him his "number 2" in return for a favor, a promise which has never been carried out. Number 24's powder blue Nissan Stanza becomes the replacement Monarch Mobile after The Monarch's lair is destroyed but is promptly stolen by a fleeing prostitute. The Stanza later inexplicably reappears in the garage of The Monarch's Cocoon. It was heavily damaged when the Cocoon crashed in the Grand Canyon. The Monarch doesn't remember much about 24 besides the fact he thinks his voice sounds like aforementioned Ray Romano. A former factory worker before he joined up with The Monarch, 24 has revealed to Dean that his ex-girlfriend married his father and that he has always wanted to be a cabinet maker. Number 24 dies in an explosion at the end of the season three finale. However, a deleted scene reveals that 24 had faked his death so as to leave the henchman lifestyle behind and is now working at the gas station his father owns. His supposed skull makes appearances throughout season 4 as an object with whom #21 converses as they did previously. In Pinstripes & Poltergeists, #24 is apparently a ghost that has decided to haunt #21 due to lack of options, the other choices being the Cocoon lair, which gets blown up frequently, or his ex-girlfriend from when he was 15, which would have been 'way too creepy' as she no longer likes him 'in that way'. In , it is revealed that 24 was not actually a ghost throughout Season 4, but a figment of 21's grief-stricken imagination. 21's acceptance of this allows him to finally accept 24's "death". Although he still harbors a suspicion that someone is responsible for 24's death, and decides that Tim Tom and Kevin are the ones responsible, and blaming them allows The Monarch's henchmen to overthrow them.
Dr. Mrs. The Monarch.
Dr. Mrs. The Monarch, "née" Dr. Sheila Girlfriend (voiced by Doc Hammer): Wife and assistant to The Monarch. For the most of her career as number 2 to The Monarch wore the former First Lady's famous short pink jacket and pillbox hat, and shares her Long Island accent. Her comically deep voice is a result of her previously having had a severe smoking addiction, and is a parody of Jacqueline Kennedy Onassis' relatively low voice for a woman. 
Tim-Tom and Kevin.
Tim-Tom and Kevin (voiced by Christopher McCulloch and Doc Hammer, respectively): Achondroplastic dwarves who were Dr. Girlfriend's assistants in her solo career as Lady Au Pair. They apparently remain on good terms with her, helping in her application to be the Order of the Triad's nemesis, helping her at her wedding, and organizing the rebuilding of the cocoon after its destruction. They speak to Dr. Girlfriend in a respectful manner, but outside of her presence, they are both surly, foul-mouthed, and utterly psychotic as they seem to ferociously attack with their matching stilettos with very little provocation. 
Watch and Ward.
Watch and Ward (voiced by Christopher McCulloch and Doc Hammer, respectively): The communications and operations liaisons for the Guild of Calamitous Intent, speaking with prospective protagonists and antagonists respectively to adequately provide proper arching assistance. Watch wears a tactical eyepatch over his left eye and appears to be bald, while Ward wears one over his right and has hair sticking out from beneath his cowl. The two frequently get into arguments based on actual conversations between McCulloch and Hammer, such as Ward being upset that Watch drank his juice box. 
Dr. Henry Killinger.
Dr. Henry Killinger (voiced by Christopher McCulloch): A highly skilled businessman and negotiator and demonstrates a keen understanding of legal matters, particularly tax law. He is shown to have magical abilities, although the nature and extent of his powers are unclear. Some characters have a great deal of trouble understanding him when he speaks. Killinger's major appearances have twice involved spontaneously offering his services as a strategist, business consultant, and/or 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 cases, his influence results in a substantial increase in the efficiency with which his clients conduct their affairs. Although, as a supervillain, Killinger is capable of dispassionately murdering adversaries, he is also shown to be capable of quickly forming warm friendships, as well as acts of great kindness. He develops an avuncular relationship with the Venture boys in "The Doctor Is Sin", to the extent that the two of them refer to him as "Uncle Henry". 
The Sovereign.
The Sovereign (voiced by Christopher McCulloch, David Bowie impersonated by James Urbaniak): The mysterious entity who runs the Guild of Calamitous Intent. He communicates principally by use of telescreens which distort his face and voice. He was seen to be David Bowie, but "O.S.I Love You" reveals that he is a shapeshifter who often appears as Bowie. It is unclear if the Sovereign is the actual in-universe David Bowie. In "All this and Gargantua-2", he murders most of the Council of 13, and masterminds an attack on Gargantua-2 as part of a grand scheme to kill the Investors, and is killed in eagle form by Headshot.
Iggy Pop.
Iggy Pop (impersonated by Christopher McCulloch): American rock musician and one of the Sovereign's henchmen. He can create spheres of energy that explode when he issues the command "Pop". He betrays the Sovereign in favor of Phantom Limb, but the Sovereign later kills him for his betrayal.
Klaus Nomi.
Klaus Nomi (impersonated by Christopher McCulloch): German singer and one of the Sovereign's henchmen. He can sing in a hypersonic voice and his bowtie can fly off as a projectile. He betrays the Sovereign in favor of Phantom Limb, but the Sovereign later kills him for his betrayal.
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 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 he is being rescued by Molotov in falls off a cliff, Brock finds it in the season 5 premiere, and finds Monstroso's "body" was a fake, and 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 arch of the Order of the Triad. He is first assigned as their arch enemy in "Fallen Arches" when he kidnaps Triana Orpheus to the Torrid Zone. He has fire-based powers. In "Showdown at Cremation Creek", he steals the All-Seeing Orb, during which The Alchemist and Jefferson Twilight start to doubt the utility of having an archenemy. Torrid's final appearance is when he attempts to open a portal to the Second World, unwittingly being 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): A truck- and Hercules-themed supervillain, and former Number One for Dr. Mrs. The Monarch, from whom she learned how to hotwire any vehicle. His upperbody resembles 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): A supervillain who is intangible. He attends Dr. Venture's yard sale to buy something, but is caught in the fight that ensues. He is later 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): A mysterious group of supervillains who first appear in "Pinstripes & Poltergeists" as members of the Guild aligned with Monstroso. They seem to have omnipotence and are able to grant the dreams and wishes of anyone by entering into "contracts"; promising those who deal with them their desired dream in exchange for a hefty price. They are on the top of both O.S.I. and the reformed S.P.H.I.N.X.'s list of targets, but they cannot be captured. They later appear in "O.S.I. Love You" disguised as O.S.I. Mister level operatives Mister Frost (voiced by Christopher McCulloch), Mister Sample (voiced by Dana Snyder), and Mister Yourname (voiced by Brendon Small), the last of which has not been properly inducted to interrogate those on board about what has happened to Monstroso and Molotov Cocktease. They kill Monstroso during Brock's interrogation earlier in the day. The ruse works until the actual Mister operatives come to interrogate, whereupon Gathers discovers the Investors have already left with all of the documentation of their own debriefing. They are present for the opening of Gargantua-2 looking to "collect" what they offered to JJ Venture by destroying the station, while The Sovereign planned to attack the station with the ultimate goal of killing the Investors before they came to "collect" from him as well. With the help of Phantom Limb, they successfully sabotage the station, escape The Sovereign, and then confront, Dr. Henry Killinger on Meteor Majeure, who kills them in a battle.
Augustus St. Cloud.
Augustus St. Cloud (voiced by Christopher McCulloch, originally James Urbaniak) is the wealthy former rival of Billy's from their quiz show days, both having been collectors of sci-fi and Rusty Venture memorabilia. He first appears at Dr. Venture's tag sale, receiving the brunt of Baron Ünderbheit's attacks due to The Monarch's interference. He later appears amongst supervillains, despite not yet being an official member of the Guild. After giving a sizable donation to the Guild's Widows and Orphans charity, he is inducted into the Guild and allowed to pick from a group of archnemeses, but demands he get Billy Quizboy, with Watch and Ward acquiescing to his demands after another sizable donation. The arching of Billy comes to a head when Billy and Pete White must attempt to retrieve several items St. Cloud bought off of Dr. Venture to fund the Palaemon Project, discovering St. Cloud's Asian albino henchman "Pi Wai". After refusing to eat $1 worth of pennies, the exact value that Billy had beat St. Cloud in an eBay auction years earlier, Billy bests St. Cloud in a trivia contest once more, winning back Venture's hovercraft, needed to deal with the Palaemon Project mutants, and H.E.L.P.er, who had also been sold to St. Cloud. St. Cloud's signature features are his short and stout stature, deadpan voice, round dark glasses, and collection of ginger pageboy style wigs. Because of his incredible wealth and somewhat bratty personality, St. Cloud tends to use money to persuade people or purchase anything that would help him get his way.
The Council of Thirteen.
The governing body of the Guild of Calamitous Intent. Known members are:
Wide Wale.
Wide Wale (voiced by Hal Lublin): A 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 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 didn'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 him 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 remains an ally to them. 
Red Death.
Red Death (voiced by Clancy Brown): A skinless red supervillain similar to the Red Skull. Despite of 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.
The Revenge Society.
A new, independent organization of villains set up primarily to oppose the Guild of Calamitous Intent; as such, a number of its members have had unpleasant dealings with the Guild in the past. Its founder is Phantom Limb, who initially created the society as his "team" to obtain the ORB for use against the Guild; however, this version of the Revenge Society was merely Phantom Limb himself along with a coffee mug named Wisdom, a toaster named Chuck, and a shoe called Lady Nightshade that he believed were real people. After escaping Guild custody later on, Phantom Limb teamed up with Richard Impossible to found the current Revenge Society, which has since had quick success in the field of villainy and they fail to kill Dr. Venture, twice in "Bright Light, Dean City". The group has effectively been broken up as of "All this and Gargantua-2".
Ünderland.
Ünderland is a micronation located near Michigan. Once led by Baron Werner Ünderbheit in a dictatorship, he ruled the land and had a forced conscription for all men age 18 and a forced euthanasia at 40. Ünderland also had no prisons, as all crimes are subject to the death penalty. As a result of "Love Bheits", Ünderbheit is deposed and Ünderland becomes a democratic society.
Fraternity of Torment.
The Fraternity of Torment is one of a handful of supervillain organizations other than the Guild of Calamitous Intent. The group was largely made up of disenfranchised men shunned by society for their various physical defects. They were frequently the antagonists to Team Venture during the 1960s, and it is shown that Jonas and his team often seemed to merely be tormenting and bullying them for fun rather than fighting them out of any sense of justice. The remnants of the original group appear in "Now Museum, Now You Don't", but it is stated they still have some level of presence in the world of organized supervillainy alongside the "Peril Partnership".
Peril Partnership.
The Peril Partnership is another supervillain union based out of Toronto. It is one of several rival organizations to the Guild of Calamitous Intent. Its members can be distinguished by their wearing the letters 'PP.' In season 7, it is revealed that the Peril Partnership has infiltrated the Guild. However, it is revealed that this is actually a splinter group made up of some of the Peril Partnership's American members, hoping to cause a war between the Guild and Peril Partnership so that they can take over as the dominant super villain organization.
S.P.H.I.N.X..
Originally a terrorist organization that was the primary adversary of the O.S.I. 20 years ago until its defeat in the Pyramid Wars of 1987. The Pyramid Wars began when S.P.H.I.N.X. seemingly claimed credit for the Movie Night Massacre on Gargantua-1, in which Jonas Venture Sr. and many others perished, but the organization was actually framed by the Sovereign using S.P.H.I.N.X. Commander's form. Several members of the O.S.I. who were disillusioned with its ineffectual bureaucracy decided take up the S.P.H.I.N.X. mantle, along with their leftover equipment, to create an organization to deal with rogue supervillains. At the end of season 4 and the beginning of season 5, the members of S.P.H.I.N.X. who were formerly O.S.I. agents are redrafted into O.S.I., leaving the former Henchman 21 as the only S.P.H.I.N.X. operative. Gary tries to recruit new members, and accidentally reunites the original S.P.H.I.N.X. members. Knowing that their S.P.H.I.N.X. loyalty chips will soon dissolve and kill them, they dedicate themselves to a final suicide attack against the O.S.I. S.P.H.I.N.X.'s rented headquarters space within the Venture compound is blown up in the season 5 episode "S.P.H.I.N.X. Rising", forcing Gary to live in the Venture's backyard. The original remaining S.P.H.I.N.X. members are: