Long time lurker and had to register because of this; I have put a ton of thought into this which is admittedly influenced by the Cwcki theories and Venture Brothers a great deal. Here's what I came up with:
Our Pet Lolcow - Leader of Cwcville and it's armed forces. Very deeply troubled character who's severe psychological issues led him to seize his father's once successful autonomous community and transform it into a Theocratic Totalitarian State run by he himself. Despite his machinations, constitutional precedents set by his father and his own incompetence keep him from completely destroying the community. He is still prone to homicidal rages from time to time, especially when things don't go his way. He unsuccessfully tries to woo numerous women, especially unscrupulous redheads. He is extremely paranoid and touts various conspiracies, which he sends the Chaotic Combo to investigate and is ultimately abducted by inter-dimensional beings (for the sake of humanity) only to return. Think Kim Jong-il meets an incompetent version of Fox Maulder.
Sonichu - Upbeat and moralistic leader of the 'Chaotic Combo' which act more or less as the secret police/special forces of Cwcville. He tends to be an extremely positive and reinforcing individual in the face of his "father's" pessimism, sometimes blatantly ignoring it and often pretending everything in the world is fine. His obsession with "father" is a typical projection of what all the citizens of Cwcville SHOULD be like and he remains the poster-child for a healthy Cwcville citizen. Those who dismiss his delusions outside of the Chaotic combo are promptly murdered by him before he returns to his typical upbeat and positive banter. With the Chaotic Combo he is generally cheerful if forceful about the directives of a mission. Despite how big he talks to opponents, he's actually only mediocre at combat and relies on back-up often though hogs all the glory forhimself when he's finished with help from Chris' and Magi-Chan's propaganda. Inspiration here is largely taken from 'Ted' from the Venture Brothers Episode parodying Scooby Doo (based on Ted Bundy himself and Charles Manson to a lesser extent), Jonas Venture Sr., and ironically Joseph McCarthy.
Rosechu - More or less a captive housewife to Sonichu, unable to think much for herself. She often asks Sonichu if she's allowed to go shopping or interact with other women, though Sonichu quickly shoots her down on either account and reminds her that "he's not made of money" or "Girl-talk is boring!". In her day to day life she completely dotes on Sonichu, reinforced by hypnotic suggestion from Magi-Chan any time she may falter in these thoughts. She does seem to care deeply for Sonichu, and their children, but it almost certainly more closely resembles Stockholm Syndrome than genuine affection at this point. When combat situations arise she generally lets the others fight, though as time goes on she comes into her own abilities, though Sonichu explains it away as luck and discourages her from being anything more than a housewife, and she complies. When she shows signs of attraction towards Reginald Sneasel for his gentle nature and a desire to "take the kids and leave!" They are both rewired by Magi-Chan and made to live miserable lives. Patty Hearst meets Supergirl essentially.
Blake - Roughly the opposite in terms of external demeanor to Sonichu, very cynical and unlikely to spout the party line, earning him the ire of Chris and disregard from Sonichu. He seems incredibly depressed about his origins and traumatized by his upbringing. When asked to go into combat however, he's often guilt-tripped into joining the Chaotic Combo and angrily goes along with their decisions. He's actually far more talented than Sonichu (who has to remind him that he is "sort of his father" as his DNA birthed Blake) and yet his role is often minimized leading to further depression. He's an alcoholic, pill popping, emotional wreck who's only solace in life is listening to 80s Punk Rock (especially Iggy Pop because he feels like he's 'The Idiot'). Often times Chris or Sonichu erroneously refer to him as 'Urban' even though he's actually just a Sonichu wih very Dark Red pigment and he points out that his DNA is virtually identical to Sonichu's with the sole addition of 'Cherry Cola'. Begins a very casual relationship with Bubbles that he cannot put any emotional effort into as time goes on, mostly because of how damaged his psyche is. His psyche is further damaged when Silvana poses as Bubbles and rapes him. Analogous to Dr. Thaddeus Venture or Action Johnny if they were actually talented.
Wild - Wild is allowed certain privleges that the other members of the Chaotic Combo are not (such as promiscuous sex and heavy drug use) because Chris and Sonichu view him as an unscrupulous and primitive savage, which he plays up in front of them. He is in fact a racist, bigoted, moron who uses stereotypes as a precedent, is actually a talented writer and a very capable speaker when he needs to be (though a bigoted one in his responses). He is virtually incapable in direct combat (though plays himself up big) and is easily outwitted. He is a capable infiltrator however, and leads the Chaotic Infiltration team, trying to keep in touch with the others via Magi-Chan. Wild later meets Simonla, a transgendered Sonichu, though he ignores this fact and constantly dismisses this reality. Because of the distorted Sonichu gene-pool they manage to conceive a child. Strongly based on a combination of Mac from Always Sunny and Early Mr. Garrison from South Park, lesser extent Oscar Wilde with his actions in front of Sonichu and Chris being based on Tarzan stereotypes.
Bubbles - A bubbly and upbeat character with a valley girl nature, Bubbles is however initially somewhat innocent and ignorant of sexual norms, much to the chagrin of Chris. Unlike many others she does not attend Date-Ed, insisting it is immoral, and is enrolled in an alternative program; which is simply to be brainwashed by Chris and Sonichu. This results in her developing a multiple personality disorder that goes between an absent minded and innocent valley girl, and a loose prostitute who aggressively pursues every man in her vicinity. This leads to extremely low self-esteem and feeling of rejection that Blake very quickly capitalizes on and they begin a non-committal relationship - despite her more innocent persona being genuinely attracted to and loving Blake. Chris demands they keep the relationship secret, in hopes that she'll "settle down with one of the good ones", which is highly unsuccessful. In combat she is easily the most incompetent, being either to afraid to fight an enemy or offering to sleep with them if they are male when her other persona emerges. When Silvana rapes Blake, her innocent personality is horrified and tries to comfort him whereas her lustful personality is intrigued and offers a threesome. I can't think of any analogues for her.
Punchy - Punchy is a chu past his glory days. Originally he was an honorable, upright warrior with dedication to Chris as "Father" so fierce that he resembled a member of a cult or Paramilitary organization. In his present state, he's a drooling moron that can hardly function on his own. Punchy had it all - fame as a fighter, fortune in the Chaotic Combo, and in turn females as one of Cwcville's most celebrated personalities. He was the most effective fighter in the Chaotic Combo prior to his "incident". While it is initially speculated that he suffers from Parkinson's Syndrome because of head injuries involving his various duels, it is actually revealed that Chris ordered Magi-Chan to Trepanate him when he began to question the need for his Date-Ed class (he had no need for it) and refused the brainwashing alternative after seeing what it did to Bubbles. He can however still fight sufficiently. His old aide, Layla that harbored a crush on him for years during his prime, is now his caretaker, and depending on Punchy's state of mind can also vary between his lover and Punching Bag. He's prone to murderous rages post-trepanation where he screams "CHRIS!!!!!" That most take as a sign of loyalty. He is in fact under the delusion that he is killing Chris and often has to be influenced away from his rage by Magi-Chan, telepathically. Somewhat based Late Dragonball/Early DBZ Tien Pre-Trepanation, Mohammed Ali/Mid-Late DBZ Tien Post-Trepanation.
Angelica - Angelica is both a member of the Chaotic Combo and the "Purity Society"; Cwcville's equivalent of the Ministry of Truth. She is a former Nun who harbors very mixed emotions about Cwcville - on the one hand she venerates Chris as "Father" and willingly goes along with his plans, on the other her religious nature brings her to question his morality and moral grips. Date-Ed brought her immense emotional scarring, compounded with her previous chastity vows, she develops severe anxiety when being wooed. She agrees to a slow relationship with Cwcvilles biggest loser; Reginald Sneasel, because she knows he'll never have the balls to try and fuck her. Despite this she does care for him, either because he is so gentle or because Magi-Chan constantly tells her she should.
Magi-Chan - Cwcville's de facto leader due to the incompetence of Chris. In theory Magi-Chan loves Chris and the Chaotic Combo, in truth he actually toys with them with sadistic glee and is far more concerned about policing it's citizens to do his bidding and easily manipulates Chris into thinking the ideas that Magi-Chan envisions belong to Chris. He can easily save everyone, but would rather place them in danger, unless Chris specifically demands he fight or his life is placed in direct danger. He, like Wild, is known for his sexual promiscuity and deviancy, which he can in fact explain away from Chris using Psychic suggestion; Magi-Chan is Bisexual and agrees to monitor Cwcville only to monitor those he can engage in sex. He later approaches Silvana for sex, thinking she has "the best of both worlds!" Roughly based on Oscar Wilde and Mr. Popo from DBZA.
Reginal Sneasel - A shy, obsessive-compulsive wreck with a penchant for approaching any female that will listen to him, Sneasel is regarded as the biggest loser in Cwcville. He deeply cares however and tries to appease women by showing this caring nature. While few women show much interest, his desire to leave Cwcville and be a reporter make him a popular steel for Rosechu when she desires to escape Cwcville. He is intercepted and brainwashed by Magi-Chan to instead stay and give up on his drams. He gradually begins a relationship with Angelica, looking for any female contact.
Mary Lee Walsh - A former attorney within Cwcville that tried to prosecute the maniacal crimes of the "father" only to be cast out. She later joins "Count Graduon" in her battle to fight Chris and largely cuts Cwcville off from the world economy via embargo. This is responded to with terrorism by the Chaotic Combo and Cwcville Armed Forces ultimately leading to a major war and Walsh resigning in shame only to return and battle Chris. It is revealed that the 'real' Mary Lee Walsh changed her name and now lives in Tahiti with her husband and that the current mantle has actually been picked up by various women Chris has harassed over the years, directed by Count Graduon.
Count Graduon - Joseph McCarthy's spirit bound to a scepter. He saw Cwcville as a sort of Communist and Un-American experiment and is hell-bent on destroying it. Most of the Walsh's just ignore him however in his rants and conceive real plans to destroy the apparatus and simply tolerate him for his magical abilities, including possession and telepathy - which he often uses against Chris to humiliate him further. He further believes in American hegemony and global conquest however few of his followers take him seriously. He was confined to the scepter as punishment by the spirits of John Pershing, Nikola Tesla and Richie Valens for his Communist witch-hunt that disgusted all three.
Silvana - A Transgendered servant of Graduon, who joined the fight against Chris to liberate her brothers and sisters. Despite this, Graduon can occasionally take control of her and targets the most vulnerable member of the Combo, Blake and forces her to rape him. Silvana is however by nature very gentle and sensitive, despising most of her actions under Graduon and often having to be comforted by the Walsh imposters. She eventually becomes immune to Graduon's hypnosis and goes to open a tiki bar in Staten Island, only to be approached by Magi-Chan for sexual encounter, which she quickly rebukes.
