I noticed how show has been largely ignored by the trans community, but I have been watching this show from the very start.
It runs on Cartoon Network's Adult Swim block. It is a show about how Two Brothers (Hank and Dean Venture), their father (Dr. Venture), and their overly masculine body gaurd (Brock Sampson) are harassed by supervillians, and their other adventures.
Normaly animated comedy shows tend to be offensive and represent the negative stereotypes of TS or worse (South Park, Family Guy, though I will admit to watching both on occasion.)
Venture Brothers though takes these issues a little differantly, with a degree of respect while still retaining humor. While they do overuse the word "gay" quite a bit (in fact overuse it) the show I have noticed is one of the most overtly positive shows regarding gender identity issues.
I will say outright, the show handles issues of gender identity with humor, without being degrading. In fact I will argue that it is presenting a well thought out discussion of gender identity that goes beyond anything I have seen on TV. The more I think about the show and the episodes I have seen, the more I realize they are approaching something special. It could all fall apart, but as it stands, the show is presenting gender identity issues without falling into common traps.
First. There is Dr. Girlfriend. She has a deep voice. I think they only did this because they do want hint in the fact she is a TS, and did not want to do it in an inherantly offensive way. From the very start of the show she has been one of the best thought out characters of the show. She is a super villan in every sense of the word, but she is also an extremely intelligent woman. Even though the show has hinted the viewer about her past, the way Dr. Girlfriend is portrayed, is that she is without question female. Instead of portraying Dr. Girlfriend as the classic man in a dress that many shows like to portray transwomen, Dr. Girlfriend is portrayed as the classic femme fatal. Throughout the show she is portrayed as easily the most balanced and intelligent characters on the show. She openly fights the misogyny that she faces from love interests and the other males on the show. The last episode of the season makes you assume that Dr. Girlfriend was honest about her past to "the Monarch" after thier marriage, basically having to come out. She is easily the most three dimensional character of the show, while most the other male characters are paperthin archetypes (there are two exceptions: Dean Venture and Brock Sampson, which I will discuss later). This may be the best TS characterizations on TV I have seen, because you are not only shown the misogyny that Dr. Girlfriend faces as a woman, but also the issues she has to face as a post-op TS, such as coming out and being read. For all the craziness that happens on the show, and all the problems that all the characters have, Dr. Girlfriend without question is one of the most sane and normal characters. The show actually handles it all very well and Dr. Girlfriend ends up being one of the best portrayals of a transwoman I can find in popular media.
Second: Brock Sampson's mentor - The show dedicated an entire episode to Brock Sampson being sent on a mission to kill his mentor. Brock Sampson is a tough guy spy/body guard of the Ventures. Only to find out the reason why he was being sent on this mission was because his mentor was a MtF transsexual and just wanted to live a new life and had just underwent surgery. Brock ultimately respects the wish's of his mentor to live as a woman. The show does make a joke about this in a later episode "But you're not dead, you're a woman" while the male head of his mentor is speaking with a female body. It is an odd dream sequence. I would not call it outright offensive though, as it suggests that Brock Sampson is still trying to come to terms with who his mentor has become and the memories that he had regarding his mentor, though he clearly accepted that his mentor was in fact a woman. Brock is an odd character because he does have observations with regards to the strange aspects of Dean, and the fact he suspects Dr. Girlfriend is a TS woman. I am not saying he is perfect by any means, he is observant of differences and points them out, but never reacts violently towards them (he reacts violently towards everything else though), and is in fact a rather tolerant character.
Third: Dean Venture. I could spend pages deconstructing Dean and the gender identity issues that he faces. He frequently cross dresses on the show, often without any issue. During one episode of the show he is mistaken as a woman while dressed. He is frequently teased for his effiminate behaviors. While there is something boyish about Dean, such as attraction to the next door neighbor. However, there is also always a suggestion there that Dean is not like a typical teenage boy, that there is not much male about him at all. The subtle suggestion in the show is when Brock Sampson said he was not quite sure what to buy Dean for Christmas. The thing is you are always intended to guess, is Dean a just a CD, a TS who has yet to be conscious of gender identity, or just genderqueer.
Am I the only one deconstructing this show this way. I kinda like it because beneath all the weirdness and humor of the show there is actually a serious dialog on gender identity issues.