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Anime and Manga
- Cat Shit One involves cute rabbits as killing machines fighting in The Vietnam War.
- Ginga Nagareboshi Gin and its sequel, Ginga Densetsu Weed are about talking dogs. Kid-friendly, right? Hardly — there's some very disturbing stuff (including a dog who castrates his enemies) in Weed, and Gin is even more violent, and that's not even counting the manga.
- Oruchuban Ebichu is a comedy about a cute little hamster and her unmarried owner. Almost every joke is about sex.
- Cat Soup is an abstract, existential short film based on the extremely dark comics of artist Nekojiru. But hey, all the characters are cats!
- Wolfs Rain is an anime about wolves. It's a violent and depressing seinen anime where in the first episode Kiba tears out a mans throat in front of a child.
- During the 1930s and 1940s the Tijuana Bible phenomenon began to blossom. These were pornographic comic strip parodies on famous franchises like Mickey Mouse, Donald Duck,... drawn by anonymous artists. As Art Spiegelman has correctly said: "These were the forefathers of the Underground Comics of the 1960s and 1970s."
- Fritz the Cat and its two Animated Adaptations, Fritz the Cat and The Nine Lives of Fritz the Cat. Graphic sex, graphic violence, drug use and satirical social commentary, all set in a World of Funny Animals. Robert Crumb continued making comic strips with antropomorphic animals doing adult stuff ever since, such as Those Cute Little Bearzie Wearzies where a fuzzy bear couple that looks absolutely cute act more like a typical Real Life couple by having foul mouthed arguments and having sex with each other.
- Omaha the Cat Dancer: An adult comic strip with antropomorphic animal characters who engage in sex, but is otherwise not vulgar. It's more about relationships between people and also touches sexual topics, but in a tasteful and thought provoking way.
- Usagi Yojimbo involves adorable anthropomorphic animals, the main character being a rabbit. The setting, however, is Feudal Japan with all of the cultural baggage thereof, including kirisute, the traditional right of the samurai to kill any commoner who offends him. There is exploration of death, relationships (including forbidden relationships, illegitimate offspring, widowhood, etc.), various extremely nasty monsters from folklore, political intrigue, crime and punishment, and a very messed up judicial system.
- Maus is a retelling of the author's father's experiences during the Holocaust, including his stay at Auschwitz. Jews are mice, Germans are cats, Americans are dogs, and Poles are pigs.
- While later iterations of Teenage Mutant Ninja Turtles were relatively kid-friendly, the original comic was rather gritty and featured plenty of violence and death.
- Benoit Sokal's Inspector Canardo is about a detective duck in a world of talking animals. The protagonist is a drunk, people get killed, prostitutes and rapists are commonplace. Definitely not for children.
- Swedish comic strips Arne Anka and Rocky are filled to the brim with funny animals. They're also filled with alcohol consumption, sex and deep, deep cynicism.
- We3, by Grant Morrison, is about three talking animals trying to find their way home; the covers feature "missing pets" notices written in childlike style. Kids'll love it, right? Sure! Except for the scenes featuring the cybernetic animal soldiers literally tearing apart the soldiers meant to come kill them, the part where the rabbit explodes while hurling itself at a car, and all sorts of graphic violence in between. Oh, and it's being adapted into a movie directed by the guy who made Kung Fu Panda.
- Blacksad is a Film Noir style series of graphic novels about a black cat private detective named John Blacksad and his various cases set in a World of Funny Animals version of 1950's America. It doesn't hold back from showing blood, fatal injuries, wounds, controversial topics (e.g. racism), and sex.
- Grandville - the main character is an anthropomorphic badger who is a private investigator. It's set in a Steam Punk fantasy setting, and features plenty of sex, violence, and politics.
- The characters in the Sandbox comics by Swedish artist Joakim Pirinen are antropomorphic teddy bears, while their plots often deal with sex, drugs, violence, and disturbingly psychedelic visions.
- The infamous Air Pirates Funnies was a short-lived underground parody comic which featured Disney characters in adult situations, such as having sex and taking drugs. Disney sued the makers of the comic for copyright infringement, which apparently was exactly what they wanted.
- The Unfunnies is this trope all over: Hanna-Barbera-style characters start talking about pedo-pornography as soon as the second page, and it goes further downhill from there. Of course, the Hanna-Barbera element also includes the occasional cartoony humans thrown in for good measure, but the comic still counts.
- Albedo Erma Felna EDF kickstarted much of this trope as a deadly serious Military Science-Fiction series where the furries usually follow up on the action with serious discussions about the sociopolitical ramifications.
- Pride of Baghdad has blood and at one point a lioness flashbacks to being gang raped (It's not shown, but still.) Also, they all die at the end.
- Tom Poes is about the adventures of a bear and his friend the little white cat. It's a children's comic strip, but has very Antiquated Linguistics and gentle adult satire that will be understood by adults better than children. Creator Marten Toonder used it to openly poke fun at the Nazis when they were at their most powerful and right on his doorstep). The series is still considered one of the most mature and "literary" European comic strips.
- Howard the Duck: The original comic strip was about a cigar chomping wisecracking duck and not intended for children at all.
- BB Wolf and the 3 L Ps uses the characters of The Three Little Pigs in an allegory about racism in 1920's America. It's quite violent - the wolf protagonist's family is killed when the pigs burn his home, and he graphically tears open two pigs as part of a Roaring Rampage of Revenge.
- Beasts of Burden, which pits adorable pets against absolute terror.
- Garfield was aimed at adults early on but as it grew more popular it became more kid friendly.
- The Harmony Trap is an M-rated fanfic with an Alternate Universe version of Captain Carrot and His Amazing Zoo Crew!.
- Memoirs Of A Master is a Kung Fu Panda story where Po and the Furious Five read the personal memoirs of Master Shifu; a tale of trials and profound loss experienced by a martial arts master who found redemption where he least expected it through Po.
Films — Animated
- Watership Down. The introductory animation has animals being killed, and this continues throughout the movie. At one point Bigwig is trapped by a snare around his neck and is clearly suffering. The original warren the protagonists come from is a moderately harsh dictatorship, and Efrafa (General Woundwort's warren) is much worse. There's also a lot of blood and at one point rabbits are buried alive.
Hazel: Don't make it too grim, Holly.Holly: "Grim"? I haven't even begun.
- Despite this all it's apparently aimed at middle schoolers and is relatively common in school. Too many people mistake it for toddlers and little kids because of the rabbits though.
- Felidae. To quote the entry: "Despite being an animated film, it is definitely not for kids. The film contains graphic violence, disturbing images, adult language, and cat sex. Yes, cat sex."
- It's basically a noir drama with cats. It has the language, sex, and violence but instead of humans in fedoras we get cute cats.
- The Plague Dogs is an animated film based on a book by Richard Adams, author of Watership Down. It's about two dogs that escape from a research lab and attempt to live in the wild. It starts with a dog drowning as part of an experiment involving how long it can tread water. The tale highlights the cruelty of animal research and vivisection. In America, the film was rated PG-13.
- As noted above, Fritz the Cat is probably the very first example in history of American animation, produced back in 1972. It revolves around the Pornomancer Fritz hanging out with stoners, having sex with everyone and...forget it, there is not much plot, aside from emphasizing the movie's X-rating.
- The oldest example of this trope may be the Reynard The Fox stories from the 13th century. It's a medieval poem about a Karmic Trickster fox character who brutally murders, rapes, steals from other animals and has to be brought to court. The story has a lot of adult content, with even a Catholic priest who is apparently married and has his penis bit off by one of the animals.
- Many fairy tales who are kids' entertainment nowadays weren't originally intended that way. In earlier centuries these stories were told to children and adults alike and often featured content that would not be considered child friendly today. A good example is Little Red Riding Hood where the wolf character was mostly intended originally as a seductive man lusting for young girls.
- Anna Sewell wrote Black Beauty as a lengthy social commentary on animal welfare, politics, religion, and social justice, including living conditions for the working-class poor. While there's probably not anything that's inappropriate for younger readers (aside from a couple rather gruesome depictions of dead and suffering horses), much of it would probably go straight over their heads. Versions of the book are frequently marketed to children, but these have typically been heavily edited or rewritten entirely.
- Animal Farm is more or less a breakdown of Josef Stalin's part in the Russian Revolution, portrayed via animals throwing a farmer out of a farm and then running it themselves. The pigs are the communists, they raise dogs as their police, and the sheep pledge their full support to everything said to them without thinking about any of it. All sorts of Fridge Horror ensues, such as the horse being sold to a glue farm while the pigs periodically read letters they claim the horse wrote to them from his retirement pasture. Fortunately, nobody really thinks of it as a book for children, although it is often taught at middle school level (13/14-year-olds can usually grasp what's going on, and if you teach it alongside the actual history of the Russian Revolution and Stalin's regime, it makes for a good introduction to the concepts of allegory and satire).
- The third book in The Wicked Years series is about the Cowardly Lion. In true Wicked fashion it's a Darker and Edgier, very adult retelling of The Wonderful Wizard of Oz
- Watership Down and The Plague Dogs by Richard Adams, as noted above under film.
- Felidae by Akif PirinÁci, the basis for the animated feature also mentioned above under film, and the eight subsequent books in the series.
- Jonathan Livingston Seagull. The author, Richard Bach, always had trouble with publishers and librarians on what genre they should label the novel. They couldn't label it children literature due to the contents being too adult (without being violent or sexual), but also they felt reluctant to label it adult due to the characters all being talking seagulls.
- Most of Kyell Gold's output.
- Conkers Bad Fur Day stars a drunken squirrel and features Toilet Humour, sexual innuendo, swearing, and an M rating...all capped off by a Tear Jerker of a Downer Ending. It originally was a normal, cute Funny Animal platformer which is why a younger Conker pops up in Diddy Kong Racing.
- A Dog's Life is a T rated game where you are a dog trying to save his love interest from being cat food.
- Lackadaisy is a webcomic about a bootlegging gang in Prohibition-era St. Louis, with plenty of gunfights, killings, and several sociopathic characters. There is painstaking attention to period-appropriate detail, with one exception: all the characters are anthropomorphic cats.
- Jack is a Furry Webcomic about a rabbit who is also The Grim Reaper. Most of the stories take place in the afterlife or involve death in some form. This comic can get very NSFW at times.
- Exterminatus Now features a comedic World of Funny Animals based on Sonic the Hedgehog... mixed with Warhammer 40,000, with all the blood, gore, death, and Eldritch Abominations that implies. Thus, it largely deals in adult-oriented Black Comedy, with plenty of profanity to go with it.
- Drugs & Kisses features the misadventures of several pot-smoking, vodka-swigging anthropomorphic animals.
- Tasakeru is a series about cute, fluffy talking animals like squirrels and rabbits... which involves bloody warfare, racism (speciesism?), religious intolerance, Mind Rape, and not a little innuendo.
- The Cat Piano may qualify, being about Petting Zoo People/Anthropomorphized cats who were being kidnapped in order for the titular piano to be played (it stabs a nail through a cat's tail every time a key is struck, making the cat yowl the note). Particularly the ending, where the catnapping human slips in his own blood and falls off a tower to his death.
- Arguably a lot of furry online roleplays end up this way. Darwins Soldiers is a good example. It features intense violence, cursing, sexual activity and some pretty heavy themes.
- Happy Tree Friends, an internet TV show about cute animals getting into bloody mishaps and I do mean bloody!
- Ruby Quest and its Spiritual Successor Nan Quest both use minimalist drawings featuring characters with animal aesthetics to narrate stories about grotesque Body Horror, Cosmic Horror and Survival Horror set in Eldritch Locations. Unsettling stuff. Once the blood starts spewing, the stories' target audience becomes a bit clearer.
- Father of the Pride was a short-lived CGI cartoon featuring cute animals living in Siegfried & Roy's private zoo. It features plenty of adult humor.
- Alfred J. Kwak, aimed at children, but alluded at very adult topics such as racism, Nazism, apartheid, AIDS,... in a way that is sometimes subtle, but other times very direct.
- Duckman: An underground comic strip adapted to a TV adult animated series starring mostly anthropomorphic characters and topics such as politics, sex, drugs, society issues,...