Foxes occupy a unique place among Animal Stereotypes. They can be good guys, bad guys, or completely neutral, but they're always crafty, clever, and cunning. Their sly nature sometimes results in illegal activies, so it's not uncommon to see them portrayed as thieves or con-artists. Although it is not unknown for them to be too clever; another term for Too Clever by Half is "outfoxing yourself". Sometimes this trope invoked under the phrase "crazy like a fox" for when the brilliant plan seems crazy to anyone who isn't quite as brilliant.
This stereotype is, to some extent, Truth in Television: foxes aren't pack animals like wolves, and they are more known for stealing farm animals in the dark of the night than outright attacking them in broad daylight. The "crazy like a fox" part has roots in real fox behavior as well; red foxes have been known to jump around and act crazy to entice curious rabbits into coming closer.
If the work in question is Japanese (or inspired by Japanese culture), expect the fox to be a Kitsune, a fantastic fox-like creature with the same stereotype of guile and trickery associated with it.
See Fantastic Foxes and Kitsune for the myths, legends, and fables that inspired this trope. Compare Those Wily Coyotes, for another stereotypically clever wild dog.
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"Mr. Fox, how many licks does it take to get to the Tootsie Roll center of a Tootsie Pop?" Though in a subversion, he actually admits that he's less well-informed than Mr. Turtle and Mr. Owl.
Similarly, Tamamo from Hell Teacher Nube is a youko, a "sorcerer fox" whose natural form is as an enormous half-fox, half-human demon who removes human skulls from his victim in order to assume a true human form. Very, very cunning as well.
Kitsune in Pom Poko were driven from their homes the exact same way tanuki are, by human cities expanding into their hills and forests. However, instead of declaring all-out war on humans, kitsune found a more cunning solution. They used their transformation skills to become humans and live in their society. You can still distinguish them by their pointy, angular faces that vaguely resemble a fox's snout.
Which refers to the Japanese term 'kitsune kao', and traditionally someone with those features is held to be this clever. The opposite is a round, wide face, 'tanuki kao', which makes sense, considering the end of the film.
The Medicine Seller from Mononoke, but you'll only notice if you're ready to read between the lines quite a bit. His Kitsune-mask-like face is not the only reason for this comparison — but it certainly helps.
The Dutch comic Tom Poes has a recurring The Barnum character, Joris Goedbloed, who is a fox.
The eponymous main character of the Danish comic Hieronymus Borsch is a fox. He is smart, but thinks he is smarter, and is often hindered by his many psychological weaknesses more than by This Week's Murderer.
Ireyon of newer Danish Paperinik stories fits the clichés, since she is a cunning thief who runs a Robin Hood-like operation of taking from the rich and giving to the poor. (Fun fact: in some of her appearances, the artist was Mĺrdön Smed, who is the creator of Hieronymus Borsch, above.)
Avoided with most fox characters in Bamse, who aren't very sly or cunning. But played completely straight with the rather recent Reinard, who is a crafty villain more or less introduced because most "bad guys" in the comic had deteriorated to the point they only worked as Ineffectual Sympathetic Villains.
“YOU HAVE LEARNED WELL FROM ME!” he whispered like moldy bread. “LEARNED WELL LIKE A FOX WHO WENT TO SCHOOL AND DID WELL AND THEN WENT TO COLLEGE”
Mary Poppins features a fox that needs rescuing from a foxhunt, but once safely on a merry-go-round horse will mock his pursuers - a common criticism of the Guile Hero is that he is, in essence, a coward.
Disney rather appropriately turned Robin Hood into a fox for the animated movie. Maid Marion is also a fox, which leads to the amusing inversion of a chicken guarding a fox (her duenna is a white hen).
Disney's Song of the South features Br'er Fox, who's clever enough to think up a Tar Baby (trapping Br'er Rabbit with his own temper), but isn't as clever as he thinks he is - something Br'er Rabbit can use to his advantage, and does.
The fox (usually female) is most always a sly trickster in Russian folklore and works based on it.
In one Russian fairy-tale, a living round bread who had managed to escape an old man and his wife, a hare, a wolf and a bear, was easily tricked by a fox and eaten.
If a fox shows up in a Scandinavian folktale, you know that it's going to at some point trick or at least deceive someone in an amusing way — and if a bear shows up in the same story, it's going to be the victim. There are several tales dedicated purely to the tricky rascal fox tricking and outwitting the simple-minded dimwit of a bear in various ways. (This is so common that the one story where the bear comes out on top Lampshades the entire thing by pointing out that this time the bear was the clever one, even if he's usually Too Dumb to Live.)
A common punchline in Hungarian fairy tales is that a fox manages to trick several people (usually of a Slavic ethnicity) until he's double crossed by a Szekler, who are also known for their wits and unusually non conventional way of thinking.
The foxes place in British folklore is as a trickster similar to other cultures. However it has a special emphasis because aristocrats began hunting them when the boar were played out. In Anglo-American culture, the term fox is often given to warriors renowned for cunning. Manfred Rommel in the intro to one history said he thought lion would better fit his father Erwin Rommel. But British preferred fox.
The foxes in Redwall tend to be much more into subterfuge than all the other bad-guy species, which often veers into Chronic Backstabbing Disorder, especially when they're the main villains of the book.
Le Roman de Renart is an anthology of tales about a cunning fox called Renart who outwits other animals (see Mythology). Those stories were satires of medieval society at the time it was written. They were loosely adaptated in an animated series, Moi Renart.
In Dick King-Smith's books, especially The Foxbusters (an Affectionate Parody of The Dam Busters), foxes are occasionally portrayed as cunning. But this is decidedly secondary to their main characteristic of being vile Nazi stand-ins. (King-Smith, unlike most of the authors here, was a farmer...)
Mat Cauthon from The Wheel of Time is associated with the fox as part of his trickster archetype. He has a fox head medallion that makes him invulnerable to the One Power and his signet ring has a fox scattering ravens. He is sometimes clever but at other times a bit of a buffoon.
So does its Russian adaptation by A.Tolstoy, The Adventures of Buratino.
Some versions of the The Odyssey have Circe saying that a fox would be a fitting animal for Odysseus, what with him being a Guile Hero. She says this because she's a sorceress who frequently does Baleful Polymorphs.
Mr. Croup from Neverwhere is characterised extensively with fox-related imagery and is generally the more cunning of he and his associate, Mr. Vandemar, who's more oafish and is compared to a wolf or a hound in the same way.
The crafty female tribute "Foxface" in The Hunger Games is describe by Katniss as sly and elusive. Foxface demonstrated her cleverness by figuring out the path into the Careers'supply pyramid and reached the bulk of supplies, takes an unnoticeable amount of food, and then runs back to the safety of the woods.
Tom McCaughren's Run With the Wind and it's five sequels (think Watership Down but with Irish foxes instead of British rabbits). All of them are depicted as being cleverer than any of the other animals but a few are crafty even for foxes like Old Sage Brush, a blind Trickster Mentor or Hop-Along, who uses an eclipse to fool a hare into thinking he can leap high enough to take a bite of the moon.
"The Fox" is also the name of the episode he was in back in season one and he returns in a season five episode called "Outfoxed".
Blackadder: Goes Forth gives us the page quote, in question to Baldrick's final?cunning plan.
Becomes a brick joke at the end of Blackadder Back & Forth:
Blackadder: Baldrick, I have a very, very, very cunning plan.
Baldrick: Is it as cunning as that fox what used to be Professor of Cunning at Oxford University but has since moved on, and is now working for the UN at the High Commission of International Cunning Planning?
Blackadder: Yes, it is.
Baldrick: Mmm... That's cunning!
"The Fox" by Nickel Creek, is about a fox who steals a goose.
Slylock Fox features a cunning fox detective. Even his name is a pun on "sly".
Pogo had Seminole Sam, a con-man. He tended to wobble between antagonist () and neutral.
He partially subverts the trope, since he was often out-bamboozled by the superior brains and cunning of his intended victims.
The opera The Cunning Little Vixen was based on an early comic strip with a similar premise.
The Cunning Little Vixen (Příhody lišky Bystroušky), best known as an opera by Leoš Janáček, tells the story of a vixen who is orphaned as a cub, captured by a forester, but eventually escapes, tricks a badger into leaving his hole and taking it for her own, finds and marries a handsome fox, and raises a family of cunning children.
Referenced in The Taming of the Shrew when Gremio refers to himself as "an old Italian fox". Ironically, Gremio is a rather foolish character (being based on the Commedia dell'Arte character of the "pantaloon"), and at that point in the play he's trying to talk down Tranio—a true trickster who's already thought circles around him.
Invoked by Wheatley in Portal 2. At least, halfway invoked. "Braindamaged... like a fox!"
Dark Lord Ninetails from Okami is an evil fox that spends more time on complex plots than most of the other villains.
Hunter Ravenwood of Suicide for Hire doesn't seem particularly cunning at first glance, being something of a Cloud Cuckoo Lander (dancing around brandishing handguns on a public street, shooting the television on a regular basis, and telling random strangers he has "banged yer sister" being just a few of his eccentricities). However, he's deeply involved in highly illegal activities and has managed not to get caught yet, so evidently he has more street smarts than are obvious at first.
The embodiment of Greed in Jack is a fox, though he's so heavily mutilated that this is a bit hard to tell.
SCP-953 is a very, very nasty nine-tailed Kumiho. She once slaughtered 27 people at a furry convention, and the first time a group of agents cornered her, she used Master of Illusion abilities and a Yamato Nadeshiko act to horribly murder all of them except the one Korean agent on the team; the rest assumed that she was a kitsune and fell for it badly. Yeah, she's smart. Really smart. In the most disgusting, horrifying way possible.
Moi Renart is an animated series loosely based on the Le Roman de Renart tales (see Literature and Folklore). Featuring much more anthropomorphic animals than the original work, Renart is a cunning fox who goes to make a living in Paris.
In The Simpsons, Homer Simpson tries to invoke this while trying to get Springfield's lemon tree back from Shelbyville's car impound, responding to the man in charge saying "Bust in here and take it?! You must be stupider than you look!" with "Stupider like a fox!" and attempting to climb over the fence. He fails.