Fate Stay Night Ultimate Master: Ben takes the fact that the Holy Grail grants any wish with a grain of salt, thinking it's a Jerkass Genie. Talking to Illya, he pumps her for info on Beserker, knowing that, while she's more than she appears, she's still a kid who'll brag when prompted. It helps he's Taught by Experience.
Avenger has shades too due to Ben's influence. For example, if she fights, she knows Ben will jump in to help.
Similarly, Archer is quick to identify Ben as a Wide-Eyed Idealist and try to take advantage of it.
Mikey: "Then you can be my escort tonight before it's too late! You'll do it, right! It's important! I need it! And you love me, so you'll do it! Right!"
Breech: "I never agree to do anything without knowing what it is first. How do I know you're the real Mikey, and not some Dai-Oni possessing his body with the intent of making me promise to do something awful?"
Mike: "Ponies don't start randomly thinking about this kind of thing unless it's about to become some important plot point in a corny story they're in!"
Calvin & Hobbes: The Series has the titular duo, though in different ways: Calvin knows a lot about sci-fi movies, while Hobbes knows the outcome of pretty much any adventure Calvin drags him along on.
Calvin: Since that information is keeping us alive, I barely think we should tell you [who we are]!
One of the hallmarks of being a resident of Angel Grove in Of Love And Bunnies is that, living amongst Power Rangers for so long, they're used to the weirdness and can predict when strange things will happen and what effects they will have.
Pinkie Pie displays a brief moment of this in Ace Combat: The Equestrian War, while observing, along other ponies and griffins, the final duel between Rainbow Dash and Gilda. When Twilight asks her why is she excited, this is her response:
Pinkie Pie: Come on, it’s a fight between the aces! Whenever it happens at the end, it’s always awesome!
Jade in Akatsuki Kitten Phoenix Corporation Overhaul actually knows exactly which author she's being written by, and what the author's sense of humor tends to lean on. This leads to instances where she quotes a movie, and reprimands herself for being surprised at the outcome.
Jade: *waves hand* These are not the droids you are looking for.
In Queenof All Oni, Jade, after her Face-Heel Turn, is FAR more Genre Savvy than many (if not all) of the villains from Jackie Chan Adventures canon, partly due to her witnessing and/or exploiting their Genre Blind moments before the re-emergence of her Superpowered Evil Side, and she even exhibits Dangerously Genre Savvy moments. Some of her Genre Savvy moments include: taking Daolon Wong with when she breaks the Enforcers out of prison, remembering what happened when Shendu left loose ends lying around, cleaning out their lair before Section 13 can react on the info Valmont gave them, and one of her best was when she nearly managed to get the masks the heroes had (SOLO), in a Batman Gambit by remembering how the Dark Hand had used Jackie Dark to gain access to the captured talismans, and if it weren't for an OC Section 13 agent with Blackand White Morality (even to the point of FIRING a gun at her!), SHE WOULD HAVE PULLED IT OFF WITHOUT A HITCH!!
In one Code Geass fic, Lelouch, upon learning he's not the only one with Geass quickly realizes that the Emperor must have it as well. Why? That's the worst possible scenario for him.
A Naruto ficlet has Naruto attempt to use magic to turn Kakashi into a chicken. Why? Because Kakashi refuses to teach them anything even after Naruto warns him that he'll continue pranking Kakashi until he does. Sakura insists it's impossible to turn someone into a chicken. Sasuke on the other hand.
Sasuke: "It's insane, would take a miracle to pull off, and I doubt anyone else would even think to try it. (Beat) I'd say he has better than even odds of doing it."
Navarone from Diaries Of A Madman is quite genre savvy, and is well aware of the cartoon logic the world sometimes operates on. It particularly applies during the Crystal Empire arc, where he recognises Sombra is carrying the Villain Ball, and takes full advantage of the cliched tactics of cartoon villains.
Harry in The Havoc Side of the Force fully expects people to screw him over the first time he does a job for them. Also, when his cover is blown after anonymously saving over a hundred slaves, he decides to leave immediately. Padme tries to reassure him that everyone present has her complete confidence, but Harry just dismisses that, saying that only meant the Hutts would learn his identity in hours instead of minutes. He's right on both counts: Bibble had the ship Harry was getting in payment stripped of almost all it's weapons, shields, and engines. And Aayla Secura (one of the slaves) sending a transmission to the Jedi Temple led to a ship trying to ambush Harry right where he should have come out of hyperspace (he had Anakin pull them out a little early so they would be ready)