Genre Savvy/Fan Works

"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?""
 * There's the wacky but surprisingly good House/Zombie Apocalypse fic The Rampant Disease, in which House and Co. invoke every trope in the book -- only some of which end up being true.
 * Nili's Lord of the Rings fanfic A Taste of Disaster shows how genre savvy Legolas, Aragorn, Elrond and company get after Aragorn and Legolas have been through a few action/adventure fics. Hilarity Ensues.
 * Often present in MS Paint Adventures forums, especially in the Fan Adventures. A sample suggestion, explaining what's going on to a new character, is clearly very genre-savvy.
 * In the Teenage Mutant Ninja Turtles fanfic The Long Walk, Michelangelo is pleading with OC Breech Loader to do something for him.

""But see, in every movie that's science-fiction or fantasy or the like, the kid always makes it. This time he didn't, and thus, this queen has broken the unwritten rule for such movies. Even an Asian martial artist cliché or the American commando cliché cannot defeat someone who is breaking the unwritten rules. But as I said, I didn't want to say this out loud, or I'd look weird.""
 * In the Mass Effect Self-Insert Fic Mass Vexations, Author Avatar Art goes through pretty much the entire fic noting the events of the game as they go on. He ends up lampshading just about everything he notices, including making an offhand comment about one of the game's Playing with Syringes examples.
 * Several characters in Total Drama Battlegrounds, though Heather deserves special mention after seeing Rodney die in one of the virtual reality challenges:

"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!""
 * Luminosity: Bella realizes that her life is a Romance Novel. Relying on her status as the protagonist may be part of why she makes some risky decisions.
 * In Harry Potter and The Methods of Rationality, Harry is a prodigy who spent his childhood a) reading fantasy and sci-fi and b) analyzing everything in sight. He constantly uses his knowledge of literature and archetypes to figure out things that his canon counterpart didn't figure out for years--for instance,.
 * In the My Little Pony Friendship Is Magic Fanfic "A Rising Light", this is one of main character Mike's defining traits, often crossing over with Deadpan Snarker and occasionally bordering on Leaning on the Fourth Wall.


 * Calvin and 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.
 * 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.
 * Switzerland in the Nineteen Eighty Three Doomsday Stories is shown as rather familiar with World War III conventions. And is arguably the first to figure out that Austria's decades-long Hope Spot that Hungary may have survived would not end well.
 * Arcanus in the My Little Pony Friendship Is Magic fanfic Whispers is stated in-universe to have become this by reading a lot. He demonstrates it by lampshading a case of Innocent Innuendo.
 * On the flip-side, he also demonstrates Genre Blindness by claiming love and friendship have little merit... in a series built on them.