Flaky in Happy Tree Friends is scared a lot of the time, and damn well should be. She always knows that danger will find her in the sadistic world of this show.
Most of the protagonists in the Whateley Universe grew up reading Marvel Comics and DC Comics, and watching lots of anime, so they're pretty well suited to be growing up as mutants in a superhero universe. Deadpan Snarker Phase is probably the most genre savvy of the group. although they all get into the act sooner or later, even the Cloud Cuckoo Lander Jade.
Deconstructed in Sonny Gets Mad Scienced. For all his knowledge about his situation, Sonny's Genre Savvy doesn't actually help him escape. He just happens to be the lucky person on whom the Mad Scientist's experiment worked. Reconstructed when he knows exactly what to do with the henchmen and the scientist when he gets free.
In Survival of the Fittest, v4 character Bounce had been a massive fan of the series prior to her own involvement in it and as such references things like The Power of Friendship never working in SOTF and the fact that, as an unfit, unpopular nerd, there's no point in her making plans because people like her never stand a chance.
In We Are Our Avatars, Awe Striker and Ozbourne, due to being humans from worlds very much like ours, often have familiarity with the fictional universes that many of the other characters come from. This is fairly common amongst most Author Avatars, but a lot of other characters happen to be as well.
This is the source of most of the jokes in the X-Men Flash cartoon "Dark Phoenix Rising". Cyclops references Jean's habit of constantly returning from the dead, the need to put Wolverine on every X-Men team possible and the fact that another group of villains will likely attack while they're being distracted with Dark Phoenix. In "Death Becomes Them", Kitty Pryde asks if the team is counting alternate timelines when they discuss which of them have died and come back to life.
In "84 Egg Sandwich", the employee manning the drive-thru station figures out that the people (Harvey and the gang) are ordering something for an Epic Meal Time project because of how much they're buying.
62. It is better to beg forgiveness than to ask permission, no longer applies to Specialist Schwarz.
87. If the thought of something makes me giggle for longer than 15 seconds, I am to assume that I am not allowed to do it.
Ani Mae, a superhero from the Global Guardians PBEM Universe, whose powers stem from the fact that she's the real life incarnation of an anime Magic Girl, has Genre Savviness as one of her superpowers. Knowing that she is essentially a living cartoon superhero, she's very good at predicting what the villains will do next, because she knows what cartoon and comic book supervillains do.
The hosts of Eat Your Kimchi, Simon and Martina Stawski are savvy with both North American and Korean popular culture
Darcy in The Lizzie Bennet Diaries. He's savvy enough to ask if he's being recorded when his sister calls him. He knows she's doing a series of demo recordings of their new story-telling application. He promptly ends the conversation when the answer is yes.
The Autobiography of Jane Eyre: Jane is genre-savvy from the start. She seems to know that she is in a dangerous situation and tries to deal with it as best as she can. However, she's lonely and doesn't have a good family or any close friends, so she must go with living at Mr Rochester's house. She uploads her video because she wants advice and feedback from her viewers (in-universe, her viewership is much smaller than in reality). She mostly expects people to be abusive to her, and some of her videos are meant as a piece of evidence if anything serious should happen.
Gaea has shown signs of this a couple times in Noob.
When she has a rare fight against someone towards whom she has a personal grudge, two of her guildmates offer to help and she refuses. However, when one of them says "Well, we might as well leave" Gaea has them stay in case she ends up needing help after all.
She later says that she would never let a rematch happen after winning a duel.