Cheshire Cat, Alice's Adventures in Wonderland
Quite possibly the first trickster I encountered, the Cheshire Cat is one of my favorite characters, especially Disney's manic version portrayed by Sterling Holloway. The right balance of wise and demented, the Cat acts as both guide and roadblock on Alice's journey. He's the epitome of the trickster in that way.
Bartimaeus, the Bartimaeus Trilogy
The initial narrator of Jonathan Stroud's fantasy trilogy, Bartimaeus is the sarcastic and slightly unreliable djinni at the heart of the books. Beneath all the snark, he has a heart much bigger than he wants you to think. His friendships with his masters make him one of the most complex characters in YA fiction.
Robin Goodfellow/Puck, A Midsummer Night's Dream
I love him so much I put him in the Albion Quartet. 'Nuff said.
The Marquis de Carabas, Neverwhere
This guy took his name from the story "Puss in Boots" and though he takes some inspiration from the titular trickster of that tale, he is far more of a wild card. He is one of the few characters I have read who is truly unpredictable. You aren't ever certain if he's really on Door's side or not. It's wonderful.
Rumplestiltskin, Once Upon a Time
I've talked about Rumple in a previous Top 10, but I want to focus on his role as a trickster here. He is very careful of his words and always makes his deals with the proper loopholes. Despite his reputation as the Dark One, he's still seen as a repository of wisdom and knowledge. What's more, his plans are always much bigger than anyone around his can guess. (This is especially true in the first two seasons.)
El-ahrairah, Watership Down
El-ahrairah is the rabbit trickster figure, the Anansi of their folklore and myth. He's the Prince with a Thousand Enemies, blessed by the Creator with the skills to evade his enemies. He often gets the better of those he encounters and is hailed as a hero by all (right-thinking) rabbits. "All the world will be your enemy, Prince with a Thousand Enemies, and when they catch you, they will kill you. But first, they have to catch you."
Bugs Bunny, Looney Tunes
One of many tricksters populating the Looney Tunes and Merry Melodies series of cartoon shorts, Bugs is the classic example. Inspired by folkloric heroes like Hare and Brer Rabbit, he wreaks havoc wherever he goes and we love him for it. Rare is the cartoon where we don't root for Bugs, and then it's usually because whoever has crossed his path (or set their sights on him) is just so pathetic that we feel terrible for them.
Peter Pan, Peter Pan
Peter is a trickster in the sense of his being an unknown factor. He seems friendly and whimsical, but he has the capacity to be fierce and frightening as well. The boy cut off a man's hand as a joke, for crying out loud. If that isn't a move out of the trickster playbook, I don't know what is.
Jack Sparrow, The Pirates of the Caribbean Franchise
The Doctor, Doctor Who
The Doctor is an odd choice for this list, but hear me out. He possesses hidden knowledge, is very clever, and may or may not be telling you the truth. He's a mythic figure who appears and disappears in the history of the world, he changes his face from time to time, and he usually gets out of predicaments with wit and a bit of luck.