"The Trickster represents the quality of randomness and chance in the universe, without which there could be no freedom. (...) The cosmos is interesting rather than perfect, and everything is not part of some greater plan, nor is all necessarily under control. "
― Starhawk, in The Spiral Dance: A Rebirth of the Ancient Religion of the Goddess (1979), p. 231
"The trickster, the riddler, the keeper of balance, he of the many faces who finds life in death and who fears no evil; he who walks through doors."
― Christopher Paolini, in Brisingr (2008)
Archetype of character who plays tricks or otherwise disobeys normal rules and conventional behavior.
Supreme Con Man
The Cunning One
The One Who Lurks in The Shadows
User is a Trickster: a god, goddess, spirit, man, woman, or anthropomorphic animal who plays tricks or otherwise disobeys normal rules and conventional behavior. The Trickster openly questions and mocks authority, encourages impulse and enthusiasm, seeks out new ideas and experiences, destroys convention and complacency, and promotes chaos and unrest. At the same time, the trickster brings new knowledge and wisdom. Even when punished horribly for their effrontery, their indomitable spirit (or sheer foolishness) keeps them coming back for more.
Tricksters can be anything from gods of chaos, bedeviling heroes for a few laughs, to master manipulators who use cruel ploys and sadistic choices. They can also be heroes (or more likely anti-heroes) who make up for a lack of strength or bravery with manipulation, planning, or outright cheating. The trickster is often a master of disguise and may have magical powers.
In mythology and religion, the trickster deities break the rules of the gods or nature, sometimes maliciously but usually (albeit unintentionally) with ultimately positive effects. Often, the bending/breaking of rules takes the form of tricks or thievery. Tricksters can be cunning or foolish or both; they are often funny even when considered sacred or performing important cultural tasks.
The Trickster & His Brigade (Doctor Who/The Sarah Jane Adventures)
The Doctor (Doctor Who)
The Master (Doctor Who)
Gabriel (Supernatural); also called Loki
Kitsune (Teen Wolf)
Bugs Bunny (Looney Tunes)
Discord (My Little Pony: Friendship is Magic)
Lotso (Toy Story)
Woody Woodpecker (Woody Woodpecker)
Luan Loud (The Loud House)
John Constantine (DC Comics)
Mister Mxyzptlk (DC Comics)
Bat-Mite (DC Comics)
Joker (DC Comics)
Mammon (Image Comics)
Flip (Little Nemo)
Gwenpool (Marvel Comics)
Impossible Man (Marvel Comics)
Loki (Marvel Comics)
Mystique (Marvel Comics)
Spider-Man (Marvel Comics)
Chelsea (Akame Ga Kill!)
Gin Ichimaru (Bleach)
Sosuke Aizen (Bleach)
Joseph Joestar (JoJo's Bizarre Adventure)
Flip (Little Nemo: Adventures in Slumberland)
Naruto Uzumaki (Naruto)
Caesar Clown (One Piece)
Capone Bege(One Piece)
Charlotte Pudding (One Piece)
Donquixote Doflamingo (One Piece)
Jabra (One Piece)
Krieg (One Piece)
Monkey D. Luffy (One Piece)
Usopp (One Piece)
Teufel Diabolos (Senyu)
Xelloss (The Slayers)
Misogi Kumagawa (Medaka Box)
Hazama/Yuuki Terumi (BlazBlue)
Queen of Maggots (The Cat Lady/Downfall Remake)
The Contessa (Sly Cooper)
Dr. M (Sly Cooper)
Cyrille Le Paradox (Sly Cooper)
Yukari Yakumo (Touhou Project)
Tewi Inaba (Touhou Project)
Trickster (Valkyrie Crusade)
Loki (Valkyrie Crusade)
Puck (Valkyrie Crusade)
Carrotjuice (Channel Awesome)
Erevan Ilesere (Forgotten Realms)
Jane Crocker (Homestuck); via spiral sucker
Jake English, Roxy Lalonde, Dirk Strider (Homestuck); via significant contact with other people in Trickster Mode
Loki (Marvel) is the Norse God of Mischief.
Naruto Uzumaki (Naruto) is able to use his skills in unique and confusing ways.
Obito Uchiha (Naruto) was so skilled in his acting, he was able to deceive almost everyone in the entire world that he is Madara Uchiha, down to his voice.
Lorenzo (American Dad!) made a deal with Roger Smith to teach him guitar lessons that will ensure his victory against Jamal at the cost of his soul...
...but Roger cunningly conned Jamal into covering the "price for [his guitar] lessons", saving Roger from Lorenzo's grasp at the cost of Jamal's soul.
Bugs Bunny (Looney Tunes) is perhaps one of the sneakiest characters in cartoon history.
While not the smartest guy around, Luffy (One Piece) can be sneaky and has some clever attacks.
Usopp (One Piece) is a highly skilled and experienced liar. His fighting style revolves mostly around outsmarting the opponent through clever tactics and trickery.
Jabra (One Piece) has been known to trick people through convincing lies so he could attack them when their guard is down.
Krieg (One Piece) lives up to his moniker "Foul Play" as his tactics revolve around using dishonest and underhanded methods to defeat his enemies.
Doflamingo (One Piece) used his Devil Fruit to overthrow King Riku and disgracing the Riku bloodline, making him look like a hero in front of Dressrosa.
Capone Bege (One Piece) is a master of bluffing...
easily tricking Caesar Clown, an expert liar himself, to surrender.
Charlotte Pudding (One Piece) is a master of deception, she feigned kindness and innocence to completely concealed her true wicked nature, her victims who fell for her trickery includes not only the Straw Hats but the entire citizens of Tottoland.
Mystique (Marvel) uses her shape-shifting powers to deceive people often.
Spider-Man (Marvel) often uses tricks to take out his rogues.
Joker's (DC Comics) cunning is matched only by his sadism.
Loki (Norse Mythology) is the god of mischief.
The Contessa (Sly Cooper) was able to fool Interpol into sending her criminals who she then steals from.
Dr. M is a skilled manipulator, tricking Sly into leading him through the Cooper Vault via a tracer placed on his cane and planting doubt in Bentley's mind about his friendship with Sly.
Cyrille Le Paradox (Sly Cooper:Thieves in Time) was shown to be an adept manipulator, having been able to persuade El Jefe, Toothpick, Grizz, Penelope, and Ms. Decibel to join him, only to betray them all in the end.
Azula's (Avatar: The Last Airbender) intelligence made her very skillful in manipulating people.
Alejandro (Total Drama World Tour) is the most untrustworthy and manipulative player in Total Drama history.
Hazama/Yuuki Terumi (Blazblue) is known as the 'God of Trolling' because of his use of obnoxious and sarcastic remarks to either hurt people's feelings or manipulate their emotional responses in his favor.
Joseph Joestar (JoJo's Bizarre Adventure) from a young age, is considered a master trickster, able to outsmart a variety of opponents with dirty and unpredictable tactics, including beings that have lived tens of thousands of years.
Trickster (Valkyrie Crusade) is a chaotic trickster goddess.
Loki (Valkyrie Crusade)
Carrotjuice (Channel Awesome) is a rabbit-like creature and a parody of Beetlejuice, taking the Nostalgia Critic's personal hard-drive and messing with him constantly.
Hisoka (HunterXHunter) is a deadly hunter with equal strengths in both physical and mental categories but his most deadly aspect is his unpredictable nature. He does things according to whether they will amuse him or not.
Xelloss (The Slayers) "Sore wa Himitsu desu~!" ("That is a secret~!")
The Trickster (Sarah Jane Adventures)
Puck (Valkyrie Crusade) is a trickster fairy.
Sosuke Aizen (Bleach) is an extraordinary master of trickery and deception, he had deceived Soul Society for a century and manipulated the entire Gotei 13 for his own goals.