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A classical example would be Perceval, in the Grail poems of the middle ages, especially in Chretien de Troyes' Perceval ou le Conte du Graal.
Twoflower of the novels Discworld The Colour of Magic, The Light Fantastic and Interesting Times.
And Rincewind from the same series. Except he pays more attention to the disasters than the luck in surviving them, and so thinks he is cursed by The Lady... which is why she loves him so much.
Colon and Nobby from the City Watch books have important clues and crimes fall into their laps by pure luck so often that it's the unofficial reason they're still on the force when it has otherwise moved on into a respectable organization.
Dondi Snayheever (really!) from Tim Powers' Last Call.
A subversion in the saga, in which the Fool knows Realm of the Elderlings precisely what he is doing.
The eponymous character in Voltaire's . Unfortunately for him, the trope is invoked only to be totally deconstructed, since he doesn't live in the Candide best of all possible worlds.
Tim Powers wrote a pair of novels — Expiration Date and Earthquake Weather — which explicitly riff on this trope, and on the idea of characters being archetypically related to the Tarot generally.
In L. Jagi Lamplighter's trilogy, Mephisto after his insanity.
Prospero's Daughter Simkin of .
The Darksword Trilogy Malachi Constant from Kurt Vonnegut's .
The Sirens of Titan Hercule Poirot's friend Hastings has some elements of this. As a detective trying to solve the mystery with Poirot, he's an abject failure. However, he's very good at pointing out the "obvious" things that sometimes slip by Poirot's notice.
Hasting's best performance in this role comes in : The ABC Murders The other detectives are distressed at the "bad luck" that sent one of the anonymous letters astray, causing it to reach them too late to prevent the murder. Hastings points out that the letter could easily have been deliberately misaddressed in order to give the killer enough time.
Plenty of P. G. Wodehouse characters. Bertie Wooster hung a lampshade on it in Carry On, Jeeves: "Providence looks after all the chumps in this world, and personally, I'm all for it." (Though Bertie isn't as perfect an example as some of Wodehouse's protagonists.)
inverts this, Ilya's only pretending to be a fool, and is in fact cursed with Firebird (Lackey) bad luck.
A Song of Ice and Fire has several fable within a book examples, including Florian the Fool and Spotted Pate. In particular, Pate the pigboy has a hundred or so Negative Continuity tales where he blunders his way into defeating villains and winning fair maidens. But in the books themselves about a dozen minor characters named Pate are killed unceremoniously
Brandon in .
The Leonard Regime Blake Thorburn in embodies this trope, even having Pact the Fool card drawn for him from the Major Arcana. Rather than be cautious and pragmatic, he acts impulsively and on instinct, which in a setting where most magicians that last are patient and cautious is usually unexpected for his enemies. This strategy gives him momentum, but Ultimately gets him defeated by a demon, who . Afterwards, he becomes more cautious, but retains his instincts-now he knows when to wait and when to strike.
severs his connections to the world and turns him into an Other