Sometimes, the powerful need to be told uncomfortable or unpleasant things. Unfortunately, there's always the possibility that they might not take it seriously or might not want to listen. At best, they may ignore it; at worst... well, sometimes the Bearer of Bad News lands themselves in some very hot water.
Thankfully, there's a powerful tool that can be used to make the point hit home for these authority figures: humor. Whether by sugarcoating something unpleasant to make it more palatable or making it more biting to impress the gravity of the matter, comedy can be an excellent means of persuasion. As the saying goes: "many a true word is spoken in jest".
This is a specialty of the Court Jester. From a meta standpoint, this is a major driving force behind satire, which often uses comedy to criticize the powerful. Compare Bad News in a Good Way and Honest Advisor.
- One Red Bull commercial involves a Court Jester stuck in the public stocks. Apparently, the king drank a Red Bull and suddenly realized that the jokes the Jester was telling were mocking him, and thus he got kicked out of the castle.
- In Irresponsible Captain Tylor, near the end of the series, Tylor is briefly held captive by enemy forces and kept around as a toy by a basically well-meaning princess who is surrounded by political enemies. He's only kept alive under the condition that he basically be drugged out of his skull. Even in this condition, while they constantly and knowingly recommend terrible courses of action, he plays the clown and points out the absurdity of the situation and gives her the best advice of her life. Unfortunately, at this point in time, she doesn't really take him seriously yet.
- Shounen Hollywood: The mascot from the amusement park seems to be one prone to doing this, at least in recent years. He's known for his "acid tongue" and often makes quips and snipes at others that are perfectly acceptable because of his crude character. He even manages to get the boys to finish their photoshoot by mocking them and forcing them to admit the things that were eating at them.
- The Comedian from Watchmen at the beginning of his career wore a clown costume, trying to invoke this trope. However, nobody got the joke, so he became a Straw Nihilist Troll who only said truthful things to hurt others without any hope that anyone would get the joke and do something to change things. At the first reunion of the Crimebusters, the Comedian was so mad that the heroes were so vain to think they could solve all of America's problems that he claimed that it would not matter because a nuclear war would destroy the world anyway. The Crimebusters disbanded immediately, but even when the Comedian thought he was trolling them, in reality, he exposed the real situation to the only hero with the knowledge and resources to avert nuclear armageddon.
Ozymandias: "[He] opened my eyes. Only the very best comedians can do that".
- Belisarius Series: Ousanas is dawazz (combination tutor, minder, and discipline-instiller) for Prince Eon of Axum. His post requires him to be a counterbalance for the prince's enthusiasm, as very few outrank the teenager. However, the humor is all his own: while he's a very intelligent polyglot with a taste for Platonic philosophy, he ranges from You No Take Candle speech up through very energetic dope slaps to make his point, and he's usually very right.
- Poet from A Canticle for Leibowitz fills the role of the Shakespearean fool, as he points out hypocrisies in the form of jokes that go over the heads of the priests.
- Christopher Moore's Fool stars King Lear's jester, and his ability to make the powers that be listen to him is one of the biggest themes in the book.
- The Knights of the Cross: Ciaruszek, Jagiełło's jester, is very good at making people laugh and turning their attention to things that need to be attended.
- New Jedi Order: Onimi is the slave jester to Supreme Overlord Shimrra of the Yuuzhan Vong. His position as Shimrra's 'pet' allows him to mock and criticize the Elite mercilessly in a way no one else can, and he seems to take great pleasure in being as offensive as possible. He's also the true power behind the Yuuzhan Vong throne, using Mind Control to speak his wishes through the practically brainless Shimrra's mouth.
- The Reynard Cycle: Duke Nobel's fool, Pierrot. He's an odd man, and speaks entirely in the form of Aesops.
- The Sea Wolf: Larsen mockingly compares Van Weyden to a jester, and though the Ghost plainly isn't a royal court, it fits. Despite being a clear subordinate, Van Weyden is one of the only people who can speak to Larsen as an equal, within reason, in large part because his intellect and naivety make him both interesting and amusing for Larsen. Though this doesn't spare him from Larsen's violent temper.
- The Stormlight Archive: The Alethi king has a position known as "the King's Wit" who insults people in the king's stead so that the king doesn't have to sully himself. He zig-zags this trope: while his primary role is to humiliate and humble the various "lighteyed" lords and ladies by mocking them, he mixes genuine criticisms in with his more straightforward insults. It's technically legal for a slighted lord to kill the Wit... if he is willing to revoke all his lands and titles.
- Watership Down: While Bluebell annoys many of the rabbits with his jokes, Holly notes that if it wasn't for his joking, both of them would have given up and died long before reaching Watership Down.
- Chernobyl: Andrei Glukhov is known for his angry, yet measured, use of this technique. Naked truth delivered to power with a carefully crafted sting they'd look the fool for punishing him for? A masterpiece.
- Game of Thrones: Olenna Tyrell's acidic quips and one-liners tend to point out the hypocrisy and fallacious thinking to whoever she's speaking to. She gets away with saying things that others would be beheaded for.
- Horrible Histories: In one sketch, some courtiers for Henry VIII recruit his jester to tell him about his wife's alleged infidelities in this manner. This is because the jester's the only one who can consistently give the king bad news and not be punished for it.
- Merlin (2008): Merlin himself plays this role to Prince Arthur, quick to call him an idiot (or a prat, or a clotpole) when he thinks he's being one, and getting away with it because of Arthur's barely-hidden affection for him. Arthur often gives as good as he gets, and at one point jokes that if he ever becomes king, he'll make Merlin into his court jester.
- Russell Howard's Good News: Russell uses comedy to spread awareness of problems and injustices.
- The aptly named German sketch comedy series Sketch History has an inverted form in one episode: The court jester is openly insulting the French king, but the king mistakes the insults for humor.
- Arthurian Legend: King Arthur's jester was Sir Dagonet, a man knighted as a joke. Many stories have him wittily pointing out the other characters' mistakes and shortcomings.
- "The Fool's Prayer" by Edward Rowland Sill tells about a fool (jester) whose king asked him to pray in front of the assembly, thinking it would be funny. The jester obliges, but much of his prayer concerns the great harm done unintentionally by foolish behavior. It makes the king regret his command.
- Godspell: Jesus is interpreted as using this technique, teaching his message through humor and clowning. The others get in on the act, and he paints their faces to mark them as his followers.
- King Lear: The Fool, of course. His jokes and clowning often have a pretty scratching criticism of Lear and his conduct attached to them.
- Twelfth Night features Feste, one of the Bard's best fools, who crosses the Countess Olivia in a bad mood and is told to either make her laugh or beat it. Feste pokes fun at the Countess's Excessive Mourning of her brother by saying her brother must be in Hell if she's so sad about his death. At first shocked, Olivia ends up laughing.
- Kokichi Oma from Danganronpa V3: Killing Harmony fulfills this role. He might be an unpleasant little guy and wears a straitjacket, of all things, but his trolling tendencies and his antagonistic attitude make the other characters start to think, and his provocations end up making the others realize things they needed to know about their fellow students.
- A large part of why Mike of Shortpacked! gets away with his antics is because he gives constructive, helpful advice... often in ways that mock or humiliate the people he's trying to advise.
- videogamedunkey: While the content of his videos is often silly and nonsensical, there are often times when the goofy jokes serve to illustrate a salient point about the subject.
- "Anthem Legends: Exodus" serves to highlight the number of similar open-world games being made, often with identical systems, gameplay, and story.
- "Youtube Gave All of My Subscribers to Will Smith" is a satire of YouTube's unhelpful and unintuitive policies, which often punish and inconvenience content creators for no reason and with little chance of appeal.
YouTube Comment: You can tell this is fake because he said Youtube notified him.
- The Japanese equivalent of a jester, the Taikomochi, pulled double duty as a military advisor and was expected to fight alongside his lord in battle, making them literal Lethal Joke Characters. The overlap in roles makes more sense when you realize that both require similar skillsets: quick thinking, an understanding of the situation, and the ability (and close relationship with their lord) necessary to speak truth to power.
- Henry VIII had a court jester named Will Sommers, who was the only member of Henry's court who could speak frankly to his king without fear of reprisal. Not even Henry's own wives were allowed to do that. Sommers took advantage of his unique privilege to jokingly draw attention to problems both large and small.
- Benjamin Franklin was known for this. For example, when the British Parliament was discussing the possibility of sending convicts to the Thirteen Colonies in 1751, Franklin published an open letter under the pen name "Americanus" where he suggested sending rattlesnakes to the British Isles in exchange, saying the British would get the better end of the deal because, unlike convicts, rattlesnakes only hurt people in self-defense and always give warnings before striking.
- Since the mid-1970s, high-profile prankster Joey Skaggs has been impressing upon the media the need for proper fact-checking by tricking them with absurd hoax news stories.
- The Clandestine Insurgent Rebel Clown Army (CIRCA) is an international anti-authoritarian activist group that combines clowning with nonviolent protest.