C-3PO: He made a fair move. Screaming about it can't help you.
Han Solo: Let him have it. It's not wise to upset a Wookiee.
C-3PO: But sir, nobody worries about upsetting a droid.
Han Solo: That's 'cause droids don't pull people's arms out of their sockets when they lose. Wookiees are known to do that.
C-3PO: I see your point, sir. I suggest a new strategy, R2: let the Wookiee win.
- In one Calvin and Hobbes strip, Calvin deliberately loses the ball to Hobbes.
Calvin: I'm losing the game, but winning an ambulatory adulthood.
- The entire events of the Black Moon Chronicles are set in motion because of Lucifer playing chess (and always winning) against his minion Pazuzu (who knows exactly how much Lucifer's promise not to kill the one who bests him is worth), who keeps losing so as not to incur his master's wrath. So they decide to play the game with mortals instead.
- The page quote (and semi-trope namer) comes from Star Wars A New Hope, when R2-D2 is playing and beating Chewbacca at dejarik.
- Referenced in Star Wars: The Old Republic, on Hutta, where a Wookiee is standing near a dejarik board, with a protocol droid, surprise surprise, missing it's arms and it's head smashed in.
- Double Subverted in Jet Li's War, which has an Asian mob boss practice sword sparring with one of his men. When he allows himself to be distracted, the other guy accidentally strikes him, and immediately begs forgiveness. The gangster calmly tells him not to worry, and that is was his own fault for allowing himself to be distracted... and then kills him anyway.
- Friday: During a game of craps.
Smokey: I won; gimme my money.Deebo: You what?Smokey: I lost.
- Foundation has a king offering his noblemen a bet about his hunting. No one dares to take the risk of winning.
- On The Adventures of Pete & Pete, a school bully with a paper motif, nicknamed "Papercut", was so intimidating to the other kids that they would always pick rock whenever he challenged anybody to a game of Rock, Paper, Scissors.
- Averted in Star Trek: The Next Generation poker game. This trope would have been Worf's edge if he were a real Klingon.
- Yeralash has an episode where two boys are playing chess, and the stronger one constantly makes hidden threats. At the end, the weaker one brings an even stronger guy to sit in his place.
- In Family Matters, Carl lets his boss cheat at Golf. Initially.
- Played with in Malcolm in the Middle. Both Francis and Commandant Spangler are highly skilled at pool, but Francis has been throwing games because Spangler will be upset about losing and take it out on the cadets. When Spangler learns about this, he threatens to cancel everyone's privileges if Francis doesn't give his best. Francis takes a third option by losing on purpose, and the match eventually devolves into a competition to see who can play the worse game of 8-ball, with both players using all kinds of trick shots to sink the cue ball at the same time as the 8. By the end of the exhibition, everyone's lost track of who has 'lost' more games, so it's impossible to declare a winner.
- Played with in Grand Theft Auto: San Andreas: His underlings blatantly let Wu Zu Mu, a powerful but blind Chinese gangster, win whenever they play anything, including moving the cup when he plays Office Golf or lying about their cards in Blackjack, which leads to funny moments when Carl, not caring, beats him regularly. Judging by his personality, "Woozie" a nice enough guy, especially to his men, that he probably wouldn't care if his minions beat him or not, but to his experienced mooks it's better being safe than sorry.
- At one point in Mass Effect 2, two of your engineers will invite you to a game of cards that you can potentially score credits from. The paragon option will have Shepard ask them to go easy on him, which makes them let their guard down. The renegade option will tell them that it's not a good idea to win against their boss, but after it's done they'll convince themselves that Shepard was just kidding.
- In the Pig King's Tower in Mother 3, Lucas must compete against several robotic likenesses of the Pig King in various events, however, in order to progress Lucas must lose the events in order to stroke the Pig King's massive ego.
- Bug has this problem with Grizzlies.
- The Simpsons: During the annual Nuclear Power Plant company picnic, everyone has to let Mr. Burns win the sack race.
- Similarly, in a comic story in Simpsons Illustrated magazine, Homer lets Mr. Burns win at golf.
- On the Looney Tunes short "My Little Duckaroo", Daffy Duck plays a game of poker with feared outlaw Nasty Canasta. Daffy deals Canasta one card, then keeps the rest for himself, giving him a "royal straight flush full house with four aces high." Canasta wins with the three of spades... and a revolver shoved down Daffy's gullet.
- Rocko's Modern Life, "Teed Off": Ed Bighead is playing a game with his boss Mr. Dupette, and is instructed to let Dupette win. The groundskeepers at the golf course strictly enforce this by shooting Ed's ball down with pianos. However, they did not count on Heffer, who rigs the game back on Ed's favor.
- Actually somewhat subverted since Mr. Dupette was actually a rather good sport and was completely oblivious to the fact that the executives are rigging the game in his favor. He didn't really mind losing and even congratulates Ed when he does win.
- The croquet game in Disney's Alice in Wonderland is rigged in the Queen of Hearts' favor, with the cards playing the wickets moving so that the ball goes through every time. When one misses, he is inevitably sent away to the chopping block.
- In Adventure Time, Jake convinces Finn to play an outlandish card game with him because his girlfriend won't play with him anymore. Finn, who's never played before, does much better than expected, causing Jake to become increasingly agitated. Eventually Beemo tells Finn that Jake gets extremely upset whenever he loses a game, so to make things easier on both of them, Finn throws the game.