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- In BlackLagoon, during the Nazi arc, after the Villainous Breakdown of the Nazi leader, Revy hands him a gun then tells Dutch that she's betting "black." Dutch replies that it's no bet and says that he's going "black" as well. The Nazi at first appears that he's going to shoot himself before attempting to shoot Dutch, only to find that the gun was empty. It's then revealed that the bet was on who the Nazi would try to shoot (himself, the black man, or the half-Chinese woman).
- At the end of Strange Powers after England and America hook up after a good deal of UST, Romano pulls out a binder and talks about some money he has to collect.
- Actually, this often happens in just about any pairing fics out there. One of the most notable example would be some FT fics. Cana & Mirajane are often the bookies.
- There are multitudinous examples from Harry Potter fan fiction, written by folks who prefer Harry shipping with Hermione, in which Ginny and Ron, the characters Harry and Hermione (respectively) end up with in canon, exchange money and say things like "We were wondering why it took you so long" when Harry and Hermione finally get together.
- Who says that's limited to the above scenario?
- Common fanon for Phineas and Ferb is that Ferb, Baljeet and Buford have a bet going about how long it will take for Phineas to figure out that Isabella has a crush on him. However, one of the most unique examples from this fandom occurs in "Summer of Love" by lowrider; Django and Adyson both have obvious crushes on each other and when she confirms her desire to be his girlfriend at a 4th of July cookout, it turns out the other boys, including Phineas, had bet on when the 2 would pair. Goes into Crowning Moment of Heartwarming when Ferb (the winner) hands over his winnings to Django and tells him to use it to treat Adyson like a queen.
- According to the Danny Phantom fanfiction, Harmless, the ghosts had a bet on what it would take for Danny and Sam to admit their feelings for each other. The Box Ghost won when they finally became an Official Couple in Phantom Planet. Tucker was disappointed he didn't get the chance to join the bet.
- In The Legend of Korra fic Repairs, Retrofits and Upgrades, many main and side characters had a betting pool on Korra and Asami getting together. Lin raked it in.
- Sinbad: Legend of the Seven Seas included among Sinbad's crew two men who passed money back and forth throughout the movie. The bets were on whether or not the earth is flat and whether or not Sinbad would survive his latest escapade.
- In Die Hard, when Hans is interrogating Takagi, who refuses to give up information, Theo says "I told you" and Karl replies "It's not over yet." After Hans kills Takagi, Karl hands Theo a bill.
- At the end of Down Periscope, there's not just a yell from the chronic gambler to "Pay Up" on the misfit's boat, but after an admiral who hated the protagonist took over the opposing boat a surreptitious exchange of a wad of cash between the CO and XO of the appropriated submarine.
- The first Lipstick Lesbian close encounter in DEBS is followed by the villain's sidekick telling the heroine's friend "You owe me fifty bucks."
- The Avengers: Nick Fury offers to bet Steve Rogers $10 that there's still surprises left in the world for Steve. We don't see Steve accept, but after the Helicarrier takes off Steve walks onto the bridge and silently hands Fury a ten-dollar bill.
- Fred and George Weasley in film version of Harry Potter and the Order of the Phoenix bet on a Hermione vs. Ron duel.
- In The Road to El Dorado, early on, Tulio and Miguel are being chased by soldiers, and need to jump off a ledge, and Miguel spots two barrels.
Miguel: We can make it!Tulio: (Looks down, looks at soldiers) Two pesetas says we can't!Miguel: You're on! (They both jump, and land safely for the moment) You lose. (Two coins flip from one barrel to the other.)
- Ocean's Eleven, while watching Yen practice: "Ten says he shorts it." "Twenty!" Later, when the real deal comes up, the side bet gets a callback: "Ten says he shorts it." "No bet."
- At the end of the first Back to the Future sequel, the man who hands Marty the letter that Doc wrote in 1885 mentions that the post office had a bet as to whether Marty would actually show up on the date specified in the letter. He lost.
- Invictus: Mandela and New Zealand PM Bolger have a bet on the final match. Bolger first offers all his country's goats against all the diamonds of South Africa. Mandela chuckles and instead suggests the wager be a nice case of wine.
- In The Hobbit: An Unexpected Journey, when Bilbo catches up to the dwarves Gandalf tells him that they'd been making bets whether he'd show. Bilbo asks what Gandalf thought he'd do - just before the dwarves toss Gandalf his winnings.
- The Cabin in the Woods. The Punch Clock Villains bet on how the designated victims will die, suggested to be a deliberate way of disassociating themselves from their Necessary Evil actions.
- In PMO, Cabinet minister Peter Tucker apparently had a bet with a friend of his that the government would lose their first budget vote, and while Prime Minister Marc Brancois scrambles to get the support they will need to survive the pending vote of no confidence, Peter calls his friend and says he owes him $10.
- Occurs in the Harry Potter series, specifically in Goblet of Fire, when the Weasley twins make a winning long-shot bet on the outcome of the Quidditch World Cup. And spend the entire rest of the book trying to collect their windfall, because they were paid in leprechaun gold, which vanishes in a few hours.
- In the film version, although the bet with Bagman is not included, Fred and George are shown loudly, publicly, and unashamedly taking bets from other students on the outcome of each Triwizard task.
- In The Truth, Vimes assumes that someone in the Watch will be running a book on whether William De Worde will survive. "Find out who's responsible, and once you've found out it's Nobby, take it away from him."
- Nobby also runs a book on Moist von Lipwig's chances in Making Money. Such is the Lipwig mystique, however, that even though he thinks he's doomed, no-one will bet on that.
- In Going Postal, the Post Office staff put all their savings into a bet on Moist von Lipwig outracing the semaphore. Moist, who at this point has no kind of plan beyond being an impressive loser, is horrified by this, and even more horrified when he hears the lousy odds they got; even professional bookmakers think he has something up his sleeve. (Shortly after the PO placed their bet, the bookies stopped taking bets on whether he'd succeed, and only accepted bets on how.)
- Done in the Honorverse novel At All Costs between Queen Elizabeth and Hamish Alexander as to whether Honor would realise that she was about to become Unconquered's new CO.
- The Wraiths make a lot of such bets. After Wedge learns that Wes set one up speculation about what he would do when he realized the flaw in a plan which involved working closely with Chewbacca when he himself didn't speak Wookiee, he decides to take his most serious revenge on Wes.
- Later books in the Stephanie Plum series make reference to Rangeman employees having a pool going on how long any car Stephanie gets from Ranger will survive.
- In Spock's World, Spock and McCoy have one on the outcome of the secession vote. Spock won.
- Hendricks in The Dresden Files has one with Miss Gard at one point. It's on if Murphy will figure out a spy. She did. Hendricks won.
- Which itself was a Callback to a bet between Hendricks and Marcone on whether Harry would get involved in a case. Marcone won.
- Carrera's Legions: When setting up a base in Yezidistan for the Sumer campaign in A Desert Called Peace, a bet is made between an officer there and Sergeant Major McNamara that Carrera would reject the double-wide mobile home set up as his quarters in favor of a regular tent. Carrera pretended to not notice the 50 drachma note being handed to McNamara to pay the wager.
- A recurring theme with smuggler or ex-smuggler characters in the Star Wars Expanded Universe. At one point in Rebel Dream, as he's taking off on a very dangerous covert infiltration, Lando Calrissian bets the traffic controller a thousand credits on his survival; after the controller agrees ("I could use ten credits.") Lando points out that the man won't be able to collect if he wins.
- In another incident, Booster Terrik is outraged when his daughter and his rival's son elope together — not because of their rivalry (which he had made peace with over the course of The Bacta War), but because fellow smuggler Talon Karrde, a man of keen interpersonal insight if ever there was one, had bet him a million credits that they would do precisely that. (And had managed to haggle Booster into giving him favorable odds, implying that Karrde knew exactly how they would do it.)
Live Action TV
- On an episode of CSI, Greg Sanders's replacement eventually cracks from the pressure to be just like Greg and quits. Nick forks over a bill to Warrick, who really shouldn't have been participating since he had a gambling addiction in the first season.
- There's also been a whole episode with a Running Gag about Nick and Warrick having a bet about what happened to the Vic of the Week, so it seems that Warrick can engage in "fun" bets with a buddy without a problem.
- Another CSI sees Catherine and Grissom making a bet over whether two murder victims' deaths were related or not. At the end it turns out they were both right, and Cathrine rips a bill apart and hands half of it to Gil after the very heavy conversation, this is a tension breaker when Grissom reminds her that doing that is a federal offense.
- In CSI: NY, Sid, Sheldon and Adam had a side-bet about whether Lindsay was pregnant. She was and Sid won.
- On Scrubs, when an exasperated Dr. Elliot tells Dr. Kelso that she came out of the (fake) closet to her mother, he deadpans, "Well, it seems the boys in Radiology owe me quite a lot of money."
- Another episode had Turk and Cox making a bet as to whether a patient would live or die in surgery. The patient lives, and Turk wins the bet. However, this gives Dr. Cox to give a nice What the Hell, Hero? speech to Turk about how callous he's become to make bets on people's lives. Turk feels appropriately ashamed afterward. Why he feels bad or cynical for betting the guy would live is not clear (as opposed to Dr. Cox who stood to gain money from a patient's death).
- When Ellen comes out of the closet, her friends ask her if she's sure about it, and, when she says yes, Joe pays Audrey, who then pays Ellen's cousin.
- In Tales of the Gold Monkey, Jake gets in a fight with a visitor and the following exchange ensues.
Sarah: (to Louie) Do something!Louie: (to Gushie) Forty francs on Jake.
- It is a common occurrence during the show's many other bar brawls, too.
- House sets up bets with his underlings, friend and boss all the time, and some of them have picked up the habit from him. Generally, the audience doesn't know a bet was in progress until money changes hands.
- In a season 4 episode, House's ducklings were making bets with Chase on which of them would be fired. At the end of the episode, even though they all screwed up one way or another, House doesn't fire any of them, meaning that Chase won all the money. Foreman then confronts House, saying that he can't believe he would do something that 'nice' without financial gain. Sure enough, it is revealed that House and Chase cut a 50/50 deal.
- Father Mulcahy from M*A*S*H does this virtually every time the subject comes up.
- Happens several times on Friends. Once, Joey was deliberating on whether to sleep with a casting director for a part. He comes in and tells the others that he refused, only to be offered a bigger part. Ross and Chandler pay Rachel and Phoebe. Then Joey implies that he did sleep with her for the better part. Rachel and Phoebe hand the money back.
- NCIS once featured Ziva, Gibbs and McGee having a bet over what interrogation method Tony would use.
- Another one had Abby, wearing a cute hat she'd cut from a clean room uniform, present a similar hat to Kate, and ask her to try it on. She does—and McGee gives Abby twenty bucks. He leaves, despondent...and Abby gives Kate her ten-buck cut.
- In an episode just before the one where McGee and Abby made a bet, there was a bet between Tony and McGee where Tony had to get Kate to admit she was Tony's wife.
- One episode of Frasier saw Lilith's husband leave her...
Frasier: ...and get this - for a man.Niles: Damn - I owe Dad $5!
- On Cheers, Sam and Diane were supposed to be getting married, but they started arguing. While they carry on their dialogue in the foreground, everyone in the bar behind them is passing money back and forth, apparently having bet on whether or not they would go through with the wedding.
- Several instances on MythBusters, either from Adam and Jamie or the Build Team, on the outcome of an experiment. In one Build Team wager, a cameraman was drafted to hold the money until the bet was resolved (Tory won).
- On a first-season episode of Extreme Makeover: Home Edition, there was a bet between the four designers over which pair (the men or the women) could make a nicer room, with the losing team cooking dinner for the winners. The competition heated up to ridiculous extremes, to the point where they were even trying to sabotage each other. Ty called off the bet, bought everyone pizza, and (off camera) told them to never do that again.
- An entire episode of The Office revolves around this, as bets are placed on the characters' quirks. Such as: Whether or not Creed will notice if his apple is replaced with a moldy potato, or the over-under on how many Romantic Comedies Kelly will mention while explaining Netflix.
- In The Big Bang Theory, Sheldon once ends up offering "his spot" on the couch to Howard in an attempt to apologize to him. While Howard is describing the advantages of the spot, Sheldon cracks and tells he wants his spot back.
Penny: "How long?"Leonard: "Ninety-four seconds." [reaches for money]
- When Alan's marriage to Dumb Blonde Kandy fails in Two and a Half Men, everyone seems saddened... because they picked the wrong month in their betting pool for when they'd break up. Everyone, that is, except for Judith, his previous ex-wife, who won the pool.
- During the second season of Food Network's Worst Cooks in America, chefs Anne Burrell and Robert Irvine had a side bet about whose team would win. If Anne won, Robert had to bleach his hair blonde. If Robert won, Anne Burrell had to lose her trademark hair and get a make-under. Burrell won, and the photo evidence is here.
- Married... with Children: Marcy once showed up at Al's with a boyfriend (the episode was from after Steve left and before Jefferson's debut) and had him ask Al what his job was. Once Al confirmed being a shoe salesman, the boyfriend gave Marcy some money. When Al told how long he kept the job, Marcy's boyfriend gave her more money.
- One episode of How I Met Your Mother has Ted finding out that Lily and Marshall have been making bets on the decisions their friends make including a long-running bet on whether Ted and will eventually give up on the idea of being with Robin and if they will end up together. Lily thinks they won't while Marshall thinks they will. At that point it seemed unlikely that they would, and Ted claimed yet again that he was over Robin, but when Lily told Marshall to pay up he said "not yet". The audience already knows that they won't except the series finale ends sixteen years in the future with widower Ted going to ask out divorcee Robin so the bet seems still unresolved.
- The team on Animal Planet's series Tanked once started an office pool for how long it would take Wayde to notice that his wife Heather had gotten braces. Answer: two days.
- On an 1995 episode of The Tonight Show With Jay Leno, Motorhead was the musical guest. Bandleader Branford Marsalis said that he bet Motorhead leader/singer/bassist Lemmy Kilminster $5 he could get them on the show. After Motorhead performed, Lemmy took $5 out of his pocket and gave it to Branford before heading to the couch to talk to Jay.
- In The Red Green Show episode "The Big Thing", the Lodge members have bet on how many tires are on the truck carrying the big thing. It turns up becoming a Brick Joke at the end: When Harold says there were 59 wheels, Red says he won because his guess of a thousand was the closest.
- In Ghost Adventures Zak at one point mentions that he has a side bet about how long it will take Aaron their equipment tech to trip/fall over something at the location. On this particular occasion he tripped over the exact same piece of debris twice an hour apart.
- In Cyrano de Bergerac, Cyrano has threatened punish Montfleaury if he acts in “La Clorise”. Raguenau and the first Marquis bet a fowl “a la Raguenau” about if he will fulfill his threat.
First Marquis (shrugging his shoulders) : He will not come!
Raguenau: I say he will! and I wager a fowl—a la Ragueneau.
The Marquis (laughing) : Good!
- In Jedi Outcast when Kyle decides to keep his lightsaber, we are informed that Lando owes Jan five credits.
- In Dragon Age: Origins one of the side conversations between companion characters Morrigan and Zevran (the side bet being between Zevran and a third party member)
Zevran: They are goddesses receiving their subjects, just as you should be. Whatever would be annoying about that?Morrigan: I have no wish to be placed upon a pedestal.Zevran: But you deserve no less. You should be admired by painters, copied by sculptors, exalted by poets! Surely you know that yours is a beauty so exotic it-it would turn the eye of the Maker Himself!Morrigan: Well, I suppose I...Alistair: By the Maker! You were right! You win.Zevran: I think you owe me five silvers, yes?Morrigan: I hate you all.
- In Dragon Age: Inquisition, if the banter is anything to go by, Varric and Dorian have these over just about everything. This includes their chances against the Elder One, which Dorian pegs at about 3 to 1, in favor of the Elder One. Other bets include whether they'll find an enemy that farts fire next, whether they are "ass-deep in trouble" (Varric being a dwarf skews that a bit), and the creepiness of nug feet.
- Emi and Rin of Katawa Shoujo repeatedly make bets on whether Hisao will keep his word and show up to events. Rin tends to lose, since she's the one betting that he won't show up.
- Kenji also loses a 1000 Yen bet over Lilly's ethnicity.
- Ace's mother in the webcomic Too Much Information is a repeat offender.
- This◊ strip from Narbonic.
- Seen here in the webcomic Get Medieval.
- Betting on who the new mayor is in this Dominic Deegan comic.
- Here in Knowledge is Power, with the twist that the character in question is wrong about winning the bet. (The bet was on whether Emjay's supposed boyfriend David really existed; the "David" her friend just met was actually an alien shapeshifter who happened to be using the name.)
- This strip from The Order of the Stick.
- Haley and Roy betting 10 gold pieces on various things has become a sort of Running Gag.
- This has been used twice in Wapsi Square. The first time, Shelly made a bet with Bud that Monica wouldn't be able to figure out how she protected herself from being shot. The second time, Bud bet Brandi that Monica wouldn't be able to keep her hands off of a supernatural artifact.
- In Girl Genius, there's a long-running pool about which corner of the Love Triangle will end up with Agatha. We see the odds getting revised and updated as new events put one guy or the other ahead, and there are even 'long-shot' wagers about a both or Dark Horse Victory.
Vesperian Squad Captain: Thirty - in gold - on Sturmvoraus!Jäeger General: Hey keed, gimme vun hunenrt on her takink BOTH uv dem!Vanamonde von Mekkahn (Keeping book): That's the dark horse, general. One will get you five.Violetta: What? You had that one to fifty!Vanamonde von Mekkahn: That was before Sturmovarus evened the odds. It's ANYONE'S race now.Random Jäeger: Really? Den hy gun bet feefty on ME!Vanamonde von Mekkahn: ...sure. Good luck.
- In Exterminatus Now, there's a betting pool concerning the outcomes of each Suicide Mission that Eastwood and company take. Simmons recognizes that they are Born Lucky and always bets on their mission success and survival...and always wins. Thanks to the horrible odds against that particular outcome, Simmons has made a lot of money this way.
- Not Always Related features the coming-out version in "Coming Out Can Be A Gamble".
- In Pay Me, Bug!, Cyrus and Ktk continually make bets with each other about anything and everything, such as the outcome of the mission, how long it will be until they wind up in trouble at this particular portnote , whether they will survive their current screwup, etc. This is, in fact, where the title comes from: Ktk is a "Bug," and whenever Cyrus wins, he makes sure everybody knows it.
- Vegeta wagers Scrooge's hat for the mysterious briefcase when they bowl in Ducktalez 7. They lose, but Vegeta was crafty and stole the hat and the briefcase, resulting in them getting chased by the Beagle Boys.
- Johnny Bravo was subject to this trope once. His sensei was arguing with a rival martial atrs teacher. When Master Hamas (Johnny's sensei) said even his worst student would defeat his rival's best, the rival picked Johnny. After the fight, it was revealed Hamas was so sure Johnny would lose, which he didn't, he made a side bet against his student. Instead of promoting Johnny to a higher belt for winning the fight like Johnny hoped, Master Hamas punished Johnny.
- When Butters in South Park tells his parents he has a girlfriend, they exchange money according to their bet on his sexuality.
- And of course, the entire subplot about the Kyle sucking Cartman's balls in "Imaginationland."
- In Regular Show, the third season finale starts out with Mordecai sharing a kiss with Margaret. He feels he screwed it up, and when he tells Rigby about it, the first thing that Rigby says:
Whoa. I owe Muscle Man so much money.
- In the WildC.A.T.s cartoon, Maul and Warblade bet on how many days it's going to take Grifter and Zealot to give in to their simmering UST. When they confess their feelings before the end of the episode, Warblade smugly collects his money.
- In an episode of Daria, Daria and Jane wage a bet on whether or not Quinn will be kicked out of the fashion club. She is, and the scene cuts to Jane handing Daria a bill.