17 Movies Where The Whole Plot Revolves Around A Big Bet

Ryan Izay
Updated May 15, 2024 17 items
Ranked By
371 votes
101 voters
Voting Rules
Vote up the grand wagers that have surprisingly big ramifications.

Gambling often appears as a plot device in movies, but there are some narratives that revolve entirely around a big bet. In these films, the story’s resolution is contingent upon the outcome of a wager made by a central character. Sometimes this may include traditional forms of gambling centered on sports or games of luck and chance, while others are focused on a more unique set of circumstances. Along with more traditional forms of gambling, there are bets involving traveling in a specific amount of time, wagers over romantic feelings, and some centered on a shift in social standing. 

Whether the reward for winning the bet is money or something less tangible, the outcome of each has a direct impact on the resolution of the plot. The protagonist often ends up victorious, even when the odds are stacked against them or cheating is involved. In a few rare instances, however, the wager results in the demise or degradation of the main character. Either way, the stakes are raised - and the resolution is determined - by the specifics of the bet.

Warning: Spoilers Ahead!

  • The Players: Randolph and Mortimer Duke (Ralph Bellamy and Don Ameche) are wealthy brothers and owners of a commodities brokerage firm with differing views of humanity. Working for them and engaged to their niece is Louis Winthorpe III (Dan Aykroyd), who has lived a life of wealth and entitlement in contrast to a street beggar and con man named Billy Ray Valentine (Eddie Murphy). 

    The Bet: One of the wealthy brothers believes human behavior is determined by nature, while the other believes it is nurture. They decide to swap the social standings of Winthorpe and Valentine to bet on the results. The wager for the bet is $1, despite their immense wealth. 

    The Results: When Valentine overhears the details of the bet, he joins forces with Winthorpe to get revenge on the men playing games with their lives. The pair con the wealthy brothers into making a poor investment decision, resulting in their own financial gain and the bankruptcy of the Duke brothers.

    70 votes
  • Dirty Rotten Scoundrels
    Photo: MGM

    The Players: Based on the 1964 film Bedtime Stories, Dirty Rotten Scoundrels follows two competing con men working on the French Riviera. Lawrence Jamieson (Michael Caine) is a sophisticated grifter who seduces wealthy women by posing as an exiled prince raising money for a revolution in his country. Freddy Benson (Steve Martin) is a small-time American hustler who cons wealthy targets out of money with stories about a sick grandmother. 

    The Bet: When the con men can’t work together, they decide the vacation spot along the French coastline is not large enough for the two of them. Lawrence and Freddy make a bet that the first to con $50,000 from a designated mark will win exclusive rights to grift in the area, while the other must leave town. They choose the seemingly naive American heiress, Janet Colgate (Glenne Headly), with each of the con men taking a unique angle to swindle her. 

    The Results: Neither Lawrence nor Fredy win the bet, as both are swindled by Janet, who reveals herself to be another con artist known as "The Jackal." The film ends with the trio joining forces in a real estate scheme together.

    41 votes
  • The Players: Based on the 1902 novel already adapted to film multiple times before this 1985 release, Brewster’s Millions follows minor league ballplayer Monty Brewster (Richard Pryor) as he discovers a recently deceased relative has left him with an inheritance, assuming he fulfills a challenge first. 

    The Bet: Brewster is informed that the only way for him to earn the entire inheritance of $300 million is by accepting a bet in which he has to spend $30 million - without a single dollar left over - in just 30 days. If he is unsuccessful, Monty will forfeit the entirety of the inheritance.

    The Results: Lawyer Warren Cox (Stephen Collins) attempts to fool Monty into failing the bet, and he nearly loses the entire inheritance. When Cox’s plot is exposed last-minute, Monty is able to complete his task and win the bet and the $300 million.

    83 votes
  • 4
    27 VOTES
    Diggstown
    Photo: MGM

    The Players: When con man Gabriel Caine (James Woods) and his partner Daniel Patrick O'Shannon Fitzpatrick (Oliver Platt) travel to the small town of Diggstown, they discover the citizens are obsessed with boxing. The town is named after the once-famous boxer Charles Macom Diggs, and his former manager John Gillon (Bruce Dern) owns almost all of the city property. 

    The Bet: When Fitzpatrick drunkenly claims to know a boxer capable of knocking out 10 fighters in one day, beating Diggs's record of five, Gillon bets him $100,000 to prove his statement. 

    The Results: Caine and Fitzpatrick enlist the help of 48-year-old former boxer "Honey" Roy Palmer (Louis Gossett Jr.), who agrees to fight 10 men for the bet. Although Gillon attempts to cheat, Caine outsmarts him by paying off the final boxer to throw the fight. Palmer wins the bet for Caine and Fitzpatrick, who expose Gillon’s corrupt ways to the town and walk away with the prize.

    27 votes
  • The Players: Held responsible by gangster Terry Benedict (Andy Garcia) for the casino thefts from the first film, Danny Ocean (George Clooney) and his 11-man crew travel to Europe for a new heist. These plans are interrupted by François Toulour (Vincent Cassel), a wealthy French baron who moonlights as a thief known as the Night Fox. 

    The Bet: Upset by the possibility that Ocean is a better thief, Toulour bets his crew can’t steal the Fabergé Imperial Coronation Egg. If Ocean and the gang are successful, Toulour agrees to pay off their debt to Benedict.

    The Results: Toulour initially believes he has foiled Ocean and his crew by stealing the egg himself, only for it to be revealed that this was a part of the plan. The egg was stolen by Ocean while in transit, leaving a fake for Toulour to steal. Ocean wins the bet and is able to pay off Benedict.

    30 votes
  • 6
    22 VOTES
    Faust
    Photo: MGM

    The Players: Directed by F.W. Murnau, Faust is a 1926 silent film adaptation of the legend about a deal made with the devil. A demon named Mephisto (Emil Jannings) and an Archangel (Werner Fuetterer) disagree on the course of humanity, using an alchemist named Faust (Gösta Ekman) as the focus of a bet to determine who is right. 

    The Bet: Mephisto bets the Archangel he can corrupt Faust’s soul, and the devil will win dominion over Earth if he is successful. 

    The Results: In order to corrupt Faust, Mephisto offers the man a series of deals risking his immortal soul for earthly pleasures. Although Faust is initially seduced by the power, he eventually sacrifices himself and everything offered by Mephisto, choosing instead to die with the woman he loves. Although Faust dies, his soul is saved and the Archangel wins the bet.

    22 votes
  • The Players: Vanishing Point follows Kowalski (Barry Newman), a Vietnam War hero and former police officer who delivers cars for a living. Also having experience as a race car driver, Kowalski enjoys driving fast and stays up all hours with the help of amphetamines bought from his dealer, Jake (Lee Weaver).

    The Bet: Kowalski’s latest assignment is delivering a supercharged white 1970 Dodge Challenger R/T 440 Magnum to San Francisco by the following Monday, though he bets Jake he will get it there by 3:00 pm Sunday instead.

    The Results: After attracting the attention of law enforcement for his reckless speed, Kowalski is forced to evade capture. He fails to win the bet when police set up a roadblock with two bulldozers. Rather than stopping, Kowalski drives the car into the roadblock at high speed, resulting in an explosion and his demise. 

    17 votes
  • 8
    19 VOTES

    The Players: As a musical adaptation of George Bernard Shaw's 1913 stage play Pygmalion, My Fair Lady follows an impoverished working-class girl named Eliza Doolittle (Audrey Hepburn), who befriends phonetics professor Henry Higgins (Rex Harrison) in hopes of learning to speak with more sophistication and class.

    The Bet: Higgins bets fellow phonetics expert Colonel Hugh Pickering (Wilfrid Hyde-White) that he can teach Eliza to speak as though she belongs in upper-class society, despite her strong Cockney accent. 

    The Results: Although Higgins is successful in transforming Eliza with the voice lessons, she becomes irritated when he takes all the credit for her hard work and leaves him. Despite their combative relationship, Higgins finally comes to terms with the romantic feelings he has for Eliza in her absence. The film ends with her return and the pair romantically reuniting. 

    19 votes
  • The Players: Adapted from a French novel first published in 1782, Dangerous Liaisons centers on the immoral games played between Marquise de Merteuil (Glenn Close) and her ex-lover, Vicomte de Valmont (John Malkovich). Merteuil is heartbroken when her latest lover leaves her to become engaged to the naive virgin, Cécile de Volanges (Uma Thurman), and places a bet with Valmont to amuse herself. 

    The Bet: Merteuil bets Valmont he can’t seduce Madame de Tourvel (Michelle Pfeiffer), the wife of a member of Parliament staying at her estate. If Valmont is able to provide written proof of his success seducing Tourvel, Merteuil agrees to sleep with him. 

    The Results: In the process of seducing Tourvel, Valmont falls in love with her but is forced to call off the romance when Merteuil becomes jealous. Valmont fails to prove he has won the bet, loses Tourvel, and is mortally wounded in a duel with one of the victims of his games with Merteuil. Cruel Intentions (1999) updated the story to modern times, with only a slightly more optimistic ending.

    22 votes
  • The Players: Based on a humorous picture book by Michele Alexander and Jeannie Long, How to Lose a Guy in 10 Days follows the relationship between women's magazine journalist Andie Anderson (Kate Hudson) and advertising executive Benjamin Barry (Matthew McConaughey). 

    The Bet: Eager to branch out from his usual projects to earn a prestigious advertising campaign for a diamond company, Benjamin bets his boss (Robert Klein) that he can make any woman fall in love with him. As chance would have it, the woman chosen for Benjamin is Andie, who only accepts his advances for an article proving she can convince any guy to dump her within 10 days of their relationship beginning. 

    The Results: Although Benjamin wins his bet, he also falls in love with Andie in the process. Anderson is upset when she discovers the details of the bet, and Benjamin is just as angry to discover their relationship was merely research for a magazine article. Though they are initially upset with each other, the couple reunites when Benjamin chases Andie's taxi down as she is leaving town.

    22 votes
  • 11
    22 VOTES

    The Players: The stars of Looney Tunes make up the main cast of Space Jam, led by Bugs Bunny (voiced by Billy West). The animated gang is kidnapped by an intergalactic amusement park owner named Mr. Swackhammer (Danny DeVito), who hopes to use them as an attraction to save the failing business.

    The Bet: In order to give the Looney Tunes a chance, Mr. Swackhammer agrees to a game of basketball to determine their fate. If the Looney Tunes can beat the theme park minions at a game of basketball, they will be allowed to go free.

    The Results: Bugs convinces basketball legend Michael Jordan to join their team to defeat the beefed-up minions in the game. Although they struggle at first, Jordan and the animated heroes are victorious, winning the bet and their freedom. 

    22 votes
  • The Players: Doctor Parnassus (Christopher Plummer) is the head of a failing traveling theater troupe who has made several bargains with the devil throughout his life. Appearing as a man named Mr. Nick (Tom Waits), the devil offered immortality and youth to Parnassus in exchange for his daughter Valentina (Lily Cole) on her 16th birthday. 

    The Bet: Before Valentina can turn 16, Parnassus makes a bet with Mr. Nick in which the winner will take the teenage girl as the prize. Parnassus must convince five people to choose enlightenment over ignorance when presented with a magical mirror serving as a test for ownership of their souls. If Mr. Nick can sway five souls to choose ignorance first, he will take ownership of Valentina, while she will be free if her father wins the bet. 

    The Results: Disturbed by the bet, Valentina disrupts it by offering herself willingly to Mr. Nick. Parnassus makes one last bargain to save Valentina and give her a happy life, though it results in him living an impoverished life away from his daughter.

    16 votes
  • 13
    18 VOTES
    She's All That
    Photo: Miramax

    The Players: Loosely based on My Fair Lady, She’s All That follows popular high school student Zack Siler (Freddie Prinze Jr.) as he recovers from heartache by using socially awkward art student Laney Boggs (Rachael Leigh Cook) to win a bet against another student named Dean (Paul Walker). 

    The Bet: After having his heart broken, Zack arrogantly insists he can turn any girl from their high school into the prom queen by dating her. Dean chooses Laney as the subject of the bet because of how unpopular she is, thinking it will be an impossible task for Zack.

    The Results: While Zack’s assistance in giving Laney a superficial makeover gets her a nomination for prom queen, the two have a falling out when she discovers the details of the bet. Although Zack loses the bet when Laney fails to become prom queen, he comes to terms with his feelings for her. In the end, the relationship developed through the bet changes Zack’s personality more than Laney’s appearance. 

    18 votes
  • The Players: English gentleman and adventurer Phileas Fogg (David Niven) believes he can circumnavigate the world in 80 days in 1872, which is met by skepticism when he makes this claim to the members of the Reform Club to which he belongs.

    The Bet: Fogg bets the members of the club £20,000 that he can make the journey around the world in 80 days before setting out on the expedition.

    The Results: Right before reaching his destination and winning the bet, Fogg is detained for suspicions of theft. Fogg believes he is too late to make it to the club on time once his name is cleared and he has been released, only to discover it is a day earlier than originally thought. By traveling east, Fogg unintentionally gained a day, leaving him just enough time to win the bet.

    19 votes
  • 15
    10 VOTES
    Life Stinks
    Photo: MGM

    The Players: Greedy billionaire and CEO Goddard Bolt (Mel Brooks) is determined to buy the slums of Los Angeles so he can tear them down and build a monument to his success. As Bolt’s biggest competitor, Vance Crasswell (Jeffrey Tambor) also has an interest in the property for similar purposes. 

    The Bet: The two business tycoons own half of the property each, and neither is willing to sell to the other, so Crasswell proposes a bet. If Bolt is able to survive in the slums as a homeless man for 30 days, Crasswell will sell the property to him. If he fails, it will go to Crasswell instead.

    The Results: Before Bolt can win the bet, Crasswell bribes his lawyers to betray him, removing his wealth and status even after the 30 days have expired. It isn’t until Bolt convinces the impoverished citizens of the slum to revolt against the proposed plans for the community that Crasswell admits to losing the wager. Changed by his experiences, Bolt announces plans to establish no-income housing in place of his original concept for the land.

    10 votes
  • The Players: The central focus of The Book of Life involves the romantic entanglement of a love triangle after two friends fall for the same girl as children and spend their lives competing for her attention. Manolo Sánchez (Diego Luna) is a bullfighter despite his passion for playing the guitar and unwillingness to kill the bulls, while Joaquín Mondragon Jr. (Channing Tatum) is a soldier and a warrior who protects the town from outside threats. Both have been in love with María Posada (Zoe Saldaña) since childhood. 

    The Bet: Gods Xibalba (Ron Perlman) and La Muerte (Kate del Castillo) also observe the love triangle and place bets on which of the boys María will choose, interceding wherever possible to affect the results. If María marries Manolo, Xibalba agrees to leave humans alone, but if she marries Joaquín, La Muerte must give up control of the Land of the Remembered.

    The Results: Xibalba cheats by giving Joaquín a medal preventing harm or death, while Manolo sacrifices himself to save María. After a journey through the land of the dead, Manolo informs La Muerte of the manipulation and returns to the living to win the heart of María.

    11 votes
  • 17
    9 VOTES
    Uncut Gems
    Photo: A24

    The Players: The hapless protagonist of Uncut Gems is Howard Ratner (Adam Sandler), the Jewish-American owner of a jewelry store in New York City's Diamond District with a gambling addiction. Despite Howard being in debt for $100,000 to his loan shark brother-in-law, Arno (Eric Bogosian), he gambles with his own life by continuing to place bets.

    The Bet(s): After Boston Celtics star Kevin Garnett shows an interest in a rare Ethiopian black opal, Howard is given the means to place a large bet on his upcoming playoff game. When Arno intercedes in this bet, Howard doubles down and places another on Garnett’s next game, knowing there will be consequences if he loses. 

    The Results: Although Howard wins the bet, Arno’s violent henchman (Keith William Richards) punishes the gambler for his insolence with a bullet to the head. Howard's demise is even more tragic because it comes immediately after his luck seems to have turned around.

    9 votes