Total Nerd

17 Movies Where The Whole Plot Revolves Around A Big Bet

List 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: 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.

  • 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.

  • 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.

  • 4
    28 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.