10 Memorable Movie Bets

Trading Places Dollar Bet
Who doesn’t love to make random bets? Let’s bet $20 on the season finale of RuPaul’s Drag Race. Let’s bet $5 on how fast it takes Taco Bell to make our Chalupa Supremes. And so on and so fourth.

The world of cinema is also filled with such random bets, and today we will be highlighting some of the most memorable. Because why spend thousands of dollars at someplace like Platinum Play Casino when you can bet $1 to see if you can destroy the life of a close acquaintance (that’s a rhetorical question, by the way). Anyway, let’s get started.

10. Funny Games (1997/2007)

Funny Games Michael Pitt

It doesn’t matter which version of Funny Games you watch (although it’s proper to say the original was better), as they are essentially the exact same movie. Director Michael Haneke first made Funny Games in 1997 in Austria. 10 years later, he directed a shot-for-shot remake for American audiences. No matter which you watch, you can’t really win; Funny Games is going to disturb you no matter what.

In both films, a family of three is taken hostage in their summer home by two young men, who bet them they will be dead by 9 the next morning. The two captors toy with the family, and use a game of eeny-meeny-miny-moe to find out which of the family will die first. We won’t spoil it for you, but we’ll just say that there isn’t anything remotely funny about these games at all.

9. Little Darlings (1980)

Little Darlings

Angel (Kristy McNichol) is a tough, poor, chain smoking tomboy. Ferris (Tatum O’Neal) is a prissy rich girl wearing the latest designs. They’re sent off to summer camp by parents who are having problems: the former’s single mom is man hunting, and the latter’s parents are on the verge of a divorce. After the two polar opposites get off on the wrong foot with a fight on the bus, the pair are egged on to settle their differences with a contest. Said contest? As the only two “inexperienced” girls at camp, they will compete to see who loses her virginity first – with everyone else wagering on the outcome.

In the end, Ferris discovers that love involves sex, which is not always romantic, and Angel discovers that sex involves love, which deeply touches her and transforms her soul. They both grow up that summer.

8. Dumb & Dumber (1994)

Dumb and Dumber Bet Scene

In this Farrelly brothers classic Lloyd (Jim Carrey) and Harry (Jeff Daniels) are two imbeciles who travel from Providence, Rhode Island to Aspen, Colorado to return a briefcase full of money (which they’re unaware is in there) to a young lady named Mary Swanson. Little do they know, a group of criminals are after the briefcase as well.

Just as their trip is starting, Harry questions if they have enough gas money to make the trip. Lloyd tells him to relax and even suggests they make a wager regarding the matter, to which Harry replies that he doesn’t bet (“never has and never will”). Lloyd then proceeds to bet Harry that he will get him to bet before the day is out, which Harry eagerly agrees to. No word on who ever won the bet.

7. Teeth (2007)

Teeth Bet Scene

Dawn O’Keefe (Jess Weixler) is a teenage spokesperson for a Christian abstinence group called The Promise. She dates in groups, watches G-rated films, and has never even kissed a boy. However, the power of teen hormones is great, so temptation beckons. After a few run-ins with a few overzealous young men, Dawn realizes that she has a toothed-vagina (a condition known as “vagina dentata”), which is exactly what it sounds like. If you stick something in there then there is a good chance that it’s going to be bitten (or bitten off).

With a premise as insane as this you could expect that there would be multiple instances of guys having their worst nightmare come true. One such moment is when we learn, mid-coitus, that Ryan (Ashley Springer) unwisely made a bet that he could lay Dawn. Dawn’s “vagina dentata” settles the score… and it isn’t pretty.

6. Cruel Intentions (1999)

Cruel Intentions Bet Scene

This modern update of the novel The Dangerous Liaisons, revolving around privileged teenagers in New York City, is an unapologetically ridiculous melodrama, but an extremely entertaining one at that. Kathryn Merteuil (Sarah Michelle Gellar) and step-brother Sebastian Valmont (Ryan Phillippe) are a deliciously entertaining villain pairing, as they respectively plan to break the hearts of naive Cecile (Selma Blair) and virgin Annette Hargrove (Reese Witherspoon).

The step-siblings make a wager about whether Sebastian can seduce the saintly Annette and Kathryn tells him that if he wins he can “put it anywhere.” Naturally, he accepts the challenge.

5. She’s All That (1999)

She's All That Beach Scene

Ah, the quintessential ugly duckling movie for the late ’90s, She’s All That – an adaptation of the classic play Pygmalion – revolves around Zack’s (Freddie Prinze, Jr) quest to win a bet by transforming dorky, unpopular loner Laney Boggs (Rachel Leigh Cook) into a Prom Queen in just 6 weeks.

It’s a thoroughly ridiculous premise because, as much as they might want to dress Cook up in paint-stained overalls, give her big glasses and put her hair up, it’s still clear as day that she’d clean up pretty well. And yup, low and behold, the make-over scene happens, and waddya know? With her hair down, some contact lenses and a nice dress, she looks smoking hot.

4. Not Another Teen Movie (2001)

Not Another Teen Movie Chris Evans

Not Another Teen Movie doesn’t really get the respect it deserves – it’s actually quite funny. The film, of course, spoofs many of your favorite (and not so favorite) teen films of the ’80s and ’90s, including; Can’t Hardly Wait, Pretty in Pink, Bring It On, American Pie, Varsity Blues, The Breakfast Club and, yes, the aforementioned She’s All That.

Not Another Teen Movie hilariously takes the absurd premise of She’s All That and carries it up about a thousand notches. This time, Jake Wyler (future Captain America Chris Evans) is the all-American football star who makes a foolish bet to turn nerd-yet-obviously-gorgeous Janey Briggs (Chyler Leigh) into a prom queen. The bet this time around is brilliant because up till then, no one really had acknowledged the fact that in movies like this they’d take an obviously hot girl that everyone could see was hot, and just put a pair of glasses on her, and hope the audience didn’t notice the ridiculousness of it. We noticed. We have always noticed.

3. Trading Places (1983)

Trading Places Bet Scene

In this John Landis comedy classic, we follow Louis Winthorpe III (Dan Aykroyd), a wealthy managing director at a Philadelphia commodities-trading firm, and Billy Ray Valentine (Eddie Murphy), a beggar, whose lives get turned upside down. The plot centers around a grotesque bet made by Mortimer (Don Ameche) and Randolph Duke (Ralph Bellamy), brothers and the owners of Winthorpe’s firm, Duke and Duke.

After a run-in between Winthorpe and Valentine, in which Valentine is falsely accused of trying to steal Winthorpe’s briefcase, the Duke brothers make a bet on whether nature or nurture is the determining factor in an individual’s life. The premise of the bet is that if they elevate Valentine from poverty, giving him all the things that Winthorpe has (money, a job, a network, and social status) – he will soon begin to act like a wealthy, entitled, successful elite. On the other hand, they wager, if they take away all that Winthorpe has, he will turn into a homeless, jobless, thieving degenerate. How much was the wager? $1. But don’t worry, the 1% get what’s coming to them in the end.

2. The Shawshank Redemption (1994)

Shawshank Redemption First Night

Hope, friendship, and survival inside a maximum security jail: what else could you possibly want in a film? The film adaptation of Stephen King’s novella, The Shawshank Redemption has taken on an almost-cult like status in the last 20 years.

In 1947, Andy – a banker – is sentenced to two consecutive life sentences in Shawshank Penitentiary for killing his wife and her lover. He maintains his innocence, but nobody is trying to hear it. On his first night in prison, the fellow inmates make a bet to see which of the “fresh fish” are going to cry first. It turns out not to be Andy but another unfortunate sap who not only sheds the first tears but then takes a beating at the hands of the guards for his trouble.

1. Caddyshack (1980)

Caddyshack Explosion

Caddyshack certainly brings out the ridiculous in the white-washed world that is the American country club. The film ends with our main characters playing a high-stakes golf match, with tens of thousands of dollars on the line. Though, looking back on it, the way the finale eventually resolves itself doesn’t seem to make much sense.

Let’s recap: The principals are playing a golf match. The referee (Brian Doyle-Murray) says “Gentlemen, this match is all even. Final hole. Doctor, you are away.” Dr. Beeper (Dan Resin) putts and misses, and makes his second putt. Ty Webb (Chevy Chase) putts, misses, and makes his second putt. Judge Smails (Ted Knight) takes out the old “Billy Baroo” and makes his putt. Danny Noonan (Michael O’Keefe) putts, the ball hangs on the edge of the hole until the course blows up, then the ball falls in, and everyone rejoices because the good guys win.

How is it they won? We don’t know much about golf, but shouldn’t this be a tie? Ah, whatever.

Are there any other memorable movie bets you’d like to add to the list? Let us know in the comment section below.

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