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The Sting: 3 Bar Bets That Can Make You a Crapload of Money

Written by Don P on . Posted in Challenge #3

(Reading time: 3 - 5 minutes) - The Sting

In The Sting, two professional con men (Robert Redford and Paul Newman) seek revenge for the murder of their friend by pulling off a long con against the ruthless mob boss who murdered him. The end result of the movie is great, but the entire setup is better and even demonstrates several different types of cons used in the profession.

The deception begins with the movie poster; just look at that image above. An older man ("Henry Gondorff") is presumably soliciting sexual favors from an obviously younger, blonde-haired man ("Johnny Hooker") in exchange for money or, perhaps, a strip poker game. And that's not a type-o, the character's name is Johnny Hooker — a name that sounds more like a crime fighting male prostitute. - Lt. Dangle

Regardless, Hooker — which is how he'll be referred to for the rest of this article — and his partner, Luther, pull off a very successful con, known as the classic "Pigeon Drop," on a man who works for Doyle Lonnegan, a big time crime boss. Lonnegan tracks down and kills Luther; Hooker flees the city and seeks the help of Henry Gondorff, the master of the long con, to take Lonnegan for an enormous sum of money to even the score. Gondorff and Hooker amass a talented group of other con artists to pull a race track based scam and cheat Lonnegan out of $500,000.

Con artists have been around for thousands of years and have screwed over thousands of innocent people for A LOT of money. But there are plenty of everyday tricks and scams you can play on friends to bank you some cash or even free drinks. I've spent thousands of hours in bars talking to thousands of people and here are some easy-to-use bar bets I've come across along the way:

#1. The Cigarette Knot

Pick up a friend's cigarette packet and remove one. Eye the cigarette carefully, turning it over and over in your hands. When your curious friend asks what you're doing, simply reply, “Well, I heard about a guy once who said that he could tie a cigarette into a knot without tearing any of the paper. I think I might have figured it out.”

Hopefully you've baited your friend into saying, “That’s totally impossible,” Suggest a small wager on the outcome of the event and add some rules: the cigarette itself must be knotted, it must be dry when you do it, and it must be smokable afterwards. The tiniest tear loses the bet. It will take around forty five seconds to win the bet. Here's how:

  • Put the cigarette down on a dry surface (remember the rule to keep it dry).
  • Remove the cellophane wrapper from the cigarette packet and flatten it out.
  • Tightly roll the cigarette into the cellophane making sure the cigarette ends up completely within the wrapper.
  • Then tie the cigarette into a knot.
  • Have the audacity to smugly ask your friend if he/she wants to pull the knot tighter.
  • Carefully undo the knot and unroll the cellophane.
  • You're left with a totally untorn and smokable cigarette!
  • Collect your money! - Cigarette Knot

#2. Simon Says

Here's an easy one: Bet somebody that they can’t do everything that you do for the next ninety seconds. Let them add all the ‘useful’ limitations. This bet will include no contortions or special athletic movements. Assure them that all your actions will be those that can be done by a completely normal person. You should have no trouble getting someone to bet on this one. Put two straws on the bar, one for you and one for them, to reel them in.

  • Turn your straw end for end. They'll do the same.
  • Take a drink from your glass. They'll do the same.
  • Mess with your straw again. They'll follow along.
  • Raise your glass to your lips to take another sip. They do so as well.
  • Spit the drink you sneakily held in your mouth back into your glass. Because they swallowed their sip they won't be able to complete this simple action.
  • Collect your cash!

Now, if you notice that they haven't swallowed their drink before you spit out yours (which would allow them to follow you):

  • When you spit the drink back into your glass, keep some in your mouth.
  • After your mark repeats the spit and reaches for your money, that's when you spit a the rest out.
  • Easy Money! - Simon Says

#3. Whiskey Winner

This little bet should win you at least a few drinks, if not some cash to go along with them. Place six shot glasses in a line along the bar. Fill the first three with whiskey and leave the other three empty. The bet is to get the glasses alternated — whiskey, empty, whiskey, empty, whiskey, empty — with the minimum amount of glasses moved. Allow a discussion and several test runs to take place. Then drop your hook.

  • Claim you can do it by moving only one glass.
  • Allow others to try to see how impossible this is (or to see if they can figure it out).
  • When the bet is placed, pick up the center of the three filled glasses.
  • Pour the whiskey into the center of the three empty glasses and replace your now empty glass where it started (see below).
  • You only touched one glass and nobody said the whiskey had to stay in the same glass!
  • Collect your cash!


Turns into:

[WHISKEY] = [EMPTY] = [WHISKEY] = [EMPTY] = [WHISKEY] = [EMPTY] - Whiskey Shots


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