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Daily Joke: The Great Depression Gambler A Hilarious Bar Bet Story You Wont Believe

05/16/2025 from Daily Jokes
#20507

Daily Joke: The Great Depression Gambler A Hilarious Bar Bet Story You Wont Believe

During the Great Depression — when money was tighter than a hipster’s jeans — a scruffy-looking guy strolled into a bar like he owned the joint. He slammed a stack of cash on the counter and declared, “Drinks for the house, on me!”

The bartender blinked like he’d just seen a unicorn juggling flaming bowling pins. “Buddy, this is the Depression. We don’t even look at money unless it comes with a bodyguard. You got the cash?”

The man grinned and pointed at the wad of bills like it was a newborn baby. “Oh, I got it.”

“Where the heck did you get all that?” asked the bartender, suspicious.

“I’m a professional gambler.”

The bartender snorted so hard he nearly sucked in a peanut. “A gambler? In this economy? What, you flip coins and cry half the time?”

“I only bet on sure things,” said the man smugly.

“Like what?”

“I’ll bet you fifty bucks I can bite my right eye.”

The bartender eyed him up and down. “You’re not a mutant. That’s impossible. Deal.”

The guy popped out a glass eye and chomped it like a snack. CHOMP.

The bartender nearly choked on his own regret. “You son of a—fine.” He handed over the $50.

“Double or nothing,” said the gambler. “I’ll bet I can bite my left eye.”

The bartender squinted. “You’re not blind—I saw you look at me. No way. You’re on.”

The guy pulled out his false teeth and bit his left eye. Like it was a carrot stick.

“OH, COME ON!” the bartender wailed. “Are you made of spare parts?!”

Smiling like a raccoon in a dumpster buffet, the man said, “Tell you what, just gimme a bottle of your finest scotch and we’ll call it even.”

Later that night, after enough scotch to tranquilize a rhino and a few hours of hustling the locals at cards, the guy stumbled back to the bar—drunker than a karaoke machine on tequila.

“Bartender… I got one last bet,” he slurred. “Five hundred bucks says I can stand on this bar… on one leg… and pee into that whiskey bottle behind you… without spilling a drop.”

The bartender glanced at the shelf, then at the man wobbling like a Jenga tower in an earthquake. “Buddy, you can’t even talk in a straight line. You’re on.”

The guy climbed up, balanced like a drunken flamingo, and let loose. Pee went everywhere — the bar, the bartender, the ceiling fan. Basically everywhere except the bottle.

The bartender burst out laughing, soaked but triumphant. “HA! Fork it over, you lunatic!”

The gambler climbed down, wiping tears from his eyes. “Nah, see… I just bet everyone in the back room a thousand bucks I could pee all over you and your bar and you’d still laugh about it!”

Funny +22
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