Cowboys Losing Jokes

4 cowboys losing jokes and hilarious cowboys losing puns to laugh out loud. Read jokes about cowboys losing that are clean and suitable for kids and friends.

Comedy Cowboys Losing Jokes to Make Your Friends Giggle

What is a good cowboys losing joke to make people laugh? Check out this list of funny stories that will for sure put a smile on everyones mouth.

If we played cowboys and Indians I wouldn't choose to be on losing team

that would be Sioux side.

Trump's battle against ISIS is the grand strategy equivalent of a Patriots-Cowboys game.

A lot of people you talk to somehow want both to lose.

New cowboy boots

Fred bought himself a new pair of cowboy boots that he had always wanted. He left them on after trying them on at the store. Upon arriving home, he walked in and said to Bertha "notice anything different".
Frustrated, Fred left the room and stripped down, leaving on nothing but his cowboy boots. He walked back to Bertha and said "NOTICE ANYTHING DIFFERENT NOW"
Bertha replied "Nope, it's hanging now, was hanging this morning, and will be hanging again tomorrow"
Fred was about to lose it, he yelled out "YA KNOW WHY IT'S HANGING DOWN, IT'S LOOKIN AT MY NEW BOOTS"
Bertha looked him straight in the eye, without flinching and said
"ya shoulda bought a hat"

A man sits at the bar drinking and looking upset.

The bartender asks him what's wrong. The man looks up and says
"I lost it all playing the ponies. A million dollars. I had it and I lost it all."
The bartender is taken aback. "If you don't mind me prying, a million dollars is a lot of money. How'd you end up losing it?"
The man downs his drink. "Pour me another and I'll tell you. I went to the track with five dollars. That's it. I was only gonna spend five and go home. So I gets a good feeling about this horse named Fedora. He had incredible odds so I went for it. Turns out he won. So I makes a five into a hundred. I'm on a roll now, so in the next race I bets on a horse named Top Hat. Again, the odds are in my favour. He wins, and I turns a hundred into six thousand. It continues all day, every race. Beret made 6000 into 120,000. And Trilby makes 120,000 into 1,200,000. That's no small potatoes. I shoulda known hat names wouldn't work forever, but I thought I had a winner with Cowboy. He lost. I lost."
The bartender is invested in the story by this point. He waits with bated breath. "So who won?"
"Some d**... horse named Yarmulke."

Make fun with this list of one liners, jokes and riddles. Each joke is crafted with thought and creativity, delivering punchlines that are unexpected and witty. The humor about cowboys losing can easily lighten the mood and bring smiles to people's faces. This compilation of cowboys losing puns is not just entertaining but also a testament to the art of joke-telling. The jokes in this list are designed to display different humor styles, ensuring that every reader at any age finds something entertaining. Constantly updated, they offer a source of fun that ensures one is always smiling !

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