One funny cowboy halloween story is about a cowboy who dressed up as a scarecrow for halloween. He went to the local saloon and the bartender didn't recognize him at first. When he spoke in his normal cowboy drawl, everyone had a good laugh. He ended up winning the best costume prize that night.
Once upon a halloween, a cowboy decided to be a fairy cowboy. He had a tutu on under his chaps and wings on his back. He carried his lasso like it was a magic wand. He was trying to catch 'evil spirits' (which were really just his friends running around). His comical attempts to fly around the halloween gathering while still maintaining his cowboy swagger made it a very entertaining sight for all.
There was a cowboy who decided to decorate his ranch for Christmas all by himself. He got these huge, wild cacti and tried to put Christmas lights on them. As he was climbing up the cacti, he kept getting pricked, but his determination was unwavering. By the end of the day, his ranch had the most unique Christmas lights display in the whole West, with the cacti looking like spiky Christmas trees. It was a story that made everyone in the town chuckle.
Horses are a common element. For example, when a horse does something unexpected like refusing to move or bucking in a funny way. Cowboys' clumsiness is also common, like tripping over a saddle or dropping their lasso. And the interaction with animals on the ranch, like a calf getting into mischief and the cowboy trying to deal with it.
A memorable one is when a cowboy accidentally mistook a reindeer for a wild deer while out on patrol on Christmas Eve. He chased it all over the place until he realized it had a shiny red nose. He then felt so silly but it became a story told around the campfire every Christmas. The image of a cowboy on horseback chasing what he thought was a normal deer only to find Rudolph was quite funny.
Sure. There was a cowboy who tried to lasso a cactus by mistake. He thought it was a calf in the distance. When the lasso caught the cactus, he got a big prick and jumped around yelling in pain. It was really a hilarious sight.
There was a cowboy who had a parrot as a pet. The parrot liked to mimic the cowboy's orders to the horses. One day, when the cowboy was trying to get his horse to move faster, the parrot started shouting 'Giddy up! Giddy up!' really loudly. But then the parrot also started shouting 'Whoa!' at the wrong time, confusing the horse completely. The cowboy was so frustrated but it was also really funny to watch.
A cowboy went to town to buy a new hat. He saw a very fancy one and put it on. But as he walked out of the store, a strong wind blew the hat right off his head and into a muddy puddle. His new hat was ruined before he could even show it off.
A popular one is where a cowboy tries to learn the Indian language to impress a girl from the Indian tribe. He ends up mixing up all the words and says really silly things. For example, instead of saying 'you are beautiful' he says something that means 'your horse is purple'. Everyone has a good laugh including the girl. It's funny because of the cultural mix - up.
Sure. There was a cowboy who tried to ride a wild bronco. He got thrown off immediately but landed in a big pile of hay. When he stood up, his hat was on backwards and his face was full of hay, looking really comical.