The best cowboy jokes

Two men walk into a bar, one wearing a cowboy hat and the other wearing a Yankees cap. The guy in the Yankees cap approaches the bartender and make a bet: "I'll bet you $1,000 that I can put a shot glass at one end of your bar and piss into it from the other end of the bar without spilling a drop." The bartender laughs and says, "You're crazy, but you're on." The man positions a shot glass on one end, walks to the other end and unzips his fly. He then pisses everywhere all over the walls, over the bar top, all over the bottles of booze, and all over the bartender. The bartender roars with laughter and tells the man to pay up. The guy in the Yankees cap pays up, laughing and smiling, too. "What are you smiling at?" asks the bartender. "You just lost $1,000!" "Well, you see that guy in the cowboy hat over there crying? Before we came in, I bet him $10,000 that I could piss all over your bar, your walls, your liquor AND you, and not only would you not be mad you would laugh hysterically about it!"
Vote:
has 68.63 % from 29 votes. More jokes about: alcohol, bar, bartender, cowboy, money
Little cowboy runs into a Bar shouting angerly "WHO's the lousy varmint that painted my horse green?" A big cowboy sidles up to him and says "I DID.. want to complain to me?" "No," says the little guy "just wanted you to know that the first coat is dry!"
Vote:
has 66.77 % from 31 votes. More jokes about: bar, cowboy, dirty, disgusting, horse
Q: Why did the bowlegged cowboy get fired? A: Because he couldn't keep his calves together!
Vote:
has 66.46 % from 23 votes. More jokes about: animal, cowboy
A cowboy rides in the desert and comes upon a Native American lying naked with a hard-on. He asks, "What are you doing?" The naked man replies, "I'm finding out the time -- it is 12:15." The cowboy looks at his watch and thinks, "Wow, it really is 12:15." The cowboy continues and sees another Native American lying naked with a hard-on. He asks, "What are you doing?" The naked man replies, "I'm seeing what time it is -- it is 3:15." The cowboy looks at his watch and that is the correct time. The cowboy continues and finds a third Native American lying naked on the ground, masturbating. The cowboy asks what he's doing and he replies, "I'm winding my watch."
Vote:
has 65.53 % from 78 votes. More jokes about: cowboy, disgusting, masturbation, time
What do you call a take-out low-calorie meal for a cowboy? A Saddle Light Dish.
Vote:
has 62.61 % from 13 votes. More jokes about: cowboy, food, men
Q: Why can't the bankrupt cowboy complain? A: He has got no beef.
Vote:
has 62.22 % from 20 votes. More jokes about: animal, cowboy, money
There were two church-going women gossiping in front of the store when a dusty old cowboy rode up. He tied up in front of the saloon, walked around behind his horse, lifted its tail and kissed the horse full on its rectum. Repulsed, one of the women asked, "That's disgusting, why did you do THAT?" To which the cowboy replied, "I've got chapped lips." Confused, the women continued, "Does that make them feel better?" "No, but it stops me from licking them!"
Vote:
has 57.35 % from 29 votes. More jokes about: church, cowboy, disgusting, horse, women
What is the definition of "derange"? De place where de cowboys ride.
Vote:
has 56.86 % from 14 votes. More jokes about: animal, cowboy
A cowboy rode up to the saloon, dismounted from his horse, and dusted himself off. He then walked around to the rear of his horse, lifted the tail and kissed it right on the rectum. As the cowboy walked into the saloon, the shocked barkeeper asked, "Did you just kiss your horse's butt?" The cowboy said, "Sure, I've got chapped lips." The stunned barkeep asked if this was an old Indian cure. The cowboy said, "Nope. But, sure as s**t, it keeps me from licking my lips!"
Vote:
has 56.84 % from 20 votes. More jokes about: animal, cowboy
Q: If a cowboy rides into town on Friday and three days later leaves on Friday, how does he do it? A: The horse's name is Friday!
Vote:
has 56.05 % from 28 votes. More jokes about: cowboy, horse, time
<<<23
More jokes →
Page 2 of 3.