April 12, 2023 4 min read

Gambling is a serious activity, but that doesn’t mean there isn’t room for some fun too.

With that in mind, we have compiled 10 of the funniest gambler jokes out there to help lighten the mood and give you a few laughs.

So roll up your sleeves and get ready for some punny gambler humor!

Ace Up Your Sleeve

From puns and riddles to hilarious stories from experienced gamblers, these jokes will surely have you laughing out loud!

So shuffle up those cards and check out these ace up your sleeve gambling jokes!

  • A man walks into a casino and says to the dealer, "Deal me in!" The dealer looks up and replies, "I'm sorry sir but you don't have any money." The man smiles and says, "That's okay, I've got an ace up my sleeve!"
  • A poker player was so confident in his skills that he bet everything he owned on one game. Sadly, the cards weren’t in his favor and he lost it all. As he was leaving the casino, he said to himself “That’s alright, I still have my pocket aces!”

Two Gamblers Walk Into a Casino…

Two gamblers walk into a casino, each with their own sense of humor and strategies for winning big. One is an experienced card shark who knows the odds and knows how to make his money last. The other is a novice player who hopes luck will be on his side.


What follows are some of the best gambling jokes that they shared while playing their favorite games.

  • Two gamblers walk into a casino and one of them says to the other, “I’m going to try my luck at the roulette table. You should come with me!” The second gambler replies: “No way! Roulette is for suckers. Let’s go play blackjack instead!”
  • Two gamblers are walking through a casinowhen they spot a roulette wheel with no one playing it. One of them turns to the other and says, “Hey, do you want to play a game? I’ll bet my last $20 on red!” The second gambler thinks for a moment before replying, “No way! That's too risky for me."
  • Two gamblers are playing slot machines when one notices the other playing with a lucky coin. He turns to her and says, “Where did you get that?” She replies, “It's my grandpa's lucky coin. Every time I use it I win!”
  • Two gamblers are discussing their worst losses in the casino when one mentions that he lost his house playing craps. The other gambler looks at him incredulously and says: “You lost your house?! How much did you bet?” He replies, “Nothing. I just rolled snake eyes!”

A Gambler Walks Into a Casino…

Gambling jokes traditionally feature the archetypal gambler: the experienced, daring type who's always looking to win big at the casino tables. In these stories, something usually goes wrong with the gambler’s plan and he walks away empty-handed or worse off than when he started. Here are some classic gambling jokes featuring this familiar character:

  • A gambler walks into a casino and starts to place bets on every table he sees. After an hour of playing, he looks around and realizes that everyone has left but him. He turns to the dealer and says: “Do you mind if I keep playing? It's kinda lonely without anyone else here.”
  • A gambler walks into a casino, looking for an easy win. He approaches the blackjack table and announces, “I’m all in!” Everyone at the table is taken aback until one of them finally speaks up and says: “Ummm… Sir, you don't even have any chips.”
  • A gambler walks into a casino, determined to make some money. He sits down at the blackjack table and starts counting cards. After a few minutes of play, he gets up and announces: “I'm done for today! I've already made more than enough money!”
  • A man walks into a casino and spots an old friend sitting at the roulette wheel. He approaches him and asks what he's doing there so late at night. His friend replies, “I’m trying to make a living - I’ve bet everything I own on this one spin of the wheel!”


As the saying goes, “all good things must come to an end.” But before you go, make sure to have a few laughs with these top 10 story long gambler jokes! So whether you're in it for the win or just for some fun, never forget that laughter is often the best bet at the casino. Good luck!

Author - Fred Felton
Fred Felton          

Content Creator / Editor

Fred Felton is a copywriter, editor and social media specialist based in Durban, South Africa. He has over 20 years of experience in creating high end content. He has worked with some of the biggest brands in the world. Currently Fred specialises in the adventure watersports space, focussing on surf, kayak and rafting. He is also a keynote speaker and has presented talks and workshops in South Africa.

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