Check out our collection of funny gambling jokes. We are sure they will make you laugh. If you have any gambling jokes as good, upload them at the bottom of this page.

Gambling Wins and Losses on a Tax Return. Gambling wins are reported on the front page of Form 1040 for tax years 2017 and prior. Gambling wins are reported on Schedule 1, Line 21 for tax year 2018. All gambling wins are required to be reported even if the casino doesn’t report the win to the IRS. Gambling wins are reported on a W-2G for. The Tax Court made it clear, and IRS now agrees, that a professional gambler's expenses incurred to engage in the trade or business of gambling are not subject to limitation, but are fully deductible as ordinary and necessary business expenses under Internal Revenue Code §162.

1) I just bet £100 at the bookies that they would find Maddie, at 1000-1 odds. That way, if they ever do find her, I’ll be able to afford a fucking good lawyer.
Check out Really Funny Lawyer Jokes

2) Chuck-E-Cheese, because it’s never too early to introduce your child to poor nutrition and gambling.

3) My wife has left me because I am a compulsive gambler. I’d do anything to win her back.

4) Poker is like sex – everyone thinks they’re the best, but most people don’t have a clue what they’re doing. Dutch Boyd
Check out Really Funny Sex Jokes

5) What’s the difference between prayer in church and prayer in a casino? In a casino, you really mean it.

6) A blond girl playing freeroll was taking her time and playing very slow. The timer was started and she still could not take a decision how to play the hand. Her friend asked her with surprise, “What is going on? Why aren’t you playing?” The blond girl replied, “I am playing! I am just slow-playing aces!”
Check out some of the funniest Dumb Blonde Jokes ever

7) Why didn’t the elephant like to play cards in the jungle? Because there were too many cheetahs.

8) They say one in every seven friends have a gambling addiction. My money’s on Dave.
Check out Really Funny Money Jokes

9) What did the giraffe say to the tiger at the poker table? I thought you were a cheetah.

10) What’s the difference between a poker player and a dog? In about ten years, the dog quits whining.
Check out Really Funny Animal Jokes

11) Whats the difference between online poker and live poker? You can cry after a bad beat online and no one will laugh at you.

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12) Sign you might have a poker addiction: your kids are named check and raise.

13) I put a thousand pounds on a horse. The fucking thing collapsed.
Check out some of the best Horse Jokes ever published

14) Chuck Norris won the World Series of Poker using Pokemon cards.

15) “I am looking for the book named ‘How to win easily and fast with poker.'” “Please check at the fantastic literature counter.”

16. Husband Comes Home After Gambling

I came home from the pub four hours late last night.

“Where the fuck have you been?” screamed my wife.

I said, “I’ve been playing poker with some blokes.”

“Playing poker with some blokes?” she repeated. “Well, you can pack your bags and go!”

“So can you,” I said. “This isn’t our house anymore.”

17. Professional Gambler Screws Everyone In The Bar

During the Great Depression, there was a man who walked into a bar one day. He went up to the bartender and said, “Bartender, I’d like to buy the house a round of drinks.”

The bartender said, “That’s fine, but we’re in the middle of the Depression, so I’ll need to see some money first.”

The guy pulled out a huge wad of notes and set them on the bar. The bartender can’t believe what he’s seeing. “Where did you get all that money?” asked the bartender.

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“I’m a professional gambler,” replied the man.

The bartender said, “There’s no such thing! I mean, your odds are fifty-fifty at best, right?”

“Well, I only bet on sure things,” said the guy.

“Like what?” asked the bartender.

“Well, for example, I’ll bet you fifty dollars that I can bite my right eye,” he said.

The bartender thought about it. “Okay,” he said.

So, the guy pulled out his false right eye and bit it. “Aw, you screwed me,” said the bartender, and paid the guy his $50.

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“I’ll give you another chance. I’ll bet you another fifty dollars that I can bite my left eye,” said the stranger.

The bartender thought again and said, “Well, I know you’re not blind, I mean, I watched you walk in here. I’ll take that bet.” So, the guy pulled out his false teeth and bit his left eye.

“Aw, you screwed me again!” protested the bartender.

“That’s how I win so much money, bartender. I’ll just take a bottle of your best scotch in lieu of the fifty dollars,” said the man.

With that, the guy went to the back room and spent the better part of the night playing cards with some of the locals. After many hours of drinking and card playing, he stumbled up to the bar. Drunk as a skunk, he said, “Bartender, I’ll give you one last chance. I’ll bet you five hundred dollars that I can stand on this bar on one foot and piss into that whisky bottle on that shelf behind you without spilling a drop.”

The bartender once again pondered the bet. The guy couldn’t even stand up straight on two feet, much less one. “Okay, you’re on,” he said.

The guy climbed up on the bar, stood on one leg, and began pissing all over the place. He hit the bar, the bartender, himself, but not a drop made it into the whisky bottle.

The bartender was ecstatic. Laughing, the bartender said, “Hey pal, you owe me five hundred dollars!”

The guy climbed down off the bar and said, “That’s okay. I just bet each of the guys in the card room a thousand bucks each that I could piss all over you and the bar and still make you laugh!”
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Related Links: 1. Gambling Jokes from Sickipedia.org 2. Gambling Jokes from Jokes4us.com

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The IRS decides to audit Grandpa, and summons him to the IRS office.

The auditor was not surprised when Grandpa showed up with his attorney.

The auditor said, “Well, sir, you have an extravagant lifestyle and no full-time employment, Which you explain by saying that you win money gambling. I’m not sure the IRS finds that believable.”

“I’m a great gambler, and I can prove it,” says Grandpa.

“How about a demonstration?”

Irs And Gambling Man Jokes

The auditor thinks for a moment and said, “Okay. Go ahead. “

Irs Gambling Jokes

Grandpa says, “I’ll bet you a thousand dollars that I can bite my own eye.”

The auditor thinks a moment and says, “It’s a bet.”

Grandpa removes his glass eye and bites it. The auditor’s jaw drops.

Grandpa says, “Now, I’ll bet you two thousand dollars that I can bite my other eye.”

Now the auditor can tell Grandpa isn’t blind, so he takes the bet. Grandpa removes his dentures and bites his good eye.

The stunned auditor now realizes he has wagered and lost three grand, with Grandpa’s attorney as a witness.

He starts to get nervous.

“Want to go double or nothing?” Grandpa asks. “I’ll bet you six thousand dollars that I can stand on one side of your desk, and pee into that wastebasket on the other side, and never get a drop anywhere in between.”

The auditor, twice burned, is cautious now, but he looks carefully and decides there’s no way this old guy could possibly manage that stunt, so he agrees again.

Grandpa stands beside the desk and unzips his pants, but although he strains mightily, he can’t make the stream reach the wastebasket on the other side, so he ends up urinating all over the auditor’s desk.

The auditor leaps with joy, realizing that he has just turned a major loss into a huge win.

But Grandpa’s own attorney moans and puts his head in his hands.

“Are you okay?” the auditor asks.

“Not really,” says the attorney.

“This morning, when Grandpa told me he’d been summoned for an audit, he bet me twenty-five thousand dollars that he could come in here and pee all over your desk and that you’d be happy about it!”

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