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How These Comedians Found the Humour in Gambling Heartbreak

When you feel like your luck has run out, and all hope is lost, it’s time for a little laugh. This funny story about gambling traps will make your day brighter! We’ve felt their sting, too—the agony of losing a big bet or even just going over budget to afford one lousy turn in Las Vegas isn’t something we like to talk about, but there are ways around that sadness, if only we know what they cause.


Norm McDonald found humour in all three gambling mishaps. Yes, he went broke and lost three times in sports betting, but this time we see that even though things got very stressful financially and emotionally, there were still some lighter moments and much more worthy of cringing.

The great thing about gambling is that you can always win. During an appearance on The Howard Stern Show, he once said that gamblers think they will never lose the money invested in their favourite game of chance.

McDonald’s career was prolific, and it seemed that his success would never end. He started on the small screen with a guest role on The Drew Carey Show and later wrote the hit show Roseanne, participated both backstage and on stage on Weekend Update during the 1990s SNL period, where he competed with Enixy – gosh, even playing himself.

He may not have the prettiest face or body of any player on this year’s field, but his skill and whale-sized personality make him beware. He’s no stranger to organizing high-stakes poker tournaments either; during the 7th HDP (High Stakes Poker) season, he took the place of Game Kaplan – Welcome Back Kotter – and has been a contender favourite ever since!


McDonald’s ability to laugh at himself and make people laugh back makes him so popular. He has used his celebrity status as an opportunity for others who may be struggling with gambling problems by telling stories on late-night talk shows like Conan O’Brien or Letterman David Letterman. He always had a smile on his face when he said these punch lines, which proves how excited he was.

Lucky numbers

Mitch Hedberg was known for his deadpan expression and surreal humour, which he used in brief one-liners. His stage presence garnered fans who often yelled punch lines before Mitch could finish their story! Along with three comedy CDs; Strategic Grill Locations (released posthumously), albums such as All Together Now Volumes 1; 2 along with Therapy Session – while continuing to appear at the Just For Laughs comedy festival in Montreal several times during 1998, 2001, 2004 – Mitch has also appeared on two television programs including The Daily Show With Jon Stewart (2000 – 2005).

“The number four billion isn’t very convenient when you’re gambling. “Come on, four billion, damn it, seven!” Not even close! I need a few more bones… At least divide by six!”

Hedberg added this charm: “I like to play blackjack. I’m not addicted, I just sometimes sit in a semicircle.” He gave his audience diarrhea from laughing after admitting he was more focused on sitting than gambling and even likened it to an addiction!

“My friend is a blackjack dealer, and he has a tattoo of an ace with another jack on his forearm. I want my next tattoo to be ten points over two clubs, but maybe we’ll add some more kings to the mix later!”

Unfortunately, the talented Hedberg passed away in 2005 due to a cocaine overdose at the age of just 37.

Super Bowl or Bust

Funny, smart Artie Lange is being chased by some demons. After making his mark on the sketch comedy show Crazy TV, he became famous for his wits on The Howard Stern Show and co-starred with Norm Macdonald on Dirty Work. Who can forget the Beer League?

With three books, four CDs and a personality to match his work are Artie Lange. He has been writing for years with titles such as Too Fat To Fish (2009) and Crashes And Burn (2014), which were recently made into an ABC show called Whiskey Diagnostic: Jack & coke. This man knows how to make you laugh and also teaches important life lessons about gambling!

Many people experience the pain of degenerative gambling. Johnny’ Stink’ Lange elaborated on this during his feature on Comedy Central, where he revealed that every Super Bowl coin toss, until he’s 42 will be worth at least $5,000!

“You realize you’re a degenerate gambler when it’s 4 am and your friends are at home sleeping, and the sun is just starting to rise. You’re sitting in front of an empty pool, and $20 depends on someone being able to find it online.” -lacrosse games so I can watch them.”

Artie Lange’s life was full of turmoil and addiction. He has struggled several times with cocaine addiction, heroin addiction, and suicidal thoughts, but today he has been clean for more than two decades thanks to hard work that pays off in the form of a successful podcast host with almost 45 thousand subscribers!

Raisins and prophecies

Steve Allen, the great comedian and TV star decades ago, admitted that he was once an avid gamer. However, his comedy routines nowadays focus more on the mental stakes than the physical ones because “that’s how I got crazy.”

The feeling of anonymity while gambling simply because you can forget the restrictions and do what you see fit. You don’t tell anyone and then lie about how much money was won or lost to keep up with other people who might be watching!

Jack Yelton joke A man goes to a casino and plays with all his heart. He wins big, but when the dealers ask him for ID to get home, he has no idea what kind of wallet to bring on such an adventure, so he leaves without it – losing everything plus a little extra change for good measure! The moral of the story is if you’re going to gamble… fill your wallet with cash (or checks) because nothing will take you away like leaving empty-handed.

The holiday season is a time for joy and reflection, not sadness. But one man’s story of how his mother lost Christmas at the slot machines gave us anger-fueled nostalgia in 2018 when he said, “But Mom, did Santa come last year?” To which she replied: “Yes, SANTA GOT THREE SIX!”

Let’s play

Chicago’s tireless comedian Sebastian Maniscalco knows how to make people laugh. He has done everything from comedy sketches and TV appearances to his newest job: putting his wife in the role of a problem gambler during appearances that detail their story of how they lost $100 in five minutes playing slot machines.

“Relax, enjoy the spin,” he said. And then, to taunt me a little more: “We haven’t even registered yet!” The sound of his voice was so calm and relaxed that I also relaxed in my seat – which should never be done during a flight because it is believed that there are planes that do not want anything but our death or death. Already unconscious!

His wife protested, “I have such a hunch,” eagerly awaiting further action. But in response, her husband only said excitedly: “Yes, baby! You’re right – we won’t eat tonight!”

Gambling is a fun and exciting way to spend an evening with friends, but it can also be destructive. Tommy Cooper illustrated this beautifully in his famous “swallowed mic” sketch many years ago!

“Gambling has brought our family together,” he said. “We had to move to a smaller house.”

Gamble responsibly, have a sense of humour and laugh about it.