Some gambling stories are downright hilarious, while others make you want to stop and think first. Like, ‘Is that funny or sad?’ Here are four scenarios that we find funny.

Gambling is serious business with potentially big wins and losses, so players are expected to take it very seriously, right? Wrong. While winning is what you expect when you get into a good gamble, you are wise to expect a loss here and there, especially when playing games of chance such as slots or craps. There have been various stories in the land-based casino as well as the online world that make you cringe, some that get you mad, and yet others that deserve a good laugh. We dig into some bitter-sweet moments that happen when people open their purses and placed bets.

Umm, and that was School Fees

A British player watched Angola thrash Mali 4-0 in an Africa Cup of Nations match. With only 10 minutes to go, he decided to put all his 4,400pounds into the match, with Angola as the obvious favorites. Well, his ancestors must have been looking sideways because, in the few minutes left till the end of the match, Mali made an unexpected comeback, matching their opponents in goals. The match ended in a draw, and the student lost his entire loot, which, sadly, was his entire student loan. Even sadder was the fact that his earnings would have been 44 pounds only and not the 440 pounds he had hoped for had his team won. When it rains, it pours, right?

Grandma’s on a Roll!

When Patricia Demauro checked into a casino in Macau, she probably only had plans to have a good time with her pals and maybe win a few dollars from playing craps. A solid plan anyone would have when checking into casinos that accept Australian players and others, right? Well, fate had other plans. While this was no Aussie online casino, she did roll the dice 154 times without sevening out. Her initial bet was $100, and for 4 hours and 18 minutes, she was on a roll, almost literally. The odds of rolling out 154 times without sevening out are 1.56 trillion to 1, and she did it!

Demauro did not reveal her winnings, but it is suspected they ran into the hundreds of thousands, or even millions, given her bet size. To make her win even more celebration-worthy, this was her first time playing craps in a while. Grammy set a Guinness World Record for her feat.

Let’s Charge that to Alcohol, Shall We?

If you thought only online casinos bring out the interesting stuff, you haven’t heard land-based gambling with funny stories. One Nebraska businessman, Terrence Watanabe, went gambling at the Caesars Palace and Rio All-Suite. Here, he spent enough to be offered complimentary drinks and food as casinos are wont to offer. He ended up losing $127 million and suing that on the house for filling him up on drinks and painkillers that he said caused him to lose himself on the casino floor. The court threw his case out when it was established that Wynn Casino had banned him from drinking on the casino floor. Couldn’t blame anyone now, could he?

You Snooze, I Win

A story is told of 8-year old Aashish Nanak from India, who snuck into his uncle’s online casino account and won an equivalent of $500,000. While the rule at many casino sites, such as Parimatch casino, is for participants to be at least 18 or the legal gambling age allowed in their country, this youngling didn’t recognize that. Because the casino he played poker at has similar regulations, they refused to pay out the rewards, claiming not to have known how young he was all along. It was later revealed during hearings that the casino’s staff referred to him as “the little poker wizard,” so they must have known he was underage. The court’s decision was unconfirmed online, but he sure deserved to be paid for his troubles, didn’t he?

A Good Laugh a Day…

Do you have hilarious real money gaming stories that have made you double over with laughter? While losing money while gambling isn’t the funniest thing, it sometimes makes for laughable lessons. In the end, everyone is urged to gamble responsibly and for the love of God, not to risk money they cannot afford to lose – like school fees.