Gambling Heartbreak is No Joke, But Sometimes it’s Funny

This is a funny story about the pitfalls, or in some cases the horrors, of gambling. Let’s call it a dark comedy. We’ve all felt the sting of an agonizing casino loss. The kind that breaks the budget and causes regret, and it can be devastating to deal with. The remorse of a wager gone wrong can not only dig deep into your pockets, but your soul as well. So why not treat it with a little humour?

Norm Macdonald is all too familiar with that raw, gut-wrenching emotion. The Canadian stand-up comedian, writer and actor has been to that place of dread and doom. Not once, not twice, but three-times. Yes, he’s gone broke and lost it all on three occasions to sports betting, and once dropped $400,000 on a single game. His team lost. Not for the faint of heart. While it’s important to note gambling addiction is no joke, sometimes it’s meaningful to have a sense of humour about it all and find the funny side. And, for comics like Macdonald, laughter is always the best medicine.

Norm MacDonald

“They call gambling a disease, but it’s the only disease where you can win a bunch of money,” he once said during an appearance on The Howard Stern Show.

If only Macdonald had the same luck in the casino as he’s had in Hollywood. The 60-year old Ottawa-native has had an illustrious career. He’s written for the hit show Roseanne, made guest appearances on The Drew Carey Show and Newsradio, and has also starred in his own sitcom, The Norm Show. He is best known for hosting ‘Weekend Update’ on Saturday Night Live in the nineties, a gig he was subsequently fired from. Macdonald has also graced the big screen on numerous occasions, appearing in such films as Billy MadisonThe People Versus Larry Flynt and Deuce Bigalow.

Poker fans will no doubt remember him from Season 7 of High Stakes Poker in 2011, when he replaced Game Kaplan (Welcome Back Kotter) as Kara Scott’s co-host.


Macdonald has the ability and humour to laugh at himself, and his now legendary rounds on the late-night talk show circuit are certainly proof of that. He’s managed to use his celebrity status to share with others the dangers of problem gambling. “I was never superstitious,” he told Conan O’Brien, during one of his several appearances on the show. A smile crept across his face, as if he was excited about the punchline he was soon to deliver.

I was always a doubting Thomas, but then I had a dream and it changed everything. It was of a giant number seven, and it was the most vivid dream I ever had. When I woke up, I looked over at my clock and it was seven o’clock. Then, I decided to go to the race track, I like playing the ponies, so I took a cab. It was taxi number seven. Now, I was getting freaked out. I asked, “what do I owe you fella?” He said, “$7.77.” I entered the track through gate number seven, and proceeded to cashier number seven. I was looking at the racing program, and in the seventh race, there was a horse named ‘Lucky Seven.’ So, I pulled out all my money, $700, and told the clerk to put it all on ‘Lucky Seven in the seventh.’ I watched the race, and damn if he didn’t come in seventh.Norm MacDonald

Lucky Numbers

Known for his surreal humour and deadpan delivery, Mitch Hedberg seemed more like a rock star than a stand-up comedian. His jokes were quick and absurd, one-liners and non-sequiturs, and his on-stage persona garnered a cult like following. The audience would often shout out punchlines before he could finish the jokes. Along with his three comedy CDs; Strategic Grill LocationsMitch All Together ad Do You Believe in Gosh?, the last of which was released posthumously, he also starred at Montreal’s Just for Laughs comedy festival three times (1998, 2001, and 2004).

“My lucky number is four-billion, but that doesn’t come in too handy when you’re gambling. ‘Come on 4-billion, f— seven!’ Not even close. I need some more dice. Four-billion divided by six, at least.”

During one routine, Hedberg left his audience in hysterics after admitting he liked to play blackjack. “I’m not addicted to gambling,” he quipped. “I’m addicted to sitting in a semi-circle.” He then followed with this thing of beauty:

“My friend is a blackjack dealer and, on his forearm, he has a tattoo of an ace and a jack. I am a blackjack player. On my forearm, I’m gonna get a tattoo of a ten and a two, and then later maybe a king.”

Tragically, Hedberg died in 2005 due to a cocaine overdose. He was just 37.

Super Bowl or Bust

Artie Lange is another funny guy, who’s been haunted by some demons. After making his mark on the sketch comedy show Mad TV, he became ultra-famous for his quick-witted humour as part of The Howard Stern Show. He has also starred alongside the aforementioned Norm Macdonald in the movie Dirty Work. Just one of his long list of film credits. Who can forget Beer League?

Lange is also a prolific writer and live on-stage performer. He has authored three books, Too Fat to Fish (2009), Crash and Burn (2014), and Wanna Bet?: A Degenerate Gambler’s Guide to Living on the Edge (2018), to go along with his three CDs, It’s the Whiskey Talkin’ (2004), Artie Lange: Jack and Coke (2009), and The Stench of Failure (2014).

In his Comedy Central feature, The Stench of Failure, Lange detailed the pain associated with degenerate gambling. “Every year, from the age of 17 to 42,” he recalled with self-deprecation. “I had at least $5,000 riding on the coin toss of the Super Bowl. You know you’re a loser when you’re down five-grand before the game even starts.”

“You know you’re a degenerate gambler when it’s 4 a.m., at the sports book in Vegas, and you’re asking random strangers, ‘have you seen the high school lacrosse scores?’”

Gambling isn’t his only vice, either. Lange has also battled cocaine and heroin addiction, and has attempted suicide a few times. Today, he is clean and sober, and only backing himself as host of the Artie Lange Podcast, which has close to 45,000 subscribers on YouTube.

Punchlines & Prophecies

Over the years, stand-up comedians have used humour to deflect the pains associated with gambling, specifically the losses. “I used to be a heavy gambler,” the great Steve Allen once admitted. “Now, I only make mental bets. That’s how I lost my mind.”

Louie Anderson, widely regarded as one of the funniest stand-ups ever, said the fun thing about gambling is “you feel like you’re a little kid getting away with something. You’re throwing money away, you’re not telling anyone, and then you lie to them. ‘How’d you do?’ ‘I’m about even.’”

Here is a joke credited to Jack Yelton: “There is a very easy way to return from a casino with a small fortune: go there with a large one.

In a live routine posted to YouTube, Billy Blank explained how his mother gambled away Christmas on the slot machines one year. “But Mom, Santa came last year? ‘Yeah, Santa got three sevens last year.’”

Let’s Go Gamble

Sebastian Maniscalco, a Chicago comedian with five television specials to his name, puts his wife in the role of problem gambler during his bits, detailing how she once lost $100 in less than five minutes playing the slots.

“Relax, enjoy the spin,” he’d say. “Enjoy the cherry and the tangerine. We haven’t even checked in yet.”

“I’ve got a feeling,” his wife would counter, anxious for more action. “Yeah, I’ve got a feeling too, that we’re not going to be eating tonight, cash-out!”

Sebastian Maniscalco

Gambling can be fun and entertaining, and a night out at your local casino with a group of friends should be a rewarding venture, whether you’ve won money or not. But, it can also be a destructive force, something Tommy Cooper illustrated nicely.

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

Please gamble responsibly, and if you’re unlucky, at least try have a sense of humour and laugh about it.

Derrick Oliver

Derrick Oliver

Derrick Oliver Dewan is the founder of High Roller Radio, and has interviewed a number of the world’s top poker players including Chris Moneymaker, Greg Raymer and Barbara Enright. A former, long-time radio and television broadcaster, Derrick has always had a passion for all things gambling (and darts too). He has even played at the World Series of Poker and other cash games all around the world.

To see more of Derrick is up to on a day-to-day basis, go follow him on Twitter @HighRollerRadio


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