As far as cushy gigs go, this one is sweet: Fly from Los Angeles to Las Vegas on a Saturday morning, do standup comedy that night, collect $40,000 in cash. But there is a potential catch. “If I’m in a casino,” Norm MacDonald says, “I’m gonna gamble.”

One of the most talented comedians in showbiz, Norm recently released a hilarious CD, Ridiculous, and has just completed a very funny script. He had a memorable run on Saturday Night Live and has appeared in more than a dozen movies. Beyond the work, though, one constant has shadowed his career: gambling. Back in the 1990s, it was everything from blackjack to Let It Ride to occasional bouts of Casino War (“The world’s most degenerate game,” he acknowledges). These days, Norm focuses on poker, which generates a couple thousand dollars a month in profits. Best of all, it’s kept him out of the money-sucking Vegas pits. But tonight, and for the coming forty-eight hours, he will revisit the belly of the beast. He’ll put his entire paycheck at risk.

I suggest that it might be expedient if Norm gets paid in chips. He purses his lips and replies. “That would be the ultimate insult — especially if they paid me extra. It would mean that they had a read on me.”

Norm performs at House of Blues in Mandalay Bay. Dressed in baggy cotton slacks, Tommy Bahama golf shirt, and a black leather jacket, he kills. A rational view on sex has Norm skewering the less-endowed among us (“People with small cocks always say, ‘It’s not how big it is, it’s what you do with it;’ like the guys with big cocks have no clue. They’re like, ‘What do you do with it again? Put it in and then take it out? This is just too confusing. If only it were smaller and easier to maneuver.’”). In a nod to tonight’s locale, he takes off on Vegas’s famous “What happens here, stays here” ad line: “I guess all that really means is that you can fuck a whore here and she won’t tell your wife about it.” Norm deadpans. He hesitates for a beat, then wonders, “But it’s not like the whores in your hometown are gossips. A woman’s not going to be in a beauty parlor and have a whore come up to her and say, ‘You’re Ned Johnson’s wife? I know Ned. He paid me $1,000 to shit on him. What a small world.’”

After closing the show, Norm stashes half of the $40,000 in his Mandalay suite’s wall-safe. Then we cab it to the Mirage, a casino where he’s endured more than his share of tragic washouts. Like the time he began with $5,000, promptly lost $2,000, and impulsively bet his remaining $3,000 on a single hand of blackjack. “Then I got dealt two aces and had no money left,” he says. “I asked the dealer how I can split them. The dealer said, ‘Sir, you can’t. Unless you have a line of credit.’ I didn’t. So I hit. Got a ten. Hit again. Got another ten. If I had been able to split, I’d’ve had two 21s. Instead I lost the last of my money. That’s when you walk away numb. You feel blank and can’t find the elevator.”

Hoping to even things up a little, Norm enters the glistening Mirage and heads straight for a scrum of craps tables. He drops a stack of hundreds upon the felt and buys in for $10,000.

Armed with twenty purple chips, Norm soon spreads $1,500 across various wagers. He’ll be employing what he likes to call his “Pensioner’s System.” It centers around betting on Don’t Pass. “I’ve devised this as a way of bleeding my money the slowest,” says Norm, acknowledging that, over the long haul, craps is unbeatable. “After I start to win, though, I always go a little crazy. Then I reign in the fucking crazy guy with the robotic approach of my Pensioner’s System.”

An old dude, wearing sunglasses and dispassionately betting thousands, throws a seven on his fifth roll. A collective groanrises from the other players. Cool Norm, who is betting against them, smiles ever so slightly while the croupier pays him off.

♠ ♠ ♠ ♠ ♠

Norm MacDonald read Beat the Dealer at age eight and learned to count cards. Growing up on a farm in rural Canada, he passed time by dealing himself endless hands of bridge and whist. By his 12th year, he had developed into such a strong backgammon player that he was competitive on the tournament circuit. More recently he perfected an impressive memory trick: Remove any card from a deck and Norm will quickly sort through the 51 remaining cards to tell you which one you selected. It’s precisely the stunt that Chris “Jesus” Ferguson performed on ESPN. However, there’s a critical difference between famously brainy Jesus and Norm: Norm does it quicker.

Despite his mathematical acuity and interest in card games, Norm hadn’t done much gambling before he made it big on the stand-up comedy circuit and landed a job writing for the TV show Roseanne. It was 1992, long before the Hold’em boom. But Los Angeles had a lively poker scene inside its venerable card rooms.

A writer on the show introduced Norm to the Commerce Casino. Norm began playing $10/$20 7-card Stud, but things quickly escalated. “After 14 hours at Roseanne, my friend and I would spend all night at the Commerce,” remembers Norm. “It was pretty disgusting. People ate while they played, handling cards with their greasy hands. Some guys wore oxygen masks. We would play through the night, then go right back to the show.”

Norm quickly moved from Stud to Hold’em, but he was not yet good enough to win. He and his friend used to joke about the Commerce denizens being “worse than us at everything except poker. So we lose money to inferior human beings.”

Once Norm discovered Vegas, in 1993, Steve Wynn’s recently opened Mirage became his weekend getaway of choice. Though he might have been able to use Beat the Dealer skills to win at blackjack, that was never the point. He went there to gamble, not to methodically grind out a low-percentage profit. Norm never wanted a sure thing.

The dark side of his approach was driven home during a weekend trip to Vegas with his visiting aunt and mother. “I booked us a room at Treasure Island,” says Norm. “While we were waiting in line to check in, I looked at the tables, and told my mother and aunt that I’d meet them upstairs. I had $3,000 with me, no cash-advance capabilities on my credit card, and no ATM card. I started betting $100 a hand. I had four splits and lost them all. Suddenly I was playing for $500, hoping to catch up. After less than half a shoe, I was finished, completely broke. I sat up in the room for the rest of the trip, watching Matlock on TV, and listening to my aunt complaining about being down a buck-and-a-half playing nickel slots.”

♠ ♠ ♠ ♠ ♠

Five hours into Norm’s current gambling quest, it’s near dawn. Norm sits on a small stool at the far end of the craps table. It gives him a perfect view of shooters shaking dice and tossing them down the felt, hoping to hit the very numbers that will break Norm.

Holding the bones now is a blowsy redhead. She’s got a pina colada on one side of her and a pack of Marlboro Reds on the other. Baring yellow teeth and flaring her nostrils, she has been rolling for the last twenty minutes. Point by point, she’s destroying Norm.

“Siiiixxx,” the woman shouts, releasing the dice, shooting them right at Norm’s face.

The cubes bounce off a back wall and land double-threes. A roar goes up around the table. Norm remains expressionless as he loses $1,000 and drops a fresh $500 chip on the Don’t.

Right now, this seems like an impossibly lucky table. For the last couple hours, players have been going on unbelievable rushes, killing the house, and ransacking Norm’ssstack of purples.

In the midst of Norm’s negative run, an attractive blonde looks over and recognizes him. She shakes his hand, kisses his cheek, and asks for an autograph. Norm, of course, complies. It reminds him of fame’s drawback in a casino. “The worst thing is when you lose a lot of money and someone at the table thinks you’re a billionaire because you’ve been on TV a couple times,” Norm tells me. “A guy’ll see you lose $10,000 and he’ll say to everyone, ‘That’s like a dollar to us.’ But of course it isn’t. I know what it’s like to lose a dollar when you’re broke, because I’ve been broke. And, believe me, everybody cares about losing $10,000 but nobody cares about losing a dollar.”

A couple hours later things get truly ugly when a fat guy defies mathematical logic by leading out with four sevens in a row. The crowd turns frenzied. Norm’s down to his last three chips. And they’re all on the felt. Then the fat guy hits a seven mid-roll, which causes everyone at the table to lose — everyone, that is, except Norm. He palms six purple chips, smiles crookedly and says, “Still alive.” Then he shakes his head and insists, “The Pensioner’s System has never taken such a beating.”

Within 45 minutes, Norm is down $10,500 at craps. He finally steps away from the table and says, “Now let’s find a good blackjack game. I just hope I don’t go on tilt.”

Norm sits down next to a skinny, dissolute guy who’s a wearing a black jersey with French writing on the front. The guy looks up from a mess of chips, recognizes Norm from television, and says, “My mouth tastes like I just ate a box of ass.”

Norm buys in for the remaining $9,500 and runs his bankroll up to $13,000, then loses a few hands and sits out the rest of the shoe. After the guy in the French shirt hits a couple blackjacks, he looks at Norm and says, “No offense, dude, but I seem to do better when you’re not playing.”

Norm nods in agreement. Then he pushes forward a few chips as the dealer shuffles. Looking exhausted, he says, “I am feeling a little tilty.”

Within about fifteen minutes, Norm has gone through the last of his money. He steps back from the table, hears the French-shirted guy applauding for the Q-10 that he’s just been dealt. “I never get that,” says Norm, strolling toward daylight and a taxi back to the Mandalay. “Guys act so proud about getting dealt good hands. Like they actually accomplished something.”

♠ ♠ ♠ ♠ ♠

Watch an old episode of Saturday Night Live and you’ll never see Norm MacDonald onstage, joining the cast for a communal wave goodbye. That’s because while they were bidding adieu, he was already on his way out the door, eager to hit the casinos of Atlantic City.

On the most fateful of those trips, Norm had settled in at a Taj Mahal blackjack table. He bought $2,000 worth of chips and rarely bet more than a couple hundred per hand. After going through a chunk of his money, he decided to make a withdrawal from an ATM. En route, though, he ran into his gambling buddy Danny, a production assistant on SNL. Danny was playing craps, a game that Norm knew nothing about. But when Danny suggested that he make a bet, Norm tossed a $100 chip on the Pass line.

He won. Then he won again. Then he kept winning for 95 minutes. Soon he was covering numbers all over the table. Every time Norm won, the dealer asked, “Want to press your bet, sir?”

“Should I?” Norm wanted to know.

“Of course,” said the croupier.

Norm has one word for the experience: unbelievable. “The place was going crazy, and every time someone rolled, the dealer handed me a big pile of money,” recalls Norm. “I was stuffing chips in my pocket because I thought the casino would get pissed if I won too much. At the end, I said to Danny, ‘I did pretty good. I think I won about $10,000.’”

He was wrong. Sitting at a Formica counter in the Taj food-court, Norm and Danny counted the avalanche of chips. It came to $75,000. “I had never won that kind of money before,” remembers Norm. “I was on a rush, so I went to the blackjack table and started playing for $5,000 a hand. I decided I would play till I lost one hand. I won six in a row. Sonow I had like $100,000 in chips. Danny and I were in shock. We didn’t know what the fuck to do.”

They filled a paper bag with the chips and each cashed out for $9,800 ($10,000 is the threshold before casinos require a social security number). Once at home in New York, Norm stashed the paper bag full of chips in his refrigerator. He and Danny went down to A.C. every Saturday night, each armed with $9,800 in chips. The plan was to spend eleven weeks cashing out. “But I couldn’t go back to playing lowstakes, and each week I lost some of the money,” says Norm. “It took six months before the bag in my fridge was empty.”

♠ ♠ ♠ ♠ ♠

By Sunday afternoon, following the craps and blackjack debacle, Norm and I have moved from the Mandalay to the Mirage. Sprawled on the couch of his comped suite, Norm channel-surfs between a Yankee game and a Masters golf tournament, rooting against the bets he had considered making (but opted not to).

A few minutes later we head down to the sports book. Norm’s got the remaining $20,000 in his pocket and he wants to wager it on an NBA game. “Shaq’s not gonna let the Heat lose at home,” he tells me.

He steps up to the betting window and says, “I’ll take Miami for 17,000.”

He’s going for the Heat against the Mavericks and giving up two points. I’m surprised that he doesn’t bet the whole $20,000. But maybe that’s logical: Even if he blows $17,000 on basketball, he can try to recreate the A.C. craps experience with a stake of $3,000. Whatever the case, there’s no doubt that the coming game will define our Vegas adventure.

Despite the large percentage of his bankroll in play, Norm is completely calm at the tipoff. In fact, he’s already expressed a willingness to write off the weekend: “I did a good show and might lose the $40,000 that I earned. But stand-up is easy and I can always make more money.”

Today’s game proves to be a nail biter. As it goes into overtime, Norm gets a burst of confidence, insisting, “I feel like destiny is on our side.”

But is it? With 9.1 seconds to play, the Mavericks are ahead 100 to 99. For Norm and me to win our bets (I had put up a measly $100), we need a three-pointer. Dwayne Wade takes an inbound pass and drives toward the basket. We pray for him to get fouled, make his shot, and convert to three. But he’s hacked before getting the shot off. Wade lands his first from the line. We want him to miss the next, setting things up for Shaq to rebound like an avenging angel and slam it in for two. But instead, Wade stands at the line, shoots, and the ball swishes in perfectly. Heat fans go wild. We hang our heads in misery. The Heat win by a lousy point. We lose by a lousy point.

Norm looks a little disgusted but he still makes a joke of the whole thing: “This would have been a great game to watch if we didn’t have any money on it.”

We agree to meet in the morning and take a last stand with the remaining $3,000.

Next day, over lunch in the Mirage coffee shop, Norm and I hatch a plan. He will start out betting small at blackjack and parlay his way back to solvency. Sounds like a good idea until, three hands in, Norm loses patience. The 3,000 is gone before the dealer’s divvied out half a shoe.

Norm heads up to his suite, appearing beaten down. When I meet him there, he presents an idea: “Loan me $10,000.”

“Norm, I don’t have that kind of money on me.”

“Use your ATM card.”

“Sorry, but I don’t have an extra $10,000 lying around. Why don’t you use your card?”

“I didn’t bring it with me. I don’t bring it to Vegas anymore.”

Then he asks, “What about an advance on your credit card?”

“I don’t think my credit card is set up for cash advances.”

“Yeah, it is. Every credit card is.”

Not a great situation. But I’m feeling guilty, like maybe if we weren’t doing the story he wouldn’t have blown through $40,000. So I agree to call Visa and see if I can get cash. Amazingly, I’ve got $50,000 available. But I’m still not comfortable borrowing the money so I can loan it to Norm for gambling.

Norm places a call to a mutual friend and asks, “How can I get some money? I want to go down and play. Kaplan obviously doesn’t trust me. If I just had $1,000, then at least I could play poker.”

It’s not an issue of trust. I have complete faith that Norm would pay me back. It’s more a lack of comfort in loaning $10,000 to anyone. But what about $1,000? “Okay, Norm,” I say, “I’ll loan you a thousand.”

He immediately hangs up and we head down to the poker room. I extract $1,000 from the ATM machine and give it to Norm. He strolls over to a $40/$80 Texas Hold’em game. I sit down at the pitiful $3/$6. A couple hands in, Norm comes by and reports that the $40/$80 table is full. “I’m going to play craps,” he jauntily tells me. “See you in three minutes.”

Pretty much true to his word, Norm is back in eight minutes. “Oh, well,” he tells me. “I bet the $1,000 and won. Then I kept doubling until I ran it up to $8,000. Then I bet table max [$5,000] and lost. Then I bet the remaining $3,000 and lost that.”

“You kept betting all your money?” I ask, a little incredulous, trying to focus on the poker.

“Yeah,” he says. “That’s what I always do at the end of a trip. But if you had loaned me the $10,000, I’d’ve run it up to at least 30, and I’d still be playing.”

Do I feel like a little bit of a pussy for not having fronted him the $10,000? Yes.

Do I think he’d be capable of running it up to $30,000 or even $100,000 and losing it all in a very short period of time? Yes.

Would I have loaned him the whole $10,000, if I thought he’d be so cavalier with it?

As if reading my mind, Norm says, “I didn’t want to tell you that I’d bet $5,000 at a time. I figured you’d never loan me the money then.”

♠ ♠ ♠ ♠ ♠

A few weeks later, Norm is back in Las Vegas, competing in preliminary World Series of Poker events and doing great. He plays eleven single table tournaments and cashes in all of them for a total of $25,000. Feeling confident, he enters a big $1,000 buy-in tourney at the Bellagio, outplays a passel of pros, and finishes second to collect $22,000. Then, on opening day of the Main Event, I happen to be in Vegas and spy Norm at a craps table.

He’s got a bunch of chips scattered across the felt.

“Employing the Pensioner’s System?” I ask.

“No,” he replies. “I’m playing like a guy on tilt because he just got knocked out of the World Series.”

Turns out that Norm was running great at the poker table. He built his starting stack up to $60,000 in seven hours and was briefly chip leader. Then, within an hour, he busted out after a succession of bad beats.

Noticing his fortress of yellows, I say, “Looks like you’re doing pretty well, here.”

“I’m ahead 25,000,” he replies. “But this isn’t where I wanted to get lucky tonight.”

Nevertheless, he winds up winning $100,000 during compulsive rounds of craps and blackjack. And, Norm assures, the $1,000 he owes me has already been put in the post.

Sure enough, when I return home and retrieve my mail, I see an envelope with Norm’s return address across the top. Inside is a check for $1,000, along with a handwritten note. It reads, “Better sorry than safe.”