Life’s a Gamble

In ‘Random,’ the second novel from celebrity magician Penn Jillette, everything rests on a roll of the dice

In his second novel, Random, Penn Jillette has taken a deep dive into a world he’s swum in for so long: Las Vegas, the frequent home of the comedy and magic act he does with Teller.

This, though, is not Vegas glitz and glamor. This is the scummy underbelly of the gambling life, Las Vegas being a zone where the visitor and tempted-gambler should never forget the house always has the advantage. An observation Jillette makes about the sad money-losing throng outside the casinos, “the slow desperation of the night of the gambling dead.”

Penn Jillette (photo: Francis George).

Jillette’s protagonist is Bobby Ingersoll, who has had the stroke of bad luck to be born the son of a compulsive, cheating gambler. Dave Ingersoll is an asshole deadbeat saddled with a $2.5 million debt. The due date is approaching. Fraser Ruphart, the Las Vegas loan shark (among other things) he’s indebted to, has no trouble at all rationalizing the murder of not just daddy gambler, but the rape and murder of his wife, daughter and son (Bobby). Sure, Ruphart–pronounced Rupe-Hart not Rufart, mind you–wouldn’t collect the dough, but it’s all about messaging: Ya think the other gambler/debtors are not going to find a way to pay up after this carnage? And, really, Ruphart thinks, he’d get as much pleasure out of ordering the killing as he would the collecting. He doesn’t get wet; he farms out the torture.

That’s the set-up for Jillette’s nasty (meant as a compliment) new novel. Random is rife with bad actors, dark humor, a name-check of the avant-rock band the Residents, the Velvet Underground and Prince, song lyric quotes from the Sex Pistols, Megadeth and Joe Ely, and cynical/realist philosophizing from Jillette.

It also veers into the flashback reality of the author appearing on Celebrity Apprentice and the author’s utter amazement that Donald Trump called him one of the three people he’d ever met who was smarter than him: “Who were the other two, a balloon twister and a ventriloquist?”

In Random, the clock is always ticking. Bobby, on the verge of turning 21 (and thus able to gamble in a casino himself), is taking it upon himself to try–somehow, against all odds–to raise the money within a very short window of time to repay daddy’s debt. He borrows from a friend. He knocks over a convenience store called Stop ‘n’ Rob. His take is not even close.  The impossible dream looks truly impossible. Certain, painful death looms.


So it’s especially fortuitous that Bobby pilots his quiet electric Vespa scooter into the maw of a bloody gang fight and, in the mayhem, recovers a Gucci bag filled with a substantial amount of drug money. He’s invisible to the gunslinging gangbangers and quietly slips away with the bag. Alas, he finds he’s not got enough cash to cover the debt. But maybe he could do something with it. As he turns legal age, Bobby enters a casino, places the entire pile on 11 in a craps game–winning is a 5.6 percent possibility–and comes up with $7,117,980.

He can now pay off the debt, buy his mom a new house, set his smart sister up for medical school, while telling dad to hit the fucking road and get out of their lives. He can also get massive body tattoos honoring the No. 11 and pay to have sex with pretty much anyone in any combination. Basically, Bobby, he can pretty much live however he chooses.

He brings Ruphart the cash. Ruphart, however, wasn’t pleased with Bobby’s method of delivery. Along with the $2.5 million he brought a Hawaiian pizza, a known insult to every human, and, yes, Ruphart takes the slight seriously. Bobby doesn’t know it yet, but he’s still on the hit list.

Bobby, like Jillette, is an ardent atheist, but he does find a higher power: The dice roll changed his life. The fact that this random number set him up. He now lives by the rule of Random. Decisions are made by a roll of the dice. Not all of the decisions. He makes some on his own, but many others he trusts to the throw of his dice. Or, as Bobby explains, “When I have doubt about what I want to do next, I give the Dice choices that some part of me really wants and all are possible. I roll the dice and all the doubt and indecision go away. I just have to lay out my options.”

Writes Jillette in the third-person omniscient voice: “The pair of Dice was now God. They felt good in his pocket.” The Dice –note the capital D–were cold and objective, showed no mercy or favoritism. And if Dice was Bobby’s religion, writes Jillette, “Religion is so easy. It’s easy to believe in god like it’s easy to believe in fat and salt. We know it’s not good for us, but we do it. We are compelled.”

Bobby knows the probability of each roll of the dice and assigns the potential choices accordingly – the thing he wants to do most will likely be in the 6-7-8 zone but those fringe things that lurk in the recesses of his mind at 2 and 3 or 11 and 12, well, he’ll follow the plan if they come up. Group bisexuality is in the mix, as is going to Starbucks.

Jillette’s point, one of them anyway, is that much of what we decide is indeed random, whether we know it or not and that’s not necessarily a bad thing. The best laid plans and all that. We consciously or subconsciously weigh a myriad of decisions, some consequential and others inconsequential, and sometimes base that decision on what we think is logical. But maybe the logic is faulty, not to mention often less adventurous. Maybe the less boring ploy would be to trust the thoroughly random roll of the dice, metaphorical for us, literal for Bobby.

It sure takes Bobby to some wild places. Like buying a detective agency, where he has the owner stay on as boss and he serves as an intern, until a big case comes and he can pursue it as an amateur gumshoe. The electronic billboard for the agency solicits losers with lost causes. The first customer is cowboy Bill, another casino guy who’s won big at craps, but for reasons that could be sketchy.

There’s also a particular sex/love interest for Bobby, Terri, a buxom blonde big-ticket lottery winner. After watching a mini-orgy with her and a couple of others in her McMansion, they meet up downstairs in the kitchen. Bobby describes her as wearing a t-shirt that didn’t cover anything below her waist “with her pussy showing, like Debbie Harry in the seventies, even the same wispy, just-fucked hair.”

On the back of the book jacket, there’s a blurb from Debbie Harry: “Bravo, Bobby Ingersoll. Encore, Penn Jillette!”

That’s about as much of Random I feel comfortable revealing. Well, one more thing about Bobby’s character: He can listen to Celine Dion unironically. Trust me, there are countless twists and turns, barbs, broadsides and magician in-jokes within the body of what I’ve just described, and this is not much more than bits from the first half of the book. So, plot-wise, I’ll leave it there.

Something that happens a couple of times: Jillette – the author – breaks through the fourth wall, steps in to explain, say, some bad-decision making on Bobby’s part that Jillette, of course, wrote reminding us this is a novel and not non-fiction.

Jillette has written four non-fiction books on his own and two with Teller. Sock was his first novel in 2004. In Random, Jillette taps into material from his own life as a wiseass magician/smartest-guy-in-the-room/very public atheist/skeptic and throws one of his magician pals Piff the Magic Dragon into the expository, humorous mix. You’ll likely find him amusing and irritating (tilted toward the former), not unlike the Penn you’ve seen onstage or pontificating on TV. But, ultimately, he’s a convincing sonofabitch and a wily tale-teller and you’re happy to go along for the ride. Just be aware there are a lot of crashes along the route.

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Jim Sullivan

Jim Sullivan wrote about pop music and culture for the Boston Globe from 1979-2005 and currently is doing the same for WBUR’s ARTery and Rock and Roll Globe among other websites and outlets.

One thought on “Life’s a Gamble

  • January 31, 2023 at 8:21 pm

    Is this just a reboot of Luke Rhinehart’s novel, Dice Man?


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