Random follows Bobby Ingersoll, a Las Vegas native who has done a fairly good job of keeping his nose clean. His dad, David, on the other hand, has not. David Ingersoll owes a lot of money to a loan shark by the name of Fraser Ruphart, and the 2.2 million dollar debt is due on Bobby's 21st birthday. If David can't pay the money back by the encroaching deadline, Ruphart has decided to make an example out of David's entire family. So Bobby has to find a way to collect more money than he has ever seen in just a couple of days, if he hopes to see the end of the week.
After several attempts to borrow, lie, cheat and steal the money, he can't help but notice that he is often racked with indecision at the worst possible times. After only a little success, Bobby ends up watching a gang deal gone wrong and by random circumstances, he finds himself in possession of a bag of money and none the wiser to who has it. He then puts his faith in that same randomness in a Hail Mary play at a roulette wheel by putting over 500 thousand dollars on eleven and walking out a multi-millionaire.
Not only does Bobby save the Ingersoll family from Ruphart's enforcers, but it also changes Bobby's life forever. Sure, the money changes his life in a lot of ways, but the biggest change is a newfound faith in Random. With a set of fair dice in his pocket, Bobby has decided to trust Random, not as a deity, fate, or even really a force of the world, but as a way to help him make decisions if he has even the slightest question about what to do. Granted, he wouldn't be able to make these decisions if he wasn't now a millionaire, but with his new world view, at any roll of the dice, he could end up giving that money away to a charity, or even some homeless guy on the street. The decision to go Random frees Bobby in a way he is immediately attracted to.
Bobby's new lifestyle is a strange way to live, and Jillette spends a good bit of the early book explaining living by Random through many examples before the story's main plot points really pick up.
Basically, Bobby only uses the dice when he doesn't immediately know what to do in a situation. He never presents himself with options he doesn't actually want to do, so when the dice help him decide, he immediately acts without looking back. The trick is, Bobby is retrospective enough to know how much he wants to do each of the options he is presented, and he knows the chances each number a pair of six-sided dice can land on has. If he has a desire to give all his money away, but only a small desire, he will assign it one of the lesser chance numbers, but if there is something he really wants to do, then maybe it gets several numbers that have a higher chance of happening. Maybe each choice is different, and maybe they are all variations of each other. The point is, they are all things he would be happy doing, he just needs some help actually deciding.
For example, he wants to order coffee. There are some flavors he might want to try, but wouldn't really order on a normal day. Those get the lower percentage chance numbers. His favorite flavors get the ones that are most likely to come up. When the dice roll and he chooses one of the unusual flavors, he finds he is delighted to try a coffee that he wouldn't normally have chosen without the dice. While Bobby uses the dice for a lot of little decisions like coffee or how to dress, he also uses them for bigger decisions like going vegetarian.
At one point, Bobby decides he wants to seriously help people, so he gives Random a few choices that range from dressing up like Batman to buying a detective agency in order to have a licensed investigator help him look for interesting cases. While the Batman option is appealing to Bobby, Random lands on buying out a PI and starting Last Chance Investigations.
While Bobby is looking for his first real case, what he doesn't realize is that Ruphart has been holding a grudge against him. Not only did the loan shark really want to make an example out of the Ingersolls, but the way that Bobby paid Ruphart off left the man feeling insulted. The problem is, everyone knows that the Ingersoll family is debt free, so if Bobby is going to die, it can't be connected to Ruphart. While killing people who don't pay your debt is an understandable response in his business, killing those that do pay means people stop going to you for loans.
Unfortunately for Bobby, Ruphart isn't the only person gunning for him. As Bobby digs into a case involving a gambler being black booked by the casinos, he inadvertently stumbles onto a more sinister plot with someone who has even fewer scruples about killing than Ruphart does. Random helps Bobby stay alive, but considering the fact that Random put him in this situation to begin with, this new life style isn't really something that can be condoned.
Bobby's story ends up going all over the place as his dice rolls lead this character in and out of some unexpected situations. And while the ending is just as unusual as Bobby's lifestyle, it is very fitting to the story as a whole. Usually a character having agency or not is a key point to how well the story is developed, but this character willingly gives up his agency. Sure, each choice is something he wants to do, but what he actually does is at the will of Random (AKA Penn Jillette). There is even a point in the book where the narrator explains to the reader that the best way to get Bobby where the story needs him to go is just to have the dice push Bobby in that direction. For most books, I would say that this is a product of lazy writing, but on the other hand, this is literally the focus of the book and I cannot condemn Jillette for using it. I couldn't help but draw some comparisons, in this regard, to Robert Jordan's Ta'veren in The Wheel of Time. Jordan built in a magic system that let him move his characters how he wanted and he could just hand wave what could easily be seen as bad writing, but is actually a part of the world. That is essentially what Jillette does in Random. It both amuses and infuriates me, which feels like exactly the type of reaction Jillette would want.
On a final note, I feel I need to address the very adult nature of this novel. Many elements of it are crude and vulgar and often in a very over the top way. Bobby's dice rolling, especially early in his life under Random, leads him into a lot of adult situations. After all, with money as no object and your every wish just a dice roll away, you could end up experiencing a lot of different things you wouldn't have let yourself experience otherwise. If you are even slightly prudish, I would pass on this book, even if the concept really appeals to you. I would never consider myself a prude, but there were times that I just had to walk away from the book for a time. All that being said, this isn't necessarily an unexpected aspect of Random. Like I said at the start of this review, those who have followed Jillette know he does not shy away from adult themes, so this should not come as a surprise to you. Just know that you are now warned.
Still, I enjoyed Random. The book explored an interesting story that could have gone very differently if someone actually tried to live by the dice in this manner, but then again, if Bobby's life had immediately crashed and burned, it would not have made for a very interesting novel.
