The Luck of the Fictional

When you’re 15 or 16 and you read On the Road for the first time, no one has ever been luckier than Sal Paradise and Dean Moriarty as they careen from adventure to adventure, taking in women, drugs, and cities like so much fuel to be burned through and discarded. Depending on your own longings and inclinations, you either end up thinking that Sal’s the lucky one — the one with the... modicum of stability and skepticism, the one for whom the road is a choice, not a necessity — or Dean, who, for all the chaos of his life and his eventual descent into madness, bears the mythology of the True Prophet. To revisit Kerouac’s freewheeling epic as an adult is to realize the ways in which, as a kid, you were likely to equate luck with unaccountability, or recklessness, but also to remember how fiercely those old longings once burned. Even if you can no longer think of Sal or Dean as lucky creatures, you realize that you were lucky to have once thought of them that way. — Sara Jaffe

One might not think of a boy as terribly lucky when the plane he’s on (ferrying him between divorced parents) crashes in the wilderness. However, in many ways, 13-year-old Brian Roberson is lucky: Not only does he survive the crash (the pilot does not), he lands in a forest of plenty. During his 54 days in the wild, Brian learns how to create fire, make shelter, and hunt, all using the titular... hatchet that his mother had just happened to give him right before the trip—luckily, it took place before TSA restrictions went into effect. After a tornado hits Brian’s campsite, he’s able to access the crashed airplane and its survival kit, which includes an emergency transmitter that, happily for Brian, still works. Ultimately, he’s rescued and brought home. If you have to be stranded alone in the woods, having luck on your side certainly helps. — Claire Zulkey

First, how lucky is the little boy who has a zookeeper for a father? You always have playmates, you’ve always got something for show and tell, and you’re never bored. However, Piscine “Pi” Molitor Patel’s luck momentarily runs out when the freighter that’s ferrying his family and their zoo animals from Japan to Canada sinks, taking his family with it. Lucky for Pi, he manages to escape the shipwreck, along with a... hyena, a zebra, an orangutan, and a tiger. The animals aren’t terribly lucky— they all, save the tiger, kill each other.But Pi is fortunate enough to survive not just by fishing and obtaining fresh water but because of his experience with animals, as well, for he’s able to train the tiger to refrain from killing him or capsizing the boat. Ultimately, the boat washes up in Mexico and, luckily for them, both Pi and the tiger survive. — Claire Zulkey

To call Hunter S. Thompson (or his fictional alter ego, Raoul Duke) a daredevil would be a gross understatement. The original gonzo journalist wrote exclusively about situations that would scare ordinary people; if they weren’t scary enough, he’d just add more drugs to the mix. In 1967, when Hell’s Angels was originally published, the eponymous motorcycle gang inspired fear and loathing throughout America. The intrepid Thompson decided to investigate their outlaw lifestyle... and hateful worldview by going to their parties, interviewing them, and getting intoxicated alongside them. This electrifying first-person narrative could have resulted in his incarceration or death, but it didn’t, and that alone made Thompson a very lucky man.

Thompson’s good fortune also came in another form: the creation of Raoul Duke. Toward the end of the book, Thompson names his alter ego as a true outlaw in the vein of Alexander King or Elizabeth Taylor. Duke later took Thompson’s luck and ran with it, emerging as the protagonist of Fear and Loathing in Las Vegas, which cemented his (and Thompson’s) status as American rebel icons. — Arianna Stern

Mrs. Dalloway, famously, begins with flowers and closes with the eponymous flower-getter entering, finally, the room in which her long-awaited party is being held, while all the loves of her life look upon her entrance with anticipation. Luck — blooming flowers, steadfast admirers — pervades Clarissa Dalloway’s life. But so does pain, and it is that struggle — how to acknowledge oneself as a lucky person in a world so rife with... pain that one has caused and felt and witnessed — that provides one of the book’s central conflicts. Clarissa is lucky to have experienced the love of Peter Walsh and Sally Seton and luckier still to have chosen the simpler, solid Richard over both of them. She is lucky to have experienced the horrors of World War I only indirectly. But one gets the sense throughout the book that Clarissa feels a deep guilt over the luck that has been afforded her. She is lucky is to be alive, but suffers, too, the guilt of living. — Sara Jaffe