7 Fictional Characters We’re Dying to Take with Us On Spring Break

The Wild Card: Dean Moriarty from On the Road, by Jack Kerouac
Moriarty, a.k.a. Neal Cassady in real life, was a key figure in the greatest road novel of all time, and was, by all accounts, the sort of deranged, try-anything free spirit every spring break squad needs. He’s the guy who pushes you to pursue adventures, disregard posted signs, and explore places that aren’t in the guide books. He’s also the reason every good spring break trip needs a generous Bail Fund, but hey, experiences of a lifetime don’t come free.

The Infiltrator: Holly Golightly from Breakfast at Tiffany’s, by Truman Capote
While a freewheeling wild card is necessary to inject that buzzing electrical line of crazy into your spring break, you also need someone who cleans up well and can talk their way into anything, and gorgeous and determined Holly is perfect. Whether it’s a party you weren’t invited to, a restaurant that claims to have no reservations, or a police station where Dean Moriarty is being held on suspicion of awesomeness, a Holly Golightly will chatter her way in and dance her way out. As an added bonus, she’s an expert party-thrower, so if things get slow she’ll soon set things right.

The Tour Guide: Boris from The Goldfinch, by Donna Tartt
When in unknown climes, it’s essential to have a world traveler who is not only connected, knowledgeable, and perhaps just a little shady, but also a lot of fun to be around. Anyone who has read The Goldfinch knows that while the actual main character can be a drag at times, Boris is always reliable fun, the sort of guy who can find anything, anywhere, and seems to always know at least one person at whatever party, bar, or jail he happens to be visiting. Spring breakers need a Boris to find supplies, to make connections, and to arrange transportation while entertaining the heck out of you.

The Outlaw Lawyer: Raoul Duke from Fear and Loathing in Las Vegas, by Hunter S. Thompson
Okay, we all know what we really mean is Hunter S. Thompson himself, and we also know that Mr. Duke isn’t the lawyer in the book, his associate Dr. Gonzo is—but we don’t mean a literal lawyer (unless, of course, you’re having a truly epic spring break, in which case yes, we mean a literal lawyer). We mean an Adventure Lawyer, the sort of person who can talk you through barriers, find loopholes in local regulations, and navigate various states of consciousness with aplomb, and that would be Mr. Duke, who can handle the local authorities and hallucinations with equal ease.

The Bank: Jay Gatsby from The Great Gatsby, by F. Scott Fitzgerald
Someone has to pay for everything, right? And that someone needs to be a person who understands and appreciates a good party. Congratulations, we just described Jay Gatsby, a filthy rich romantic who sees a grand party as the best way to communicate his thoughts and feelings. Whatever Gatsby is feeling while you’re on spring break, he will seek to express that feeling by funding a lavish party, and one can imagine Gatsby, with his links to organized crime, is also no stranger to funding bail on occasion, also a key skill for any spring break squad member.

The Security Detail: Deadpool
The best spring breaks are like the best weddings: there’s gonna be fisticuffs. Whenever various groups of people are wandering around seeking fun and adventure, those groups are going to find themselves at odds with each other, and you’re going to need someone who can kick a little butt and keep everyone safe and the party on course. At the same time, you want someone who’s fun to hang out with on those rare occasions when you’re not fighting with opposing party people. Plus, a man who can heal from almost any wound is ultimately very useful, because statistics show at least 50% of all spring break trips end in West Side Story–style knife fights.

The Wizard: Harry Dresden from The Dresden Files, by Jim Butcher
Finally, since we’re imagining literary characters accompanying us on our spring break adventure, why wouldn’t you want a wizard? Magic solves a remarkable number of problems, ranging from hobgoblin attack to bogarted beer kegs, possession by demons to incarceration. While someone like Gandalf or Dumbledore might have the magical chops, they don’t exactly seem like monster party people—but Harry Dresden would be a lot of fun to hang out with even when there’s no need for magic. Plus he doesn’t dress like a priest of some sort, and it won’t look like you’re hanging out with your grandpa while you’re on spring break.