Illustrations by Anne Scotti

There is rarely any consolation prize for getting the middle seat on a plane—but, as staff writer Naomi Sharp found on a recent Spirit Airlines flight, sitting next to and meeting Jimmy Failla was one of them. “Maybe we all forgot to pay the extra fee for departure,” he reasoned good-naturedly, as passengers on the notoriously cheap airline grumbled about delays. Failla is not a worrier—as he puts it, “things don’t stress you out that much once you’ve driven a cab in New York.” The stand-up comedian, radio host, and soon-to-be author will chronicle his experiences as a cab driver in his first book, scheduled for release in the fall of 2013. This B&W staff writer from seat 10B (who, she has been informed, sleeps like his dog), sat down with Failla to hear his take on offensive humor, New York City, and why the best conversations in the world are between prostitutes and cab drivers.

The Blue and White: Your book is called Follow That Car: A Cabbie’s Guide To Conquering Fears, Achieving Dreams, and Finding a Public Restroom. Which is the hardest of the three?

Jimmy Failla: Definitely the restroom. It’s not even close. What is the easiest? Achieving dreams.

B&W: Really?

JF: Yeah, because you can adjust them. I had different dreams before I started driving a cab. It started out like, “I’m gonna sell this screenplay,” and “I’m gonna host the Tonight Show,” and then twelve hours later it was like, “I do not want to get stabbed doing this.”

I drove a cab for nine months in 2008, before the birth of my son. I originally drove it because I needed the money and I wanted to learn things, and then I kept driving it because I was crazy. And you have to be a little nuts to drive a cab.

B&W: Most other drivers are a little nuts?

JF: It really depends. There are a lot of guys driving cabs that are geniuses in other countries that aren’t licensed to practice heart surgery here. Then there are a lot of guys who are driving cabs in their 70s and 80s. It’s a lifestyle for a lot of people. You have two twelve-hour shifts you can work, but you do whatever you want during those twelve hours.

B&W: You do stand-up comedy. Do you think that New Yorkers need comedy more than other people?

JF: We have more self-made problems than the rest of the country. The rest of the country’s really easy-going. They aren’t as competitive as us, they aren’t as judgmental as us. and I think they live a better life in the sense that they’re not as bothered by a rat race.

Do New Yorkers need to know how to laugh more? No, but I think they laugh easier, because they’re more self-aware. I just think it’s that we are a lot darker.

There’s so many of us. There’s such a cross-pollination of classes here. A cab’s the best example. You’ll drive a billionaire, and then you’ll drive some borderline homeless person. You’ll drive a pro ball player, but then you’ll drive a hooker, and then you’ll drive a nun. I’ve driven a nun and a hooker back-to-back. I’ve driven Clay Henry, the beer-drinking goat.

B&W: Excuse me?

JF: Yeah, yeah. From Texas. I drove a guy, I picked him up on 14th street, and his goat was drinking beer. Long-neck bottles of beer.

B&W: You drove a drunk goat.

JF: A drunk goat.

B&W: Was that your strangest passenger?

JF: I had a woman get in with two sock puppets, and only communicate with them. That’s up there. I had a guy in my cab who was in the plane that crashed in the Hudson. I dropped him off at LaGuardia and I had his flight papers still in my cab when he got out. And when I heard the flight number, I was like, I know one of those guys. I had someone leave a bag of cocaine the size of a pillowcase in my cab. That was the scariest thing.

B&W: Your book is a collection of the different advice that you got from passengers in your cab.

JF: It’s the best advice I was given while driving a cab. And I did not solicit it. I’ve repeated it to other customers to get feedback on it, but only if it came up in conversation. If somebody got in and was really depressed, I might share a depression strategy that somebody gave me.

A woman once explained to me spiritual currency. She said it was basically just the power of compliments—like, if you are really feeling awful and you can just bring it upon yourself to go compliment somebody, you’ll see them animate a little bit more, and it’ll make you aware of your own power. Because you know how depression kind of tells you you’re pointless and you’ve got no wherewithal to do anything? She called it spiritual currency.

B&W: What’s the best advice you’ve ever gotten from a passenger?

JF: Dennis Hopper basically told me that your whole life is just about being authentic.  Just surround yourself with people you can be yourself in front of. Date the person who makes you feel like yourself, hang out with the people who make you feel like yourself. If you’re policing yourself, if you’re editing the content of your life so it can fit into this little cookie cutter that these people have built around you, it’s not sustainable.

B&W: What’s the worst advice a passenger ever gave you?

JF: Take the 59th street bridge to LaGuardia. That is definitely the worst advice. You’re never getting there. That is like vehicular purgatory.

B&W: The jobs that you’ve done all require you to interact with people in some way. Is reading your audience a skill that you think you have naturally, and to what extent did you develop that consciously?

JF: The best conversationalists in the world are the best listeners—they’re not the best talkers. If you listen to your audience, they tell you what you want more of. I think I’ve acquired that skill—I got used to listening to people. In a cab, you can tell where they want to go in conversation if you’re listening. If you’re driving, you won’t get there.

The best conversations on this planet have taken place between cab drivers and prostitutes. They’re the only two people in society who truly interact with everybody, and get to know the city the way a proctologist gets to know a patient. Everybody a hooker picks up—they know, within a minute, what that person’s life was.  They know if it’s a cheating spouse, they know—let’s say you’re a male prostitute. The minute you pick up a customer, you know if he’s a married guy claiming to be straight. They know your demographic when they look at you, because they do it in such volume that it becomes impossible not to know.

You can tell when someone wants to buy something from you—emotionally or physically, whatever it is—and they don’t know how to reach for their checkbook, so you get it out of them. You can tell when somebody wants to unburden themselves.

B&W: So if people tell you some sort of confession, are they usually the ones who start that conversation?

JF: Most people talk to you. If you talk to them, they talk back. Because instinctively, we want to talk to people. Even though technology is driving us away from human interaction, our instincts prefer a person. It’s like when you call customer service and you have to shout the prompts into the phone. There’s nobody in that moment that doesn’t wish they had a person. Do you know how many people a day scream “Give me an effing person!” into voice prompts? Because your instincts are people. People want people.

People just need to unburden themselves. People confessing to cheating is the biggest thing, because they need to get it out of their head. They assume they’re never going to see you again.

B&W: What’s your favorite story you put in the book?

JF: I had a pregnant woman who was fleeing a bank she had robbed. She confessed the whole thing to me on the way to Newark airport. She moved up to New York to meet a guy, only to find out that he was married with a kid. She was stuck in New York and figured out three weeks into it that she was pregnant, and didn’t have anywhere to live. And she was going to put the kid up for adoption. She told me that, and she cried. She left a tip in an envelope—$2,000 and a note that said ‘Thank you for everything.’ And I have the receipt, I kept it to this day. She told me, “I’m keeping this kid. I made $31,000, and I’m gonna go live in the middle of the country.” She was like, “I know I got away with it.” She was hardcore.

It wasn’t about the money because I gave back the money, but you feel a weird obligation to the person. I probably could have helped the police and given enough detail [about her], but I wasn’t contributing to it. If someone had said to me, “You’re doing six months in jail,” I probably would have done them.

B&W: How does spoken humor prepare you to write—do you think that translates?

JF: You learn how to position your reader, because comedy’s a trapdoor. You want to make sure your audience is standing over the trapdoor when it opens so they can fall through it properly. And I think in real comedy, because you’re competing with discussions and drinks being spilled, stuff like that—because you get used to fighting through so much, you develop an economy with how to get audiences to where you need them to be standing. There’s a lot less resistance in the book than there is in real life. I think if you wrote a book first and then tried to do stand-up, it might drive you crazy, because as an author you’re used to having their eyes.

B&W: What’s the worst joke you’ve ever told?

JF: Topical humor is always the most offensive joke you can tell. That’s the one thing that’s horrifying about comedy clubs to people who don’t frequent them. Everybody in the world grieves differently. And a lot of people in the time of a tragedy want to hear jokes about whatever it is we’re all grieving about, because that’s their cathartic way of getting through it. It’s not something I want to take away from these people. It’s also not something I want to celebrate, but I think they’re entitled to it, if it’s not malicious.

B&W: Like after 9/11 happened, the late-night shows stayed on and pretty soon afterwards started—

JF: Oh, and the comics were horrific. I was just starting comedy. When I was watching the comics downtown, blocks from the World Trade, there was a guy who was Iranian. He opened his set with dynamite strapped to his chest, and said “I want to open this show by doing something in the name of Allah.” I mean, that’s pretty heavy. And we’re talking like a week later. But people laughed at that for an hour, because there was something unburdening about it. You can do a joke about everything—the only time people really give you a hard time is if it’s really not funny.

B&W: There are some people who say anything can be funny, and then some people who say, “A rape joke is never funny, ever. It’s never okay.”

JF: It’s really tough. I get why, because there’s a sensitivity to it. So yes, you have every right to say there’s no such thing as a funny rape joke. But you don’t have the right to take the laugh away from the five thousand people that do. They have a right to their laugh, you have a right to your offense. The two just shouldn’t mix.

Comedy of all things cannot be written and regulated for the people that get offended. As a comedian, you’re supposed to be who you would be in your regular civilian life if there were no repercussions. That’s what we give to the crowd, that’s the cathartic thing we’re trying to give them. That 45 minutes when they don’t have late bills, or a bad relationship, or some crazy student debt, or whatever it is. Our job is to give them those 45 minutes where they can laugh at those things instead of being tormented by them. That’s kind of like our societal contribution.

B&W: Cab driver, radio personality, standup comic—those are very male-dominated professions. Do you have any insight into why that is?

JF: Societal attitudes have evolved, and these are older professions. I think comedy and cab driving are specific to a certain lifestyle, too. Comedy’s really lonely. You’re on the road, a lot of weird hotel living. If driving a cab paid enough actual good money, I would never do anything else. It’s the best job in the world. Your brain is never not stimulated. You interact with 35 one-man demographics a day, so your perspective is constantly getting sharper. You just realize how much of the world there is that we don’t know about. There are people in scuba diving suits repairing pipelines under the ocean. Military counterfeiters, guys that run speakeasies. There’s just so much life out there that you’re not privy to.

I think your whole life is really this quest for perspective and authenticity. One of the coolest guys I know has driven a cab for 55 years, and he sleeps in a taxi garage between shifts. And he’s not in denial, he just gets it. He’s a self-actualized human, he just gets what makes him tick and he’s faithful to it. And cab driving has definitely taught me this—you are who you are. You have these limitations, these flaws—it’s not to say you can’t challenge them, but there’s something inside of you that makes you who you are, and if you can just figure that out, you enjoy your life a lot more.

You know how in comedy you want to distract people from their problems? I think the allure of a cab is because they can unburden themselves to a stranger, you’re giving them a chance to be real for fifteen minutes. Or ten minutes—depending on how you drive.

This interview has been edited for clarity and brevity.