Talking ‘Look Alive Out There’ and the Importance of Humor Writing with Sloane Crosley

Sloane Crosley may be an accomplished writer, but she’s still humble. Crosley is the acclaimed author of essay collections I Was Told There’d Be Cake, How Did You Get This Numbertoday’s release Look Alive Out There, and the very funny novel The Clasp, which deals with jackhammering outside her apartment and the general day-to-day grind of living in New York. “I still get my card punched at the coffee place so that I can get a free cup,” she told me during a mid-afternoon phone chat. For someone who was a frequent guest on Craig Ferguson’s incarnation of The Late Late Show, this insistence on living a normal life might be atypical, but Crosley isn’t the type to give into the trappings of fame.

As a writer, Crosley invites empathy into her essays examining everything from the experience of freezing one’s eggs to the bizarre experience of playing a fake version of yourself on Gossip Girl. The essays are notable not just for their ability to scrutinize a very micro or abstract aspect of life, but for being genuinely funny – not clever, not cute, not playful, funny. This combination of literariness and comedy makes Crosley one of the few living essayists to be designated as a humor writer.

Recently, Crosley took the time to speak with me about the craft of humor writing, privilege, the weirdness of playing yourself on screen as a writer, and the strange ways we distinguish between humor writing and writing that has humor in it. Throughout our long chat, she remained nothing short of great company.

Has the way you approach using humor always the same? Obviously you were the first contributor to The New York Times op-ed series, Townies, which has a brisk, wry tone to it. Writing humor for The New York Times can be complicated, but your sensibility meshes so well with it. I’m curious if you’ve always written with that sort of humor, or if you partly honed your voice by contributing to that series.

There’s something about my writing…my voice is a little bit old-fashioned, especially when it comes to my writing about New York. It’s not necessarily in the exact wording or imagery, or the things I’m saying – I’m not in mourning for subway tokens – but the actual structure of it, the beats of it, the way it’s either tied up or not tied up neatly. When I say old-fashioned, I don’t mean Elizabeth Mitchell/Joseph Hardwick old-fashioned, although that would be nice. More the This American Life heyday model. I suppose you could say those elements appeal to Times readers, but I don’t run the Times and I don’t know who is and isn’t reading them. I didn’t have to bend over backwards to fit into someone else’s mold, I can tell you that. I think that when you start writing for magazines, newspapers, things of this nature, you just sort of learn about the economy of words, and brevity, and when to make jokes, and also the fact that there has to be meaning behind most moments. In other words, when you’re writing for a publication, it’s not standup but is a balance – a balance between fitting a certain amount of funny material in before 1000 or 2000 words is up, but also having some sort of larger point. You have to amuse people quickly but not at the sacrifice of meaning. This isn’t a Most Jokes Per Square Inch contest.

When your debut, I Was Told There’d Be Cake, came out, the essays were brimming with humor, almost as a shield. Look Alive Out There is coming out almost a decade after that first collection, and your use of humor has become more patient. Is that a result of your becoming more comfortable with ambiguity, with not having those answers? 

Sure, that’s probably true. Dorothy Parker said humor should always be used as a shield and not a sword, so there’s that. But maybe the real answer to your question is about the idea of one’s own mortality. I mean, how many books of personal essays am I possibly going to write? There could be four more, or there could be one. It’s sort of this feeling of taking advantage of the platform and the time you have on stage. When you’re younger, that manifests itself as the feeling that you have to say every damn thing in your head and say it with authority, not ambiguity. Now it’s more this idea of “This is exactly what I want to say.” The trick is to not become so indulgent or meandering with that.

I went to see a famous comedian perform last night, and it was so god-awful, because he drank his own Kool-Aid, I guess. He was workshopping material on Trump just into the ether, with no regard for the audience. Writers and comedians are in a rarefied position, talent aside, and I believe you just have a real obligation to sing for your supper and remember that no one really needs you – you’re not a doctor or a plumber, which is sort of depressing, but it doesn’t have to be. Over the years, I think I’ve gotten better at balancing the idea of, “Hey now, people are interested in what I have to say, so I’m going to say it to the fullest extent I can,” while also remembering that I’m here to entertain people. I suspect what you’re picking up on is me going, “Yeah, these first four paragraphs are going to be only tangentially related to the essay, but there is value to be had in and of themselves, in these training wheels. They don’t have to be taken off. You might appreciate easing into somebody else’s thoughts as long as we both sign this silent contract that you’ll laugh.” If a writer like me doesn’t sign that contract, that’s how you end up with books that feature five-page descriptions of an oak tree.

In general, has the way you think about humor changed?

Well, I feel like it’s a little less pressure to make these jokes every five seconds. Hopefully this new collection is a good balance between the first and second, more of an evolution than a balance. I wrote the second one during a tough time, and a depressive person writing humor has a specific result. Not bad, just specific. But the first one was a bit of a “dance, monkey, dance” vibe, and that can distract from whatever you’re trying to say. It just looks like you’re trying too hard, which just smells bad. I’ll go through and pluck them out, just because you’re living with someone for a while with these essays. In theory, a book of essays is less of a commitment to a personality than reading someone’s memoir, but actually it’s more of a potential landmine. There’s a constant shifting of, like, “Oh, do you wanna know what I think about thing A? And thing B? And thing C?” You have to balance out the humor, otherwise it can be grating. You don’t want to be the guy at the party who thinks he’s hilarious. It’s important to not ask to be congratulated for being funny when you write funny. That’s a good lesson.

Do you have an innate instinct for when things need to be punched up?

I mean, sure. My instinct is to keep an eye out for when things are too complain-y, which sometimes needs to happen to get from point A to point B. There are certain things you have to do in writing that’s sort of like eating your vegetables. You know, for a novel like The Clasp, there are going to be times where you have to have a character open a door without fanfare. He or she just has to open the door. Not everything is verbal pyrotechnics, and you have to suck it up and write a couple paragraphs of “and then, and then, and then” in order to get to the next magical destination. With the essays, there are times when I’m writing something that has that sort of New York Seinfeld-ian quality to it and it can come out as a little self-pitying or self-centered, especially if every sentence starts with “I.” So I wouldn’t say I “punch up” my writing so much as I “take the indulgent edge off.” I’m not taking flat writing and making it funny, I’m just conscious that talking about yourself can be exceedingly boring. My books have to come out both as specific and universal as possible – the humor of exasperation – or even I don’t want to read them.

Between your last collection and this one, you worked on a screenplay for an Apple Music project and wrote the comic novel, The Clasp. Do you think working in those different mediums impacted the way you think about writing now? 

To sort of pan out a bit and answer a different way, I had a different career for twelve years. The idea of not going to an office every day and working from home is still weird, so I’m just trying my best to do whatever I can and to do as much of it as I can and not pass anything up. It’s not about impact, it’s about trying. If you told me I had to write a poem or play, even though I’m not a poet or playwright, I’d figure out how to do it functionally enough if it was the only way I could express myself and get paid to do it. I’m not saying this to be an egoist, I’m saying it to be a survivalist. I know that’s sort of a blunt answer, but I’m not alone. I’ve also written pilots and movies and, as other people always tell you and it’s true, the thing is a screenplay is more like math. Action just has to happen at a certain point, by a certain page. That’s a different medium and a different muscle for me. I will say, the nice thing about a screenplay or TV pilot is that no one is going to come after you for having too many jokes. They might come after you for unrealistic dialogue, but one doesn’t influence the other. A lot of the time, when someone starts off in a sketch comedy or TV and then moves over to books, well, it’s either Jessi Klein or Tina Fey or Steve Martin, or it’s…significantly not that. I don’t know why that is. It’s not like my people fare any better [in different mediums], but I don’t know. I can’t help but think it’s because if you’re an essayist or a novelist, you’re accustomed to more longform gratification. A marathoner needs less help to become a sprinter than a sprinter needs to become a marathoner. I assume. I’m not a runner.

One thing that was immensely satisfying in reading the new collection is seeing how the concept of privilege was scrutinized. But I think you will get asked about this. Like, not everyone can afford to take cabs to the airport, and you mention that. But you start with the micro – the privilege of unnecessary sympathy – and move on to discuss writer, New York, white, celebrity, and romantic privilege. How organic was this theme? 

What is romantic privilege and how do I get in on it? Listen, whatever world you’re in, it’s important to reflect on your advantages and disadvantages, especially if you’re going to call yourself a writer, and if you don’t do that naturally in today’s day and age, that’s actually just weird. So I’m glad I’m not weird. But it should be organic or feel organic. If I intentionally acknowledged society’s kid gloves with me, a white Jewish woman, at every turn, it would make for really bad writing. There’s a woman I admire who’s a nonfiction writer, and I was so excited to read her new book a while back, but I was bummed out because every time she would scrutinize something – and it was clearly one of those “the smallest violin in the world is playing for you” topics – she would then overly check herself. She would constantly be like, “I know it’s not civil war, but…” “I know it’s not the Arctic melting, but….” “I mean, it’s like I’m getting shot in the street or anything!” “Could be worse, could be the Holocaust!” So I’m reading this book and I’m going: Yeah, I know that. Have a little faith that when I want to read about social injustice, I’m not turning to you.

Maybe this question is a female thing – the expectation that we hedge and apologize and our instinct to that. You know who doesn’t get asked to explain his privilege or apologize for the life he’s worked hard for? Name a male writer. I am, of course, conscious of the fact that a couple of these essays in the new book sprung out of magazine assignments and I say so. So there will definitely be a few readers thinking, “Oh, someone sent her to X city, bully for her. And she took a cab!” But…oh well? It’s my job. And, more importantly, funny things happened. And privilege always depends on who’s asking, anyway. I am very aware that I have the ability to wander this world and know that if I go into any store, no one will see me as a threat. Not everyone gets that. And you have the ability to wander into the alley behind the store at night and feel safe. I don’t get that. So let’s laugh about it until we fix it.

Both you and John Jeremiah Sullivan have written about the strangeness of interacting with the world of television. In both essays, you cover the way fabrication bristles against your own actual lives as Sloane and John, not just the personas the public might project onto you. Since readers largely know you as a dialed-up version of yourself, complete with all the assumptions one might make based on that version of you, why do you think you found it important to capture and dig into the surrealism of not being depicted as you exactly are?  

I love that piece of his. I would be willing to bet that the seed that was planted in John’s mind was the same seed that was planted in mine. I think we both felt like foxes in a henhouse, which is rare, because our whole jobs as writers, and as comedic writers very specifically, is to feel like you’re at the edge of the party, not that you’re part of the center. You have to be there to observe, which means you have to be functional enough to be invited, but you have to have one foot out the door. I think we both felt like these TV people let the wrong person in with open arms, and we got to be spies. We got to see this world of the WB network for other people, which is a different vibe from the other essays, for me at least. In all the other essays, the relatability comes from me seeing the same things you also see, but just saying it in a different way. But guest starring on Gossip Girl or, in John’s case, having One Tree Hill take over your house…these are not daily occurrences. So both of us, if I may even group myself with him, we are starting from a different place than normal. Then the question becomes: How is this relevant to people beyond a cool story I’m telling at a party? How do I let people in on this lost but rare feeling, a reckoning they can trust? It’s strange to talk about yourself as a characterization of yourself. It has the potential to heighten your most annoying qualities. We spend too much time wondering what people think of us as it is. So to write an essay that asks “What do you think of me as a character?” is tricky and strange and I hope I pulled it off.

It’s definitely strange. I wanted to end by asking you about this: In your interview at The New York Public Library, you mentioned that you don’t identify yourself as a humorist, since the point of your work is something other than the joke. I’m curious about your feelings then on the popular idea that since one’s work has comedy elements, they are relegated to the humor section, or get the label of “humorist.” Specifically, I wanted to ask how you felt about this in nonfiction, since novelists like Lorrie Moore, Gary Shteyngart, Sam Lipsyte, Paul Beatty, and Ottessa Moshfegh don’t come up against those boundaries in the way that you and David Sedaris might. 

I don’t know if I agree that there’s a genre difference. I think it’s an equal opportunity issue. Like I would not put Gary on that list. I’ve never had this conversation with Gary, but I also think the humor of his writing does get him penalized in some abstract way. His talent is as real as any National Book Award winner and he’s hilarious to boot, so that’s what people commend him for. And then they take the structure and seriousness – the grand achievement of the thing – for granted. It’s not a curse to be beloved for humor, but maybe ask any actor who wants to do a serious role how he or she feels about this. Ask all the comedic actresses who’ve never won an Oscar in the history of the Oscars. But it doesn’t take a great leap of imagination. I think we can all agree that it would be annoying to do twice the amount of circus tricks and have the net effect be one-half a trick. So is it any wonder humorists don’t like being called humorists even though they’re really obviously humorists? I’ll give you a concrete example: I was a judge for the Kirkus Prize when Roz Chast won for Can’t We Talk About Something More Pleasant? It was a tough call but we picked her book because she’s tackling an incredibly serious and complex issue and plotting it and wrestling with it and making us laugh just like everybody else. And she’s doing the illustration. So why turn “and” into “only” when it’s “and?” Does that answer your question?

I was curious about how you felt about the fact that the category wouldn’t have to come up if you were just writing, say, novels…

Well, I want to be a humorist. And I can’t turn back time and say how the word would be used if I had written four novels instead of one novel and three books of nonfiction. All I know is I don’t want to lead people astray. Aside from producing a bad book, or not producing any books, I would say third on the list of author fears is the idea that your book is going to get into the wrong hands. So, if you have a goofy cover on your serious book about North Korea, no one interested in the topic is picking it up, and everyone who does buy it is left confused about why you’re not making enough jokes about North Korea. Similarly, the label of “humorist” I find to be a little bit dangerous. I’m not writing for Shouts & Murmurs every week. I have no desire to do standup. I just don’t ever want to disappoint people in terms of what they’re reading. I mean, if they know what they’re signing up for and don’t like what I write, I’m fine with that. Them’s the breaks. I hope they find my writing funny but dark and sad and heartwarming in weird places, but maybe they don’t and okay. But if someone thinks they’re signing up for something else entirely – if they read “humorist” and are like “Where is my list of things this bitch finds under her bed?” and “Where is my political satire?” and “Where is the letter from the point of view of the dog?” – then that’s not fair to anyone. This being said, I’m probably more comfortable with the label than when I gave that interview at the library, which I barely remember giving. Ask me in another ten years if I’m not still concussed.

Eric Farwell has written for the physical or digital arms of Brooklyn Rail (forthcoming), The Paris Review (forthcoming), The Village Voice, Guernica, The Los Angeles Review of Books, Salon, Esquire, Vanity Fair, Rolling Stone, Vice, The Believer, The New Yorker, McSweeney’s, and GQ. He teaches English Composition at Monmouth University in New Jersey.

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