An Embarrassment of Riches

I had been invited to witness a typical “brothers hang,” as Nathaniel Rich had dubbed it over the phone from the Paris Review office in the Tribeca, where he works as an editor. It was a mid-August evening, and Nathaniel and his younger brother Simon and I surrounded a four-person table at Waterfalls, a family-style Middle Eastern restaurant in Cobble Hill, Brooklyn. This is a place the Rich brothers know well; they both live within a few blocks of it—six blocks apart from each other—and they order takeout from there several times a week. This night, they deviated slightly from their custom and visited the place for a Tuesday dinner. Every now and again, the sound of a blender making fresh juice dominated the tiny, tiled space with walls the color of a ripe tangerine.

This marked the last time the brothers would hang out for several weeks. Twenty-eight-year-old Nathaniel would be out of town for a 10-day vacation with his mother, then return to a pile of manuscripts to read before the Paris Review’s next deadline. And in one week, Simon, who is 24, would begin his second season as a staff writer on Saturday Night Live. His second collection of humor pieces (or as he prefers to call it, his second book of jokes), Free-Range Chickens, would be published the following week by Random House.

We were more than an hour into our conversation before I brought up their least favorite subject—what they like to call, with a healthy dollop of cynicism, “the family angle.”

A fun dinner with two bright, young literary talents was about to turn unpleasant. Of course I knew they didn’t like to talk about it, but how could I avoid the topic? Their famous father, Frank Rich, has been an op-ed columnist for the New York Times for the last 14 years; from that pulpit he has preached a liberal agenda that has won him a huge national following and led to a bestselling book, The Greatest Story Ever Sold, published in 2006. Before that, he’d been the paper’s respected and feared first-string theater critic for 13 years, a position in which he’d earned the unofficial title “the butcher of Broadway.” With his garrulous personality and marriage to novelist (and New York Times Magazine staff writer) Alex Witchel, Rich has become an A-list New York media personality whose views matter to millions.

Nathaniel and Simon’s mother, Gail Winston—she and Frank divorced in 1987—is an executive editor at HarperCollins. The notion that Nathaniel and Simon’s burgeoning fame might somehow be related to their father’s position has been fodder for journalists, who’ve been tracking Nathaniel and Simon for the past two years. Since his graduation from Yale in 2002, Nathaniel has already written two books: His second, a novel called The Mayor’s Tongue, was published in April by Riverhead and received rave reviews from the Times, the Los Angeles Times and the Washington Post. Its surreal plot borrows from Samuel Beckett and explores writing, communication and love. (It reminded me of The Master and Margarita by Mikhail Bulgakov; when I told that to Nathaniel, he happily acknowledged that Bulgakov’s work had inspired him.) Three years earlier, his first book—San Francisco Noir: The City in Film Noir From 1940 to the Present—this one nonfiction, was published by the Little Bookroom. Simon has met with similarly sudden success. His first published humor collection, Ant Farm: And Other Desperate Situations, came out in 2007, just months after his graduation from Harvard; it earned good reviews—from the Times as well as People and Time Out New York—and led to the job at SNL.

Short articles and on-air interviews with Nathaniel and Simon followed, though the two never appeared together and the articles were mostly Q&As. The brothers were gracious during interviews, patient with questions about their celebrity pedigree and flattered to participate. Authors understand that more publicity means more sales and that more sales mean more opportunities. But it ground on their nerves that one way or another, either posed as a direct question or included as an aside in the eventual article, their relationship to their father always came up.

I too was curious about Nathaniel and Simon’s experience being the sons of such a prominent writer. Simon already had a contract for two books with Random House before he graduated from Harvard—his father’s alma mater—where he was president of the Lampoon. (Frank served as editorial chairman at the Crimson in 1971.) When Ant Farm came out, Jon Stewart (who has had Frank Rich as a guest) pronounced it “hilarious.” Upon his graduation from Yale, Nathaniel became an editorial assistant at the New York Review of Books before moving to San Francisco to work on his book about film noir. He was then hired at the Paris Review as an editor.

But the two young men have avoided the topic of their enviable (and still developing) career arcs as much as possible and, until our dinner at Waterfalls, had given no joint interviews. Their colleagues and friends typically describe Nathaniel and Simon as charming, unassuming, sensitive and thoughtful. To this day, the brothers seem unfazed by their father’s fame, or their own. Those who know them say they simply took the opportunities afforded them and made the most of them. To members of the Rich family, the notion of a concerted effort by the father to ensure the success of the sons runs counter to the reality of their family life. “They’ve never rebelled in the sense of rebelling against careers in writing,” Frank said. “I think part of the reason is that we never really pushed it. You hear these stories of parents who push their children to be in some profession or another.

Often you hear parents pushing them to be lawyers or doctors. The children will revolt against it and go in the other direction.” In this case, the children joined the family business.

The nature-versus-nurture debate has roiled family life since long before Freud came along. We live in a world in which children of presidents become presidents and children of movie stars become movie stars. The notion of pre-destiny dominates daily discussion on millions of therapists’ couches, as children work out issues of independence versus inheritance and gratitude versus resentment. All of us bear obvious traits of our parents; it’s how we deal with them that defines our identities.

“It’s a funny thing, this nature-versus-nurture thing,” Gail Winston said. “I go to a lot of classical music concerts, and I always read the programs, and I always notice that the musicians tend to come from musical families. And I always think, uh-huh, OK, that’s what it is. Some sort of familiarity with the context. That’s how it works. But then I see friends of mine who are in the arts, and their kids are scientists. So I don’t know how that all actually plays out. But in this particular case, obviously the context is one that they ended up in. But who knows?”

Others can’t help but see Simon and Nathaniel’s personalities and successes in the context of their high-profile family.

Steve Bender, a teacher at the Dalton School (where both Simon and Nathaniel attended high school) who has remained friendly with Simon, said that Simon’s amazing mind was evident from the moment he met him. “Obviously, he comes from good pedigree when it comes to intelligence,” Bender said. “His dad is probably the smartest writer in New York.”

And about being compared with his father? “Another friend and former student is Sean Lennon,” Bender said. “Believe me, it’s worse for him.” Josh Koenigsberg is a family friend who went to Dalton with Simon. They’re still close enough that in August, his recipe for burritos became the topic of an Alex Witchel column in the Times’ "Dining In" section. “I think Simon’s dad has both the intellectual part of him and sort of the more fun-loving emotional part to him,” Koenigsberg said. “And I think he divided those traits equally between Nat and Simon, respectively. Nat is definitely the guy who writes about politics and who’s all about theory, and Simon is the guy who takes his dad’s love of dramatic conflict and dramatic construction and stories.”

Bill Hader, a 30-year-old Saturday Night Live colleague, considered the family context as he recalled Simon’s SNL sketches, including one about the strained relationship between Captain Hook and Peter Pan. “Peter Pan comes in and does these funny, silly dances, and it’s like, why doesn’t Captain Hook just shoot him? Right there. Shoot him!” he said. “He’s a voracious reader,” Hader added. “He comes from a very literary family. His family reads a lot. He loves to talk about books—outside of comedy. If he comes to my apartment, he immediately walks over to my bookshelf and is like, ‘Oh, what are you reading? Oh, this is good. Oh, I don’t know about this. This is not very good.’”

Even their father can’t help but see their success through the prism of his own. “They have trod their own paths,” Frank said in August during a phone interview from Denver, where he was covering the Democratic National Convention, “and if you look at the response to stuff that both of them have done, as time goes along there will be less and less mention of me, except maybe of saying that I’m their father, not that they’re my sons.”

Still, I needed to ask the question. I had to bring up the family angle, if for no other reason than that like so many other journalists, I was curious about their father’s role in the lives of these two ambitious and successful young men. I knew that my doing so would further their cynical belief that the media wanted to tag them forever as Frank Rich’s sons, privileged kids who didn’t deserve their success. Having spent a bit of time with them, I didn’t think of them that way; I saw them as talented individuals struggling to find their own identities in a culture that looks for easy explanations. I just wanted to know how the question made them feel.

"Does it bother you when people imply that your father’s influence has something to do with your early success?” I asked.

Simon leaned forward. He is slight, 5-foot-8 and boyish, with longish straight hair and hazel eyes that look green in the sunlight. He’s partial to the T-shirt-and-blazer look of a young writer with no interest in shopping.

“He should exert his power more,” Simon said, his eyes fixed on mine. “Like, for instance, I’m still writing my own books. I feel like I shouldn’t be made to write my own books. If I had such a powerful father, shouldn’t he pay somebody to do it for me? Or just force somebody somehow?” He was making fun of the premise of the question, but he wasn’t laughing. “Also, we’re always trying to get him to review our work in his columns, but he always claims that there’s some kind of political thing going on. And we have no choice but to accept that.”

Simon paused. Nathaniel broke the silence. He’s bigger than his brother—6-feet tall—and his thick black hair offsets his fair skin and large, round eyes that resemble his father’s. He wore a polo shirt and khaki pants.

“When we were growing up and he was reviewing plays, there it was a lot more of a direct—if he gave someone a negative review, they would be angry at him,” Nathaniel said, fingering his fork in a manner more measured, and less hostile, than his brother. “And if I went to a play with him, I guess it could be conceivable that someone would be angry or not. In our lives now, it’s not—it’s a totally different context. He’s writing about national events, political events that are pretty removed from anything we do in our day-to-day lives or that we do in our professional careers.”

Simon, who had been listening intently, picked up Nathaniel’s thread. “I think we had way more advantages in our lives than just having a father who writes for the greatest newspaper in the world. We grew up in Manhattan. I think that, you know, there’re plenty of—at a certain point, it’s not about—”

Simon didn’t finish the sentence. He does this a lot. He’s known among his friends for either pausing at length in the middle of a sentence and either completing it or just abandoning the articulation of the remaining thought. Koenigsberg explains that it’s not because Simon is rude or doesn’t want to connect with people. It’s just that his brain works really fast, and he may wait until he has something better.

The silence returned to the table. For a moment, all of us returned quietly to our meals.

------

Earlier that evening, I had met the brothers at Simon’s groundfloor apartment on Hicks Street in Brooklyn Heights.

He lives just two blocks from the Brooklyn Promenade, from which we could see the sun setting behind the Statue of Liberty.

I rang the bell of his apartment. Simon pulled the door open and shook my hand. He wore a white T-shirt. As I stepped inside, he repeatedly ran his fingers up through his longish hair, pushing it out at the sides. I saw his brother standing in the living room behind him. The place looked like a typical 24-year-old guy’s first apartment. The rug was more like an extra piece of carpet to wipe your feet on, and the stench of stale beer hung in the air. In the living room, a handful of smallish oil portraits hung high on the walls, almost at the ceiling. There were two big, black velvet couches; a wooden chair; a table; a stereo; a TV; and an electronic keyboard. His bedroom door was open slightly, revealing an unmade bed. The hallway led to two other bedrooms.

Simon asked that I excuse the place because they were still cleaning up from a Saturday-night party they had thrown for a roommate who was moving a couple of blocks away. Both of Simon’s roommates had worked with him at the Lampoon. Simon jingled quarters in his hand and tugged at a bag of laundry; he went to put a load of beer-soaked towels in the washer. I was curious about the extent of the party that had left the apartment smelling of beer. A few days before, when I had first met Simon, I asked him about his social life. He’d responded in his usual way, with sentences full of blanks that make you anxious to fill them in. “Um, ah, I don’t know—I don’t know by what—standard—I mean, pretty normal—pretty normal 24-year-old life.”

The reference to normalcy made me laugh. In Free Range Chickens, Count Dracula is the main character of several pieces. The Count paints himself as a regular guy seeking regular human things through a Match.com profile: I am normal human looking for human woman to come to castle. I am normal, regular human. I like the popular music and television. You come to castle. I brought this up. Simon said that a lot of his characters insist they are normal when clearly they are not.

The latest leisure-time activity of the “brothers hang” was systematically watching every DVD in the New York Mets 1986 World Series Collector’s Edition that Frank gave Nathaniel last year for his birthday. The first game alone lasted five hours. While Nathaniel seemed less than eager to share this kind of detail, Simon couldn’t stop. They talked about the importance of 1986, when Nathaniel was six and basically became a “cognizant and sentient being,” as he put it. But Simon said that he was obviously not at the time, since he was two. So now as they watched the series, if Simon tried to look up the score of a game on Wikipedia, Nathaniel would shut the IBM ThinkPad before Simon could catch a glimpse of the screen.

Even though the collector’s set had no commercials, Simon liked to pause the games where commercials should have been and try to re-create ’80s commercials, using the electronic keyboard that was sitting next to him. Simon has a knack for captivating people without leaving them sure exactly why or whether the stories he’s sharing are true or just jokes he’s trying out on them. At Dalton, his best friend recently recalled, the two of them would go to the library, where there was a strict no-loud-noises rule. They would stand out of sight of the librarian but still in sight of other students and act out long, intricate, detailed fake battle scenes. Eventually the librarian would grow curious at what soundless attraction all the kids were looking at, and come over and catch them.

The brothers like to play off each other. Simon recalled being furious with Nathaniel for not watching Mets games on TV with him because “at some point Nathaniel had to go to high school and be serious and study.” Still, whenever anything of note would happen in the game, Simon said, “I would scream at the top of my lungs so Nathaniel would come running out away from his biology homework.” What Nathaniel remembered most was Simon screaming, “Oh God!” as if he were stabbed and then hearing a huge flop. Simon had thrown himself onto the floor and waited there on his stomach until Nathaniel came out.

Much of this took place at their mom’s apartment, where the brothers spent weekdays after the divorce. Nathaniel’s room there remains untouched, while Simon’s has become a guest room. Nathaniel described his room as a shrine to his childhood. “I’m very sentimental about possessions,” he said. “I guess another word for that would be materialistic.”

“I’d say craven and perverse,” Simon said, and they laughed.

Although the brothers seemed close, they weren’t caught up on every one of each other’s many professional activities. Simon was talking about how the Los Angeles Times had written about the comedy Web series “The Line,” which he and Bill Hader had written over the summer. I remarked that Simon had been named again that morning in the New York Times for the series.

“You were?” Nathaniel said, sitting on the couch. “That’s great.” Nathaniel opened Simon’s laptop to look up the series. “I wanna watch that shit.”

“You should watch it,” Simon said.

“Holy shit,” Nathaniel said when the article came up onscreen. “So are they closely monitoring hits?”

“It’s one of those things like the L.A. Times tries to make every Internet thing seem like the next big thing,” Simon said.

“The New York Times piece was very logical,” Simon said. “It didn’t try to make any grand claims about the state of Internet comedy or the state of media. The L.A. Times…whenever they write about anything me or my friends do, I always feel like they are trying to point out trends, like the next big trends, to stay relevant.”

“It’s funny, they did a piece on my book where they didn’t talk about the book at all, but just me and two other editors,” Nathaniel said. “And it’s like, what is this new, young—young men who are editors? Even though the two editors were 10 years older than me.”

Simon agreed. “The New York Times piece was like really, crazily long,” Simon said. “I mean, it was just this really small little thing we did.”

------

Back at the restaurant, Nathaniel and Simon continued to wrestle with my question. It was clear that they’d rather be home watching a Mets game, but at the same time they took on the topic with the relish of an intellectual exercise.

“The biggest advantage, I think, in our lives”—Simon was saying—“has just been the incredible opportunities that any prep school New Yorkers have, which are already so incredible, you feel like, that’s, you know…”

“Sure, if you look at all the people we went to school with, they’re artists, extraordinarily wealthy businessmen, lawyers, surgeons,” Nathaniel said.

“I think it’s Harvard and Yale,” Simon said. “The schools seem to be pretty powerful.”

Simon had ordered a giant falafel-and-feta-cheese sandwich that arrived in a pool of sauce. It didn’t slow his conversation. “I had a lot of advantages by having gone to a really good high school, where I was able to focus on the kinds of things I wanted to write,” he said. “So by the time I got to college, I got on the Lampoon on my first try. But I think a lot of it was because I had been writing jokes for a number of years at that point, whereas a lot of people, when they get to Harvard, they haven’t necessarily written a lot of jokes before. So it takes them a little longer to learn how to do it.”

“Simon’s being modest,” Nathaniel said. “He’s just really, really good at what he does.”

Simon paused to let the blender in the background finish its business. “All you can really do is”—Simon paused again as the blades started to whir—“try to write every day. That’s the only way to be a writer. It’s not the most helpful to think about it only in terms of how your writing is going to be perceived by magazines, trend story writers, or”—he looked directly at me—“people doing profiles.”

Nathaniel appeared eager to speak, but Simon wouldn’t let him break in.

“So when people in interviews ask me questions like,‘What do you think people say about you and your unfair advantages,’ my usual response is that they’re the ones, they’re the ones saying that. Like when you ask me whether or not other people are going to say about such and such that, you know, you’re not talking about them, you’re the one who’s asking me.”

“There’s a lot of truth to that,” Nathaniel said. “Because no one ever—the only people who say to me, you know, how did you get this piece in the Times Book Review or did your dad write your novel and get it published by a publisher who’s, like, invested money in you and the success of the novel, the only people—I only get that in interviews.”

“We only get that at interviews,” Simon said quickly.

“I don’t get that on book tours,” Nathaniel added.“You know, I don’t get that when readers write to my website. We don’t get that from our editors or from our bosses—”

“Who are paying us money to produce work for them,” Simon interrupted. “But what we do get it a lot from—magazines. And there are a lot of articles about it.Which is fine. I understand everybody needs to make a living. But it just seems like it’s not the most original. It’s just not our job to talk about it. It’s your job to talk about it, if you want to. I feel like it’s not our responsibility to talk about that subject.We’re not the ones getting paid to do it.The people who write for—”

Another sentence left uncompleted; Nathaniel picked up the thread.

Like I said to Kimberly when we met the first time, when somebody’s writing a piece about a book—especially if it’s by a young writer—usually those pieces are sort of exceedingly biographical in nature because there’s not a body of work to compare it to,” he said. “You get personal stories about the person’s life. One hopes that if he writes a few more books, maybe they stop talking about his dog and they start talking about what makes his work special. I think I understand writing a novel. It’s a lot easier for a writer, especially one who hasn’t read the novel and thought it out in any kind of literary context, for the story to be biographical. And in that case, the thing that most people know about me, who are writing a column about me, is the profession of my father. Which I understand. My hope is that someone who is a serious reader or a serious writer, ah, maybe will discuss qualities of my work—”

“That’s not even really relevant,” Simon interrupted.

“But even then, there is an element of someone who’s always unsatisfied by that anyway,” Nathaniel continued. “So I guess the way I think of writing is the relationship between— any time you read something, there’s a relationship between the writer and the reader. I think when someone is reading my novel, they’re not thinking about whose son I am.”

“It doesn’t even matter,” Simon said firmly.

“It doesn’t even matter,” Nathaniel repeated, resigned that maybe his point was futile to keep arguing. He nodded and leaned back in his chair.

The conversation shifted to small talk and stories of their childhood. We finished eating soon afterward, and as we prepared to part on a happy note, I felt compelled to apologize for asking questions about their father.

“No, no.We talked about it yesterday too,” Simon said. I wasn’t sure what he meant; I had seen him on Friday. Today was Tuesday. Did it just seem to him that we talked about this every day? Or did he mean that he and Nathaniel had talked about it yesterday, when I wasn’t around?

“Unless you want to ask it a third time,” Simon said, followed by silence. ------

Gail Winston once thought Simon might grow up to be an artist.When Simon got a little older, but before he could write, he would dictate jokes to his mother, who would write them down on sheets of paper. Simon would then staple the pages together and sell them on the sidewalk to people coming home from work. He watched a lot of TV as a kid, but that never concerned Winston. She didn’t have strict rules about, for example, how much homework needed to be done before the television could brighten the living room. Her kids were excellent students, so she let them indulge their passions. “I believed at the time that he watched it differently,” she recalled. “I thought he really watched it. He was really getting something out of it, but I didn’t know exactly what. But it was important to him, and I could tell.”

Nathaniel focused his attention more on baseball than television; he spent most of his childhood alternating between the Mets and the movies. He chose to go to Yale instead of Harvard because he fell in love with its curriculum and its campus. He was a literature major with a focus on early-20th-century European novels, and he didn’t ever read much contemporary fiction. At the Yale Herald, he wrote long essay-type pieces similar to the kinds of articles he would eventually write for the New York Times City section. Meanwhile, at Dalton, Simon continued to develop his passion for joke writing. He and Josh Koenigsberg started a humor magazine and began dominating assemblies with announcements about the publication, Liquid Smoke, which they turned into Andy Kaufman–esque performance pieces.

“It was really all about how could we be the most popular at parties as we can be,” Koenigsberg said. “Because, you know, Simon and I aren’t exactly like football stars, you know. So we used humor and our humor magazine to try and gain popularity.”

After being accepted early at Harvard, Simon immediately set about trying to join the Lampoon. He graduated from Harvard a semester late and opted out of the honors-degree program; instead he enjoyed his right to “sit in a castle all day and write jokes and have it help your career.” In that time, he reached out to Daniel Greenberg, a prominent New York literary agent who represents hip young writers like Chuck Klosterman, and then spent several months writing what would become Ant Farm.

Greenberg sent the Ant Farm manuscript to Daniel Menaker, executive editor in chief of Random House. Menaker had been the fiction editor for years at the New Yorker, where he was the first editor to publish David Foster Wallace and Michael Chabon.

Menaker recalled the first time he put it all together—who Simon’s father was. “I felt, first of all, that you know, there was something sweet and nice about it, being involved with the next generation of a talented family,” he said, remembering his first reaction. “I also feared a little bit that people who were sort of knowledgeable about the world of publishing and writing would think that it was somehow nepotistic or incestuous or something like that, whereas in fact it just wasn’t. And the fact that there was considerable competition for the book I hope sort of shows that others also felt that this was simply a talented young person that they wanted to sign up.”

Nathaniel, after publishing his film noir book, heard from a friend and former New York Review of Books colleague—Jon-Jon Goulian, himself an emerging author—of the job opening at the Paris Review. Goulian made an introduction, and editor Philip Gourevitch hired Nathaniel in 2005. Goulian also introduced Nathaniel to Elyse Cheney, the agent who represented Dave Eggers, among others. Cheney took Nathaniel on immediately, recalling that she was “thrilled by his promise” as a fiction writer.

“It’s more about the writing than the person having media contacts,” Cheney said. “But eventually he started working at the Paris Review, which really gave him a nice platform, and he developed a lot of contacts in the media, and that helps. He’s written for the New York Times Book Review, so he’s more likely to get reviewed by them.”

Once at the Paris Review, Nathaniel continued to work on the second rewrite of The Mayor’s Tongue in his spare time. He finished it in 2007, and it was published a year later.

------

My nose is running,” Nathaniel said at last, breaking the latest silence that fell over us as we prepared to separate. As usual, he was the brother more inclined to talk things out. In this instance, he was referring to the hot sauce the brothers had ordered for the table.

“That was really hot,” he said, bringing his napkin from his lap to his mouth and then to his nose.

“We finished it, though,” Simon said. “It wasn’t easy, but we accomplished something.”

“It’s true,” Nathaniel said.

Another 10 seconds passed quietly.

“What do you think is going to happen in Game 6?” Nathaniel said.

“Wish I knew.Wish I knew,” Simon said. “There’s only one way to find out.” His voice brightened. “Five consecutive hours of concentrated watching.”

“It’s too bad they don’t have the commercials,” Nathaniel said.

“We’ll simulate the commercials,” Simon said. He then mentioned to Nathaniel that SNL work was going to start on Monday. Nathaniel seemed disappointed to learn that his brother would become busy so soon.

“It’s terrible,” Nathaniel said. “It’s like you’re going into some bubble.”

“I know,” Simon said.

“I’ll come and make you food on Sun—”

“On Sunday nights!” they said in unison.

“And also you’ll come to the show, so we’ll hang out Saturdays,” Simon said.

We left the restaurant, stepped onto a mostly dark Atlantic Avenue and lingered for a moment outside of Waterfalls in the warm light coming out through the glass. I broke the silence by asking for directions to the R train.

“We’re both going this way,” Nathaniel said. And so I turned to follow the brothers back to Simon’s apartment, hoping to continue the conversation. But Simon pointed me in the opposite direction.

“You’re not coming this way.”

A version of this story originally appeared in 02138 magazine at [02138mag.com].