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Lunch with the man described as “Instagram’s first comedy superstar” has been booked at Rick’s Cabaret, a strip club and steakhouse in midtown Manhattan. Josh Ostrovsky, 33, and professionally known as the Fat Jew, assures me that he didn’t pick the venue for the naked girls: “I come for the Caesar salad,” he says.
It’s 1pm on a beautiful summer’s day but inside the club, in near darkness, electronic music is blaring and it’s already filling up quickly. Men arrive in groups. A slightly built young woman wearing black lingerie under a transparent robe is working the pole that rises floor-to-ceiling on the stage next to the bar. Anastasia’s particular trick is to bend over backwards at the waist so far that her face appears again between her legs. Then she looks up and winks at the silver-haired punter sitting in front of her, who likes what he sees and throws dollar bills up in the air — “making it rain” in strip club parlance.
No one here is likely to attract as much attention as the strippers but even the man with silver hair looks away from his lap dance to gawp when the Fat Jew turns up wearing a onesie with the zip undone to his belly button (revealing a gold medallion and a tattoo bearing New York magazine’s logo) and his hair styled in a vertical ponytail he calls his “Jew unicorn” or “hair erection”.
Pulling up a stool, he greets me in a thick New York accent: “John! What’s up, how you doin’?” Turning to the barmaid, he requests she “Mix me up something slutty, please. Something with peach. Know what I’m saying?” Anxious but keen to jolly things along, I finish my beer and say I’ll have what he’s having.
More than 5.2m people follow the Fat Jew’s Instagram account, which consists chiefly of photos of animals, babies and the rich and famous presented with wry, profane captions. The only people with more followers than him are either traditional celebrities or those related to the Kardashians. Yet, if you don’t use the social photo-and video-sharing app, which was bought by Facebook in 2012 for $1bn and today has more than 300m users, his name probably means nothing to you. At once hugely famous and totally unknown, the Fat Jew’s rise reflects the increasingly disparate ways in which we consume comedy.
“I want as many people as possible to know that I’m very fucking funny,” says the Fat Jew, “but why would I fly around the world to do a stand-up show to hundreds, maybe thousands of people when I can reach far bigger numbers through my Instagram?” As we all spend more time on our phones, he reasons, it’s there, too, that we laugh. “And because we live life in fast forward,” he says, “for a joke to be funny, it has to be fast.”
The barmaid places two cocktails on the counter in front of us and declares: “Boys, I made them extra special for you. They’re a fruity floral combination of chartreuse, gin, peach schnapps, cranberry/pineapple punch and a splash of tonic. Is that slutty enough?”
“Damn, yes!” the Fat Jew replies, before sampling the bright pink liquid through a straw. “So. Fucking. Good. Tastes like air freshener!”
You can’t eat at the bar, so we move to a table in the corner of the room. Once settled in, the Fat Jew explains how, each day, from an office he rents in the back of a nail salon in Queens, he and three interns search the bowels of the web for unusual, often slightly ridiculous images — so long as they haven’t already gone viral — to post to his followers.
Last month, celebrating the Supreme Court’s decision to approve same-sex marriage across the US, he posted a Photoshopped picture of rapper Kanye West kissing his double. Below it, the Fat Jew wrote: “Finally, Kanye can legally marry himself absolutely anywhere in this great nation.” The picture gained almost 238,000 likes.
Outlandish taste runs through his comedy — in one picture two pizza slices are positioned together so that they look like the Star of David, with the caption “This is my religion” typed below. He also mocks our dependence on the internet. Take the picture showing a message saying: “Home is where your WiFi connects automatically,” beneath which a caption reads: “Meaning not my parents’ house, where the WiFi password is RHXFGJIJ0000055$T.”
With this sort of content, which people seem unable to resist regramming or telling their friends about, the Fat Jew has found fame and financial success. Still, he says, it’s difficult to explain to “proper adults” what he does.
“Not getting all high and mighty about it but it’s more like performance art than comedy,” he says, draining his cocktail. “I won’t ever open a soup kitchen but what I do is the next best thing. Pictures are what I can give back to the world. A lot of people have steady careers, health insurance, a pay cheque at the end of the month, a wife and three kids. But that kind of life can get boring; sometimes you need to see a fat guy sitting in a giant bowl of chilli.
“Because being an adult sucks. It fucking sucks, man. You have responsibilities. You can’t go out and do a ton of coke, spiral out of control. So if I can make your day a little less shitty, help you 0.001 per cent while your life is falling apart, that feels like a noble undertaking to me. It makes me middle of the pack. Maybe I won’t go to hell after all.”
A stripper comes over and asks me if I would like a lap dance. “He loves you but no thanks,” the Fat Jew replies before I can muster a response. “Just the menu.”
When it comes, there’s unexpected news: the Caesar salad has sold out. “Three courses for $10 — you can’t complain,” says my guest philosophically. For that price, I dread to think what the food will taste like but we are meeting for lunch so I order tortilla soup to start, followed by steak frites and a chocolate mousse. The Fat Jew also orders the soup and the mousse, though chooses crispy shrimp for his main. “And two more of the same,” he says, pointing to our empty glasses.
Instagram has tolerated his profane humour — up to a point. Since he started his account in 2009, he has been kicked off the app three times for posting content deemed inappropriate — most recently in 2013. “But that time I wasn’t given any reason why,” he claims.
In protest, he chained himself to the Instagram and Facebook offices, then located in Manhattan. His sandwich board read: “They’ve stolen my memories, my freedom of speech and the joy of those I bring laughter to every single day . . . Join the fight, use the hashtag #freefatjew and demand they return my Instagram to me. Freedom!!!!”
According to the Fat Jew: “Suddenly the street was packed. I struck a nerve as I was prepared to go to jail for literally forever. I’m like Nelson Mandela in so many ways except fat, white and Jewish.” The hashtag started trending and the protest was live-blogged by media companies such as Vice. Within 15 minutes his account was reinstated.
“Back then,” he recalls fondly, “Instagram was definitely my bitch. But recently I’ve been happy to tone it down, play by the rules. Instagram is helping me move into the mainstream. Mark Zuckerberg, I come in peace.”
For the past few years, companies have started to pay for exposure to his audience. Clients ranging from Burger King to Virgin Mobile to Stella Artois have all hired him as an “influencer” to feature product placement in his posts.
Advertisers are said to be willing to pay around $6,000 for each mention of their product in an Instagram post (it costs roughly the same for a shout-out on Twitter). The Fat Jew tells me he doesn’t like to talk about how much he earns but, based on the rates commanded by other successful Instagrammers, his income from advertising alone could now be running at a rate of several hundred thousand dollars a year.
How does corporate sponsorship fit with his edgy ethos? “It’s snowballed recently, although it’s not about the money for me. I could be earning a lot more but I like to have complete creative control over whatever I do, so the brands aren’t as trusting yet. They know I won’t go along with their ideas. Yes, I’d like to get dirty rich and buy some exotic animals, but only if the content stays good.”
By “good”, he means he is willing to take more risks than other Instagrammers. He recently starred in a Bud Light campaign for the Super Bowl. Playing up to the beer’s motto, “Up for whatever”, he took his grandmother to a party and got a friend to tattoo her lower back. “I could have taken the brand’s money and posed in a photo holding a beer. That’s the kind of thing other big Instagrammers would have done. But I was like, ‘Let’s do this for real, let’s make this memorable’. I take the time to make this shit really good. I’m a giver.”
What does he think about the oversharing — or TMI (too much information) — that people now do online? “I’m all about having no boundaries and I’ve been putting it all online for years. But a lot of people — like Lena Dunham, let’s say — are ‘confessional’ in a way they know people will like. Her kind of ‘honesty’ feels really PC. She is pandering a little bit. Whereas nothing is too embarrassing for me. I’ll make fun of myself and I’ll make fun of others.”
But never, I’ve noticed, his wife, Katie Sturino, a publicist whom he married in late 2014. Why not? “The internet is beautiful, my favourite place on earth. And yet it’s also a fucking trash can, an endless ocean of horrendousness. And some people aren’t ready for it. I’m not hiding my wife — she has a nice symmetrical face — but if people say horrible shit about her online, she’ll take it personally. She’s an internet amateur.
“Me, on the other hand: I’m the president and first lady of the internet. I can troll better than anyone in the world!”
Our second cocktails arrive and conversation turns to the opportunities the Fat Jew has to build an offline career. Now, he explains, is the time to translate his huge web presence and smartphone success into an old-fashioned entertainment career. Everywhere you go in New York, there he is: plastered all over buses eating a hot dog in advertisements for Seamless, an online food ordering service; appearing on Bloomberg News every few weeks to talk about “how to market to ‘millennials’ and use the internet to promote your brand, boring stuff like that”. And now, he continues, he has sold scripted TV shows to Comedy Central and Amazon; and last month he signed a plus-size modelling contract with One Management; and Money Pizza Respect, a collection of personal essays and images, will be published by Grand Central Publishing in October. Writing a book, though, felt too much like hard work, he says. He rented a cabin in the woods in Connecticut but spent more time at the local bar than he did writing.
Surprisingly, for someone who lives so much of his life online, he thinks “IRL” (in real life, i.e., stuff that happens not on the internet) will make a comeback in the next five years. And he has elevated aims: “I’m doing Money Pizza Respect to become the book industry’s accidental hero, to reinvigorate reading on a mass scale!”
Soups, steak and shrimp are brought to the table all at once. The soup is almost inedible — lumpy and salty — but I tuck into the steak with enthusiasm after all the sugary booze. “I told you the food here’s the best,” says the Fat Jew, signalling for the waitress to come over and ordering us both another cocktail — rum punch this time.
We also have an uninvited guest. “I’ve been dying to come over!” Anastasia the pole dancer tells the Fat Jew, sitting down next to him. She is 21, from Russia, and her friends back home are fans. She is new to dancing, and enrolled at university, but won’t say which, studying for a degree in human resources management. “Keep living the dream, girl,” the Fat Jew tells her.
Anastasia has been sitting with us for 15 minutes, and has pertinent questions of her own. She’s midway through asking him about growing up in New York when the DJ calls her to the stage over the loudspeakers — it’s time to dance again. The Fat Jew agrees to reconvene on the roof terrace for a photo once the interview has finished.
We continue talking about his upbringing. He was raised in the well-off surroundings of the Upper West Side. Taking out his iPhone neither for the first time nor the last, he shows me pictures of his mother, Rebecca, who formerly worked as a nutritionist and his father, Saul, a radiologist. He was sent to private school where, he says, he was exposed from a young age to the glamour — and hedonism — of the moneyed elite. “Comparatively, to the rest of the world, we were rich. But the New York private school scene is such a bubble. The money was crazy but we were at the lower end.
“I mean, I was going to school with the kids of international business moguls, kids that took helicopters to school, that did coke at 15. Kids going hard. Totally fucked by the time they turned 22 but, whatever, it was awesome and ridiculous. Kids that grow up in big cities are always ahead of the curve.”
He says he dropped out of New York University because it was “boring” and got kicked out of another college before enrolling in 2004 at State University of New York Albany to study journalism. It was here he decided to forge a career in being “professionally ridiculous”, joining a rap group described by one newspaper as a cross between Barbra Streisand and the Wu-Tang Clan. In 2009, he began focusing solely on comedy and founded his social media business. What did his parents think?
“They were hard workers. Very focused. My dad was born in Russia. He had a beard and a factory job by the time he was 13. They found what I did funny but it blew their fucking minds how I’d ever make money from it. At first, they were right. But I was doing it all for the notoriety then. Now that I’m able to monetise it, they’re feeling it.”
So how Jewish is he? “Religiously, hmmm — I used to go to the synagogue to pick up girls; culturally, very much so — I have so much unfounded anxiety; genetically, 100 per cent — my pubic hair’s longer than my penis. Seriously, though, when Jewish kids come up to me to say thanks for making being Jewish cool again, that makes me proud.”
His conversation, while often verging on hyperbole, is never less than engaging. I drink the last of my rum punch, a final jolt of sugar, and we head up three flights of stairs — past four stages and private VIP suites — to the roof. Anastasia has taken off her vicious metal stilettos and is removing the wad of dollar bills secured to her ankle with a rubber band. The manager of the strip club has also joined us for the impromptu shoot.
Lighting a cigarette and posing for more selfies with fans, the Fat Jew gives one final insight into his happy-go-lucky philosophy. “Social media platforms come and go. Look at Facebook, it’s not cool any more. So I’m getting ready for life beyond Instagram,” he says. “I can still be cool from the mainstream. And if I get rich along the way, I’ll buy a giraffe — and comprehensive dental insurance. That’s the Jew in me.”
John Sunyer is commissioning editor on FT Life & Arts
Illustration by James Ferguson