Josh Ostrovsky, AKA The Fat Jew, Wants You To Be Talking About Him

The Instagram sensation discusses sex workers, dolphin tranquilizers, and getting into “dad weed” culture.
Josh Ostrovsky, AKA The Fat Jew, Wants You To Be Talking About Him
Courtesy of Josh Ostrovsky

It’s 4:20pm EST on 4/20/20 when Josh Ostrovsky aka “The Fat Jew” and I connect by phone. The specific time, of course, is his request. Ostrovsky, known for his popular Instagram handle @thefatjewish, says the current quarantine has him unhinged. “I gave myself a haircut the other day and now look like a middle-aged bald dad. I bought a couple of karate gis. Today, I took a bong hit from a bong filled with milk. I’m definitely unwell.” Ostrovsky goes on to list some of his other recent purchases, most notably a watercolor set and a bunch of new butt plugs, one of which is affixed with a fidget spinner. He’s also trying to cook a 69-layer dip while listening to Peter Tosh. “I’m trying new things, I just don’t know if I’m well or not.” One thing is for sure: Josh is insanely entertaining.

Are you buying all of these items through Instagram ads?

Josh Ostrovsky: I’m definitely getting scrapped because I’m talking about stuff and then Lord Zuckerberg, the Jew Overlord, is serving me ads for them. I’m sure of it. Some of [the purchases] are definitely things where I was like, “If ever have the time, I would buy a butt plug with a fidget spinner on it.” But most of my time is being spent going deep into the Internet and watching weird Japanese squid pornos.

My fetishes have become so specific. That’s my problem. Now, he has to be Dutch, he has to be a backpacker, circumcised, there has to be a squid, or something involving a pottery wheel. It’s gotta be a woman who kind of looks like Ellen Barkin but has big legs. It’s gotten super niche. A lot of things have to line up in order for me to actually shoot ropes. I can’t watch hardcore anymore. That’s for the kids. I’m too old, I’ve seen too much.

Perhaps now you’ll get bombarded with ads for Japanese squid paraphernalia.

Josh Ostrovsky: I’m sure Jew Overlord Zuckerberg is going to serve me something related to it. I don’t know what he’ll serve me, but it’s going to be something. Other than that, I’ve been smoking insane amounts of pot and going to bed sometimes at 9pm, while waking up at 5am. It’s been fun.

You’re stepping into the role of your grandparents, understanding their lifestyle and why they like to eat at 5pm.

Josh Ostrovsky: Totally. Living on “Boca Raton hours” is kind of sick. Staying up super late and waking up late is very “no parents, fuck off, dad.” 

Speaking of “fuck off dad,” how were expelled from both NYU and Skidmore?

Josh Ostrovsky: Skidmore was classic 80’s-style shenanigans, not in the 80’s, but in the early aughts. It was a lot of getting caught by security doing a mangina and shooting boiled potatoes out of a basketball machine. Straight up classic college antics.

For anyone reading this, don’t go to a small liberal arts school. It’s the lamest shit you could ever do. Go to the University of Alabama and go completely mental. Do not go to fucking Vassar and take bong hits with four-thousand kids. Go to a state school and go full blown moron.

Getting kicked out of Skidmore was actually kind of a gift. There were a lot of white kids with dreads and it just wasn’t really what I was going for. I ended up getting [the expulsion] expunged from my record and then got into NYU. But the problem with NYU was that I was from New York City. Going to NYU, I was basically hanging out with guys that didn’t go to college, who were the most absolute savage degenerates, and I ended up getting very experimental. We were doing a lot of Special K and a lot of other animal tranquilizers. I think if I remember correctly, we got our hands on some dolphin tranquilizers or something for a large sea mammal. Once you start getting into dolphin tranquilizers, your schoolwork is probably going to suffer.

The old adage.

Josh Ostrovsky: My grandfather used to say that all the time. “Once ya get into dolphin tranquilizers, ya never gonna do homework.” But yeah, once I got thrown out of NYU, I was like, “Fuck this. I want red-cup college antics.” So I went to SUNY Albany with a bunch of guidos from Staten Island who had huge uncircumcised dicks and had never met a Jewish guy before.

People sleep on the Capital City, but the Capital Region is so gnarly. Every couple years in like Schenectady, a stripper gets busted for doing coke off her baby. We knew a group of sex workers in Troy and would have them over to our place off campus on Quail Street. These dusty-ass hookers would come over and we had no intention of having sex with them. But we’d do nonsexual stuff with them, that was the whole shwang.

I actually did this later for a TV thing, but I remember we cleared all the furniture in the living room and played a huge, high-octane, full-contact game of dodgeball with these 40-year-old prostitutes. One of them was really strong and had grown-ass woman strength. She threw a ball that hit me square in the face and busted my nose open. It was so funny. I was bleeding everywhere. We would also pay them to do stuff like read us stories. Just no sex.

Not that any of them were put-off per se, but since it was their occupation, did anyone try to throw in a blow job with the dodgeball game?

Josh Ostrovsky: Sex workers are used to having a disgusting human being on top of them flopping aound while they sit there and think about how they need to support their families. What’s interesting is, they get very thrown off when you say, “Hey, do you think you could just act out this scene from ‘Mighty Ducks 2’?” They basically think you’re a murderer. At first, they almost seemed like they’d rather have my horrible cork-sized penis inside them, but once they realized we just wanted to do fun shit and pay them their full rate, they were like, “This is great,” and it became sort of a regular thing.

One of [the sex workers] had a rugged C-section scar. Again, I never had sex with them, but I imagine if you were going to, you’d have to blow the dust off, a la when Nicholas Cage finds the constitution in “National Treasure.” Very “Indiana Jones.” It would be like “Indiana Jones and the Meaty Vagina from Troy.”

What’s cool is we can use that title for one of the custom made pornos under the Fat Jew banner.

Josh Ostrovsky: That’s what I’m saying. A sex worker from Troy with a rugged C-section scar and a five-year-old who plays little league. Her husband is in prison for running a cologne ring, stealing cologne from local malls or whatever. That’s the stuff that will give me a raging hard-on. That stuff I can really jack-off to. But just some regular anal? I’m past that. It’s for the twenty-five-year-olds.

You need the stuff where the son is sitting out in the hall with an iPad while his mom is inside.

Josh Ostrovsky: And he’s super smart. His name’s like “Romeo” and he has a ton of potential. It’s that kind of backstory that really makes me spray seed.

When you were at UAlbany, was there ever a thought that hey, “I’m going to turn ‘Fat Jew’ into a brand?”

Josh Ostrovsky: It was never that calculated. I think a lot of the kids now who have Instagram accounts think about these things from an “I’m a brand” [perspective]. My ridiculous antics were my friend. I’m old enough to where I had a public access show where I was running around in a diaper through the street, being completely insane. It wasn’t designed to get views and monetize. There was nothing like that. It wasn’t that kind of thinking.

After college, I did mostly TV. I was on the E! channel for a while and I used to do a lot of Vice stuff. I would write all their “Do’s and Don’ts” and do weird videos for them. My fans were coke-smoking maniacs in their twenties, so it wasn’t like, “Let’s make a brand,” it was really just me being a complete American fucking muppet and entertaining people. It organically grew from there. Once Instagram took off, I knew I’d be able to grow past the twenty-something coke-smoking morons because there were rules. I’ve said this before, Instagram widened my base because Lord Zuckerberg has rules. I couldn’t just put up a picture of stiletto heel jammed into a dickhole. Because of the rules, I could reach more people. I think that was the point where I was like, “Yeah, I could probably make some money off this.” But also, because there were rules, I got thrown off Instagram three or four times.

I held a rally to get my Instagram back outside the Instagram offices and put the word out on Twitter. My rabbi was there. A bunch of degenerates drove down from Pittsburgh. Guys with calf tattoos. Just a bunch of real pieces of shit. If you apply for a protest permit, you get cops, barricades, and all this shit. All these cops were there because they had to be, and they were like, “I dunno, some guy – somebody took this guy’s computer.” They had no idea why we were there. Meanwhile, crimes were being committed citywide. 15 minutes later, Instagram was like, “Please get this fucking moron out of here,” and they gave me back my Instagram.

I think people have taken the position on me for a long time that I started an Instagram and then boom, just got paid. But I had been a TV writer, I had sold shows to multiple networks and had worked for a ton of different outlets making content. I’ve been an idiot since forever. Instagram was just the biggest platform with the most viewers. I was writing tv shows out the back of a nail salon we had rented out. We weren’t thinking, “How do we monetize content?”

And in the process, you were leaning into who you were and doing what you wanted to do.

Josh Ostrovsky: I wasn’t running around in a diaper through the streets of Manhattan because I thought one day Burger King would want to do a “disruptive ad campaign” featuring a grown man in a diaper. Nobody thought like that.

Now, kids almost think of things from a content monetzation perspective first, whereas for me, I’m naturally a fucking idiot. People just happened to have an appetite for [my stuff] and that led to being able to do it as a job of some sort.

It sounds like, at baseline for whatever comedy you were cultivating, the plan was to just do you.

Josh Ostrovsky: Yeah, pretty much. Although I’ve never been in a comedy club. No disrespect to comedians, but they’re generally cantankerous losers who got their heads flushed into toilets in high school. That was never me. For me, it was more about being performative and making people say, “What the fuck?” rather than get a laugh. I’ve never done stand-up, it was never about being a comedian. I don’t think anyone knew what box to put me in so they just put me into the comedy box. But some of what I was doing was a little more cultural commentary, a little more cutting, a little more ridiculous. It’s more about doing something brand new, doing something different, and definitely doing something “me.” I mean, using the word “authentic” is my actual nightmare. White people love an “authentic” experience. In relation to this, I’m willing to use [the word] because I really was doing exactly what I wanted to do.

Wasn’t there a weird thing a couple of years ago where some comics said material was lifted?

Josh Ostrovsky: Yeah, they were just mad because of the general nature of meme culture and how jokes sort of get passed around. A thirty-five-year-old stand-up comic is a lot different than a seventeen-year-old Korean kid who’s on a fucking blog with images like a pic-dump. The comics just see everything as, “their IP is their IP,” and they don’t believe in the creative commons or any shit like that. They just kind of made me the face of [meme culture backlash] because I was the one who was doing it at the highest level.

I’m a troll at heart. I’ve been trolling forever, whether it was “Jerky Boys”-style prank phone calls, or shitting on people on the Internet. I think things definitely got a little bit intense. At one point, my Uber got followed by like TMZ. Honestly, I’m down for the controversy, but I don’t go home at night and unscrew my head dildo like, “Ah, another day at the office as a provocateur.” At the same time, I’m also out here to piss people off. I’m a troll.

Now, I’m a little bit tired of it. I started my wine company to sit back a little more and am more into jacking-off to Dutch guys and stuff. That kind of makes it sound more gay than it is, but whatever. You know what I’m saying. Niche porno. Back then, I was there to troll. I was trying to piss the comedians off. They missed the joke. They really thought that I was trying to get one over. I’m actually just acting like a fucking idiot who doesn’t give a fuck. I sold my wine company to Anheuser-Busch. In three years, I’ll be doing something completely different. I could be coaching middle school girls’ basketball in Baltimore. I don’t give a fuck about the Internet, all I give a fuck about is that you’re talking about me one way or the other.

Do you have any other businesses you’re thinking about in the works?

Josh Ostrovsky: Now, it’s funny. We’re officially living in a world where someone is taking me seriously. That’s fucking dark. You think COVID-19 and the melting polar ice caps is scary, we’re in a world where I spoke at Harvard Business School and [the students] actually took notes and listened. That’s fucking scary.

I’ve spoken at Harvard, Yale, the University of Chicago Business School, fucking Penn. I’ve basically been speaking at Ivy League businesses schools. The world is completely fucked. It’s basically WrestleMania all the time now. At this point, I can get somebody to give me money to do the next ridiculous thing. [Because] people are taking me seriously, I’d love to take someone else’s money and completely throw it away.

We’re making it up as we go along and giving the people what they want. I didn’t start a wine company because I like wine, I started a wine company because people wanted to shotgun rosé from a can. Everyone’s overthinking this shit. I was like, I want to live in a world where a girl named Lauren at the University of Michigan can do a rosé keg stand. That’s my legacy. I want my children to be able to do rosé keg stands. I give people what they want and I’m not taking any of it seriously. All I care about is making a scene. So whatever it is next, you can bet it will be off the nose. Like, “Why the fuck is Fat Jew doing that?” Maybe it’s a line of fucking ovenmits. I’m always going to try to be exactly where you don’t expect me.

What a legacy. Down the road, your daughter finishes that keg stand and screams, “My dad created this!”

Josh Ostrovsky: And then just immediately blows a guy. What will guys in college be named in like 2050?

If we make it that far.

Josh Ostrovsky: [Laughs] It’s sad to think that the world might end before my daughter ever has chance to do a rosé keg stand and suck off a guy who actually has a horrible personality, but she’s just basically molding him and projecting good stuff on to him to make him whoever she wants him to be. But he’s actually a trash bag. I want that day to come, but I don’t know if it ever will.

My whole thing with building the wine was that I knew my celebrity couldn’t last very long. I think people connect with the fact that I say whatever the fuck I want and do whatever the fuck I want. But at the end of the day, it’s not going to last forever. How long are you really interested in a fat adult baby with a fucking head dildo? I’m not George Clooney. I knew that my window was small and that people were only going to be interested for a very limited time. So creating something with lasting value was something I was focused on from the beginning. I had to start a brand, something that had nothing to do with me, that people actually wanted, like a consumer product. Now, I want to help the next generation do the same.

Kids now will take a fast check and promote some bullshit for a brand that pays them fucking peanuts, leverages their platform, and then completely moves on to whoever the next flavor of the day is. I think they [the kids] have really really good ideas and can do things that will last way past their Internet personas, but I don’t think they actually know how. So, I’ve been doing some VC stuff. I’m on some straight up “Shark Tank” shit. The Internet has sort of leveled the entrepreneurial playing field and you need guys like me who are actually willing to fucking help and give money and do shit. I’m not even looking to invest. Like, I’ll give you money to start your company. I just want to see the kids do sick shit.

It’s kind of cool that your ridiculous antics are – in a sense – potentially fueling the next beneficial company to society.

Josh Ostrovsky: All these Gen-Z kids, they care about shit. Back in the day, nothing was less cool than caring about shit. Caring was for nerds. But now, [the kids] care. And they have sick ideas on how to like clean water in Ghana. They’re learning to not trust the adults in the room, the adults don’t know what the fuck they’re talking about, and before we let the earth explode in the next 50 years, they want to try and change shit. So at the very least, I’m going to try and help them. It’s definitely accidental. I was not attempting to help with any of this shit, but it just kind of happened.

People always say, “Why don’t you use your platform for good?” but that was never for me. I never wanted to be like, “Hey guys. Here’s the thing I want to shed light on.” It’s my job to put something stupid on the Internet so you can take your mind off your life for two seconds. But I ended up finding a whole new world of kids who would email me and be like, “I’m fat and you made it cool to be fat.” Or, “I’m a Jew in Iowa and there’s no Jews in my town. You’re cool and Jewish, now everybody likes that I’m Jewish.” Shit that I’m like, “What the fuck?” I was just trying to smoke dolphin tranquilizers and play full contact dodgeball with prostitutes.

Cannabis has been part of your life for a good minute. What role does it play in your lifestyle?

Josh Ostrovsky: I think New York City kids had a unique experience with marijuana. We never had mids. I was smoking straight up indoor, engineered, chemical-laced fire. Always. Mids were never a thing that were part of my life. We bought pot from Dominican dudes who lived with their grandmothers. It was so strong, it would make you feel like your eyeballs were bleeding. They were engineering some real dank indoor in the late 90’s with ridiculous names. So I’ve been smoking strong pot since absolutely always.

Do you come up with ideas for antics while you’re high or do you use it more to relax?

Josh Ostrovsky: I feel like it goes in waves. Sometimes, you go into a valley of weird self-reflection. You start smoking weed and you’re like, “What are friends? Who are my friends?” Right now, I’m more in a period where you smoke a bunch of weed and you do a mangina and get super fucking loose and wacky. I’m moving into more of a “dad” style. Wearing crocs and weird kimonos. I want to get into some real “dad weed” shit. Smoke a joint and take a dog for a two hour walk.

“Dad weed” shit.

Josh Ostrovsky: First of all, “dad weed” shit is the tightest weed culture. The problem now is, people are doing pot drugs. You smoke some shatter and you’re basically doing heroin. If you start doing thick, creamy dabs, all of a sudden you wake up and it’s Wednesday and it turns out you deepthroated a Haitian guy with beet-red eyes. You have no clue what happened.

I’m trying to get on some classic “dad” shit. Smoke a reasonably sized joint, maybe eat some low carb crackers and think about aliens and stuff.

The other nice thing about weed is it will lead you down the deepest Internet rabbit holes.

With weed and the Internet, you can never have the same journey twice.

Josh Ostrovsky: I mean, weed and Wikipedia. What page do you start on and where do you end? You start by reading about Denmark, and somehow you come out the other end of the rabbit hole reading about Steven Seagal.

I smoked so much weed during this quarantine, I went on a full-blown investigation trying to find the identity of the black dude with the big dick in those memes. I know some publications have run articles about him since, but for a minute I was leading the charge. I was basically on “The Wire.” Who was he? Where did he come from? I ended up getting so deep that I emailed his co-workers and found out about his funeral and all this crazy shit. Now, I’ve been texting with his brother and his ex-girlfriend and we have plans to meet up post-COVID. And it was all thanks to pot.

Follow @thefatjewish for ridiculous content.

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