New York Cartoons

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Sneaking Into The Good Room with Meryl Streep: A Wild Night of Bottomless Martinis & Parasol Churros
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Sneaking Into The Good Room with Meryl Streep: A Wild Night of Bottomless Martinis & Parasol Churros

A Pickleball Player's Guide to Crashing a Fancy Fundraiser Party

Jason Chatfield's avatar
Jason Chatfield
Nov 22, 2024
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Sneaking Into The Good Room with Meryl Streep: A Wild Night of Bottomless Martinis & Parasol Churros
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November 19, 2024
Hell’s Kitchen,

New York, NY

Every New York party has two rooms: one where people eat hot dogs off trays, and one where people casually buy $80,000 European castle vacays. Through what I can only assume was a glitch in the Matrix, I found myself in both.

The Ice House looms over the Hudson like a glass wedding cake, with the USS Intrepid providing the kind of casual military backdrop that says, "Sure, we could start a war, but first, let's have a cheese slice at Joe's." I was there because me and my Pickleball crew (a sentence I never thought I'd write) had been invited to the after-party of WNYC's centennial fundraiser by Ronny Chieng and Hannah Pham.

We couldn’t afford to be in the big room for the main party, so we just attended the afterparty. Our host for that part was New York Nico, the city's unofficial chronicler-in-chief, whose new book sat in welcoming stacks by the entrance. Being chronically early —a habit that's saved me from more social anxiety than therapy ever could— meant we were first in line for the photo booth. This turned out to be a tactical victory as the queue later stretched longer than the wait for a Sunday table at Russ & Daughters.

We celebrated our efficiency by grabbing what the party billed as "authentic New York hot dogs," though any local knows that true authenticity requires at least a hint of danger and a vendor who remembers when going to Times Square was a dare.

The passed hors d'oeuvres included churros hanging from parasols, a sight that would make any subway platform vendor drop their paper bag and swear in Spanglish. But here's where the night took a turn from "fancy party" to "surreal fever dream": Hannah, master of the gentle infiltration, somehow snuck our little gang of Pickleball enthusiasts into the main event.

Suddenly we were standing in a room where Meryl Streep had just casually dropped $80,000 on an Austrian castle vacation like she was ordering dumplings on Seamless. Seth Meyers appeared as if summoned by the collective net worth of the room, to introduce the next act. A jazz duo started playing "Autumn in New York" while our little clump of Pickleball players did our best impressions of load-bearing columns.

I spent the entire song frozen in place, fighting the urge to make a fart joke. I scanned the room and peeped a half dozen A-list celebs that I had no business gawking at without plexiglass between us. There's nothing quite like the pressure of trying to look like you fit in a room where people buy Cybertrucks as casually as I tap on at a subway turnstyle. I’m told

The Bob
was also lurking at one of the tables— the difference is, he actually knows how to behave himself in public. I make witty cocktail party banter with all the grace of someone eating chicken over a bin.

When it became apparent that we did not belong in the room, security slowly moved towards us with pursed lips. We crept out the door and back into the afterparty where there were several people milling aound who looked like they’d run for NYC mayor once. (Or at the very least, Comptroller).

The after-party was peak millennial New York: Joe's Pizza boxes were circulated by beautiful looking waitstaff, free martinis flowed like Hudson River water (post-cleanup), and a mix of people that could only happen in this city mingled loudly – it was a heady combo: Hedge fund managers in Loro Piana sharing slices with artists in thrifted suits and sneakers. I was wearing my one good suit, which at this point is basically a costume I put on whenever I need to convince people I know which fork to use first.

After one too many slices and precisely too many martinis, we emerged onto the West Side Highway to find a Mister Softee truck positioned with the kind of strategic genius that would make Sun Tzu proud. Because if there's one thing this city teaches you, it's that there's always room for soft-serve, even after three slices of pizza and a buttload of imposter syndrome.

Splitting an Uber back to Chelsea with Ronny and Hannah, I realized this is what makes New York unique: the ability to move between worlds, from Pickleball courts to rooms where people bid on castles, from hot dogs to high culture, all in a single night. However, I still can't shake the feeling that one bad joke could get my New York Socialite card revoked. At least I nabbed a copy of Nico’s book.

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By Jason Chatfield · Hundreds of paid subscribers
A free cartoon hits your inbox every Tuesday + live videos & stories from my sketchbook that prove being a New Yorker cartoonist & comedian in Manhattan is exactly as unhinged as you'd imagine.
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Sneaking Into The Good Room with Meryl Streep: A Wild Night of Bottomless Martinis & Parasol Churros
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Dan Ilic's avatar
Dan Ilic
Nov 22

I miss New York... Such an incredible town.

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Jeff Knurek's avatar
Jeff Knurek
Jan 4

Come to Indianapolis, my pickle brother. You can play all the free pickleball you can handle with me a my pickle/covid crew!

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I hid these cards around New York and got the weirdest emails back.
How a real-world experiment to 'find my rat people' resulted in some of the craziest responses from Real New Yorkers.
Aug 4, 2024 â€¢ 
Jason Chatfield
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I hid these cards around New York and got the weirdest emails back.
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Silencing the Court Jesters.
10 years ago, cartoonists were murdered for drawing offensive things. Things have not been getting better since.
Jan 5 â€¢ 
Jason Chatfield
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New York Cartoons
Silencing the Court Jesters.
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Sketchbook: Live Drawing the 2025 Westminster Dog Show in New York
So many good boys and good girls. So many.
Feb 16 â€¢ 
Jason Chatfield
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New York Cartoons
Sketchbook: Live Drawing the 2025 Westminster Dog Show in New York
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