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The Legend of Tiger Hood
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The Legend of Tiger Hood

Boxing is a lot like Comedy. (Except it hurts less when you do it badly.)

Jason Chatfield's avatar
Jason Chatfield
Aug 12, 2022
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September 12, 2015
New York, NY


After a long night of terrible gigs, I wobbled down MacDougal Street to my spiritual home: The Comedy Cellar.

I collapsed into a booth and started scribbling in chalk on the table. That night’s MC, Wil Sylvince, came over to say hey as I ordered tabouleh and whiskey. Eventually, Outside Steve1 wandered in after loading the audience in for the late show and leaned against our booth to trade war stories from that night.


#10: Overheard at the Comedy Cellar

Jason Chatfield
·
September 29, 2022
#10: Overheard at the Comedy Cellar

Diary Entry: September 29, 2022 The New Yorker has been sending their cartoonists out into New York to eavesdrop (or as I’ve been calling it, “Eavesdraw”) on its inhabitants, and publish their findings in their collection “Overheard in New York”.

Read full story

Steve mentioned Louie and Schumer had dropped in to work on some new gear tonight. One audience member had been offended by a comic on the late show and later got into a fistfight with him outside. The comic had been wearing rings on his hands, and they sliced up the guy’s skin. He was bleeding all over the sidewalk.

Wil is a comic from Haiti with the most infectious smile in New York.

He often hosts the Cellar2 shows and sometimes does a bit of back-and-forth with Dave Attell after he brings him up at the end of the night. It’s my favourite thing to watch. Wil came to Australia to do comedy for a festival and then toured around the small towns afterwards. “Your country people are crazy down there.” he told me. “…And they had some fuckin’ racist words for me.”

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He talked to me about boxing3 while I stuffed my face with pita and hummus. I told him I’d just started working with a boxing trainer in Alphabet city: a Russian heavyweight named Yuri4 who beats the shit out of me twice a week for money. I love it.

I really enjoy boxing; It’s the only physical activity I’m remotely good at. For every other sport I’ve tried I look like a demented, flailing racoon trying to punch its way out of a sleeping bag. Boxing is a lot like comedy— I said that to Wil between mouthfuls and he went on a long, excited tangent about the many correlations between the two.

My comedian friend, Ed got me to do his comedy series called “Defend Yourself” —the show featured comedians getting in the ring and being interviewed between rounds. I did really badly at it.

“Tiger Hood”

After about 1am, I finished up my drink, said goodbye to Wil, and stumbled into the corner of Minetta Lane. I pulled out my phone and started reading my texts when I almost walked right into a tall black man with a golf club chipping milk cartons into an upturned crate behind a parking cone.

He had a grubby old rug on the ground with a $100 bill design on it. All the crunched-up milk cartons were in a perfect line, ready to hit. He expertly swung his sand wedge and tapped the parking cone nearly every time. It was mesmerizing.

He scrunched his bearded face up in a smile, turned to me, and asked, “You want to have a go?”
I shook my head, “Too drunk.”

I later found out he calls himself, “Tiger Hood” and is a bit of a legend5 around these parts. You can read more about him here.

This city never stops surprising me.

I saw Tiger the other night at about 2am outside the Village Underground on 3rd. I said, “Hey, I drew you the other day.” He replied, “Ooh shit, let me see it!” I showed him. He liked it. He reached into his pocket and gave me this…

1

Outside Steve is the guy named Steve who works outside. So they call him Outside Steve. He checks audience members in at the door and has gone on to become a good friend for over a decade.

2

The Comedy Cellar, Greenwich Village, NYC.

3

*Wil ended up trying to make a movie about boxing years later.

4
5

Not long after, Tiger Hood got a golf gear sponsorship from Nike and was featured on Will Smith’s Web Series.

BONUS CONTENT BELOW



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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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darren harley
Apr 16, 2023

exquisite art, JC 🙏🏼

g'day,

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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 • 
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 • 
Jason Chatfield
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Silencing the Court Jesters.
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4
Sketchbook: Live Drawing the 2025 Westminster Dog Show in New York
So many good boys and good girls. So many.
Feb 16 • 
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Sketchbook: Live Drawing the 2025 Westminster Dog Show in New York
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