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#24: Larry David Hated My Caricature of Him.
"Katie Couric wants you to draw a caricature of Larry David for the wall at Sardi's. She would like to present it to him at the restaurant, live on her show."
Diary Entry:
February 11th, 2015
I've been commissioned to draw thousands of caricatures of people since my 8th-grade geography teacher asked me to draw the school gardener.
It was a terrible caricature but he gave me 20 bucks for it. It seemed like a crime that I could get paid for doing something I love. (Scene missing: I didn’t go to university... became a cartoonist.)
26 years on, the only thing I love more than drawing school gardeners is watching Larry David do literally anything. It was with immense anxiety, then, that I accepted the most intimidating commission of my life.

I can't quite explain why, but being insulted by Larry is a great honour. For a comedian, it's like being blessed by the pope.
The job came through a fellow New York cartoonist, Ed Steckley. He passed the job on knowing full well my eyes would pop out of my head when I read the brief. It was a very generous prank. Essentially, the brief was as follows:
"Larry David's Broadway show is a hit. Katie Couric wants you to draw a caricature of Larry David for the wall at Sardi's. She would like to present it to him at the restaurant, live on her show.
We need it hand-delivered in 2 days."
There isn't enough valium in the world to take that in without swallowing your tongue.
You're going to have to pardon the hyperbolic fanboy drool. I generally feel the idolizing of anyone -comedian or otherwise- isn't always the healthiest of life choices, but let me just say, Larry is the exception that proves the rule. He continues to have the finest observational mind in the business. His takes on social intercourse are bordering on genius. (If he'd let anyone use the term around him.)
Read my post on Creative Partnerships here:
Curb.
Curb Your Enthusiasm is the only show I've ever watched on rotation constantly for over a decade without ever tiring of it. I love it more than Seinfeld. I know more of the idiotic minutiae of the Larry universe than I know about my own medical records. Which brings me neatly to…
The Broadway Show.
I snapped up the last tickets to the first night of previews of his new show, Fish in the Dark and took an old friend of Larry's as my man-date. Without a hint of fanboy bias, I can honestly say it was the funniest, best-written comedy I’ve seen on or off Broadway.
No bells and whistles, just great writing and brilliant performance. It was basically one giant episode of Curb with a theatre treatment. The moment he broke into an epic “Prett-aaaaaay Prett-aaaay Prettay good” garnered an incredible roar of excited laughter I’d never heard from a theatre audience.
In previews, it had a couple of kinks, but nothing fatal. The show itself is a singular piece of art I’m insanely lucky to have seen in its infancy. It has broken box office records, and it is now, unfortunately, impossible to get tickets.
Seeing LD in the flesh is incredible. He moves like a lanky 30-year-old. It’s baffling. It makes it even harder to land the most perfect ‘imperfect’ caricature of him. For Sardi’s.
What even is Sardi's?
Sardi's Restaurant is a New York institution, in the oldest sense of the word. More specifically, it's as much a part of Broadway as theatre itself. When its original owner, Vincent Sardi Jr. died in 2007, The New York Times wrote of his iconic restaurant:
"Mr. Sardi ran one of the world’s most famous restaurants, a Broadway institution as central to the life of the theater as actors, agents and critics. It was, the press agent Richard Maney once wrote, “the club, mess hall, lounge, post office, saloon and marketplace of the people of the theater.
Sardi’s shone brightest on the opening night of a Broadway show, and in the 1960s, a show opened nearly every night. The ritual never varied. In a line that stretched down 44th Street, theatergoers, theater folk and celebrity watchers clamored for a table, hoping against hope to be seated on the first floor, where they could see cast members, producers and the playwright of the moment entering the restaurant after the curtain rang down. As the actors made their way to their tables, the diners would stand and deliver an ovation.”
To be asked to draw a caricature for Sardi's is crazy. I have no business drawing caricatures for these people. Whether it gets hung on the wall or not, it's ridiculous that I was even asked to do this job. I won't write anything disparaging about the existing caricatures, but you can read up on the history of the restaurant and the tradition of the four artists they've used over nine decades here: Secrets of Sardi's
I was once booked by an agency to show up at Sardi’s to draw live caricatures of the child actors in Matilda and School of Rock. It did not end well.
The Caricaturing Process.
“It needs to look 'less' like him for Sardis.”
I really agonized over this caricature. I didn't sleep for three days. I started out drawing roughs from every reference photo I could get my hands on.
Larry is a devotée of Woody Allen, and every official portrait of Allen has his head being propped up by his hand. The first season of Curb had this image of Larry as the promo photo, so I worked with this as a starting point
.
The problem is, of course, that was from 1998. Larry doesn't look quite the same as he did back then, and the photo doesn't really capture his essence much these days. That, and the caricature itself wasn't very good. We scrapped that version and moved on to version 2.
The producer sent back a few reference photos, insisting we do one of Larry smiling.
Larry's not really known for being a big smiler. He has a smirk he wears when he's stirring people up, being a social assassin, but he's not a big smiler overall. The smiling version wasn't my favourite, but the producer and Katie's team liked it. I wasn't thrilled with it.
Dozens of frantic, sleep-deprived emails flew back and forth over the two days of drafts, changes, and amended amendments. I was throwing everything into this. I was sending roughs to trusted friends to get feedback on likenesses and styles.
Finally, the producer said they really wanted to go with this reference photo of Larry so I was to work from that one for the final caricature. I was also to make it more of a portrait, not so much an exaggerated caricature.
At this stage, I just wanted to get it out- I'd been agonising over this thing for days and I'd grown a full beard.
I jumped on the subway uptown, sleep-deprived and clutching onto my scribbles for dear life. I handed the final version to the producer to get framed. They used it in the shoot that weekend.
I wasn't happy with the finished product, but I'm that way with literally everything I've ever drawn. All I ever see is the errors- the flaws, the ways it could have been way better, but the deadline was tight, and so was my chest by this stage. I slept for 14 hours the next day.
The producer did a fantastic job- The final interview is brilliant. The reaction to the caricature is exactly what I anticipated. I love that he hated it. I now have a copy of the caricature for my studio, signed by Larry.
Pret-tey pret-teeeey prettteeey good.
Curb has been renewed for a 12th season, due out later this year. After 24 years, it is HBO's longest-running scripted series.
#24: Larry David Hated My Caricature of Him.
omg jason i did not know that you did this (i love sardis)
Great story accompanying great art. I'm glad he liked it!