Pencils Process: Personalized Portrait Place Cards!
(Try saying that without spitting all over your screen...)
Drawing the New York Literary Elite: An Artist Interloper at an Upper East Side Soirée
The invitation arrived via Paperless Post—the modern equivalent of a wax-sealed envelope delivered by footman. "Private Dinner Party. 6:30pm. Friday. Upper East Side."
I have another book coming out at the end of the month. I’m new to the authoring world, so being summoned to a Manhattan mansion opposite The Met is not a common occurrence for me —a cartoonist who still gets excited about free bread at restaurants. It’s the New York literary world's equivalent of being called to Hogwarts. Except the other students are dressed in haute couture and drinking 25-year-old scotch. These can be the kind of parties where book deals are conjured out of thin air between the amuse-bouche and the main course while I'm still trying to figure out which fork to use for my endive salad.
I got a follow-up email from the hostess, Deborah Roberts. My inclusion was clearly a clerical error that had been discovered. Or so I thought… that was until I received a very novel request from the hostess:
"She wants to commission me to draw portraits of the guests for custom place settings," I read aloud, which was true but sounded like something I made up to get the doorman to let me in. It was ingenious, really. Most of these parties have printed place-cards; some have a calligrapher hand-write them, but I would be creating hand-drawn original artwork for each guest as a place setting and a take-home party favor.
Just when I thought the value of my hand-drawn art was drying up, a new idea like this popped into the world, and I was animated to get scribbling again. I hope hand-drawn, tangible art like this is valued in the future over cheap, soulless AI-generated slop.
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Art Made by Human Hands.
There's a new piece of "art" haunting the New York subway system, and for once, it's not a chalk outline.
I got to work right away, sourcing reference images from the hostess and their individual author pages and Substack bios. After a bunch of experimentation, I landed on simply drawing them on paper, in pencil, then pasting them onto cards to fold over for place-cards.
(Above: Portrait of the writer Francesca Fartaj of A Life Considered)
There’s something nice about going back to basics with drawing— not adding a hat on a hat with ink and colours, washes and paint splodges; just basic pencil lines and a bit of shading. I used a blending stump from Blick Art Supplies for some of the art, where I needed a softer edge on facial features.
Drawing exercise for you:
Try drawing something in pencil, but push as gently as you possibly can— try to get to the point where you’re barely making a mark on the paper. See how gentle you can push. Set this as your base level for pressure when using pencils from now on. There’s nothing worse than a deeply engraved pencil line that you can’t erase. Try also holding the pencil on its side, for an extra gentle grip.)
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I worked away day and night to try and land on a good likeness for each guest, drawing multiple versions of each face to get it just right. I used a lightbox to get the rough shape of the face, then worked from sight on the features to make sure it didn’t just look like a facsimile of a photo (Difficult with portraits from photo reference. Caricatures are easier to add flair to.)
I’d like to say I used a fancy mechanical pencil to do it all, but in truth, I just used a basic number 2 pencil I bought in a box from my local CVS. Once in a while, I switched to a basic Bic pencil for small details, but that was only for 1 or 2 of them.
The great chronicler of New York City: Anne Kadet of CAFÉ ANNE (above)
Author Cici Sullivan
I arrived fifteen minutes early, which is twenty five minutes too early for a New York dinner party but precisely on time for an interloper with crippling impostor syndrome. I had the drawings tucked under my arm in a dog-eared folder, ready to plop on the beautifully decorated dining table with moments to spare before the rest of the guests arrived. The immaculately dressed doorman gave me a once-over that started at my scuffed shoes (I took a bike) and ended at my hastily-combed hair with an expression that said, "I've seen better-dressed people trying to deliver Amazon packages." I mumbled something about the dinner party, and he switched gears: smiled broadly, then let me through while tipping the shiny brim of his cap.
I was warmly welcomed by the hosts*, and glared at skeptically by the true boss of the house, who was named Sophie. It was not the first skeptical glare I’d received from a Sophie that week.
*(Both writer and editor of Sparks from Culture by David Roberts)
David and Deborah’s apartment was incredible: they’ve hosted several writer events before, inviting authors, journalists and substackers of all stripes to their epic abode with floor-to-ceiling bookshelves, a vast array of artwork from around the world, and a guest bathroom bigger than my apartment. The kind of New York I’d only seen in old Architectural Digest features and scenes from Gossip Girl. (Yes, I watched it. xoxo.)
Twenty minutes later, I was positioned near the entrance, Dutch courage in one hand and a pencil in the other for last-minute panic edits to the portraits, though I briefly considered using it to stab myself in the thigh should I say something mortifying.
The doorbell announced the arrival of the guests, who flowed in as we sipped drinks in the sitting room (the sipping room?): A prize-winning novelist, a formidable editor and journalist, a renowned poetry teacher and author, and a slew of best-selling writers and substackers. I introduced myself in what I hoped was a casual, professional manner, but sounded more like a peacock with an antipodean accent being gently strangled to death.
The editorial team of The Metropolitan Review filed in, led by
, who gave me a collegial nod as if to say, "Yes, we both belong here," even though I absolutely did not. and followed, engaged in what appeared to be an intense debate about the proper use of semicolons. Ross has a novel out this May called The Glass Century— putting any combination of words together around him feels like I’m still learning English as a third language.I’d actually drawn a totally different version of Django’s portrait, before throwing it away and working from a photo I’d taken of him at another event the night before. The first version looked as much like him as I do George Clooney.
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Sidenote: I’ve since been enlisted as the Cartoon Editor for the The Metropolitan Review. So I guess I retroactively now belonged at the party.)
To my relief, the reactions to the portraits ranged from genuine delight to polite appreciation, with no one discovering they'd been accidentally given a third eye or errant mustache—always a risk with my hasty line work.
The dinner conversation flowed like the expensive wine being liberally poured. Topics swirled and eddied: the death of the publishing industry (announced annually since 1901), the impossibility of getting good reviews ("Times critics these days!"), and whether audiobooks counted as "real reading" (My feeling: yes, but only if narrated by someone with a British accent).
We all shared bits of business and publishing horror stories before retiring for post-dinner drinks in the sitting room. (I’ve always wanted to say I retired to another room. It’s less impressive when I say it in my one-bedroom apartment.) I got to meet Sarah Fay (PhD, MA, MFA) who is re-launching her book this year. I’d just seen her that week at a reading event,with
where she read from her incredible novel Pathological. She invited me onto her Substack live show to discuss book publishing, which you can watch below, if you’re interested in the nuts and bolts of the book business.As the night wound down, we each peeled off into the cool New York air, pencil portraits tucked into pockets, reeling from the buzz of being around other people who do the insane thing we all do; flinging words into the world, and hoping for the best.
And yes, I did have to draw my own portrait for my place setting. It now lives face-down in my flat files with the rest of my terrifying self-portraits.
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The great Kyle T Webster wrote eloquently about working with pencils on his Substack
. I highly recommend you read it and subscribe to his newsletter.
I also enjoyed Siobhan Twomey’s post about drawing as part of her study series of Kimon Nicolaides’ “The Natural Way to Draw.” Give it a read. The video is also very helpful.
