Spilling Ink at the Hotel Chelsea
Substack invited me to live-sketch a rare night with iconic writers, Mary Gaitskill and Tavi Gevinson.
June 27, 2024
Hotel Chelsea,
New York, NY
The room was completely silent. I hadn’t seen anything like it since my Best Man speech bombed at a friend’s wedding in 2006. (we haven’t spoken since.)
The only sound that could be heard was the dull scratch of my temperamental bastard of a nib against my sketchpad as some of New York’s best authors, songwriters, journalists, actors, musicians, and artists (and me) sat, captivated in the Piano Room of the Hotel Chelsea. We were there to witness a rare conversation between
and Tavi Gevinson, hosted by .The fireside chat between the two iconic writers was ostensibly about their creative process, but the conversation unfolded into something much deeper. I was there to blend into the wallpaper and live sketch the night— something between reportage and clandestine portraiture. I’ve been calling it ‘Eavesdrawing’. This is something I’ve been lucky to do at previous Substack writer events in New York. (Finally, an advantage to remaining in the city after the artistic exodus of 2020.)
But first, I want to share a dirty little secret…
Since moving to Chelsea four years ago, I’ve spent entire nights posted up at the lobby bar of this hotel, sneakily sketching guests and recording overheard conversations in my sketchbook. The people-watching in here is some of the best in New York. I order the cheapest thing on the menu and sink into the the far corner. The bartenders are nice to me— they top off my drink and refill the saucer of bar snacks. I try not to give myself away by crunching too loudly. If some ugly brute catches me drawing him one night and decides to beat me senseless, I like to imagine they’ll hang a small bronze plaque; “Chatfield’s Creepy Corner.”
The reason it’s a guilty confession is because I only do it when I’m meant to be finishing other work. Which is often.
OK, it’s every Sunday.
A book deadline looming? ‘Perfect!’ I think. ‘I’ll just do a little eavesdrawing at the bar before getting back to the studio.’ The real work invariably gets pushed into the next morning after I wobble off at Last Call with an un-shareable sketchbook full of incendiary caricatures and baffling non-sequiturs.
At one point, the New Yorker paid me to do this for their ‘Overheard in New York’ series. They planted their cartoonists at locations around the city to vacuum up anonymous conversations in iconic settings: Roz Chast at Grand Central Terminal, Ed Steed at the Central Park Zoo, Liana Finck on the L Train, Emily Flake at an Irish pub in Queens, and yours truly at his spiritual home in Manhattan: the Comedy Cellar.
During my previous seven years in the East Village, I’d pull the same shit at the lobby bar of the Ludlow or the Bowery. But as the years wore on, they went from being populated by international travellers with interesting faces to tech bros parading Insta-fluencers through on Hinge dates to pose with an overpriced cocktail. The same insufferable bullshit began happening at Bemelmans after Meghan and Harry stayed there. The Carlyle is now less of a hotel and more of a TikTok backdrop. Amid this vapid fuckery, The Chelsea has maintained its mystique, undiluted by the shallow whims of whatever the algorithm is rewarding this quarter.
I digress.
The Hotel Chelsea is an iconic New York landmark and historic beacon for artists, writers, and musicians. Established in 1884, it stands as a testament to the creative energy that’s rattled through its ornate wooden corridors for over a century. From literary giants like Mark Twain and Arthur Miller to rock legends like Bob Dylan and Janis Joplin, these rooms have hosted a myriad of influential figures. Andy Warhol filmed here. It was also the home of punk icon Sid Vicious and his tragic love story with Nancy Spungen. The hotel’s Gothic Revival architecture, paired with its storied past, makes it a cultural touchstone in the heart of Manhattan and the perfect place to host this conversation.
The provenance of tonight’s chat was when Substack’s Head of Writer Relations (and fellow Chelsea resident)
, was reading the comments under one of Gaitskill’s posts. She stopped on one from Tavi Gevinson. After briefly wondering if it was that Tavi Gevinson, she thought, “Of course Gevinson is a fan of Mary Gaitskill. That makes perfect sense.” She went about planting the seeds for the two to meet, and talk about their respective creative process for a select audience of fellow creators. It was a stroke of genius.Gaitskill is an iconic American author renowned for her provocative, insightful explorations of human relationships, sexuality, and emotional complexity. If you’ve seen the movie ‘Secretary’ starring James Spader and Maggie Gyllenhaal, you know her work.
Gevinson is hard to sum up in a single paragraph. She seems to have done more in her 28 years than most people do in 80. She’s a writer, actress, and cultural critic who gained fame as a teenager for her fashion blog Style Rookie and later founded Rookie Magazine. She’s known for TV shows like Scream Queens and on Broadway. She is known for her insights on fashion, feminism, and youth culture.
When I arrived early to meet them both in the Piano Room, I’m not going to lie, I got a little …flustered. I’d just read a profile on Gevinson published in GQ the week prior, and she was every bit as stylish and charming as anticipated. I wish I could say I came across the same way; I tried my hardest not to look like a complete cretin when I asked both guests if they’d be OK with me drawing them tonight. (I had to repeat myself because my Australian accent makes a dog’s breakfast out of basic vowel sounds.) They agreed before I promptly slid away to let them prepare.
The significance of the Hotel Chelsea’s Piano Room for this event cannot be overstated. The intimate space, with its vintage chandelier, eclectic lounge chairs and lamp shades, has an air of timeless elegance. It has witnessed countless impromptu performances and creative collaborations. The room has been the backdrop for many legendary songwriting sessions, contributing to the rich tapestry of creative history associated with the hotel. And now, my cheeky little scribbles.
If you read my other Substack, you know my ‘road kit’ is replete with dip pens, water brushes, and an inky mess that would need me to set up somewhere with a table. I nabbed a glass of wine from a passing tray and set myself up in the front corner to get the best view of the guests, who were now streaming into the Piano Room. Trays of hors d'oeuvres circulated as I started sketching guests, employing helpers like Substack’s
and to sneakily walk past and drop the finished art in the victims’ laps.
(*I didn’t get permission to post all the portraits from the guests, but
posted hers on social, so I’m assuming it’s OK to share it here.)The room was filled with the roar of guests sipping cocktails and trading war stories from the front lines of the writing world. I sketched Nick Gillespie, founder of Reason (which got spilled on, so I need to re-do). Scribbled a portrait of the inimitable
of The Hyphen, in town from London. I had to stop myself from getting caught up in conversations with fellow Substackers whom I’ve come to know these past few years as we trade notes on gradually building our different readerships on the platform. I really love this community— a curious clump of minds actually trying new things amid the chaos of the media ecosystem and being rewarded for their ingenuity.
There was an excited buzz in the air. Drinks flowed as
tinkled away on the baby grand in the corner until, finally, everyone settled into the lounges or sat cross-legged on the rug for the fireside chat they’d all been waiting for. Mere seconds after the bustling madness, the room fell silent. You could hear a pin drop. Sophia introduced the guests of honor, and the talk got underway.
The conversation delved into Gaitskill’s recent revisiting of her Secretary story, published in the New Yorker and the reading of her work in the context of the #MeToo movement. They spoke about the vast difference between their generational experience. They’ve both had such varied experiences, but worked hard to find their success among the ever-evolving mess of traditional and digital publishing.
Gevinson is a natural host, but seamlessly moved between the role of interviewer and interviewee as Gaitskill posed questions back to her. One notable observation about the interaction is that neither writer felt the need to fill every ounce of dead air with noise— there were few umm’s or like’s— just thoughtful pauses. (I’m a card-carrying fan of the thoughtful pause.) Both writers have a deft ability to build out a cogent opinion without diluting it in equivocation. This is what people came to see. They hung on every word.
Tavi sketch: I still feel bad for making her left eye so big, but I was nervous drawing her. When we spoke after the event, she was kind to ignore it.
I sketched more captivated audience members as the talk wound to a natural close. I managed one last scribble of
1 sitting on the ground next to Cristin Milioti. I’m not sure if I stuck the landing on the likeness, but the sketch did get a nice reception when she took it with her.I wound out the night sharing whatever I legally could about my recent publishing horror story over a cocktail with
of — easily my favourite newsletter about the publishing industry. Putting faces to usernames is invaluable.Nights like these are rare and I pinch myself that I get to be part of them, if only as a passive human camera.
PS - Big News! I’ll be appearing at the New Yorker Festival in October doing— you guessed it— live drawing. 😋 See details below, and book here.
Kimbra’s “Vows” is still one of the most inventive albums I’ve ever heard. You might also know her from her duet with Gotye in “Somebody That I Used To Know”.
Ok, I am in a diner, and I sketch a customers. They always love it. But I am afraid to do caricatures myself doubt seems to overcome my talent.
Beautifully captured in pen and pixel!