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Wilfrid Wood and the Delicate Art of Drawing Without Mercy

Sitting for the 57-year-old London artist means being seen exactly as you are. From queer dating apps to Hackney family portraits, Wood finds beauty in awkwardness—and proves that politeness and provocation can coexist.

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“Can you draw me?”

It’s the eternal question. One asked of every artist who ever picked up a pencil and did something good with it. Some artists roll their eyes at it. Others make a living from it. This is the third time I’ve shown up at 57-year-old Wilfrid Wood’s townhouse in Hackney to sit for a portrait. I’ve known him for 7 years, and it’s safe to say he’s turned that simple question—Can you draw me?—into a full-blown career.

Wood’s portraits span a range of media: Painted studies of families, charcoal sketches of naked men, and sculptures of political figures. He has an uncanny eye for likeness, whether or not his subjects appreciate it. From his point of view, that tension is part of the fun.



A former i-D intern (in 1990, at Terry Jones’ house, FYI!) and Spitting Image crafter, Wood eventually carved out his own niche. His self-directed career took a turn as his portraits gained traction online and soon enough, much of London seemed to be making its way to his home-studio—via Instagram and Grindr—to sit for him. His work is kind of a textural fine art caricature, exaggerating features while somehow revealing something true underneath.

The hardest part about sitting for him isn’t holding still, it’s the anticipation of seeing what he’ll make of you. Once I settled into the chair he’d adjusted to perfection, he hit play on his Spotify “Liked Songs” playlist, and the 3-hour session began.

James Dean: What makes a good sitter and a bad sitter?

Wilfrid Wood: More important than how anyone looks is their attitude. I just need someone relaxed and on board with me. Sometimes I get couples, and it’s obvious one partner is keener than the other. You can feel when someone’s fed up or just not into it. All I really need is a willing person to share this thing we’re doing together. I know I’m technically “the boss,” but everything I get comes from you, the sitter. 

Do you think it shows in the work when someone isn’t into it?

Hard to say. Sometimes I make better portraits when I’m a bit irritated by the person. If I really like them, that usually doesn’t help. But there are always exceptions.

The last time we saw each other was at the Duke of Wellington. Do you go there a lot?

Yeah, I tend to sort of end up there. I don’t really know what to do anymore. I’m on this app called Feeld—just looking for models. Kind of gone full circle, really. What I used to do on Grindr, I’m now doing on Feeld.

Probably also get a bit more variety there.

Exactly. I’m chatting with a few people. Hopefully, they’ll become models.

What’s the difference between finding models online and doing family portraits or couple sittings around London?

Probably what you’d expect. If you’ve got a mum, dad, kid, and dog, they’re usually nice people trying to make everything look good for the kid. But if it’s someone off the internet, you’ve no idea who’s turning up. They might be lovely or weird. I wouldn’t want to only do one or the other.

I think your comment about not knowing what to do anymore—bars, apps, whatever—really resonates.

There’s always a few things going on. But mainly, it’s age. It’s hard to tell if it’s me that’s changed or the world—or both. My 60s are on the horizon, and I don’t know what to expect. Maybe it’s foolish to still be in that scene, but I’d be happy to go to bars and see what happens. It doesn’t seem to work that way anymore, even for younger people.

Do you think being gay affected your career in any way? 

I don’t walk around thinking I’m gay, the way some people do. I’m not that into “gay stuff.” I just came out this way. I’ve had girlfriends. I guess it gives me a funny overview. I can understand what it’s like to be straight and gay… I’ve never put all my eggs in that one basket. 

You did a whole series of my friend Bella. She said you were “fed up with drawing loads of men.”

There was definitely a period—my Grindr period—when I was drawing lots of guys. Which was great, but it’s nice to change things up. I like variety: Thin, fat, old, young, every race and every type. Going back to the gay question, I’m just interested in whoever’s in front of me. Rather than thinking about what my “gay persona” brings to it, I’m thinking “Who is this person?” Francis Bacon painted portraits completely soaked in himself, in how he saw the world. But there’s also something beautiful about surrendering to the model. About making it about them, not you.

You could say this interview is doing both at once. I’m trying to get inside your brain whilst you’re studying me.

Yeah, I guess that’s what a conversation is. We’ve just accidentally defined it.

Do you read your instagram comments?

All the time. I used to get loads of funny ones, but less so now. People are used to me. They see my posts and think, “Oh, that’s just what he does,” instead of, “How dare he do that to those lovely people?” Maybe that’s why I’ve been thinking about doing landscapes, to break out of being predictably me.

Your Instagram bio—“Politely upsetting people”—is perfect.

Well, I am quite polite, and I was well brought up. But I do enjoy poking people a bit.

When someone sees your version of them, you’re really showing them how you see them.

Of course. If someone’s got a big nose, I’m pouncing on it. A lot of people have wildly unrealistic views of themselves. We all do. My worst work happens when I’m timid.  Frank Auerbach once said the worst thing an artist can be is timid, and he’s right. Who wants a timid work of art?

How do you feel when someone draws you?

Fine. Just… a bit bored, usually.

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