In September 2024, I was asked to paint a portrait of an 86-year-old man. Apparently, he had always wanted a formal portrait of himself, and after binge-watching Portrait Artist of the Year, he finally decided to go for it. I’d been taking on painting commissions for about three years, so I knew the routine: get a photo, paint something that wouldn’t look out of place on a county cricket clubhouse wall, and pocket my semi-hard-earned money.
He had a clear sense of who he was – and it had nothing to do with how he looked now.
This time, there were two immediate problems. First, the sitter wanted me to paint him in person, which meant commuting from London to Reading and making small talk – in my opinion, the worst kind of obligation. Second, to quote his WhatsApp message, he wanted me to “capture him.” How hard could that be, I thought?
What I didn’t realise was that my sitter and I had something in common: we both struggled to recognise what we look like. For portrait painters, looking in the mirror is part of the job. Every decent artist has spent hours, days, or even months staring at their own reflection and recreating it on canvas – it’s as much about vanity as it is about skill. But I don’t enjoy it. My eyes go straight to the flaws and imperfections. I torture myself, wishing I were slimmer, more sculpted, had a stronger jaw or smaller ears. In a world full of people trying to maximise their looks, I feel like I’ve been seriously short-changed.
So when I started painting this gentleman, I put together a simple composition – I sat him in front of a plain wall and did a head-to-elbow painting – aiming for a likeness I thought he’d be happy with. It took about a week, and by the weekend I sent him a photo of the work, about 80% finished.
He didn’t hold back with his criticism. He said he didn’t recognise the man in the portrait – that I hadn’t “captured him” at all. I had failed.
He also sent me a long list of notes: his eyes weren’t as I’d painted them – they were kinder and wiser; his hair was fuller, his smile brighter. So I tried again. I flattered him so much that by the time I finished the second painting, it looked like Paul Newman and Brad Pitt had a child who fell out of the handsome tree and caressed every leaf on the way down. But this attempt was also met with indifference. He could tell he’d been “yassified,” and he wasn’t happy about it.
I felt confused and frustrated. I could see that, like me, he had a fixed idea of who he was – and it didn’t necessarily match how he looked now. He wanted me to bring to life the image of himself – inside and out – that he held firmly in his mind.
I knew I had to try a different approach. Instead of just trying to recreate his features on canvas, I needed to go deeper. I started chatting with him, drawing out details of his life and learning more about who he felt he was. I discovered he had a romantic side: he was a dreamer and a storyteller, a big reader of detective and historical novels. He loved fiction so much that he sometimes embellished or exaggerated his own story. What I painted became a collaboration between what he saw and what I saw. Art is a dialogue, and the final portrait went beyond just paint – it became a product of our conversations. Comparing the two, I can see that his smile became a bit more mischievous than in my first version, and his eyes had more of a sparkle.
Sadly, the man died before he could see the finished painting. But I take comfort in knowing that what he really wanted was to be seen, maybe for the last time. I had shown him a work in progress, and he had…He grinned broadly, and I can only hope he would have approved of the finished piece.
During the process, I also learned more about the disconnect—some might even call it a kind of dysmorphia—that I often feel when it comes to how I see myself. I always find plenty of room for improvement: weight to lose, blemishes to remove, crooked teeth to straighten. But when I get down about my appearance, I remind myself that my negative self-talk is just one side of the story—it’s not necessarily how someone else would paint me. Even if I gain weight, lose my hair, and definitely age, that doesn’t make me any less “me.” Despite the urge to control how others see us, we’re all a work in progress, right up until the end.
Tom Neenan: Portrait of a Tom as a Young Neenan is at Underbelly, George Square, Edinburgh from 5 to 30 August at 15:15pm.
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Frequently Asked Questions
Here is a list of FAQs about the article A moment that changed me I painted a mans portrait and he hated it written in a natural conversational tone with clear answers
BeginnerLevel Questions
1 What is this article about
Its a personal story about an artist who painted a portrait of a man only to have the subject strongly dislike the final result The experience changed how the artist thinks about their work
2 Who wrote it
Its a firstperson account usually published as part of a column where someone shares a lifechanging event
3 Why did the man hate the portrait
The article usually explains that the portrait captured something the man didnt want to seemaybe an honest expression a hidden sadness or a flaw He felt it wasnt a flattering or accurate representation of how he saw himself
4 Is this a real story
Yes its a true personal essay written by a real artist recounting a specific event that actually happened
5 Whats the main lesson from the story
That art isnt always about pleasing the subject Sometimes the most honest work can upset people but that honesty can be more valuable than flattery
Intermediate Questions
6 What are the benefits of reading this story
It helps you understand the emotional risk artists take Its also a lesson in handling criticism managing expectations and the uncomfortable gap between how we see ourselves and how others see us
7 Whats the biggest problem the artist faced
The conflict between their artistic integrity and the subjects feelings They had to decide should they change the painting to make the man happy or stick with their honest vision
8 Can you give a specific example of a similar situation
Imagine a friend asks you to take their photo but you capture them crying or looking tired They hate it because its real not because its bad The portrait story is like that but with paint and hours of work
9 How did the artist feel after the man hated it
The article often describes feelings of failure embarrassment and selfdoubt But over time the artist
