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Portrait of the Headmaster as a young man? September 1, 2010

Posted by Alex, Managing Director in Independent Education.

It is the tradition in many of the leading independent schools across the world that a departing Headmaster or Headmistress sits for a stately portrait, to be hung in a hall or staircase with previous incumbents, a memorial of their dedication and service.

After a summer of long and patient sittings in dusty studies, several prestigious schools will soon be unveiling such portraits.

Tom Wheare, editor of Conference and Common Room magazine, spoke to portrait painter Emma Kennaway, shortly after she had finished capturing Steven Winkley on the eve of his retirement from Uppingham School.

Are Head teachers any different from other sitters?
No. Certainly not at the onset. Everyone arrives for their first sitting with approximately the same levels of nervous anticipation. The differences, though, do always manifest themselves in that first session. As the artist, I can quickly
gauge what level of commitment I am going to get from the sitter.

Colin Niven, departing as Head of Alleyn's, puts the finishing touches to his own portrait

Headmasters are under orders to have their portrait painted so I can say they are generally not the most biddable of subjects! They are a restless breed, by turn commanding and curious. Colin Niven of Alleyn’s had never tried oil painting and was very keen to have a go, so I let him paint in the colours on his tie. Technically, I suppose, you could say the portrait was done by Emma Kennaway and Colin Niven!

The best sitters, for the record, by miles, are thespians. They expect to be directed and then do exactly what they are asked to do.

Do Heads tend to ask for symbolic inclusions to give future viewers a clue to their character? Does everybody?
Absolutely. Headmasters like symbolic inclusions, and, I would say, more than most. Stephen Winkley, along with more mundane props, was keen to include his cat. Another wanted to have a badge of a saxophone pinned onto his lapel. These things are designed to show that the sitter is more than just a stereotypical headmaster, and I don’t suppose they get the opportunities most of us do to show people what they’re really like, or, at least, what they think they are really like.

How important is size, shape and where the portrait will hang in determining what and how you paint?
Size, shape, composition and colour are all considerations to be factored in. Because these paintings will usually be hung alongside previous headmasters, I think it’s important to have some kind of stylistic continuity.

Is it possible to paint an interesting or artistically worthwhile portrait within the constraints of an institutional commission?
Yes! These are always interesting, clever men and women, so firstly you invariably have lots of character to paint, and also nowadays there aren’t any constraints, if indeed there ever were. People are very nice to portrait artists you know; I would go as far as to say almost deferential.

What’s the best portrait of a Head you’ve done or seen?
Well mine of course are very good! More seriously there is a cracking painting at Uppingham and the painter has made a terrific drama of the sub fusc black robe.

And the worst – you’ve seen, of course!
No comment!

One of a Chairman of Governors, obviously! Is there such a thing as an over-modest sitter?
If a sitter was disingenuously modest I would find out. It would be hard to keep up such a pretence over a series of sittings. But real modesty would be nice to convey as part of the sitter’s character.

Or an impossibly narcissistic one?
Narcissism is a problem. It’s one reason why I don’t altogether enjoy painting beautiful young women. Grown-ups have more self-confidence so feel more at ease with being honestly scrutinised.

What do you talk about?
Anything and everything. I try not to let the sitter get too involved with their own thoughts because when people do, generally speaking, their faces tend to collapse into some kind of frown or look overly sad.

Are Heads discreet or do they treat you as a surrogate psychiatrist?
Heads in my experience do say some marvellous things. I know really though that they are much too astute to say anything unless it has been carefully run past the editor/censor that resides in their own heads! They can be good company and very funny. Any conversation you have during a sitting does not travel beyond the room you are in. If you are with someone one-to-one for many hours, then inevitably things of a sensitive nature are occasionally said.

Does the conversation influence the development of the portrait?
The conversation during a sitting most definitely affects the way you paint a face. It is a key to facial expressions, especially the ones where I can’t always work out what they signify. It’s really helpful, provided it doesn’t completely take over so you get no work done.

How many sessions do you like to have?
How long is a piece of string? I wish I could say for certain how long it would take. On average I like six or so sittings. Sometimes things fall into place really quickly, sometimes it can be more difficult.

Have you ever cut the number of sessions down because you can’t stand the prospect of spending any more time with the sitter?
Not with a Head, of course! I must have done approximately 90 portraits to date and only once in all these years have I wanted to cut the sessions short – well you can’t win them all!

This interview first appeared in the Spring 2008 issue of Conference and Common Room magazine.



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