Woodlawn starred in the Warhol films Trash and Women in Revolt and was name-checked in Lou Reed's famous anthem Walk On The Wild Side. She went on to have a career in film, published a celebrated memoir and is now regarded as a transgender icon.

In this interview, Lee talks about the process of painting and Woodlawn's response to the portraits.

Why do you paint?
That’s a good question. It seems like a ridiculously archaic, uncomfortable, unfashionable thing to do in this virtual, modern age. I paint because I can’t not paint. It’s like an obsessive compulsive disorder, I feel compelled to purge myself of it.

How did you come to paint Holly Woodlawn?
Through the ego-less generosity of a friend of mine, Jane Czyzselska (now editor of glossy dyke-mag Diva, then freelance journo for various broadsheets.) Jane was flying to Amsterdam where Holly was appearing in order to interview her for The Times. I bumped into Jane at a gig two weeks before she was going and as soon as I heard what she was doing I knew I had to paint Holly Woodlawn. With her help I ended up going to Amsterdam and the ball started rolling from there.

What do you learn about a person and yourself in the process of painting their portrait?
Portrait painting is being given permission to stare for longer than is comfortable or polite. In fact I don’t call myself a painter, I think I’m more a professional voyeur.

When the person stands next to their portrait you then realise it’s not always a strictly accurate rendering of their features. It’s more like an idea of a person, their personality, mood, confidence and insecurities, based on their features and body language. I don’t know why that’s more likely to be expressed in some manipulated paint than in a photograph but that’s often the case.

I don’t do flattery, I frequently stylise the features which can make it appear superficially unflattering. I inadvertently tend to go for what they’re trying to conceal. It’s not deliberate, it’s just that I find that more interesting. That can make the painting hard to look at for some sitters.

The paintings depict Holly Woodlwan and Harold Danhakl (her birth name), could you say a little bit about your approach to gender in these works?
My work is about the representation of gender and looks at traditional stereotypes as possibly constructed identities. Holly is a drag queen, suggesting much of her female persona is reinforced through artifice and the trappings of femininity as performance.

In reality Holly is an ambiguously gendered person who displays physical characteristics of both sexes. But the paintings are not about a man becoming a woman, Holly is both and neither. Also, the paintings are a record of a real person, I’m not using her as some sort of example.

Holly is a glamorous superstar of the 70s and an older figure in your work, what are your thoughts about ageing as a theme?
Holly’s connection to Lou Reed and Andy Warhol is obviously fascinating and that’s how I knew about her in the first place. But in a way, that’s about who Holly was and I’m interested in who Holly is now. The fact that she allowed me to show her practically naked, vulnerable but proud, is so much more interesting than a celebrity airbrushed and stage-lit to perfection.

I think ageing bodies and the sexuality of older people is like the last taboo in art. Painting older flesh is much more inspiring technically than smooth flawless bodies. Up to date, people have felt moved by the work and it’s prompted debate about our own unofficial cut-off point regarding what’s acceptable to look at and show.

What does Holly make of the paintings?
Holly hasn’t seen the paintings. I decided not to send her prints of the finished work as she’s coming over for the opening and I thought it might be better to take her into the room privately and explain some of the decisions I’d made.

Last week I called her and she said, ‘Oh, I’ve seen the paintings, my friend found them all on a website.’ I was completely shocked and terrified that she might not like them. She said she loved them, especially the one of her with the walking frame, which was the one I was most worried about her seeing.

Obviously she posed for them so she must have had some inkling but it’s different when you see them stylised and massive. She said all her friends had said how unglamorous they were and she said ‘I told them, so what, glamour you can buy in a jar’.

Read our review of And Then He Was A She.

And Then He Was A She: Paintings Of Holly Woodlawn, by Sadie Lee
The Drill Hall
16 Chenies Street
London, WC1E 7EX
020 7307 5060

1 October-11 November 2007

For opening times and related information www.drillhall.co.uk. Official website for the exhibition www.andthenhewasashe.com.

Get the classic Warhol transgender superstar movie Women In Revolt, starring Holly Woodlawn. Buy the DVD online and save money!