21st century education
Self-portrait in Drag

Self-portrait in Drag

Kinky Boots

Polaroid photograph of Andy Warhol in drag.
Self-Portrait in Drag, 1981, Polaroid, 10.8 x 8.6 cm, The Andy Warhol Museum

On Thursday, I drove in traffic, through the rain into NYC to enjoy the Broadway musical Kinky Boots, in which a drag queen comes to the rescue of a man who, after inheriting his father’s shoe factory, needs to diversify his product in order to save the business. Watching the play I was struck by the themes of sexual identity and “Be Who You Want to Be.” I’d been thinking about the series of 356 Polaroids shot by Christopher Makos on two days in October 1981. And now the Polaroid Self-Portrait in Drag, 1981, came strongly to mind. I’d like to talk about the processes, themes, and opinions I see in this image. And also about Cindy Sherman, who I see as Warhol’s successor.

Sex, Image, Identity, Neodrag?

Out of the many combinations of poses, facial expressions, and wigs, I chose this red-lipped, eyelash-batting drag queen who is not fully aware how beautiful she is. Ironically, as David Carrier has written, the man under the make-up found himself homely, ugly, and unlovable.

In The Philosophy of Andy Warhol: (From A to B and Back Again) published six years before Makos’ photo shoot, Warhol brainstorms about which people think they are working the hardest at being “sexed:”

Men who are trying to be women… do all the double things: think about shaving and not shaving, of primping and not primping, of buying men’s clothes and women’s clothes.

Andy Warhol

On an episode of the 1980’s MTV show Andy Warhol’s 15 Minutes, Warhol and Jerry Hall conversed about the term drag queen.

Jerry: So Andy, I [bet] you love [the word] drag queen.

Andy: Drag Queen is such a down word. We need to give it an up word.

Jerry: Dress-up!

Andy: “Dress-up, yeah…but…but…that, that could be, that’s just dressing up. You know, like a new word like, like, the new word Neo-geo and Neo…uh…Neo-up?*

Then, the scene changes and Debbie Harry brightly explains,

Neodrag is what we call the drag of the 80s.

as the word pops up on the bottom of the screen like an adult version of Sesame Street. 

Warhol in Neodrag

To complete Warhol’s Neodrag persona, friend and clothing designer, Halston offered a sequined dress, which was turned down by both model and photographer. Cristina Rouvalis wrote that they weren’t going “the traditional drag queen route” and Makos recalled, “Our idea was that if you changed a man’s face, it became something else.” By wearing a man’s shirt and tie on the body, and drag make up and a blonde wig on the head, Warhol represented transformation and exuded ambiguity. Warhol lived his own philosophy about a man trying to be a woman (or a Diva) during the extensive make up session.

Jane Wainright quotes Warhol’s comments and complaints to make up artist John Matthews: “It must be hard being a girl or a drag queen”; I am involved in the “same old act” of “putting your face on”; “Keep the look just natural” or “a little liner there…just a thin line” or “not too much eye shadow”; “Oh God it’s real, it’s a pimple.”

There’s No Place Like Postmodernism, There’s No Place Like Postmodernism, There’s…

[a photographer] can make any number of prints; to ask for the “authentic” print makes no sense.

Walter Benjamin

During Warhol’s early career, photography was not considered fine art. Walter Benjamin believed that authentic works of art should be unique. Warhol belongs to a postmodern world where, according to Helen Molesworth, repetition is apparent “in the ‘age of mechanical reproducibility’.” Catherine Morris lists other features of post-modernism:

  • Artists begin using any Medium they want, often employing several at once
  • Artists want to take apart and examine the myths they’ve been taught: deconstruction
  • Challenge the modern idea of originality by borrowing images from the media or from history: appropriation

Don’t you wish that Warhol could stare Benjamin in the face and say, “I told you so!”?

Cindy Sherman

black-and-white self-portrait by Cindy Sherman

Untitled, 1977
, Black and white photograph.

She’s good enough to be an actress

Andy Warhol

With her cropped blonde wig and horizontal striped shirt, it seems as if Cindy Sherman is impersonating Andy Warhol impersonating a woman: heads cocked back, full slightly parted lips, and cool unwavering stares, although Warhol’s seems a bit more vacant. Sherman’s character is just as beautiful, but she knows it; maybe she has had more practice. These are not self-portraits but “ready-made” lives that on can choose to emulate.



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    1. Hi Jennifer! Thanks so much for contributing your lovely article! As you know, Art History conveniently ignored that Warhol was gay for many years! It’s very nice to have you talk about Neodrag and Kinky Boots. Also, yours is the only article to explore his use of Polaroids, one of the most essential media in Warhol’s large oeuvre. Projecting forward to another great maker of portraits, Cindy Sherman, gives us plenty of food for resonant thinking.

      Thank you Jennifer!

  2. Excellent article; I enjoyed reading it so much! I have always loved Warhol’s drag series, and am thrilled to now have read this perspective of it. And it’s so well-written too.

    1. Elliott,
      Your comment is a pleasant surprise being that I composed this article over a year ago. I am so glad that you enjoyed it.
      The research for my article was intriguing. The plethora of information I discovered written about and by Andy Warhol pulled me into a euphoric state. I almost felt like I was sitting on his couch in the silver walled studio at the Factory.

      Jennifer Walk

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