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Olan Montgomery

Alan Cumming by Olan Montgomery

Rufus Wainwright by Olan Montgomery

Rupaul by Olan Montgomery

Amanda Lepore by Olan Montgomery

Profession Pop Artist
Hometown New York
Website http://www.lipstickchic.com/

Olan Montgomery’s art shines the light on gay club life – its drag personalities, go go boys, the sex, the drugs, and the pageantry.  His portraits include notable party gays like Boy George, Rupaul, Rufus Wainwright, and transsexual Amanda Lepore.

According to the artist, the gay community has a lot to learn to from its colorful nightclub denizens.  He asks that we not only respect the artistry of these creative individuals, but appreciate them for their uniqueness. “In my mind, all creative individuals are walking art installations,” explains Olan Montgomery. "They inspire me and I am pleased to pay homage to them in my creations.”

Interview by Manuel Dawson.


For a world that thrives underground, why bring it up into the daylight?

Even before Stonewall, gays have gathered in dark corners drinking and dancing in and out of drag and even in our underwear on table tops.  The “underground” is hidden, not by choice – but because it was pushed there by bigotry.  I believe gays have a responsibility to 'bring it up into the daylight!".  Hell, it should have always been there to begin with.  The world that I portray in my art has always been as much a part of my nightlife as my day life.

Who have been some of your favorite subjects?

I recently took an acting class where I got put with this woman who proceeded to tell me how I should be doing everything from reading the lines to where I should be standing. She was so controlling that if I was an inch off from where I was supposed to be standing she would lash out in a rant of "why are you there? That's not where you are supposed to be!" She basically was policing me. So to answer your question, my favorite subjects are the ones that allow themselves to be caught in a moment of pure honesty and integrity without being policed. I want my subject to be as true to their own nature as they can be without me putting my own crap off on them.

Do you see these people as more than the characters they represent?

I have never thought of any living person as a character they represent. They are complicated intelligent artistic beings who cannot be described as 'a character.'

Is Kevin Aviance more than a bald, black diva?  Is there something beneath the surface that you’re interested in exploring?

I love Kevin’s "W is for work" skit on Youtube. The reality here is if we can come out of the closet, laugh at ourselves and make a difference we are more than the 'surface'.  If the younger me had just found one skit to look at, humorous or not, in bad taste or irreverent, that spoke to me on an honest non-judgmental level, I might have understood more of what I was going through as a gay teen. I might have had a stronger self worth.

Are you a fan of Jonny “The Gay Pimp” McGovern’s work?

Not only does Jonny McGovern make his own important art that speaks to a generation, he finds original, true-to-self talent and shines a light onto it.  Take a look at Linda James doing "Bad Bump" and Adam Joseph and his “Faggoty Attention”.  It’s a wonderful new generation of homophiles cranking out the faggotry.

Do you think these personalities have a chance of being remembered through history?  Will future generations look back on the early millennium and think of Amanda Lepore?

I am pretty sure there was no reporter asked Vermeer or his muse, also known as the Dutch Mona Lisa, if there was a chance of her personality being remembered throughout history.

Time is the true test of that. I can say that I try very hard to reflect the people and the time that surrounds me so if those Greek urns showing the migration of the Amazons from Russia to warmer climates is any indication of art not only presenting history but recording it, then I am pretty sure I have created a few original historical artifacts of my own.

Is Amanda your muse?

Photographer David Lachapelle has already laid claim to Amanda, however I find Amanda inspirational.  Amanda as an art subject reflects the birth of a time when people began the process of living their lives by how they see themselves both physically and sexually. She is the predecessor to a new generation and sex: born male on the outside but female on the inside. Her own female self-creation, Amanda is the birth mother to a futuristic transgender population.

Do you remember your first club experience?

It was the 80s but I remember those days like they were yesterday.  I loved going to a party and knowing it was a party simply because Andy Warhol was there. I loved watching Farrah Faucett and Ryan O'Neil at Studio 54, and making love to Donna Summer records.  Yes, I said records: the vinyl kind that had to be played on a turntable.

How does the 80’s gay dancefloor compare with today’s gay dancefloor?

Going out back then meant hanging out with the celebrities of the time. There may have been a curtain separating the VIP section from the masses but walking into that area was not like going through airport security.  The whole point of the atmosphere was to allow people to enjoy the music and place without posting it on Facebook, Twitter or Myspace. You went out to relax, hang and enjoy; not to network, be discovered or have your five seconds of fame.  In fact, those that were so obvious about their desire for fame were usually the ones to avoid.

Do you look back on the 90’s club kid phenomenon with the same nostalgia?

In the 90’s, I got bit by the love bug and so most of my 90sn involved a man who stamped an expiration date on my forehead.  Not only did I get to experience the love of my life but the dumping of my life. All of it was a good thing because that relationship inspired me to really look at everyone around me and paint what I saw.  My art today is a reflection of my life experiences as well as a desire to understand the people and what they are experiencing around me.

How does the next generation of downtown queer artists – Cazwell, Jonny McGovern, Kevin Aviance – compare with their predecessors?

I think they should all become educated about what and who has come before them so that they are more able to give new and deeper perspectives in their art.  Understanding what has come before is a start to being able to give more. We all need to appreciate the work of Keith Herring from the Subways. We need to learn about Tish and Snookie from Manic Panic, John Sex and the Screaming Mimis, Anita Sarko and Sally Kirkland. Understanding the evolution or the process is not only educational but can really give an artist a great sense of being a part of something bigger than themselves.

What can the gay community learn from its nightlife personalities?

They can learn to appreciate true diversity and be tolerant and accepting of one another. Respect the artistry of these creative individuals.  Don't shoot the queen in the head just because she is wearing spandex, talking with a lisp, doing a few snaps with her fingers and twirling. The minute we gay people begin to ‘judge’ one another with the societal stereotypes, we've asked them to put the gun to our heads and accept the beating or even worse, the death sentence.

How would you like to be remembered?

I would like to be remembered as the artist that cared and hopefully was able to use my art to bring people together or at least provided the platform through art to begin a dialogue based in mutual respect without preconception and judgment.  I would hope that the work be remembered as a moment in pop culture when the importance of the individual became relevant and no longer reduced and devalued like washing powders and news headlines.  We are vibrant individuals and we all count.

What's the most overrated thing about New York?

Nothing is ever overrated in New York.  It may be over exposed, over done, or over killed… You might have to get over something or someone in the big apple, but NEVER is anything ever overrated – this isn’t Los Angeles.


I can tell you most definitely the most underrated thing is the true fact the city never sleeps so if you want something or need to find a place open any time of night - or even just don't want to go to bed at all - New York is always open - 24 hours.

And that is the one thing that I forget to appreciate until I leave New York City and find myself flying to the store, bar or restaurant before they close in pretty much any other place I visit.

Is there such a thing as a New York City boy?

Yes there is - but you'll need a large net and some duct tape to catch him first.

The three things you always bring in your carry-on luggage?

I check my baggage at the curb but I always have my I-phone loaded with a good movie in case boredom sets in.

For more info on Olan Montgomery, visit www.lipstickchic.com. Interview by Manuel Dawson.