Portrait of an Artist: Bill Westmoreland

When Bill Westmoreland was about 12 years old, he like so many other boys wanted to be like the Beatles. The band had recently made a splash and Bill let his hair grow out to emulate the superstar quartet. His father, wanting him to cut off the shaggy do, told him, “If you cut your hair, I’ll buy you a Polaroid camera.” Young Bill figured his hair would just grow back anyways so he cut off the shaggy locks, got a Polaroid camera from his dad, and a lifelong love of photography was born.

In college, he focused on painting and drawing as an art major, but he continued to cultivate his love of photography by minoring in it. He’d long had an affinity for the art world and as such, he found himself more drawn to abstract and conceptual art. For his senior thesis photography show, he pitched an idea that would meld his love of abstract art and photography: a conceptual show, meaning no photographs. In place of the photograph would be text explaining what the photograph was, so the viewer could imagine what the photograph would be. The powers that be wanted actual photographs, not metaphorical ones, so Bill turned his attention in a different direction, but that early affinity for the duality of art forms and going against the grain never left him.


“While everyone was photographing cats and dogs and people walking down railroad tracks, I was taking girls in my class and doing fashion photos with them,” he said.

Using his friends as models, he photographed them as well as doing their hair and makeup. Hair styling wasn’t something he’d trained to do but he said in his brain, it was less about training and more about geometry.

“If you pull the hair this way and cut it that way, it will fall this way,” he said. For the boy who cut his hair to get his first camera, he’d found a way to merge hairstyling and photography into his own art. After college, Westmoreland worked as the assistant fashion director at Saks Fifth Avenue in Houston but wound up moving to Paris with his boyfriend who was a model.

“They wanted him right away for the collections,” he said, “and I didn’t want to sell clothes anymore so I contacted the fashion editors, told them I was moving to Paris and offered to take pictures for them. I went to Paris, photographed the collections and the models and I started getting more work. My job as a makeup and hair person didn’t really exist in Houston so I moved to New York and got an agent. I still took photos but went the hair and makeup route because that’s what took off for me.”

And take off it did. Over the years, he’s worked with some of the biggest names in fashion, photography, art and the stage. One of which, only a few years after coming to New York, was Andy Warhol.

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JM & Interview Magazine photos by Scavullo. Hair and makeup by Bill Westmoreland.


Westmoreland worked with Warhol four or five times and perhaps the most memorable, he says, was when Warhol handed him a tube of Clearasil and told him to use it as makeup because it was tinted. Warhol wrote about the experience in his diaries which were published in the book, The Andy Warhol Diaries.

Excerpt from Tuesday June 14, 1983

At 10:00 I had an appointment to do a modeling job for the Jordan Marsh catalogue at Scavullo’s. I used my own makeup after reading the AIDS piece in New York. I forgot my lip gloss though. And for the first time in a long time I haven’t had one pimple. Karen Burke’s treatments are working. She gave me this stuff called Ten Percent, and its benzoyl peroxide. Which is what Clearasil is. But then Clearasil has the coloring, so I can use it like makeup. (Warhol, Andy. The Andy Warhol Diaries. New York: Warner Books, 1991.)

“He was thinking that because I would maybe be a gay makeup artist, maybe I’d have AIDS and maybe if I used my makeup on him that he’d get AIDS. That was how nuts it was at that time because no one knew what was going on,” Westmoreland explained.

Despite professionally working with Warhol multiple times, Westmoreland says he was still in awe of him and his celebrity.

“Once we were shooting him at The Factory which was in Union Square and it was for a cover of Penthouse Forum, a small magazine published by Penthouse. They had one of the girls wearing a T-shirt that said, “Andy Warhol is a Virgin” with an arrow pointing at him. Well everyone in The Factory was furious. They couldn’t believe we were doing this because they didn’t think it was funny. They didn’t see the humor in it, but Andy did. Another time, I was walking down the street with friends and I saw him. My friends were excited and said, ‘Oh my god there’s Andy Warhol.’ I’d already worked with him at that point but I was still in awe of him. He walked up to me and said, ‘Hello Bill, how are you?’ Of course my friends were flabbergasted. He said it was nice to see us and to have a great day. You never knew what to expect. Once I was doing a fashion shoot in a gallery that had been completely taken over for the shoot. Andy walked in and everyone on set was amazed to see him. He walked right over to me, ‘Hey Bill, are you doing a fashion shoot?’ We didn’t use this phrase then but I wanted to say, ‘Look around. Duh.’ He always remembered me.”

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Photos by Robert Mapplethorpe. Hair and makeup by Bill Westmoreland.

In 1986, referred by his agent, he began working with photographer Robert Mapplethorpe on various projects which included shooting Susan Sarandon for the cover of Interview and the cover of Esquire.

“The first time I met Patti Smith, Robert told me she wasn’t a fan of hair and makeup but that they loved my style because I was very natural. That’s my forte; making people look beautiful but not like they’re covered in makeup. I told Patti that her skin looked gorgeous. I said, ‘Your skin looks like the skin of a pregnant woman, you have that glow about you.’ She said ‘thanks,’ but that was it and we took the picture. A year later, she came back to New York from Detroit and said to me, ‘Bill, I was pregnant and couldn’t tell anybody at the time that I was. When you said that, it freaked me out.’ We got along great.”

Working with Mapplethorpe, they shot singer Tracy Chapman for what was intended to become her first CD cover.

“We sat down afterwards to chat and she pulled out another picture and said, ‘I did this photo too.’ Robert looked at that photo and said, and this is what I learned from him about being an artist, he said, ‘That’s a beautiful photograph, that should be your cover.’ The photo was someone else’s work, not his, and it ended up being her first CD cover.”

He worked with Mapplethorpe until 1988 when HIV was taking its toll on the photographer.


Patti Smith by Robert Mapplethorpe. Hair and makeup by Bill Westmoreland.

“He photographed Carolina Herrera, which was her last portrait by him. It was interesting watching him photograph all of his friends for the last time. It was moving. There wasn’t any comment about it at the time but everyone knew. I also did Patti’s last pictures with Robert. You’ve read a lot about his supposed ego, but I never saw that side of Robert. He was the nicest guy. To say what he said to Tracy Chapman – as an artist, you want your work to be chosen, but if you see something that’s really great, you have to acknowledge it. That’s what I got from him: Acknowledging other artists when their work is great instead of feeling like they’re one-upping you.”


Keith Haring by Annie Leibovitz. Hair and makeup by Bill Westmoreland.

Another legend from the art world Westmoreland worked with was Keith Haring. In a photoshoot for Vanity Fair with Annie Leibowitz, he was on set for what would become an indelible and iconic photo of the artist.

“They’d built a living room within the studio and Keith was going to start in the corner and paint the entire room – the sofas, tables chairs everything. Everything in the living room set had been painted white with a brush, not spray paint, so there was texture to it. I got to sit and watch him paint the entire room, which was amazing. He wore white jeans and I painted his body, face and hair white. He painted on the black stripes in his style and then he handed me the brush and told me to paint the stripes on his shoulders and back. It was like painting on Picasso, one of those moments. Annie had him in front of the room on a bench and told him, ‘I think you have to be naked.’ So we took off his pants and I painted the rest of his body. I did the black lines on the bottoms of his feet and legs and he did the rest. He jumped on the table and that became the picture.”

Beyond the final product that went on to be so acclaimed, Bill’s work with Leibowitz inspired him despite their occasionally tenuous working relationship.

“She was tough and we got in many arguments over the work. But I’m inspired by her; I like the darkness of her work. I think some shoots and work are over-lit and I like how she does it.”

Not only has he worked with famed artists and painters on photo shoots, but he himself has been a painter since childhood, something he carried with him into college.

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“Drive By” by Bill Westmoreland

“Then,” he said of his post-undergrad studies, “I flipped it and got my masters in photography and film. So I got to do both things. It all works together. Right now I’m working on a series called ‘Drive By’ which is a series of photographs I take from my car, going about 45 mph. There’s a horizon line theme to a lot of my work. In the paintings I’ve been doing for years, I’ve painted horizon lines as well. Now I have car photos that are similar. These two art forms both inform each other. It was the melding of the photos with the paintings. Now my photos look like my paintings. This is what is exciting for me now.”

That duality of art forms rears its head again when the conversation switches to the pros and cons of digital photography versus the film cameras which have become all but forgotten.

Martha Wilson Van Gogh

In 2015, Westmoreland collaborated with Martha Wilson of The Franklin Furnace. “She had me recreate a Van Gogh self-portrait, using her as the subject. I painted her, the backdrop, the clothing, added the beard and then photographed her. This was in her show at PPOW Gallery. I also painted her like a Panda Bear which was printed 4 feet by 8 feet. She booked me for this based on the Keith Haring photo,” he said. Photo: Martha Wilson PPOW Gallery

“The pro for digital photography is that if I’m shooting, everything I shoot instantly comes up on the monitor and can be adjusted. I used to have to use a film clip to figure out exposure and then I’d have to scan every image in. There were a lot of steps between the beginning and the end. Now, I can shoot someone and retouch in the same day.”

But as someone whose first camera was a Polaroid, he still loves the look and feel of film photographs.

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“Grass-scapes” by Bill Westmoreland

“I did a series of grass-scapes with my film camera and the depth in those photographs is so different than it would be in digital. It’s very different. I kept trying to figure out what it was – could I have gotten that same photo on a digital camera? Yes. But the depth and richness of film just isn’t there in digital.”

It’s that consideration and attention to artistic detail that’ve made Bill an enviable talent among both admirers and friends.

“If you ask me what makes Bill Westmoreland a great artist, I would have to say his quiet, gentle way with people,” photographer and friend Thomas Smallwood said. “Also, his witty sense of humor and his dedication to excellence in his work. He’s the total package.”

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(L-R) Ian Macrae by Bill Westmoreland, Gabrielle Reece by Frank Schramm, Veronica Swift by Bill Westmoreland, Norman Parkinson & Robert Mapplethorpe by Annie Leibovitz.

Westmoreland has long been inspired by the photographers he regards as the masters, Ansel Adams, Irving Penn and Richard Avedon. Avedon became someone Bill eventually got the opportunity to work with on a shoot late in the photographer’s life.

“There’s an image you have of people: movie stars, celebrities, and famous people in their field. You think they will be a certain way. But I didn’t think he was going to be as loose and spontaneous as he was,” he says of Avedon. The day of their shoot, he said Avedon didn’t use a rigid lighting set up. Instead, an assistant held the light by hand, enabling him to move it until he got it where it was best for the photo.

“He had a guy holding the light, ‘move over here, there, hold it there, that’s it.’ He moved things around until he got what he wanted. Sometimes you go into a studio, the lights are set up and they’re ready to go. You seat the subject and take the picture. To know that even the best of the best maybe don’t have it all figured out until the moment they see the shot – that spontaneity made the art more realistic for me. I’ve been able to work with Annie Leibowitz and Steven Meisel and Avedon – these incredible photographers – which has been inspiring to me as a photographer. Some of my best friends who are photographers know I’m a photographer. Others don’t because I booked those jobs doing hair and makeup, not photography, but when you work with famous photographers, you have to sit back a little bit and watch.”

Liza Minnelli + The Guys

Liza Minnelli and the cast of Liza’s At the Palace by Bill Westmoreland

That learned-love of spontaneity came in handy when Liza Minnelli was performing on Broadway in Liza’s at the Palace and asked Westmoreland to take photos for the show. He jumped at the opportunity, not just to take pictures of a living legend, but to take pictures of people he’d been friends with for a decade. Cast member and friend Jim Caruso remembers a whirlwind day of shooting.

“[Liza] had always admired the photos Bill had done for me and many of my friends, so when it was time for production photos, she called Bill. He photographed hours of rehearsal, then set up a beautiful studio shoot. Among other things, he wanted to recreate some wonderful vintage Hollywood photos, since much of the show was a recreation of Kay Thompson’s cabaret act from the late 1940’s. Sets were built and painted. Lighting was tweaked. We were placed in the appropriate poses around our seated leading lady. All of a sudden, Liza shrieked that the seat of her sequined pants had gotten stuck on part of the set,” Caruso said.


Liza Minnelli and the cast of Liza’s At the Palace by Bill Westmoreland

“It was my dear friend and fashion stylist, Karen Kleber who knew immediately what to do when Liza was ‘stuck’ in her vintage Halston sequined outfit,” Westmoreland explains. “First we pulled Liza out of the pants, leaving them stuck to the cube which was still tacky from a paint job by Liza’s crew the night before. Karen grabbed a credit card and pried each stuck sequin! Saving the day and the vintage Halston!”

“Needless to say, we were all hysterical. Liza’s…pants,” Caruso said, “had rarely gotten so much attention, or been so well taken care of!”

“It was great,” Westmoreland said. “We had to shoot at a studio downtown, pack up and go to a dance studio and be done by 6:00 pm. I’d known Liza for maybe ten years at that point. The choreographer for Liza’s at the Palace was having them hit poses and if I was off by a second, he’d yell at me, but it was a great series of photographs to work on and I was honored to be included in that process.”

“Bill isn’t just a random photographer,” Caruso said. “He’s a master artist. But he’s also been a makeup artist and hair stylist for decades of fashion shoots. That experience keeps his eye and his taste level current and sharp. He’s a filmmaker. He’s a painter. He designs houses. His love and respect for other artists and their talent shows in every frame. With Bill, you don’t just get a one-time shoot. You get a member of your company for as long as you want him, which is usually forever.”

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Lin-Manuel Miranda by Ben Hassett for TIME, Erich Bergen by Bill Westmoreland, BLEEP Magazine cover by Bill Westmorland

Today, Westmoreland is doing makeup and hair plus photography and video for ARTIS, the makeup brush line he also uses in his shoots. Having worked with legends of yesteryear like David Bowie as well as recently doing the cover of Time with Lin Manuel Miranda (“I got him to take his hair down out of his bun by the wayand that image became the cover of the magazine. He is the nicest person!”), he says the commonality he sees in successful artists is their desire to be true to their vision. “Some people get into the art scene and they do one thing and it sells, but they aren’t lasting,” he says. “I think when you’re really true to your vision, it strengthens as you go. If you’re not true to it, that doesn’t make for success.”

But while working with such luminaries is inspiring, Westmoreland says his truest inspiration doesn’t come from the stars in the photographs, but from his friends in his everyday life.

“I have a very good friend, Edward Gómez, who is an art critic. He and I are in constant dialogue and he inspires me to stay challenged. He’s a big believer in my work so he’s always referencing art I should check out. I’m inspired by my friends. They push me when I’m questioning things. I’m inspired by a lot of famous work I see, but it’s my close friends who inspire me the most.”

Perhaps one of those friends, Jim Caruso, put it best when he said, “Who is Bill Westmoreland? If you’re in showbiz, you don’t have to ask, but for the uninitiated, he’s the most caring, the most interested and the most forward-thinking artist around, who makes magic on a daily basis.”

Story by Ryan Brinson
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