Stephen Wayda is one of the world’s most celebrated photographers, with an ever-evolving Rolodex of photographs of the who’s-who of the world, from A-list celebrities to pop culture icons, supermodels, musicians, and the “girls next door.” Wayda quickly gained his reputation due to his style: he emphasized the attitude and personality of each subject above all else.

On November 22, 2022,  eleven of Wayda’s classic photographs of Jack Nicholson, Linda Evangelista, Demi Moore, Danny DeVito, and Denzel Washington will drop on MakersPlace.

In a sit-down interview with Stephen, I not only got the answer of how he became a photographer of cigar-smoking celebrities, I also got an insight into the 11 photographs and the behind-the-scenes process and philosophy it took to get these incredible shots. 

Tell me about the inception of the cigar series. Why cigars?

Like most of my career, it was serendipitous and unplanned. Playmate of the Year 1989, India Allen became a fan of cigars. At a Cigar Aficionado convention, she pitched the owner, Marvin Shanken, to do a nude pictorial of her with a cigar. He signed off on the concept and gave me a small budget for a shooting.  

Since I had a day job at Playboy, I could put my entire budget into production. I rented the Penthouse suite at the Peninsula Hotel in Beverly Hills, shooting India Playboy style, smoking a cigar. Shanken published the pictures, but he realized this would be a one-time pictorial. 

Liking the storytelling style of the pictures, Shanken gave me Jack Nicholson as my first Cigar Aficionado cover and pictorial for summer 1995. Linda Evangelista followed for Autumn 1995 and Tom Selleck for Winter 1995/96. Between 1995 and 2000, I photographed Arnold Schwarzenegger, Demi Moore, James Woods, Denzel Washington, Gina Gershon, Danny DeVito, Michael Richards (Kramer), Chuck Norris, Claudia Schiffer, and Bo Derek for Cigar.

It made a big difference being able to put all of my budget into production. I could do the pictures that I wanted to do without much limitation. I could pay the crew a regular fee, hire a brilliant makeup artist, the best stylist and set designer, and I could rent a great location. 

At that time, the celebrity agents only wanted to give you an hour for the shooting, usually in a studio. An hour was not going to work for me. I told the agents I wanted a day. The agent, of course, said no. Once the celebrity looked at the Polaroids and liked what they saw, they would give me all the time I wanted. The celebrity stayed because the pictures were about them, a collaboration between them and me. It was never my pictures, but always their pictures. From a viewer’s point of view, it was obvious the celebrity was having fun.

Your first cover assignment was the biggest movie star in the world. What was that like?

Now Jack’s a different story, but a real fun story. We went to his house on Mulholland Drive overlooking the lights of Beverly Hills. It’s a very modest house, not what you’d expect for the highest-paid actor in the world. Eight rooms, a bit over 2000 square feet built in 1947.

It is, after all, JACK, and from the start, you realize Jack is in charge.

I had a makeup artist. I had a stylist. I had an assistant, and we were going to shoot in the house. We had pulled all these clothes for the shooting, and he said, “No, I’m not going to wear any of your clothes. Marvin (his friend and the magazine’s publisher) can’t afford me. Anything I put on or touch, I keep. So I’ll go get something from my closet to wear.” 

The makeup artist is saying, well, let me just do a little makeup on you. And Jack says:” No makeup.”  She says just a little. Jack again says “No, no makeup… no makeup.” So she goes up to him saying:  “Let me get this hair.” She smooths down the hair, and because she touched him, she can now put in her resume that she groomed Jack Nicholson. That was our styling and makeup. 

So I set up two lights for what seemed to be developing into a relatively quick shooting. Everything he does in front of the camera is in character. On the green chair, he’s sitting there smoking his cigar, at one point putting his thumb to his mouth. He’s animated. He’s charming, and he’s serious. It’s great. That’s a memorable picture. 

We moved to another piece of furniture. We talk, and Jack says:  “Okay, how about this?” [Wayda makes  an impersonation of  Jack’s face], mugging for  the camera with a wide open grin that said, “IT’S JACK!” Priceless. Iconic. The unexpected. Historical. Okay, that’s THE picture.

He  then says, “I’m done.” What can I say: It is Jack! But then he surprises us by inviting us to walk through this house on a personal tour of his incredible artwork.

For about two hours, we walk through every room in the house while he explains the history of the work and its artist for every piece hanging on the walls or sitting on a table. The art was exquisite, the best of the best. He was very proud of his world-class art collection, and he wanted to share it with us. It was a once-in-a-lifetime honor.

There’s only one Jack. Getting to photograph him in his home, getting to see and hear about his art collection was one of the biggest events in my photographic career.

The photos of Linda Evangelista are amazing. Can you tell me about the process of going from almost cartoonishly formal to the state of casual half undress?

We flew to New York and rented a downtown studio. Linda arrives expecting what she always gets on a photo shoot: that she’s gonna be dressed up as a fashion model. Instead, it was, No, I don’t want to shoot you as a fashion model. We have an alternative wardrobe we want you to look at. 

When I’m shooting, it’s a collaborative effort, and I want the subject to choose and make suggestions. Whenever I’m taking pictures, I need the subject to be happy with the shooting.  It’s about them. It’s not about me. It’s about them and how they see themselves and how they would like to be portrayed, and that it’s going to be unexpected and fun.

So she goes through the wardrobe, and there’s this old 1930s antique dressing gown, a little fluff of marabou feathers on the sleeves. Putting the gown on, Linda says, “No one wants me to wear clothes like this. I’m so tired of being fashionable.” She sat on the floor, she got up, she moved around in that beautiful silk gown, and she loved it. She didn’t need to be fashionable. 

Next, we had the black top hat, a women’s tuxedo with a white dress shirt and bow tie. Again, she doesn’t want to be a fashion model. I don’t want her to be a fashion model. I want her to be excited about what we’re doing. She starts goofing around. She’s being silly here. She’s being silly there. She’s tipping the hat, and she’s got that big mischievous smile.

After a while of shooting her in men’s formal wear, Linda says:  Well, I want to do something in just a white shirt. So she takes everything off, leaving her barefoot in a white men’s shirt with an open tie around her neck. She moved around the studio carefree. She sat down, she laid down. She got up, she laid on her belly. She put one leg up, one leg down. And she just kept moving. 

That’s one of the things I like to do with people: keep them moving. Posing is boring. 

When I started at Playboy, everything was done as a pose. Photographers would put their models in these excruciating positions to try and make them look like 1940s pinups, which is impossible for a living body to duplicate since these pinups are drawn and painted. And the poor models — it was painful. I was the new kid on the block. I was just plucked out of obscurity. I didn’t go to photo school. I didn’t do anything other than send in some pictures. And I looked at this and said to myself, this doesn’t make sense because, in sex, you don’t pose. 

So I then developed a style and a lighting system, and a set system that let the model move. And she could then express her sexuality, her sense of self, her sense of being. So, of course, everybody hated me because I was changing everything. And I did. And they disliked me even more.

How do you balance your own creative vision with giving subjects latitude and space to play and express themselves?

On creative vision, I don’t know if I know what that means because when I get a subject, I think, What might they like? How are they going to have fun? 

If you look at all these cigars, there’s one common denominator, they’re all having fun. Okay? So I made the situation fun for them. I didn’t make it like work where they have to go in and pose like most other photographers would have them do. 

I’ll pick a location, like with Danny [DeVito]. We picked a big old grand and glorious theater. He was in that to start, and then we went to the beach. 

And he hammed it up in the theater. The picture of him where he’s smoking the cigar, and he’s looking right at you — I think that’s the best picture he’s ever taken. He looks handsome. He looks great.

Again, the agent says, You got a couple of hours. 

I don’t think so. When Danny sees the Polaroids, the agent leaves.  I now have Danny for the day.

After the theater, we take Danny to the beach, where I have a diminutive leather loveseat and an antique movie camera as props. I think to myself, What am I going to do on this beach? 

Again it’s a collaboration. I’m working with the greatest actors in the world. Who I am to impose my sense of style on their image? We work together. We create together. We make great pictures together.

One of the things that always happens when I go on location is I look around, look this way, that way, and go, What am I going to do here? And then magic happens because I’m talking to the other people. 

I’m talking to my crews. My crews are like family. They’re whispering on my shoulder. I’m telling them to sit on my shoulder and talk to me. I might do what they’re saying. I might not. I might do it later. But come on, give me your input. And the same with the subject. It’s a collaboration, okay? We go back and forth. Let’s do this. Let’s do that. Let’s do this first. So it’s always spontaneous. Even though there’s a setup.

Danny is a good example. He is five feet tall and dressed in antique silk pajamas. He’s looking over a five-foot-wide loveseat set in the sand with waves breaking behind him. It’s absurd. It doesn’t make sense. But for the comedian Danny DeVito, it is great. He’s laying on the loveseat as he exhales cigar smoke. He’s moving here, moving there as we change the angle of the loveseat to match the moving sun. He’s on the beach with an antique movie camera, putting his hands up like he’s framing a scene. If you look at these pictures, he’s having fun, okay? 

When you produce magazine pictures of a big-name celebrity, like Denzel or Jack or Danny, there’s a plan, okay? Other photographers will take the talent onto a set or location, telling them to stand here, stand there. 

Fuck. I don’t know why anybody would do  that. Yet, even with digital, there are still photographers that set up a scene and ask the talent to pose. And they talk about how they got their shooting done in an hour and a half, 40 pictures, da, da, da, da, or something. And you go, well, they’re all standing there doing the same thing, but okay. 

It’s  spontaneity that you gotta go for. Let the talent be themselves. Let them have fun. 

You managed to get perhaps the most playful shot of Denzel Washington on the planet. How did you get him to pose like a teenage girl reading her bed? Of all the actors in this series, he’s a Serious Actor, and to see him in such a playful pose speaks to your ability to disarm your subject and to make the shoot fun.

You’ve never seen Denzel smiling like that, being a clown, being silly, moving all over the place. He just gave me his all. 

There’s one picture of him standing against the wall with a shadow smoking a cigar. But everybody can do that. Not everybody can get him to lie on the ground and put on this silly hat. We just bring the wardrobe. and he decides what he puts on. 

And then the smile. Have you ever seen Denzel smile like that? where he’s laying on the ground with his feet in the air? And I have hundreds of pictures of him goofing around like that. In a white sweater, Denzel Washington has his knees out, while he’s leaning forward grabbing his toes…. he’s grabbing his bare toes. That’s not what you expect from Denzel Washington. He is a serious, serious actor, and he’s usually killing somebody in the movie. And here he is, just hamming it up. 

All of these cigar people had fun. I’ll go back to that. I use that as kind of a motto whenever I do photographs: You just wanna have fun. And also, in my recreation and my relationships, I just wanna have fun. The problem is I had too much fun playing polo, breaking up my body way too much. It was all broken from having too much fun. So,  hey. It’s the price you pay, ’cause when you’re dead, you can just lie there.

How do you get your subjects to relax and feel at home on set so quickly? If an agent’s telling you that you have one hour and you want the subject for two days, you’ve got to establish that trust and fun right away.

I would set up a situation, a location, get it propped, get wardrobe brought in, have crew there, have lights there, and then I would improvise. And again, I would ask them what they would like to do. 

Usually, they say, What do you want to do? 

Well, come on, let’s try this, I would say. 

It’s what I capture in the first 15 seconds with them, on Polaroid in the film days or on the digital screen. I mean, that’s all you got. Okay?  You got to grab their attention in that first 15 seconds. And then you got another 20 seconds to get them pulled in. And then after that, you can reel them in, and they’re yours. 

So in doing that, I always tell them, “I need one Polaroid or one snap on the digital to set things up. Then I’ll make adjustments. If you don’t like the second picture that I show you, we’ll call it a day.”

Kim Kardashian, when I photographed her for Playboy, neither she, her mother Kris, nor I knew we were going to reshoot her pictorial. We thought it was only for a cover. I was told on set — imagine, if you will, being told on set — that I had to get a full shooting with her. How do I do that? I don’t have any wardrobe. I don’t have any set. I don’t have any plans. I don’t have anything. 

I had redone the cover, and it was nice. It was pretty. The lighting was nice. Even with that, Kris said, “Well, no… no more shooting.” I talked Kris into giving me one more opportunity, let me set something up. I said, give me two frames. One to see where I’m at, and a second frame after making adjustments. If you don’t like the second frame, we’ll call it a day. That’s how we proceeded for four setups, Kris saying no to each setup, me saying: One more opportunity, I’ll show you the setup before I shoot.

We were there just for a cover. I was there to get a full nude shooting. And so it was the same thing. Two snaps. Okay, great. We love it. I’d like to do a little bit more. Two frames and then go ahead, and continue shooting, Kris seeing and approving every frame as they appeared on the digital monitor. 

Kim was great, but it took getting her’s and Kris’ trust…and getting memorable pictures fast.

You’re auctioning off two pieces with Demi Moore. One is this alluring and powerful Demi we all know, and love, and the other is a proof sheet where the viewer gets a peak into the process. 

Okay, let me tell you Demi’s story. Because every shooting has a story, and a moral, behind it. 

I flew in from my ranch in Utah to Jacksonville, Florida. My assistant flew in from Los Angeles with equipment, lighting, and some props. His plane got delayed, then he had to get on a different plane. While he arrived the morning of the shooting, his baggage and equipment were on another plane somewhere in another city. He only had the cameras he carried on with him.

Demi was there to do GI Jane, and she was getting her hair shaved off later that afternoon. She had a 12-hour turnaround — 12 hours on, 12 hours off. In those 12 hours, she had to sleep, eat, shower, rest and do whatever else that needed to be done to get ready to be on set. 

So I have no equipment, I have no wardrobe. Demi has her own makeup artist there from the movie set. I asked her what wardrobe she has, and she goes: “I didn’t bring much. I’m shooting a movie. I’m not going anywhere. “

She’s in this little rental house in Jacksonville, Florida. It’s not gracious, it’s not cool, it’s not interesting. It’s brown. I don’t like brown.

So she takes a shower, and she comes back out in a loosely fitting white robe, hair slicked back. And you’re going, Oh my God, this woman is beautiful. 

I should have given her a cigar and started shooting. Instead, I thought, That’s not what the client’s gonna want. Big mistake on my part. I didn’t follow my own advice of working with what you’ve got, being spontaneous, and innovating. 

So I said, do you have something else? So she goes back into the bedroom. When she returns, she’s dressed in a completely see-through black sheer bodysuit. 

My assistant is standing there with his mouth open… ah, ah, ah, ah, ah, ah, ah. He’s not supposed to do that. He’s seen plenty of naked women, but this is Demi Moore, currently the highest-paid actress in the world, and one of the world’s most beautiful women. 

Again, I should have said, let’s get a cigar. Let’s get this shot. Instead, I said, No, that’s too nude for the client. They’re not gonna want that. Again I didn’t follow my own advice. 

She said, I don’t have anything else. Returning from the bedroom for the third time, Demi has this brown shirt on — you know. I hate brown. My mission now was to minimize the clothing and deal with the beauty of her face. I put her in this study, and she sat this way and she sat that way. She was great, making beautiful pictures out of a difficult situation. 

While Demi told Arnold Schwarzenegger she “loved her shooting,” I was disappointed in myself for not being true to my idea of being spontaneous and taking the opportunity with whatever I had. I was structuring it. I was trying to please somebody else, the client, rather than please myself. And that was a mistake.

This is the only person in the series for which you’re offering the proof sheet. What’s so special about seeing the process here?

The proof sheet is interesting because it demonstrates how film was edited and pictures selected. In the edit there are large red Xs for definite nos, red slashes in the upper left-hand corner designating the first edit, then small red Xs for the second edit, and finally a single frame is chosen for printing. It has been over 25 years since proof sheets were a staple of the industry. I think seeing the process tells a different story than the current digital photo world. The proof is very cool.

What’s one piece of advice about creativity and art-making that you would give your 20-year-old self?

Well, at the beginning of my career, what I would have told myself is to trust my instincts, go for spontaneity, and do what I wanna do because I can’t please everybody else. 

Just do what you feel is right and be spontaneous and stop trying to pose and control. Leave the ego at home. It’s not your shooting, it’s their shooting. 

If you’re doing landscapes or animals and stuff like that, that’s a different thing. But if you’re doing people, it’s a personality, and it’s very, very fragile. When you’re doing people, it’s like having an ice cube. You’re holding that, and it’s constantly melting. And as it melts, you’re getting less and less and less. So work fast, get the job done. And then, if you do it right, you can get another ice cube. 

For any of the photographers that are out there, that’s the bottom line. What do you produce? Not what went wrong. There’s no: Well, this was this, that was that. There’s no disclaimer. You have to produce. If you don’t produce, go find another job.

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