Meet the Model Who Dated Madonna and Played Film’s Most Famous Gigolo

Tony talks: the original male supermodel opens up to Rick Castro about life then as Madonna’s toy boy and life now as a dad of three – plus, he discusses the role that made him a gay pin-up: playing ‘Monty’ Ward in Hustler White

A combination of Joe Dallesandro, Alain Delon, Jeff Stryker, Cary Grant, and Rasputin, Tony Ward has worked with nearly every major photographer from the late 20th and early 21st century; numerous brands, big-name designers and models, pop stars, living legends, gay icons, and two cult filmmakers.

I have known him for a very long time. We have a history, a karma, and have shared both good and bad times together – from my first obsession, when he modelled for my first ever photo, to being house model for my men’s clothing line (for Michèle Lamy). Together, Tony and I have been panned by the New York fashion press – once we were denounced, “Too California; a male Frederick’s of Hollywood.” Tony starred in my first film Hustler White (1996) and we toured the world together with the movie; he also featured in my two photography books, Castro (1990) and 13 Years of Bondage (2004).

Way back in 1996, I photographed and interviewed Tony for my self-published zine, The Bondage Book. The photos and interview were very revealing – I asked probing questions and Tony answered all. Now, 22 years later I am photographing and interviewing him again; this time as mature men, with his two daughters – Lilli Sato Ward and Ruby Love Sato Ward. This is what went down...

Rick Castro: How did you get into modelling?

Tony Ward: I was at college in San Jose, California and I met this guy on campus, Joe House. We ended up doing my first shoot: Joe met me at a mall parking lot, walked into a sporting goods shop, bought some dolphin shorts and a tank top, and shot me right there under a tree on a patch of grass, and gave me $75... Joe went on to teach me about art, show me art and photography books... One time I went to his house. He had wood panel on cinderblocks as a backdrop for our shoot and used a crummy little flash camera... He talked me into taking my clothes off, and being friendly... He put his arm on my shoulder... I complained about being sore from a workout and he massaged me. That was my first time with a man...

Rick Castro: Did you feel you were violated?

Tony Ward: No, I was curious. I wanted it. I’d been with girls... I had a girlfriend... No girl had ever told me I was good-looking. I didn’t see myself like that. Joe showed me how desirable I was.

Rick Castro: What’s your heritage?

Tony Ward: Half-Portuguese, the rest Scottish, Irish, English and Swedish.

Rick Castro: Has this impacted your cultural interactions?

Tony Ward: Yeah, in a big way. When I was young, all the Americana nationalism – I didn’t get, it wasn’t me. People assumed I was Italian. I would respond with, ‘No I’m half-Portuguese, the rest Scottish, Irish, English and Swedish.’ I didn’t consider myself American.

Rick Castro: What’s your mother’s maiden name?

Tony Ward: Castro.

Rick Castro: Does that make us related?

Tony Ward: Uh huh... you’re my sister.

Rick Castro: Fuck you.

Tony Ward: You’re my daddy, my brother, my master!

Rick Castro: Where and how did you and I meet?

Tony Ward: At an Albert Sanchez shoot?

Rick Castro: Are you asking or telling me?

Tony Ward: My memory is fadey... It had to have been with Bob Stickle, my manager. Bob was an advertising guy. He promoted me...

Rick Castro: He went by ‘blue leader’. I only ever talked to him on the phone.

Tony Ward: I remember staying with you downtown in a loft?

Rick Castro: That was the brewery building circa 1986.

Tony Ward: Wow!

[Through ‘blue leader’, I booked ‘Anthony Borden Ward’ for our shoot. I was working as a stylist for Albert Sanchez (West Coast photographer for Interview) and was creating an editorial based on Paul Cadmus for InStyle. I thought Tony would be perfect for our sailor. I picked him up from Union Station and he was so innocent and so beautiful... Like everyone before me, I was smitten. He really had an allure all his own. We went to dinner and I did most of the talking. He was very shy. He stayed the night at my loft at the Brewery Building, (now an overpriced artist complex). Once in bed, I made a play for Tony, to which he responded with the immortal line, ‘No thank you please.’ I used that line in the Hustler White script.]

Rick Castro: Did you know my shot of you in leather gear (1986) was my very first photo?

Tony Ward: You told me! I was mildly blown away.

Rick Castro: Thanks...

Tony Ward: I didn’t mean like disparagingly, I had no idea... What a fab pic. If I remember correctly I was probably 23... I was a pup.

Rick Castro: Did you know I hooked you up with Herb Ritts?

Tony Ward: Um... I thought it was through Bob, who took me to meet my first agent Dennis Vaughn... Bob said Dennis went to Herb’s studio and there was my Polaroid.

Rick Castro: That Polaroid was from me... Michi (my business partner at the time) and I took it to show Herb. We were working with him as wardrobe stylists.

Tony Ward: Herb fell for me eventually, but I digress...

[After my first shoot with Tony I was eager to present him to Herb Ritts. Herb wasn’t as open at the time and responded to my Polaroid, ‘I don’t know Rick... he’s like... I don’t know what... I don’t like his nose.’ ‘His nose is amazing!’ I replied, ‘It’s romanesque! It’s like a second dick!’ Herb made a face... ‘He’s just not my type.’ ‘What do you mean?!’ I exploded, ‘He’s the world’s type!’ Herb eventually used Tony for the first Calvin Klein Underwear box, numerous nude shoots, books, editorials, and then took him to Madonna’s birthday party.]

Rick Castro: What does Montgomery Ward mean to you?

Tony Ward: It’s the place my mom took me shopping and I hated it... My body didn’t match my age range. I was so tiny... I wore little boys’ clothes well into middle school. Also, that’s my character in Hustler White... I love the connection and the history to that name. I haven’t watched the film in a very long time... I’m remembering coming off dorky and nerdy... I don’t remember.

Rick Castro: We asked you to be that way. The character was supposed to be sexy and dyslexic.

[I was writing a script with Bruce LaBruce based on my hustler photos and interviews from Santa Monica Boulevard. I had cast a real hustler as the lead but after getting a girl pregnant and stealing a car, he dropped out of the production a few days before the shoot. I originally wanted Tony as the lead, but didn’t think he would do it. Post-Madonna he was very famous. I called asking him to please just read the script. He called me three hours later and said, ‘I definitely want to do this movie!’]

Tony Ward: It was my first film. I was nervous all the time when we were making it. My ego was a mess... I had self doubt. When you met me I was clueless about this town and the industry... I was taking it so seriously, I wanted to do it right. And Hustler White did affect my career, as did my relationship with Madonna. At that time models were not respected... Especially if you wanted to segway into an acting career.

Rick Castro: Which was worst for your acting career, Hustler White or Madonna?

Tony Ward: I would saying being with Madonna... I was a ‘boy toy’... All the press and tabloids... In a heartbeat you would be trashed. Ultimately it was my own fault that my acting didn’t take off... I wasn’t good at the politics but there was also a bit of self-preservation of not getting sucked into the Hollywood madness.

Rick Castro: What reactions have you received from being the star of Hustler White?

Tony Ward: People contacted me saying ‘I’ve watched Hustler White 100 times,’ and, ‘I used to fuck my boyfriend while watching you in Hustler White’ and of course ‘Watching Hustler White changed my life.’

Rick Castro: Who has most influenced you as a model?

Tony Ward: Rick Castro… I love Ricky.

Rick Castro: You’re a kiss ass.

[In the late 70s, early 80s I had a clothing line called I Love Ricky with my then business partner Michi. We transitioned into wardrobe styling and kept the name, so Tony first knew me as, I Love Ricky.]

Tony Ward: No one photographer... I get energy from all I’ve worked with, but it comes from inside of me... What I think is cool. As a model I see myself from the photographer’s perspective. I know every inch of my body when I’m modelling. The position of my fingers, my nose, my ass. I understand photographers. OK, I’ll give props to Joe House, the first guy that ever shot me. That was a turning point for how I viewed myself... ‘I’m something someone wants to look at?’ I didn’t know that.

Rick Castro: What are most famous for?

Tony Ward: My ass... I lost it... I want it back.

Rick Castro: What are you most infamous for?

Tony Ward: There’s a lot of fantasy around me... My affair with Madonna...

Rick Castro: Are you the longest-working male model?

Tony Ward: Yes... To be certain I don’t know... In my own mind, yes... I still do it.

Rick Castro: Will you ever retire from modelling?

Tony Ward: There’s no need to... I won’t give up on my end. That’s up to other folks.

Rick Castro: Shoulda-coulda-woulda – do you have any regrets?

Tony Ward: Yeah, hurting people that meant something in my life. For many years I put myself before everybody else. I regret that. But I get to be different now and that’s inspiring.

Rick Castro: Where will you spend your golden years?

Tony Ward: Hopefully in nature on a piece of land with people I love. Sometimes not with anybody. To have a place where people can come stay with me, or on their own. Creating with me, and on their own.

I have memories of my past golden years, like working with Colt StudiosJim French was a sweet man. He flew me to Los Angeles for our shoot. He was always very respectful of me... When Colt came out I had a lot of men liking me... I began to question my sexuality, but I decided I’m not a sexuality... I’m me.

I met Madonna through Herb Ritts... I did the Cherish video and we hooked up in 1990? My world changed quite a bit once I met her. With Herb I worked a ton. The other guys fizzled out quicker. I didn’t do the big campaigns. I was an ‘acquired taste’ and people liked me as an anomaly. Who was I without my connection to her? Me as an object rebooted me in the industry. In some ways good, some ways not so good.

The editor of Italian Vogue called my agent and said ‘Don’t ever send that disgusting person again! He looks like a rapist,’ because I had a few tattoos and piercings. At the time it was just too much. That went on for a while until it became a fad.

Then there was all the stylists, the gay contingency, ‘Oh we know you!’ It was after Hustler White – you’re a hustler, you did porno and prostitution! I was like, ‘No I didn’t.’ They were like, ‘Yes you did!’

Rick Castro: They considered Hustler White a porno.

Tony Ward: Yeah, this showed me the truth didn’t matter... they want their fantasy. ‘You’re not anything like you said you were?’ ‘Well I didn’t tell you what your fantasy was of me... you got what you wanted.’

Rick Castro: That’s a great answer...

Tony Ward: I thought for sure you would ask about the time we had sex?

Rick Castro: That’s not so interesting.

[The ‘no thank you please’ became ‘yes please’.]

Rick Castro is a photographer/filmmaker, writer & blogger living in Los Angeles his entire life.

Tony Ward’s clothing can be found on his Instagram page. His website will launch in February, 2019.