The actor behind Ryan O’Reily discusses working with a stellar ensemble of actors (including his own brother), the moments that still stand out, and what it’s like to watch the show 20 years later. Spoilers follow.
HBO: When did you last watch an episode of Oz?
Dean Winters: About two months ago. Someone showed me the episode of the night before Cyril, my character’s brother, gets the electric chair, and it just brought back so many memories. That was a really hard day on set for me because Scott [Winters, the actor who plays Cyril] is my real brother. To be there that day I felt like I was on a different planet -- it was really weird.
HBO: What’s it like to watch the series now?
Dean Winters: I’m blown away by how much of a visionary [creator] Tom Fontana is; he sees into the future like no one else. You look back at 1997 and he had a lead character who was Muslim. He had lead characters engaging in gay sex. He was so ahead of the curb that it was mind-blowing.We would read the scripts and wonder, Who is going to watch this? In the first episode you follow Dino Ortolani [played by Jon Seda] through the whole thing and he dies at the end -- which I don’t think had ever happened on television; the guy you think is going to be the main character of the series dies in the pilot. Tom was taking risks no one else had.
There was no template; there was nothing to refer to. It really was like the inmates were running the asylum. We’d read these scripts and be like, What are we doing? When are they going to tell us we have to stop? It was this fantastic kind of smorgasbord of newness. We were all so young. A few of the guys had been around for a minute, but most of us were newbies.
HBO: How did you and the rest of the cast get along?
Dean Winters: The content was so volatile, but for a show as rough and graphic as it was, we all got along famously. There were the more-trained theatrical actors on set, and then there was the wild bunch -- I was absolutely part of the wild bunch. There was definitely a clash of styles, but I think each one ended up respecting the other.
I would go in when I wasn’t working, when people like Elaine Stritch [Judge Grace Lema], Betty Buckley [Suzanne Fitzgerald], Uta Hagen [Mama Rebadow], or Rita Moreno [Sister Peter Marie Reimondo] were filming, just to watch the masters at work. Tom was so good about blending in guys like B.D. Wong [Father Ray Mukada] and Edward Herrmann [Harrison Beecher] who were just amazing theater actors, with us the kind of “street rats.” Walking onto the prison set, it was like we were just a bunch of puppies in a sandbox. We really had a great time and a lot of us learned from each other. It was the best acting class I ever had.
HBO: What did you think when you first read the role of Ryan O’Reily?
Dean Winters: When Tom and I first met, I was a bartender and a total hustler. I’ve said this a million times before, my motto was: If you left my bar with cab fare then I failed. Tom watched me bartend and manipulate the crowd a bit, and that’s kind of where Ryan O’Reily came from. When I read the first script, I was like holy s**t he really nailed this character. He was able to capture my voice without blinking an eye.
HBO: Did that make it easier to get into character?
Dean Winters: Tom based the character on watching me bartend, but also on Iago from Shakespeare’s Othello so I studied that play intensely, and drew a lot from that. Ryan is the only one in the prison who didn’t have a gang behind him, so he was a lone wolf who had to survive on his own. But in the second season Ryan’s brother, Cyril, who is mentally handicapped, comes to prison so then it was all about looking out for his family.
I’m very protective of my brothers and my sister in real life, and here I am on this TV show having to be protective of my brother, played by my actual brother [Scott Winters]. So there wasn’t a whole lot of work that had to be done there. Tom’s writing is so great for an actor because, yes, you do the research, but a lot of it is spelled out for you. It’s all there.
HBO: Which storylines still stand out to you?
Dean Winters: The moment when Cyril first comes to the prison and I realize he’s been raped by Vern Schillinger [J.K. Simmons] was a really hard for me. I saw this happening to my brother on screen, played by my real brother. I just remember being affected to the core. That brought a real depth to what I was trying to achieve in the scene work. Working with him and my other brother Brad, who wrote for the show, was a dream.
The one I enjoyed equally was the Ryan O’Reily/Dr. Nathan storyline, and working with Lauren Velez. It had so much fire and heat that bubbled up every time we had a scene together.
HBO: Was there any moment where you thought, “How am I going to do that?”
Dean Winters: When I was in the hole in the first season. I was the first one to be thrown in on the show. We had this guy who had been in prison, Richard Stratton, watching over us, giving Tom guidance, and he told me when you get thrown in the hole, you go in naked. And I thought, Oh man, really? I went to Tom and said, “I think my character has to go in naked,” because that’s what happens. I wanted to stay true to the storyline; I didn’t want to be naked.
I did it and that set a tone for the entire series. Every character that went into the hole had to go in naked; of course everyone hated me for that. It was all because of my conversation with this guy. The kicker is that Stratton eventually told me he was just kidding -- I think at the series finale wrap.
HBO: Do fans ever approach you about the show?
Dean Winters: It’s funny, I’m a real New Yorker so I ride the subway a lot, and I get people that come up to say, “I did time,” and “I have family in jail,” and “You guys got it as close as anyone did.” There was no Hollywood bulls**t about Oz. When people talk about that, or tell me they use it as a scared straight tool -- “I showed my kid Oz to make sure he doesn’t f**k up”-- that’s a big thing for me.
HBO: As we approach the 20th anniversary, what would you tell someone who is just starting to watch?
Dean Winters: The big take-away from the show is still true to what’s happening now: It’s about really trying to work together. I think that was the point of Oz; You have all these different types of people -- religion, race, sexual preference, whatever -- and the only way you are going to make it work is if you blend. It didn’t really work out well in the series, but I think there is a real lesson there for everyday life -- more glaringly so today.