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by David R. Guarino

This article shared 11068 times since Wed Jan 22, 2003
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If there is one positive thing that can be said about Em City Prisoner # 97P904 in Tom Fontana's fictional world of OZ, it is that Ryan O'Reily is a survivor in every sense of the word. In fact, it is precisely his uncanny ability to survive just about anything that makes the subtly savage character of O'Reily at once powerfully arresting yet disturbingly fascinating. Make no mistake; this is one prisoner who definitely knows how to take care of himself.

Bringing to life one of Em City's most infamous and resilient residents, actor Dean Winters consistently delivers a chilling performance as the sexy, wily sociopath Ryan O'Reily, who somehow always manages to beat the odds against injury and/or death amidst the unending nightmare that has become his daily existence. Among the obstacles that Ryan manages to overcome are: surviving breast cancer in a male-dominated society where anything perceived as weakness can bring about one's premature demise; living through the anguish of the unrequited 'love' he feels for prison doctor Gloria Nathan (Lauren Velez)—an obsession than eventually prompts him to have his brother Cyril kill Nathan's husband, thwarting blackmail attempts by Corrections Officer Claire Howell (Kristin Rohde) after a brief affair between the two cools off; feeling the anger and pain of his brother Cyril's rape by Aryan leader Vern Schillinger and against whom O'Reily vows revenge.

Throughout all of this and more, O'Reily manages to dodge numerous betrayals and threats on his life yet spends a great deal of time looking out for his brain-damaged brother Cyril. (Flawlessly played by Dean's real-life brother, Scott William Winters). Despite his apparent amorality, Ryan's devotion to the sibling he helped put behind bars is unwavering and intense.

Resourceful, streetwise, and ostensibly fearless, O'Reily survives as he simultaneously spreads around his signature brand of deceit, premeditated retribution and violence, including murder, which eventually lands him an additional 77 years in OZ.

In actor Dean Winters' hands the core of O'Reily's disarming malevolence is not only explored but also expanded upon with apparent ease. Winters has clearly made this character his own in every way, and he knows exactly when to pull in the reigns on O'Reily's sinister machinations. Undoubtedly the instincts and talents of the New York-born Winters have enabled him to both master this complex character and also capture the inexplicable appeal of the shockingly mercenary O'Reily and his crafty survival skills. A master at playing both sides against the middle, O'Reily can neither trust nor be trusted. As the body count rises and tensions grow, Ryan manages to keep his hands clean as he does whatever is necessary to ensure that he will see the light of the next day. Capable of the most insidious acts, such as hatching a plan to feed ground glass to an enemy mob leader and later shift suspicion for the crime to another inmate, O'Reily invariably manages to deflect responsibility for his depravity and manages to come out smelling like a rose. Obviously what makes O'Reily so compelling is also what makes him dangerous. There are few limits to what Ryan will do; besides having his brother Cyril kill Gloria Nathan's husband, he later murders Nathan's rapist with a set of barbells in a psychotic fit of jealous rage. Another example of O'Reily's subtle treachery is pointed up in the OZ boxing matches, in which Cyril O'Reily has a distinct advantage in match after match since Ryan has drugged the water jugs of his brother's opponents. Occasionally O'Reily gets caught, but is never totally shut down.

Winters digs deep to find the humanity within the sociopathic personality of O'Reily. O'Reily seduces and repels, evokes revulsion but also empathy. We want to despise him, but find ourselves admiring his unwavering resiliency, empathizing with his misguided need for affection and love, instinctively understanding and relating to his paternal need to protect the weaker, more vulnerable sibling for whom he feels responsible.

This is a strong, powerful, multidimensional portrayal of a man who is indeed a prisoner, not only of the penal system but also of his own inner demons.

Winters said the role of O'Reily was actually written for him by Tom Fontana. Candid and open, the 38-year-old readily acknowledges a crossover of his real-life survival instincts from his 'pre-OZ' days into his on-target portrayal of O'Reily. Says Winters, 'I have the survival instincts. You know, I was a bartender for eight years in the city, and when you're a bartender in New York City you have to be a real hustler.'

After those bartender years, OZ creator Tom Fontana (one of Dean's frequent customers), took an interest in him, and Winters soon found himself signed for the role of Tom Morans on three episodes of Fontana's popular series, Homicide: Life On the Street.

The son of an Irish middle-class family, Winters traveled and lived throughout the West Coast, Hong Kong, Europe (Paris, Milan) and Florida before settling in Manhattan. He majored in English at Colorado College.

Winters considers his role as O'Reily to have been his first challenging acting assignment, and in 1997 he debuted as a member of the original cast, becoming Prisoner # 97P904, receiving a sentence of life imprisonment for two counts of vehicular manslaughter, five counts of reckless endangerment, illegal possession of drugs, criminal possession of a weapon and parole violation.

Readers might recognize Winters from his many TV guest appearances including his thoughtful portrayal of good guy Detective Bryan Cassidy in Law and Order: Special Victims Unit, in 1999. Prior to that, Dean appeared as Sara Jessica Parker's neighbor John Mc Fadden (a.k.a. 'The Fuck Buddy') in a 1999 episode from the second season of HBO's Sex and the City. Other roles include: 'Larry' on NYPD Blue in 1996 and a part in 1999's Payback. Dean briefly appeared in Conspiracy Theory, and had the lead opposite Yasmine Bleeth in the lighthearted Undercover Angel. Winters also had the lead role of 'Trevor' in the sixth installment of Clive Barker's Hellraiser series, Hellraiser: Hellseeker, and in the 1997 films, Firehouse and Lifebreath. Dean also had parts on Millennium, both in 1997 and in 1999.

In 2001, Dean starred in the action thriller, Snipes, set in Philadelphia, billed as an expose of the dark side of the rap music industry. The film spotlights the underworld of music industry hustlers, thieves and killers, who will do just about anything to stay on top of the business. Winters plays a slithery hip-hop record mogul named Bobby Starr opposite rapper Nelly.

DG: What would you say is the biggest difference between you and O'Reily?

DW: Well, that's kind of a tricky question; it's a good question. It's tricky only in the sense that this character was written for me. I didn't read for this character; I had worked for Tom (Fontana) a few times beforehand … I gotta be honest, there's not a whole lot of difference between the basic structure of (Ryan) O'Reily and me. I have the deep love for my family; I have the survival instincts. You know, I was a bartender for eight years in the city ... . So I think I was able to bring all that (into the character). Obviously I don't have the killer instinct do you know; I don't have that in me.

DG: Tell me more about the survival instinct.

DW: The survival instinct is probably what we (Dean Winters and Ryan O'Reily) have the most in common. Besides the love I have for my brother (Scott) which kind of goes without saying. When Tom Fontana met me I was going through a very difficult period in my life. Without sounding too dramatic or too corny, there was a certain amount of survival (instinct) that I was relying on at the time. I think he saw that.

DG: I have always felt your character is one of the most amazing on the show, because you are able to elicit empathy from the viewer. I often find myself sympathizing with your character and yet your character carries out some of the most horrific deeds.

DW: Crazy, right? It's not something that I consciously think about. I think if actors constantly started thinking about that (gaining empathy), they'd get in trouble. I've never once thought, 'OK, how can I get empathy from the audience?' Or sympathy, or whatever you want to call it. I think that there are a lot of bad actors out there who do that, and I just think that it's so obvious. You know, in this show I literally just show up to work, and I do the lines the way Tom wants me to do them, and that's it. I mean, the writing is so clear and so understandable. I'm lucky, I haven't been in a position where I've had to deal with bad writing yet. Maybe when you're in that position then you do have to start figuring, 'Now how can I make this person more likable?' I detest that in actors and I see it all the time. I think that the audience is really dialed in to what you just touched on, David, which is basically understanding the survival instinct. There's definitely some kind of twinkle in the character's eye, but it's never something that I've consciously set out to achieve.

I think one of the reasons that people do like the character is that Ryan is able to get away with a lot of stuff that people would secretly like to get away with. I mean, who wouldn't want to grind up glass and put it in their worst enemies' food, you know? Yeah, I think the fact that I'm able to do (things like) that and get away with it … I think that everyone's got a dark side, and they see me getting away with this stuff and they can't help but get a little bit of a grin ...

DG: I've seen some of the work you've done on other shows, and I think it's quite good. I did see Undercover Angel, in which you costarred with Yasmine Bleeth … (Dean chuckles) That was really a different kind of movie for you, wasn't it?

DW: Oh, Jeez! That was strictly a need to make some money. (We both laugh) The truth is, I've had a lot of people who really like that movie for some reason. I thought it was kind of corny and cheesy, but for me, that was obviously as different from Ryan O'Reily as you could possibly get. So, in that respect I kind of enjoyed doing that film. It's Michael Jackson's favorite movie!

DG: Then there's this new movie you're in with rapper Nelly, called Snipes, set in Philadelphia. You play a sleazy hip-hop mogul named Bobby Starr.

DW: Snipes opened in NY in October and it closed about two weeks later. It's coming out in DVD, I think, Feb. 22nd. Let's see, I think it'll be great on DVD on a small screen. It had a good young cast, and Nelly was quite able. It was his first movie and he did a good job.

DG: Did you like playing this scumbag?

DW: I did. I had a good time with him. Again, this is not a nice person but in a different ilk than Ryan O'Reily. Bobby Starr is a straight-up asshole and the owner of this hip-hop label. It was fun. Once again, it was a learning experience. Most of the films I've done to date have been learning lessons. I'm really looking forward to doing a film where I can just be real proud of the finished product and go to the movie theater and see it.

I would never rely on any performance to insure a career, but I'll tell you that if I don't get any work out of this next season of OZ, then there's something wrong with the world. Basically my whole story line is with Scott this year. It's just absolutely beautiful. People are literally just going to get emotionally and physically ill from the scenes.

DG: The two of you work beautifully together …

DW: Yeah. Absolutely. And I think that Scott, hands down, has the hardest job on the show (OZ). And after that, he's equally as good an actor as anyone if not one of the better actors on the show. I think everyone on that show gets a chance to walk the walk and talk the talk and there's posing going on. Everyone's macho and the testosterone is through the roof, but Scott really has to play this little kid. You're talking about a complex character; Scott does a lot of work on this show. I get a little sad because I really don't think he gets any recognition and he deserves more recognition than anyone does. He's incredible. This year, man, I'm telling you he takes it to another level! People are going to have to turn their TV's off. They're going to be physically sick. And not by rapes or anything like that, but just by what goes on with his character. And the way he portrays it. There were a few times when we were shooting these scenes and in between takes at one point I walked off the set and I threw up. I was so emotionally spent.

DG: It was emotionally draining?

DW: Draining. I couldn't take it. I actually couldn't take it. I'm looking forward to the (upcoming) season of OZ; too bad it's the last one, but that's just the way it has to go. It'll be the highest watched season because last year was the highest watched. It's good to go out on top. But it's tough also, because there's just so much crap on television and there's not a lot of good work out there.

DG: Of all of the evil things you've been asked to do on OZ, was there one thing that was really rough for you to do?

DW: No. Some of the most evil stuff that I did I came up with. I guess there were some rough things. I'm not a big fan of walking around in the nude in front of 50 people. (Dean laughs) I never had to deal with rape or being raped. Actually I think I was the only person on the show that got to have sex with four or five women. I know that that was not easy for some of the guys, especially the guy who played (Peter) Schibetta. He had a hard time with that (being raped). Let's put it this way, I never got a script that made me think, 'I've gotta talk to Tom. I can't do that.' That was the great thing about this cast. If Tom would ask an actor to do something, he/she was happy to do it. There are not many casts like that. If someone didn't want to do something, there were two instances where he (Fontana) just literally got rid of the actor. It wasn't fair to the rest of us who had to do things we didn't necessarily like doing.

DG: Did you have a problem playing a cancer victim?

DW: No, I didn't have a problem with that, but it was difficult and that was in the second season and that was when Tom was really starting to kind of trust me and write for me and he gave me a difficult story line. I lost a lot of weight for that and I shaved my head. And I actually got awakened to the whole world of male breast cancer. [And his character gets this] in an environment where it's all men, with everyone trying to be the strongest. And (with Ryan) not really wanting anyone to know what had happened…

It was tough. The other guys on the show made it tough, as they should have; by the way they made fun of me, etc. I think emotionally the toughest one is coming up.

DG: How would you have felt if your character, Ryan O'Reily, was scripted as having been raped or written as having a homosexual encounter while he was serving time in OZ?

DW: I'd do anything for Tom, you know? I mean, seriously. And most of us felt that way. Because we'd all known Tom before OZ; we'd all worked for him. When he was doing the show and he came to us and he said, 'Look, this is not going to be an easy show,' we said, 'Bring it.' I'm not saying I would do that on any show. But on OZ I would have done it for Tom. I think you need to be careful in doing that stuff; it's easy for it to become stupid and crass. What's that show called, 'Queer as Folk?' I think that's just embarrassing. I'm very in tune with the gay world in New York; I've got a lot of really good friends who are gay, and I've worked in the clubs for a long time. I'm very comfortable around them. I know that most of them think that show is just crap. So like I said, I wouldn't do it for just any show. For Tom I would do it because I'd know that there was a reason why I was doing it. And I would know that the writing would be there.

DG: As a native New Yorker, what's been the hardest part of dealing with the Sept. 11, 2001 attacks for you?

DW: Well, at the time my girlfriend's uncle died, he was in one of the towers, and I live around the corner from one of the first fire stations that was on the scene. Twelve guys died and I probably knew eight of them. And I live downtown so everytime I walk out of my building, those towers aren't there anymore so it's always going to be difficult ... I was born and raised in New York City. It's not something that anyone in New York City, especially native New Yorkers, is ever going to get over. It emotes sadness. But at the same time this city really has bounced back and it makes you proud to be here.

DG: At one time, you described yourself as a 'street chameleon.'

DW: Well you know I grew up in a good family, middle-class, but there's really not a situation I can't adapt to. I think that's one of the things I got from my father, because my father basically grew up in an Irish ghetto. I think the thing I got from my Dad was my street smarts, and that's also something that New York gives you. I've always felt like a real chameleon in that whether I'm in a street situation, in a bad situation or at some tuxedo function at The Plaza, New York has provided me with the ability to be a real chameleon, to blend in. When I was 14 we moved to Arizona for a while. It was out there that I realized how lucky I was to have been from New York. Most of the people that I know here (in NY) have that kind of survival instinct. I haven't seen that in a lot of other places. I've lived in Paris, Milan, Hong Kong, Los Angeles, Miami … I've never seen it.

DG: New York is your first love …

DW: Ah, yeah, definitely. The fact that I love New York is probably going to be hard on my career, and I'm kind of resigned to that. I will not live in Los Angeles.

DG: What would your castmates say is the most difficut working with you?

DW: (Dean laughs) You might have to ask them that. I think for method actors, and thank God we don't have any of them on OZ, I don't take things very seriously in between takes. Or in between scenes. I like to keep it light. Because it's a serious show. So sometimes I might drive everyone a little bit crazy … (We laugh) You know, we're all such good friends. There's really not a bad bone in the bunch. And (regarding) the few people who came in and it didn't work out; Tom (Fontana) simply had them killed. (I laugh) Tom knew who fit in there and who didn't ...

DG: What is 'Project Innocence' and the OZ soundtrack that came out of that. I heard Method Man and Nate Dog got together to do that.

DW: Yeah, they did. Also Lord Jamar of the Brand Nubians. But it was really Barry Scheck, who was one of O.J.'s lawyers who started the whole thing. He has this group, a legal clinic called 'Project Innocence.' The group raises money to afford DNA testing for guys in jail. Because this DNA testing now is releasing everybody, but there are a lot of these guys who can't afford it. So 'Project Innocence' raises money to help fund the DNA testing. Method Man and all these guys got together to do the OZ soundtrack, but Barry Scheck started it all.

DG: You've had a lot of famous directors come through OZ. Do you have a favorite?

DW: Probably Steve Buscemi. He was terrific. We had Kathy Bates and Chazz Palminteri. Matt Dillon, Brian Cox. But there was something about Steve's way that was just real soothing. Kathy was great too. I've got to tell you, that's a tough call. They were all great.

DG: I would think it would be really hard for a woman to come onto a set like OZ that's made up primarily of men …

DW: Yeah, but have you ever met Kathy Bates? She's a tough chick, man. She owned that set. I won't mention the name, but we did have one woman come on the set and she shouldn't have been there. She was too fragile. The sheer volume of men and the content matter … it got to be a little too much for her. I will say that that also happened with a few guys. OZ is a weird animal, you know?

DG: What have you learned from portraying Ryan O'Reily, Dean?

DW: As an actor I've learned everything I possibly could. I mean, I don't even remember going to acting school after doing this show. I've learned that it's going to be very difficult for me to get work. The writing was so good on this show. We wrapped in August, and most of the scripts I've read are unacceptable. Most actors will tell you that with a script you don't love, acting just becomes tedious! I was a real wild child and I did get into my fair share of trouble. And I've come to learn how lucky I am. Because I know I don't ever want to wind up in prison.

DG: How long do you think you'd last in prison?

DW: (Dean smiles and laughs) Not a day!

For info on 'Project Innocence' go to

Copyright 2003 by David R. Guarino


This article shared 11068 times since Wed Jan 22, 2003
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