Welcome to Random Roles, wherein we talk to actors about the characters who defined their careers. The catch: They don’t know beforehand what roles we’ll ask them to talk about.

The actor: Dean Winters made his first major impact on TV critics through his dramatic work on HBO’s Oz, then proved his comedic chops on 30 Rock, while most mainstream viewers know him best as Detective Brian Cassidy on Law & Order: Special Victims Unit (or, more recently, as Mayhem in an ongoing series of Allstate commercials). Currently, Winters can be seen playing a different breed of detective—and in a decidedly different locale—on the new CBS action-comedy, Battle Creek.

Battle Creek (2015-present)—“Detective Russ Agnew”

Dean Winters: They came looking for me last January, and when I got the script and it had Vince Gilligan and David Shore and Bryan Singer’s name on it… I mean, how do you freaking say “no” to it? It was just one of those trifectas.

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The A.V. Club: So how would you sum up Russ Agnew in a nutshell?

DW: The guy’s basically this kind of altruistic Midwest guy, a Battle Creek local homeboy who wants to make his town better, and he’s doing everything he can, but the department’s woefully underfunded, and he runs into a lot of obstacles trying to get things done, so he’s frustrated. So they hook the city up with an FBI satellite office and he gets teamed with an agent, played by Josh [Duhamel], and his world gets thrown upside down and becomes a nightmare, because Josh represents everything he hates.

AVC: You guys have a great awkward on-screen chemistry.

DW: Oh, yeah, it’s incredible. We definitely have great chemistry.

AVC: You said that they came looking for you for the role, but how much of Russ was on the page when you got the script, and how much was tweaked once you signed on?

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DW: I think there was a certain irreverence that they weren’t ready for. You know, I tend to bring that to my jobs. [Laughs.] But I think that ends up adding to the chemistry with the characters.

AVC: If you had to define Battle Creek’s percentage as far as being comedy versus drama, where would you say it lies?

DW: I’d say 60/40 drama. It’s not a straight-up half-and-half, but it’s definitely a blend. But that’s fun. Because it goes week by week, so there’s the through-line of my relationship with Josh, but as far as the cases go, it goes week to week. So as an actor, every week you get a different take. That’s nice. I never knew what was going to be happening till the table read.

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AVC: I’m presuming that you didn’t actually shoot this in Michigan, but did you get to the real Battle Creek at any point?

DW: Nah, we shot in Los Angeles for Michigan. Which is difficult. [Laughs.] Josh and Kal [Penn] have been, though. I haven’t yet.

AVC: As far as the series itself, it seems like a unique creative team, with Vince Gilligan coming up with the concept and David Shore fleshing it out. Did you find that their sensibilities blended pretty well together?

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DW: Yeah, they did. They’re very different people, but they both had the same goal in creating Battle Creek. David picked up the reins from where Vince left off, and it was just perfect.

Homicide: Life On The Street (1995-1996)—“Tom Marans”

AVC: So was Homicide actually your first on-camera appearance?

DW: Yeah, that was my first time on national television.

AVC: That’s not a bad first gig.

DW: No. And then Tom Fontana ended up writing the part for me on Oz after the Homicide episode.

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AVC: How did you end up getting that first part? An audition, presumably, since it was your first time on national television.

DW: Well, the way it happened was, I was bartending on the Upper East Side with my brother, and I met Tom Fontana. He came into our bar at, like, 2 o’clock in the morning. We had never met before, but he was doing the first season of Homicide, and he and I became really good friends. He offered me a part for my 30th birthday, and I passed on it. I told him I wasn’t ready to be on TV yet, because I was still living downtown and doing theater. I’m, like, the first person that ever passed on him in that position. [Laughs.]

But, anyway, he and I continued to become really close friends, and then a year later I did it. I did three episodes. I did a three-episode arc. And then a year or two later he wrote the part of Ryan O’Reily for me on Oz. He actually wrote that based on watching me bartend. When I was a bartender, I was a total hustler. Like, if you walked out of my bar with cab fare, then I failed, because I would do everything I could to make sure you were broke. [Laughs.] And he kind of based Ryan O’Reily on that, and the rest is history.

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AVC: So how did you find your way into acting in the first place?

DW: I was 28, and I was a little bit lost. I’d been living in Europe and—well, I was living all over the world for a couple of years. And my brother Scott, who played my brother on Oz, he was an established actor, and he saw that I was going down the wrong path, and he got me down to meet his acting coach, William Esper. So I met William Esper and took a class, and when I took my first class, I finally felt like I had found a home. And then I kind of buckled down, started bartending more in the city, and then became part of a theater company in Tribeca. And that was it!

AVC: Did you always envision yourself jumping in front of the camera at some point?

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DW: Yeah. Ever since I was a little kid. I just wanted to wait. It was never the right time for me. And I’m actually glad I became an actor at a later age. I feel like I bring a lot more gravitas to the table than these kids who grew up on film sets when they were 10.

Oz (1997-2003)—“Ryan O’Reily”

AVC: Oz was a pretty intense series, particularly for its time. What did you think when you first heard about the premise? Did you wonder if they’d be able to pull it off?

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DW: I thought it was genius. But there was no television like that at the time. It was the first one, so there was nothing to compare it to. And when we made it, HBO left us alone—it was really the inmates running the asylum—and we never thought anybody was going to watch it. And then people watched it, and it became what it became. And then they green-lit Six Feet Under and The Sopranos and Sex And The City, and that basically changed the landscape of television. So I’m proud to say that I feel like Tom Fontana and the cast of Oz—I feel like we were pioneers, because none of these shows on none of these cable stations like Starz or Showtime, none of them would exist if it wasn’t for Oz. And I think Tom Fontana deserves a lot more credit than he’s gotten.

AVC: Certainly TV connoisseurs and actors, writers, and directors tend stand up for Oz. But you’re right, it doesn’t seem to get a lot of play in the mainstream.

DW: Right. I mean, J.K. Simmons is a shining example of how good Oz was. You know, the guy that just won the Oscar? [Laughs.]

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AVC: Do you have a particular favorite among Ryan O’Reily’s storylines?

DW: For me, the best storyline was working with my brother Scott when he was on death row. And my other brother Brad wrote that storyline for us. He was one of Tom’s writers, and Brad knew our shorthand, the way we spoke, and so that stuff was really, really close to the heart and close to the vest. When Scott gets executed on Oz… I mean, that’s the most powerful moment I’ve ever had as an actor. I was, like, throwing up on the set, I was so disturbed by the whole thing. And it shows! There’s a scene the night before Scott gets executed when we’re in his room, and we’re talking about life, and it’s so brutal and so emotional that I can’t even watch it. I can’t. I get sick when I watch it. To me, that’s good writing, and that’s good acting.

AVC: When I talked to Christopher Meloni, I asked him if he was happy with the way Chris Keller’s storyline wrapped up, and he laughed and said, “No, but that’s between me and Fontana.”

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DW: Yeah.

AVC: Were you happy with the way Ryan’s storyline ended?

DW: Of course I was. And anyone who’s not happy with Tom should, like, really check themselves before they say that, because… people like J.K. and Chris and Lee [Tergesen] and Harold [Perrineau] and Eamonn Walker—nobody would have a career if it wasn’t for Tom. Not the career that they have, that’s for damned sure. Look, we got the bad news about Oz right at the very end, so Tom didn’t really have the chance to wrap it up the way he wanted to wrap it up. But I’ll put Oz up against any show ever. Breaking Bad, Sopranos… Those shows can bring it, and we’ll crush them. Oz was otherworldly. It was Shakespearean. And Breaking Bad is amazing, and Sopranos is amazing, but even Vince Gilligan tells me, “We could never have written Breaking Bad without Oz.” Oz needs deferential treatment. It needs to be revered, and it needs to be a little bit more of the conversation of television.

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It’s funny, though, because now with HBO Go, there’s a whole new group of Oz fans out there. There was a long time where people didn’t talk about it, but now I walk down the street in New York, and it’s amazing how many people talk about Oz. And the cast—we had Rita Moreno and Betty Buckley and B.D. Wong, and we had Elaine Stritch and Joel Grey. We had the best Broadway actors in the world on the show. And we had all of us, who were complete unknowns, and we were all, like, punk upstarts. [Laughs.] But it all played. And then you had guys like Ernie Hudson, and we had great guest stars. It was an incredible show.

Terminator: The Sarah Connor Chronicles (2008-2009)—“Charley Dixon”
Life On Mars (2008-2009)—“Vic Tyler”

DW: I loved The Sarah Connor Chronicles and I loved that character, and the fact that that show and the show Life On Mars didn’t get more love make me nervous about Battle Creek, because those shows were so different and the casts were great, but no one was ready for them, and they didn’t last more than a season. Well, actually, I guess Terminator ran two. But, anyway, you just never know. I had such a crush on Lena Headey, and she and I got along so great together. Just working with her and Thomas [Dekker] and Summer [Glau] and everyone—that was a really great job. That was also the first job where I played a really nice guy. Usually I play guys who are kind of twisted. [Laughs.] But I played, like, a nice guy. And it was easy to fall in love with Lena Headey. Yeah, I loved that show.

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AVC: You also mentioned Life On Mars. Were you doing those more or less simultaneously?

DW: Yeah, I did Life On Mars right after Terminator, I think. And Life On Mars—Scott Rosenberg and André Nemec and Josh Appelbaum, the writers and producers—they were, like, my mijos. [Laughs.] We were such good friends. It was so much fun. And to be able to work with Harvey Keitel and Michael Imperioli—it was too good. And then when ABC canceled it, I was just, like, “What?”

AVC: Did you enjoy the period costuming on the show?

DW: I did, yeah. I mean, it’s always good to go back in time and be a cop. [Laughs.] I’d rather go back in time than into the future. I’ve never seen a good-looking future cop outfit.

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Conspiracy Theory (1997)—“Cleet”

DW: That was my first movie job. That job took me out of bartending. My last night of bartending was Thanksgiving ’96, and I started filming that movie either the next day or a couple of days later. Julia Roberts, Mel Gibson… I was a fish out of water on that film. We were in California, and my part—I had a much bigger part, but it got completely whittled away. I spent a lot of time on the set twiddling my thumbs, trying to figure out how I was going to quit the business. [Laughs.] It was a rough job!

But it was still cool. I would go to Julia Roberts’ trailer, and she and I became friends. I used to walk her dogs for her on the set. So she and I became friendly, and Patrick Stewart was very friendly to me. But it was so rough that I actually tried to get my bartending job back during that, but the owner wouldn’t take me back because I told him to go fuck himself when I quit. Because I wanted to make sure when I quit that I wouldn’t have a way back in! But then two months later I needed a way back in. [Laughs.] He said, “Nah. Sorry.”

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Brooklyn Nine-Nine (2013-2014)—“Detective Pembroke”

DW: Anytime you play a character called The Vulture, who’s such an asshole like that… That was fun. I got to work with Andre [Braugher] and Andy [Samberg] and Terry Crews, who I have, like, a man crush on.

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AVC: We all do, man. It’s okay.

DW: [Laughs.] Yeah, everyone was great on that show. I’m actually supposed to go back on the show, but I’m not really sure what’s going on. When I went over to CBS, they said I could never do SVU again, but they’re, like, “You can do one more Brooklyn Nine-Nine,” so I’m just waiting to find out what’s up.

Hellraiser: Hellseeker (2002)—“Trevor”

DW: That was just a bizarre experience for me. I took that movie at the last minute, I got to Vancouver, and if there were 120 scenes in the movie, I think I was in 116. And I got sick, like, at the end of the first read-through. It was a four-week shoot, and I was sick for the last three weeks. That was brutal, man. That was a brutal, brutal job. But it ended up being a really good experience. I wanted to do a horror film—I’d never done a horror film—but we ended up shooting in a real psychiatric hospital, which completely fucked with my head. No, seriously, I was having nightmares and seeing visions in the hospital. It was just bananas. But it was cool. I got to work with Pinhead, which was a dream come true. So that was fun.

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AVC: So you’re a horror guy, then?

DW: I’m not, like, a big horror junkie. But I like myself a good horror film. And when I was younger, I was, like, “I want to be in a horror film, I want to be in a Western, I want to be in this, I want to be in that…” I still haven’t been in a Western, but I’ve been in a horror film. So I can check that one off my bucket list.

John Wick (2014)—“Avi”

DW: That was one of the funnest jobs ever, because I had a front-row seat to this amazing stuff and this amazing world. Most of the stunts that you seen in that film are real. There’s really no green screen. And I got to hang out with Keanu [Reeves] a little bit, who’s just a sweetheart. I had a small part, but it was a fun part, and I got to be there a lot. And it was shot it my backyard—in Manhattan and Brooklyn. It was a fucking blast, man. A total blast.

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Happy Town (2010)—“John Haplin”

AVC: I’m curious about the experience of the Happy Town pilot.

DW: Yeah?

AVC: Obviously things did not go spectacularly immediately after you filmed that.

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DW: Uh, yeah. [Hesitates.] But which story are you alluding to? Because there’s more than one story.

AVC: I was referring to your bacterial infection.

DW: Yeah, things went south. I don’t really talk about that much anymore, because it’s kind of old news. But, yeah, it was rough. Happy Town was by the same guys that did Life On Mars, and we went up to Toronto and shot this show, and it was great. And the show got picked up, and then a few weeks later I fucking died in the back of an ambulance, so they had to replace me. And they replaced me with this actor whose name I’m not going to say out loud, and of course he told everyone in the press that ABC wasn’t happy with me, so that’s why they replaced me. And I was, like, “Really, you cocksucker?” Because that wasn’t the case at all. And it was a bummer, because I felt like I had caused the demise of that show. I’ve always felt guilty about that. But it is what it is. I mean, no one tells you that you’re going to wake up in the morning and die in the back of an ambulance in Central Park, you know what I mean?

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Law & Order: Special Victims Unit (1999-2014)—“Brian Cassidy”

DW: That’s been a great job for me. I was on the show for the first season, but then I had to leave because I had a contract with HBO, and there was a bit of a dispute. But then they had me come back in—the 13th season? The 13th or 14th. But how it happened was that I was in my apartment, and there was a film crew setting up outside my apartment. It was 5 a.m. and I was trying to go to bed, but everyone’s making a lot of noise, so I lean out my window and I yell, “Would you guys shut the fuck up?” And Richard Belzer yells back up. I had no idea it was SVU! [Laughs.] So I went outside and saw everyone, and then I went over to Mariska’s [Hargitay] trailer to say “hi,” and she was, like, “How come you’ve never come back on the show?” And I said, “No one’s ever asked me!” And the following week I was back on the show!

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AVC: But you said a moment ago that you’re not able to return, at least for the time being?

DW: No. And that doesn’t sit well with me, because I really love that show.

Rescue Me (2004-2011)—“Johnny Gavin”

DW: That was the first job I did after Oz, and I waited a year to take a job after Oz. But I got to work with Denis [Leary]. Denis was my brother. I got to work with him and a great cast: Lenny Clarke, Bobby Burke, Tatum O’Neal played my sister. I saw Jack McGee in the airport the other day. He’s the real deal, that guy. So, yeah, it was amazing. It was an amazing group of people, and it was a great experience.

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Bristol Boys (2006)—“Randy”

AVC: Do you have a favorite project that you’ve worked on over the years that didn’t get the love you thought it deserved?

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DW: Most of the ones I really loved got the love. I did this really small independent film called Bristol Boys, which was about these weed dealers in Bristol, Connecticut, and the movie was pretty good, but the way the movie was made—it was made by these young kids who had a lot of energy and a lot of resources, and they were hustlers, man. I had a lot of respect for them. I wish more people had seen that movie.

Sex And The City (1999)—“John McFadden”
Third Watch (2002)—“Bill Stram”

AVC: We’ve tackled your series-regular roles and some of your recurring roles, but do you have a favorite one-off appearance on a show?

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DW: I played a bounty hunter on Third Watch. It wasn’t the greatest show, but it was a fun part. So, yeah, that was a fun one. But there’s been a lot of fun ones. [Hesitates.] No, you know what? Let me back up: The best one-off I’ve ever had was Sex And The City. That was great. John McFadden. That was awesome.

AVC: Well, when you’re in an episode called “The Fuck Buddy,”odds are that it’s going to be memorable, at the very least.

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DW: Girls would walk up to me and say, “You’re the fuck buddy!” And I’m racking my brain: “Did I fuck you? Oh, no, that’s right: I was in an episode called ‘The Fuck Buddy.’” [Laughs.] Yeah, that got kind of confusing for a while.

Lifebreath (1997)—“Chrystie’s Lover”

AVC: I’m mostly curious about this one because it’s such an early role, and your character doesn’t even have a real name. You’re just “Chrystie’s lover.”

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DW: Yeah, I played basically—okay, so Francie Swift wakes up, and you think that she’s banging Luke Perry, and then I roll over, and… it’s me! That was my first movie ever, and that was an interesting gig because I showed up and went to wardrobe, and they gave me, like, a banana hammock for my cock. I’m like, “What is this?” They’re like, “This is your wardrobe.” I’m like, “Excuse me?” Because I hadn’t read the script. [Laughs.] I got called in because the actor who was playing my part got stung in the face by a bumblebee in Central Park, so they called me to come in right away, because I knew Luke. And I came in, and I had to crawl into bed with Francie, and then I had to simulate sex with her, and it was really rough. And then they called “cut,” and they took Francie out of the bed, and they brought in the Penthouse Pet Of The Year as her body double. And I’m in the bed, naked. I’m, like, “Is this a fucking joke?” And it got awkward, as you can imagine. It was just a really, really weird day.

AVC: But memorable, it sounds like.

DW: Memorable, definitely. I told her, “Look, I’m an all-American male, so just don’t expect for nothing to happen.” [Laughs.]

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30 Rock (2006-2012)—“Dennis Duffy”

DW: Next to Oz, that’s the best job I’ve ever had. When you’re working with Tina Fey, Alec Baldwin, and Tracy Morgan, it’s like, no one’s better than that. And it was the first time that anybody ever let me be funny. Tina took a real chance in giving me that job. She didn’t have to give me that job, because I had done nothing in my career to prove that I was funny. But she gave me that shot, and it opened up a whole new bunch of doors for me.

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AVC: Did you ever get any clue as to what inspired her to give you that shot? Did she ever say?

DW: I think it was just the way that I did the audition. Like, I did it differently from everyone else, and I was the last one to come in. And the director, Adam Bernstein, had directed Oz, so he was in my corner, and I think they had a real powwow, and he was, like, “Look, I know Dean, and Dean’s funny in real life, so we can get him funny on-screen.” And it just happened that way.

But you want to know a funny story? I went to the audition for 30 Rock—I walked in, and there was, like, 30 guys up there reading for my role, and they all—they were the funniest guys in New York City. I’m not going to mention any names, but they were all a bunch of funny guys my age. I walked in, I signed up on the sign-in sheet, I looked around the room, and I’m, like, “I’m fucking out of here.” And I left, and I went to Central Park, because I knew I wasn’t going to get the job, and I didn’t want to waste their time or my time.

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So my agent was in New York, and I get a phone call from his assistant, and the assistant says, “Hey, how’d it go at 30 Rock?” And I was, like, “Oh, it went pretty good. I’m not sure I’m right for it, but it went good.” He said, “Really? That’s interesting.” I go, “Why?” He said, “Because they’re waiting for you. They said they haven’t seen you yet.” And I was, like, “Okay, well, you know, the truth is, I’m not going back. I’m not going to get this job.” And the assistant goes, “Dean, if you don’t go back, we’re going to drop you.” I’m, like, “What are you… What the fuck are you talking about? You can’t drop me, you’re the assistant!” He says again, “If you don’t go back, we’re going to drop you.” And I’m, like, “What, motherfucker?” So I went back. [Laughs.] And they were waiting for me! And I did the role the way you see it on-screen, just as a guy who really believes in himself, no matter how dumb he is. And that’s what they were looking for. I didn’t know that. But it just clicked. And that’s how I got the job.

AVC: Is there a favorite Dennis Duffy-ism from your back catalog that still makes you laugh?

DW: I mean, just calling her “dummy” was enough, you know? [Laughs.] It was just so nice to call someone like Tina Fey “dummy.” Because she’s so not a dummy. Although I have people who walk up to me on the street in New York, and they’re, like, “Call me ‘dummy.’ Please? Please call me ‘dummy.’” I’m, like, “You’re a fucking dummy. Now get out of my way!”

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