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: Steven Weber is probably best known for his role as Brian Hackett in the long-running 1990s sitcom Wings. But the actor has stayed busy ever since in a number of memorable movie and TV roles on series like House Of Lies and NCIS: New Orleans. Weber has specialized in douchebag villains on shows like How To Get Away With Murder, Wilfred, and iZombie, but has also proven himself in a number of comedic roles in shows like Party Down and Community. He talked to The A.V. Club about his his long career as an actor, which he credits to never running from a challenge.

How To Get Away With Murder (2014)—“Max St. Vincent”

The A.V. Club: Your role on How To Get Away With Murder helped define the show by showing how those characters legally defend people who are morally bankrupt. Your character, Max St. Vincent, is an eccentric millionaire. In the end it’s pretty clear that he killed his wife, but they still get him off.

Steven Weber: He’s sort of like a better dressed Dexter.

AVC: How did that role come to be?

SW: It was offered to me, which is always a good feeling. I am a huge fan and admirer of Viola Davis, who is about the most beautiful woman I’ve ever seen. And who they treat on set like a thoroughbred. By that I mean, she’s wholly real and down to earth in every sense, and she takes her work and her art and her craft very seriously. Her concentration level is always at peak and her standard is always so high. And the production knows what they have in her.

AVC: Did you feel like you had to up your game to keep up with her?

SW: Yeah, as much as I was able to without being totally distracted by this person. This force. And in the best sense. Not in a way some egomaniacal actor would be, she’s a woman that deserves every accolade. And it was a real privilege to see that she’s appreciated by the crew and the cast, and it was just great. The role they gave me was a really showy fun role.

AVC: There’s a moment when you’re walking through the murder scene and there’s blood everywhere and the students are looking on in horror. You don’t seem like a terrifying guy who could murder his wife. How do you channel that?

SW: [Laughs.] I don’t seem like it. How do I channel it? As a fan of acting and actors and films, I’ve watched enough actors in roles of psychopaths from Dennis Hopper to Michael Rooker… just crazy people in various degrees of subtlety. As an actor, I feel more fearless than I do in real life. The idea of getting on top of the actor I was working with and getting really homoerotic and frighteningly in his personal space is something I absolutely relish and do without hesitation, so that was a great aspect of that role. A guy who is absolutely fearless and so sure of himself was so fun to play. And also like I said, it was just fun to be in Shondaland. I’d love to do more in that world. It’s rich.

The Shining (1997)—“Jack Torrance”

SW: The show Wings was more or less winding down, and I auditioned for and got the role that was made famous by Jack Nicholson. And again, I was pretty game. I wasn’t prepared or cognizant of any immediate comparisons that would be made between me and Jack Nicholson. But that hung in the air later on after I’d done it. I kind of hit it off with Stephen King and Mick Garris, who directed it. And it was a great opportunity for me, to learn what The Shining was really about having been a huge fan of the Kubrick film.

What I realized it was about, was alcoholism. And addiction. Rather than real monsters and demons, it was about the demons that were in this man, this poor guy. And I was able to learn a little bit about it because Stephen King was present on set a lot. And we shot it in the hotel called The Stanley, in Colorado, which is where he originally conceived of the book and wrote some of it. The whole thing was very exciting. I realized I formed a lot of subtleties. In retrospect, I made erroneous choices. I made the wrong acting choices at the time.

AVC: Do you feel like there was some pressure coming off of Wings to define yourself against Brian Hackett, a comedic character?

SW: I don’t think there was pressure as much as there was an opportunity there that I didn’t quite seize. Even though I did the work, I didn’t do it fully enough and lacked the seriousness that I described Viola Davis having. Choosing an opportunity rather than pressure to differentiate myself from that more popular role that I had been doing. This was an opportunity to go deeper and I went as deep as I could, but I didn’t quite go deep enough. There were aspects of that role and character that eluded me. If I could play it now, it would be different. I would have a deeper understanding.

AVC: What do you feel would be different? What do you think you could bring to the role now?

SW: An understanding, for instance, of that kind of disturbance, and compulsivity. The fear of mortality and desperation. I’m not an addict or going crazy, but after having become a parent and going through middle age and life and having to observe death and all these things… my life just formed me in ways that my life experience up until then had not. And moreover I have an understanding of that now that I didn’t quite grasp them.

Even technically I would do things. I have a better understanding in-camera now. Concentration and all that. You also have to understand that at the time, we were still making TV movies. The graphics were in their infancy. Production, they tried to animate a main element in the original shining story: the topiaries in the hotel garden that come to life in these animal-shaped bushes. So when they did that in the show, it looked like an old Davey And Goliath cartoon, Claymation. It wasn’t so hot, and it tended to distract.

And there were other aspects that made it okay but not perfect. The purists aren’t happy with it, as with Stephen King himself. Because the Kubrick version was a real bowdlerization of his story, and in fact he was legally bound not to discuss his relationship to the Kubrick film. He was not happy with what Kubrick did. I don’t exactly know why. The circumstances were as the creator and author of the book, he was just not happy with where Kubrick took it.

He was really fun and I had a great experience with him. He was the most accessible, down-to-earth, cool dude. At one point I had the book and came across a passage that was very musical and interesting. Something like, “Médoc, are you here? I’m sleepwalking again my dear… The vines are moving under the rug.” I was like, what does that mean? What symbolism is that? Hell, I’ve got Stephen King here. I’m gonna ask him. I said, “Steve, what does this mean?” He said, “Médoc? Oh that’s a red wine, I was probably drinking that at the time. ‘Are you here?’ I don’t know… I was wondering where the wine was. The vines are moving under the rug? I probably looked down and there were probably vines on the rug.” And it was very amusing to me.

We project so much onto our heroes or stories and the reality is, he’s just a writer that saw value in these most mundane things. I was hoping for some major explosive truth that he was going to give me, some great metaphorical insight. But he takes a snapshot of any room he’s in, and he writes it down and knows how to organize in a grammatically compelling way.

Jeffrey (1995)—“Jeffrey”

AVC: This movie really does bring comedy to a subject where it was lacking.

SW: Exactly. There’s gravity in it, but it’s all so delightful. I expect it’s a bit dated, but it was so much fun. I got to kiss Patrick Stewart.

AVC: In 1995, the fact that a film like this decided to focus on this topic with big-name actors was a pretty big deal.

SW: That was the point. The idea that Patrick Stewart was going to take the role after having swagger as Captain Picard and was going to be this flamboyant designer, wearing a pink beret. That was considered very risky and important at the time. So, I think with some films, it’s valuable to say that this could have been done better, but in the case of Jeffrey, it was at the dawn of the mainstreaming of gay cinema and media.

AVC: At that point, it was just important that people even start telling these stories in film.

SW: Oh, absolutely. And I learned just from interacting with people over the years, this movie, among others, was instrumental in helping people in areas of the country that did not have a support network, that felt kind of unsupported in the arts. So I was privileged to do something that was also out of my wheelhouse and experience. And I was welcomed for it. I rarely had such a good reception that continues to this day.

AVC: You were still shooting Wings then, so was there any pushback of taking the role, when your Wings character, Brian, was supposed to be kind of a ladies man?

SW: No, and that’s the weird thing. It was pre-Twitter, pre-explosive social media, where the smallest thing is equated to the biggest thing on earth. While Jeffrey was reasonably well known, it didn’t get that wide release, it wasn’t advertised as a top 20 movie, so I never received any pushback. That was part of the interesting thing. It might be that Wings wasn’t that huge a show. For instance, if someone from Friends had done it, then maybe it would have caused a bigger response.

I had a good friend who died from AIDS, and there wasn’t very much I could do for him or understand about it. So this was again, another opportunity for me to do in drama what I was unable to do in life. Which was to contact the subject matter and do something literally rather than existentially. That helped me personally; it was kind of therapeutic.

Studio 60 On The Sunset Strip (2006)—“Jack Rudolph”

SW: I was lucky to get on it. I originally auditioned for one of the roles that Matthew Perry got, but I asked them to audition for the role that I got. They didn’t originally see me in it, so they were intrigued that I would even want to read for that. But when I was reading it, it fit me better than any role I’d been in. The dialogue came easily to me. The way I stood, suddenly I just knew for the first time in my career—and almost since, I think—that the role was such a perfect fit. It was like stepping into a suit right off a rack. I found myself joyfully in the company of all these creative people who I admired so.

AVC: Jack Rudolph runs into a lot of conflicts with the guys who run the show. But at the same time, he’s willing to go up to bat for them.

SW: On the face of it, he’s this corporate dick. But the beautiful thing that Aaron Sorkin does is that he never makes just a two-dimensional villain or hero, and quite often, the elements of both archetypes are interchangeable. So this guy, Jack Rudolph, you know immediately who he is, a corporate weasel who is capable of snapping back and lying.

Later on, he began to exhibit great self-awareness. One of my favorite scenes that I had was with Bradley Whitford on a plane [in “Nevada Day”]. We’re flying back, and he and I are just sitting on a private plane and doing schtick with a stewardess. I sit next to Brad and I start talking in a way that was so amazingly, of course, this beautiful Sorkin dialogue, but it was just really simple and it described the inner-workings of network TV. And I remember Brad and I were just kind of freaked out by the gentle intensity of the dialogue, of what he was saying. It was great dialogue, great writing.

AVC: Due to the intensity of that kind of dialogue, the show faced some criticism because people said it was “too Sorkinesque.” Did you feel that on set?

SW: Here’s my view of what happened. Coming off of The West Wing, there were such high expectations for Aaron Sorkin. Not only as a creative producer/writer but as the now infamous personality. He’d battled his own demons and high-profile drug stuff and relationship stuff, so that was as compelling to the press as the possibility that he would have another great show. But to me, something happened with Studio 60. People for some reason, and this happens, had been sharpening their knives for Aaron Sorkin and I don’t know why. It’s like you’re about to give birth and people are standing around and the baby is born and immediately they start saying, “Why is he crying? Why isn’t the baby standing and talking? You’re not a good parent!” And that’s what they did to Studio 60, they immediately leapt on this new creation and immediately compared it to West Wing and any other movie he’d done and attacked the admittedly dramatic dialogue. He loves language, he’s not equipped with low-brow exchanges that pass for a lot of drama. He loves the written word and goddamn it, actors love to hear it, love to say it. It was really enjoyable. There were also things that went wrong because there was not a lot of love for that show. There was network pressure. We suddenly found ourselves in some unlikely and ridiculous competition with 30 Rock.

AVC: That came out around the same time, and people were comparing them, although they’re very different shows.

SW: It’s just the lowest and simplistic comparison. That’s a comparison that people in the third grade would make. But secondly I think, I suspect that there were a lot of financial issues with the show, even though the actors did it for relatively low sums, for the possibility of working with Aaron Sorkin. Matthew Perry, who was by no means making what he made on Friends. For that matter, I wasn’t making what I could’ve made. Everyone took “pay cuts” but they were relative to what anyone would have gotten. Everyone just said, “Fuck it. Let’s do this.”

But I think that technically it was a hard show to produce, because a lot of the episodes were long and dense. They were expensive to shoot because the sets were huge. We had an actual practical TV and movie studio, so that if I was doing a scene with you and the cameras turned to you, behind you were 300 feet of actual working set that has to be lit, populated with background, designed. And that costs… millions of dollars. And after a while, that took a toll. And ultimately, people ganged up on the show. And it may have thrown the writers to a certain extent. They were not getting love. It’s hard to create when people are throwing rocks at your window. And that’s kind of what happened. It definitely deserved another season. Easily. People around the world still love that show; it’s really a great show.

Party Down (2009)—“Celebrate Ricky Sargulesh”

SW: That was about my favorite thing I’ve ever done, probably. Really fun. Everybody on that show, every person on that show was a gifted improviser. Lizzy Kaplan, Ken Marino, everybody. Comically hilarious.

I had never seen the show by the time I was on it and it was very low-budget, which I was getting used to at that time. I had done a lot of low-budget things, so this was really particularly fair. But right away, it was contagious, and I knew the director, Bryan Gordon, and it gave me a lot of freedom as far as how the character was. I suggested a mere wonky eye, and he said, “Yeah, sure.” And so I hired a makeup person and we just kind of creased my eye and stretched it in a weird and menacing way.

AVC: So that was your idea?

SW: Yeah, I’m proud of it, so I’m going to boast. But everybody was absolutely great. Down the line, that actually led to me working on iZombie with Dan Etheridge and Rob Thomas.

AVC: Did you have any improv experience?

SW: A little bit. One time I was doing a movie in Chicago and went up to Second City and went on stage. And over the years once in a while I’d done a few things at Groundlings, UCB. I don’t have extensive improv experience, but I was able to hold my own, I think, a little bit with all those performers on Party Down, who are absolutely down the line brilliant. Each one. There’s not a weak link. And it kind of made it easy because it was all so easily distributed that all you had to do was respond, and you were improvising. Not even trying.

Community (2015)—“Detective Butcher”

AVC: You had a small part in a Community episode, “Ladders,” where you’re a detective on The Butcher And The Baker. How did that come to happen?

SW: They offered it to me, and I hadn’t been in a network comedy in the longest time so I was like, shit yeah. And it just so happened to be a really funny little fake episode of something.

AVC: It makes fun of NBC and its horrible programming decisions. Was it kind of fun to poke at them a bit?

SW: Oh yeah, and clearly I was. First of all, I love Yvette [Nicole] Brown, who is so sweet. Every time we’d see each other we’d be like, “Why can’t we do that show? That would have been a hilarious show to do,” and in all its satirical glory. Sometimes fans come up to me and say, “That should have been the show that went on after Community. That should have been it!” It’s always fun to work with people who are knowledgeable and take the piss-end of themselves in the industry that sees that so well, that’s the case here. It’s fun to be involved. I’m a guy that likes to work and is hopefully going to work for some time to come and the good thing is that there seems to be more material with comedy, more actors believe it or not. The rough thing is the structure of the industry, pay and viewership has altered since I started. So you just have to adapt and accept certain limitations. By the same token, TV is way, way out there and that’s where I like to go, follow it.

Wings (1990-97)—“Brian Hackett”

AVC: My mom is obsessed with Wings. She is so happy I’m talking to you right now.

SW: Tell her to stop texting me. [Laughs.]

I was a huge fan of network television growing up and Wings was of that world, the old powerful NBC comedy juggernaut that had Cheers and Taxi and Friends and Seinfeld. Wings was one of those shows that was popular because again, viewership was different than it is today. People still gathered in front of the TV, and it was that appointment viewing that was so important in the industry. So they put us on after Cheers, before another show, and they were able to get a pretty large audience. Bigger than some big hits today, which shows you just how viewership has changed.

AVC: It’s a show that much like Cheers and Frasier and that whole group, holds up.

SW: Look, it was a far less observant show than either Cheers or Frasier. It didn’t necessarily take any risks with any current topics or sexuality. It was good, a fairly standard comedy but it was almost always well-written. After a couple seasons, we developed better chops than the beginning but we developed a style that is still very watchable. It’s not very dated. The only thing that’s dated is… clothes. The clothes I wore, high-waisted jeans and too-large shirts. But the dynamic between me and Tim [Daly] was a tried and true dynamic that still works today. Worked 50 years ago, will probably work 50 years from now. And it turned out to be a springboard for a lot of writers. It was a great time all around. Looking back now I realize it was at the tail-end of network drama experience. We all had great schedules, made good dough, had a lot of fun. And made a lot of good friendships.

Single White Female (1992)—“Sam Rawson”

SW: Single White Female was incredibly fun. They actually cut out several more graphic sex scenes between me and Bridget Fonda. That was beautifully shot: It’s got funny cult themes, horror-status that it refers to a lot. It was fun for me to be involved with.

AVC: Did you have any reservations about doing the nudity?

SW: I’m fairly fearless. I did a production of Hair out here in L.A. in 2000 and it was full-on nudity and just fuck it. Just do it. I have no worries about it.