Jimmi Simpson loves doing Westworld, but also calling David Letterman “Nancy Reagan”

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: Jimmi Simpson has been appearing in projects large and small since 2000, and during that time, his versatile skills and distinct appearance have earned him a reputation as a valuable addition to any cast. The A.V. Club included him in our list of the best character actors working today, and since then, Simpson has continued to impress, most recently with his rare starring role in the new HBO drama Westworld. He sat down with us recently to talk about the complex sci-fi Western, appearing in beloved cult films, and how much it sucked trying to get acting jobs prior to everyone having cell phones.

Westworld (2016)—“William”

The A.V. Club: You’ve been a series regular before, but presumably this one feels different to you.

Jimmi Simpson: Oh, well. You know, I have been a series regular but I’ve never really been kind of part of a narrative story like this. I’ve been a series regular on a procedural.

AVC: Is it Breakout Kings that you’re referencing?

JS: Exactly, yes. And then I was a series regular, kind of a satellite character on House Of Cards. For this, I’ve never actually been dropped into one of the main narratives of a story, where the story just stays with me and I am a part of the story instead of coming in and interjecting a distraction or a change of pace. So, to me, it was a completely different angle on this craft that I’ve been practicing for 20 years or so. It was difficult and it was wonderful. And I learned a whole bunch, because luckily it was the most difficult work I’ve done yet and I had the most talented people to work on it. I really lucked out with Evan Rachel Wood and all these directors and creators.

AVC: How much were you aware of the massive scale of the project before you began shooting?

JS: I was truly none. I had no awareness. Because I generally don’t have that much awareness. I know what I’m doing, but I just don’t know what’s happening. I don’t have my finger on any pulses in this town. I really, truly auditioned in the dark, not knowing the history of this show already, with [Anthony] Hopkins and Evan Rachel Wood and Mr. [Ed] Harris. And so when I did get the job and I got that list, I was like, “Oh my goodness.” And then when I arrived on set and I understood the scope, and [saw] they were shooting a television show on film, I caught my breath and I really understood how careful these people were being in creating this story.

AVC: It can’t always be the most relaxing atmosphere, for example, when you’re spending shooting days in the middle of giant simulated orgies.

JS: Well, sure. But even that was taped, was done so carefully. Whether we were shooting in the Moab desert under scorching sun or whether it was 300 people who didn’t know each other in different degrees of undress, it was always so carefully executed. And you know, somehow it wasn’t stressful, but the scope was so huge. And that’s why I was kind of always—I had my mouth agape at how Jon [Nolan]and Lisa [Joy, the showrunners] truly had everyone at peace the whole time. So, I think when you have a production of this size, it’s all about how the people at the top are taking care of the masses. And somehow, it was like an old-school movie and everybody did their job and did it well. And so it was both the most difficult job I’ve ever had—the longest hours, the most work—and also, I felt the safest I’ve ever felt. Pretty rare.

Loser (2000)—“Noah”

AVC: According to IMDB, your first credit is as Noah in Amy Heckerling’s Loser from 2000. Is that right?

JS: That’s the truth.

AVC: You played Jason Biggs’ asshole roommate. Was that your first real experience on a set?

JS: It was absolutely my first experience on a set. I was an understudy on a little Broadway production of a play called The Rainmaker and so I was a farmhand, I was carrying some set pieces around. This was the ’90s, so you didn’t have a cellphone. You call your voice service in New York City and you get your messages. So I called my voice service before the play. I had auditioned for that role, did not get it. They started shooting, they fired the guy after a couple days. My agent said, “Hey, they want to fly you to Toronto tomorrow to pick up this role.” And so I had to go, and asked the director, I said, “Hey, what’s happening? I have—” And he said, “I’m not using you, get the hell out.” [Laughs.] And then one of the lead actors on the play, he was excited for me and he goes, “Hey, you gonna share me your per diem?” And I had no idea what he was talking about—it’s the stipend you get to eat when you’re up there. I was clueless.

And I went up and I had one of the greatest experiences of my life, also at the hands of Amy Heckerling, who ran that show. Not everybody saw the movie, but the shooting of it was a wonderful introduction. It was actually a great introduction all around for me, to be honest, because not only did I realize the benefit of a real familial relationship on set—everybody working hard for the love of each other and the craft—but also, that movie—I was a lead in a big movie at the time and then nobody watched it and then nothing really happened. And it was a wonderful introduction to that very thing that happens way way way way more often than not. Instead of working for 10 years to try to get a movie and finally getting it, then have my hopes dashed, it happened right off the bat. And you know, I just proceeded with caution and not too much expectation and really just knowing the only thing that mattered was what I was doing right then. And nothing leads to anything. And so you just try your best. It was a great experience for me, actually.

AVC: As you were filming, did you have that initial youthful assumption of, “This is gonna be huge and life changing”?

JS: Here’s the thing. I’m always cautious. So like, as far as that kind of thing… I don’t buy into shit right away. But I will tell you that when I called my agent that time from the theater, she did say, “Get ready. Your life is about to change.” And I was like, “Oh shit. Hmm. Let’s see.” And then it didn’t. It didn’t at all. [Laughs.] So you know, I think everybody does go in expecting they’re making Gone With The Wind on their first movie. But you know, that’s just not going to be the case, everybody. Hold onto your hat. Buckle in. It’s probably going to take a few.

Late Show With David Letterman (2008-2009)—“Lyle The Intern”

AVC: That’s an awesome credit, but how the hell did it come about in the middle of you doing a bunch of other work at the time?

JS: Again, serendipity. It was not a plan. I was doing a play in New York City. Somehow, I auditioned for a California production of a new Aaron Sorkin play and I got the lead role in this small theater, La Jolla Playhouse. And then somehow that play gets produced by Steven Spielberg and brought to Broadway. And so all of a sudden, I’m on Broadway doing an Aaron Sorkin play. I had no business being there, but I was there and my picture was on posters. And the two writers at the time, the Stangel brothers, were walking by my theater and they had just conceived of the idea of having an asshole come on stage as an intern for Dave. And they saw my face and they said, “That looks like our guy.” [Laughs.]

They called my agent and said, “Hey, David Letterman wants you to do a thing before your show. Like, do a thing.” I’m like, “Yeah, I’ll do a thing.” And so I went in, and I talked to the brothers and they showed me what they had written and then I read it through with them. And then after the top 20, they just pushed me on stage and said, “Just go sit down and do the lines.” And there were cue cards, I probably said half of them. And Dave and I gave each other some shit. I was so unaware of what was happening. I’m used to live theater so it’s—it wasn’t like a big deal, but it was just like—Letterman was talking to me. And I was there with him. And it just worked. And he ended up asking me to do it another dozen times because he had fun, and so the brothers would say, “Hey.” I don’t think the guy knew my first name, David Letterman. But the brothers were like, “Yeah Dave is like, ‘Let’s get Lyle here. Where’s Lyle? Let’s bring Lyle back.’” And then I’d go up and we’d play.

AVC: Wow. So it would just be every once in awhile with David.

JS: Yeah, because I was in New York for six months for that play. So they brought me in like three more times. But then I got back to L.A. and they started flying me out there to go do that bit. So someone flew me on the airplane to go do Letterman. To make fun of him.

AVC: So you would fly in, do the bit, and fly right back out again?

JS: Yep. And they’d let me write some of the copy. And then Letterman would write some of it. And, you know, my buddy Hank Azaria was such a fan of the Lyle stuff and he was just like, “Hey, can I get you to call him a name for me?” I was like, “Sure.” [Laughs.] He’s like, “Will you call Dave Nancy Reagan?” I’m like, “You got it.” And I called him Nancy Reagan. So, I let Hank write one of the insults.

AVC: Do you have any particular lines or things that you remember you wrote for Lyle that you’re particularly proud of?

JS: Oh man. I don’t know. I won’t want to misquote, because they wrote so many lines and Dave came up with so much great bullshit. And a lot of the stuff, he would just say it out of the blue, and I would have to riff on it out of the blue. I know my initial take, I just wanted to keep talking to Paul every time I left with that weird walk I do. And then we just made a bit out of the Paul thing.

AVC: Almost nobody has that kind of experience.

JS: Oh. Dude. I feel so lucky.

It’s Always Sunny In Philadelphia (2005-2013)—“Liam McPoyle”

AVC: For eight years you got to be the Alpha McPoyle.

JS: That’s kind of a product of me and Charlie [Day] being old pals. We lived together in New York City in the ’90s and then we lived together in L.A. when I moved here. He came out and moved in with me. And we would make video after video. This was pre-YouTube and pre-us working. So we would just work ourselves. We would get a 40 at the end of the day and we would shoot stupid bullshit of each other doing sketches. And Liam was kind of a product, or an amalgam of those characters. And he was like, “Hey, I want to do one of your guys on the show.” And you know, the fans were just appalled, delightfully. And so they kept bringing back these disgusting characters. It’s always a pleasure because Chaz and I, we still are thick as thieves and it’s just like playing with buddies when you’re on It’s Always Sunny In Philadelphia. You know, you do one pass on script, and then it’s all whatever you want to come up with. You know, like fork stab. A lot of that stuff was in the moment.

AVC: Oh wow. So for example, your fist bump style just developed spontaneously?

JS: Oh yeah. A lot of that shit, man. Most of the things that I say grotesquely, I’m just saying because I’m trying to crack Glen [Howerton] up or some shit.

AVC: It’s such a great character to get to do. One of my colleagues describes that guy as a “Garbage Pail Kids version of The Dude,” which I think always seemed really accurate to me.

JS: Oooh. I like that. I like that very much. I’m a fan of both of those references. Huge fan.

AVC: Are there notable differences in your experiences playing him from the first couple times you did it to the most recent in 2013?

JS: Ummm… no. [Laughs.] They’re changing—you know, he’s got one eye now. But it’s the same. That’s the thing. A lot of stuff, when you get to play a character over time, you get to change them but I think all of these characters are kind of hobbled fundamentally, and I think that’s the trick of It’s Always Sunny is that no one is really developing. No one is really growing in any way. The execution, I do feel like I can get—just like with any craft, any person, whatever you’re doing, as you do it more, you feel a little bit more bold so you can make some riskier choices, I guess.

Rose Red (2002)—“Kevin Bollinger”

JS: Oh shit. Yeah. That was a huge turning point in my life.

AVC: Not only did you get to do a Stephen King story, you got to play a murderous ghost.

JS: I did. I got to do so many wonderful things from that film. That film, just superficially, I was a huge Fangoria fan growing up. I would save my allowance to buy the magazine. It’s this kind of horror/gore film magazine. And this guy, Greg Funk, was my makeup artist and he did this beautiful, 3-D, gel effect and so they wanted to highlight it. And so I got to be in a two-page spread in Fangoria when I was doing that movie, because I had the zombie makeup. And then on a non-craft scale, I met the woman who I ended up marrying. I met Melanie Lynskey on Rose Red and you know, that changed my life hugely, and for the better, with that relationship. We’re divorced now, but we’re really wonderful friends. That was a huge deal.

That’s also like the first job I got after Loser. Nothing else had really happened until Rose Red. And also, huge Stephen King fan. That man taught me how to read. My father, God knows why, gave me Pet Cemetery as my first novel once I reacted really strongly to Moby Dick, he was like, “Read this.” And it scared the shit out of me, but the writing was so good. So I read everything he ever wrote. It was just after his accident, so he wasn’t around, but I sent him The Eyes Of The Dragon, which is this wonderful kind of D&D-style book he wrote that not many people have read. And Pet Cemetery, because my father gave it to me. And I had him sign them, you know, Pet Cemetery for my dad and The Eyes Of The Dragon for me. And he sent them back and he sent me the money I sent him for postage back. He was very sweet about it.

Gravy (2015)—“Stef”

JS: I like this selection of yours.

AVC: Thank you. I assume that role came about because of your guest appearances on Psych?

JS: Yes. And the guest appearances on Psych came about because of my very close friendship with James Roday. And so James actually wrote the role of Stef, which I play, for himself. And when he was finally able to make this movie he wrote, he decided he’d rather just be behind the camera and for some reason, asked me to play the role he wrote for himself—and that’s what I obligingly did, gratefully.

AVC: Talk about like a murderers’ row of great character actors in one film, between you and Michael Weston, Sutton Foster, Gabriel Luna, Gabourey Sidibe… what it was like while filming?

JS: Oh my God, it was like summer camp if all the kids knew what they were doing. It was beautiful. It was just a really—another tightly oiled group of people really working hard. But this one—the budget was very low. And so all we had was each other. And all we had was our love of James. Everyone was doing it because of a relationship with James on some level. And whether it was special effects or DP or whatever, that was everybody trying to jump into James Roday’s brain and execute his vision for him.

AVC: When you think back on making it, were there any unusual moments or things that stand out, memory-wise?

JS: The day where my girlfriend bit Gabby’s voice box out, it was one of the gorier days, and Molly Ephraim had to be showered. Showered with blood splatter. And [my character] had to be put off because it was just really, she really got her priorities wrong. It wasn’t supposed to happen that way. That was about a two-day experience. So we spent two days with blood just sticking all over the floor, no one being able to move during any break and just there for the love of the craft and for the love of some gore. And Gabby, being the biggest trouper of all, she just fucking made us all laugh and she was the one that was totally covered and had all these prosthetics and she was always up for it. She’s one of my favorites.

Herbie Fully Loaded (2005)—“Crash”
D.E.B.S. (2004)—“Scud”

AVC: I know other actors we’ve spoken to have said that filming those big Disney movies can be a little absurd. What was your experience like?

JS: Well, again, it’s just like serendipity. I just really do approach this craft like everyone I’m working with can be potential family because it’s a really weird thing we’re doing and they’re often asking me to do stuff that’s uncomfortable. So I did this little movie called D.E.B.S., directed by this woman Angela Robinson. And, you know, it was this stressful, low budget—not stressful because of the material, just because we had no money. So, we’re all there working for very little because we thought it was really cool. And we were doing it for Angela because it was a great idea she had, and the result of that was when this independent film director got Herbie Fully Loaded, she asked me to come on and do a role. So, I mean yeah. It’s not like an ideal place to hone your craft, maybe. But Angela made it as close to that as possible. And that was just another thing that was really helpful because all of a sudden I got a Disney paycheck in the middle of being a really broke actor. And so I wasn’t really noticing how lame it was. I was just like, “This is pretty cool that I get to step into this realm and try this hat on for a minute,” and I actually thought the experience was pretty fun.

AVC: Oh, that’s good.

JS: I thought that Disney treated Angela okay as far as I could tell. I mean, I’m sure they didn’t and she didn’t show it but like a good parent, I didn’t know that she was broke.

AVC: [Laughs.] That’s funny that you mentioned it coming from D.E.B.S. because I swear to God that was the next one I’m going to ask you about—from the year before, where you played Scud.

JS: Another interesting monosyllabic name.

AVC: At this point, you’ve been in a few pretty beloved cult queer films, but that one is so over the top and fun. How did you get involved with it?

JS: I swear to God, my career is like this weird origami thing. I was living in New York and I did this NYU student film called Slo Mo. And it was just a kid’s thesis project and another student at NYU at the time happened to see it and she liked my performance and it was Angela Robinson, okay? I don’t know how many years later it is. She’s casting her little independent film, being produced by Power Up, this great pro-women film organization and they gave her some cash to finally get to do her little idea. She had made a short film of that feature. She’s trying to cast this weird little role and she keeps not finding the guy she likes. She’s going through the headshots that the casting director gave her, saying she doesn’t like anybody. She looks at the pile in the trash that the casting director had rejected, and she starts sifting through those. She sees a picture of the kid she really liked from the NYU short film she’d seen almost a decade before. And she’s like, “Let’s bring this kid in.” She brings me in a couple days later and she’s like, “Holy fuck, that was what I want.” And so I did the movie.

AVC: Origami doesn’t quite do justice to how unlikely that is.

JS: It’s full of shit like that. I know! [Laughs.]

AVC: Was that your first time doing lots of that action-type stuff?

JS: D.E.B.S.? Absolutely. What a great observation, I never really thought about it, because I did kind of notice at the time, “Oh, this is something I don’t do.” But it’s a comedy version, so it feels like the stakes aren’t, like, “I gotta be cool.” It was a really comfortable place to start taking a punch or doing a one liner or something like that.

AVC: You spend so much time in that film with just you and Jordana Brewster, and it plays like you guys are having a ball throughout it.

JS: Yeah. I was half having a ball and half amazed at how pretty the person I was in a scene with was. [Laughs.] She was really nice. And I’ll tell you as I tell anyone on the street who says, “Hey man, loved you in D.E.B.S.” It’s literally my favorite reference anyone could make from my work. When someone says, “I loved D.E.B.S.”

House Of Cards (2014-2015)—“Gavin Orsay”

AVC: It seems like a Netflix series like this would be one of the few things comparable maybe to working on an HBO show.

JS: It was similar. They’re the two shows that I’ve worked on that do live up there in that realm—well, maybe The Newsroom as well—where everything is so well oiled that you can’t help but do your best because the machine is there and it’s beautiful and it’s working. And if you’re kind of slow, you lose a hand or you’re going to cause something to go wrong. But it’s not a fearful thing, it’s just the level we’re operating at, so that’s just how you are. And those three shows really did do that well. It was a pleasure to work on something so well thought out.

AVC: As you were saying earlier when you were differentiating it from your role on Westworld, you have this very key arc but it’s also this side plot. It’s not like you’re interacting with Kevin Spacey in the oval office.

JS: Well, here’s the thing. I believe that character was intended to just have those moments with Sebastian in season two. I get that, and it all made a whole lot of sense and I enjoyed my entire arc of both seasons on that. But on the second season, which I think was the result of me and Beau [Willimon, showrunner] getting along and him enjoying writing this character, you know, he goes into that next season. And it felt a little bit like a diversion from the show as opposed to a twist of the main story. It was always my pleasure coming to work, but I did wonder, if I’m being completely honest, “Am I like the Jar Jar Binks?” Do you know what I mean?

AVC: [Laughing.] Totally.

JS: So I was just like… I want to do well. But, why? We’re coming from the Russian president to this guy? Okay.

AVC: That’s some serious doubting of your own work.

JS: If you overthink this, which I like to do. It’s my favorite. You’ll seek out all the reasons why what you’re doing is terrible.

AVC: Do you tend to do that with a lot of projects? Where you’ll overthink it and then you have to pull yourself back and be like, “Calm down.”

JS: Oh, absolutely. I go through life that way. Because I’m not neurotic. I’m one of the most chill people I know. But as far as “the craft” or my relationships with other humans in my life, you just want to do your best. And sometimes you start discounting yourself.

White House Down (2013)— “Skip Tyler”

AVC: I have to ask about the experience of doing a role in a Roland Emmerich blockbuster.

JS: It was awesome. I was actually in a dim phase of my own life, personally. To be asked to fly to the beautiful city of Montreal and shoot with Roland Emmerich, who is basically a white-haired child with a video camera and an endless budget, allowed to make his dreams come true. With a movie starring James Woods where there’s explosions in the White House—it was exactly what I needed. The character was kind of ridiculous but he was also intensely smart. It was just a lovely diversion from my real goings on and that was great. All I did was talk to James Woods about Videodrome and talked to Roland Emmerich about Independence Day and it was a pleasure.

AVC: Did James Woods have good Videodrome stories?

JS: Oh my God, yeah, alternate endings and everything. He was great to talk to. It’s piecemeal in my brain right now, but yeah. If I could recall some of them, I’d tell you. White House Down happened in a kind of dim part of my life. And House Of Cards at the same time. It was just like this little bit of—from being a weirdo in weird things, generally, to House Of Cards asking me to… well, definitely [be] slightly weird. If not very weird. But, like, in a legit project. Allowed me to reevaluate my own self, in a way that gave me a little bit more confidence that I greatly needed at the time.

Hap And Leonard (2016)—“Soldier”

AVC: Are there any roles or projects that you did that you don’t feel got the love they should?

JS: Oh, absolutely. One. Hap And Leonard. Do you know what that is?

AVC: Yeah, the SundanceTV series.

JS: I think that is a gorgeous work of current independent television. I think what [creator] Jim Mickle did was, he brought this gripping noir storytelling to a serial six episode experience for Sundance Channel. I think it’s the counterattack to what Westworld is doing with the new medium of television. Where they [HBO] are saying, “Hey, if we have endless resources and the greatest storytellers in the world, we can actually make commentary and push our cultural needle forward.” I feel like on the other end, what Jim Mickle and Sundance are doing is saying, “If we have no money and just a great director and storyteller—and you know the novels that were so beautifully written—this is what we can do on the other side with very little resources.” And then in the middle of the pool, currently, we have all of this shwag where it’s like, “Hey this is super specific to these brains and so we don’t really have to worry about the craftsmanship. They’ll consume it.” I like what Jim Mickle and [Westworld showrunners] Jonah and Lisa are doing more. And I’m really proud that I was in these two beautiful examples of what current television can be.

AVC: That was a very good, impassioned answer to that.

JS: [Laughs.] Well, my pleasure. I feel strongly.

AVC: Last year The A.V. Club published a field guide to character actors we liked. And we listed that your specialties included playing “psychos and quiet nerdy types,” which is really running the gamut from one end of things to the other. Do you feel drawn to certain types of roles more than others these days, or no?

JS: It’s the same thing I’ve always been drawn to, and it’s funny. I think it’s the definition of why I’ve played those roles. My dream while performing is connection with the person and then the people I’m in the scene with, and so that’s always where I’m shooting. And because I look the way I look—and let’s be honest, it’s not your typical matinee idol—coming into a pool of auditioning actors, I would have been sifted into offbeat types. And then my personal attack on this craft has to do with connection. And so I’d imagine it would have been refreshing to a lot of people, because a lot of actors want to be leads and see themselves as leads. So when they come and play satellite characters, they’re like, “Well, this guy is twisted, so he’s twisted.” And that’s not really my take. I know a lot of different weird people and they always think what they’re doing is the right way. And that has always been my take on the nerd or the psychopath, so people respond to it.

And now, as I get older, people are seeing me as slightly more… consumable, I guess? I’m still doing the same thing, as far as that’s my main goal. And now that I look somewhat more approachable, I guess, now I’m able to do that in different roles. It’s always going to be that for me. I’m going to be looking for someone who is interesting, and who is thinking about what they’re doing, whether or not what they’re doing is evil or good. And, someone who is connecting with other characters in the story. And that what ties all this stuff together. It’s just how people see me that’s adjusting my roles, I think.

AVC: Do you feel like you’ve noticed the way people see you in terms of roles that you’ve been doing and stuff, seems like it’s changing as you get older?

JS: Absolutely. I got cast in what I could get cast in, you know? The medium of television, there’s a consumer so things do have to look a certain way, and I looked weird. My hair was always weird and I was pretty scrawny and awkward and I acted as uncomfortable in my body as I felt, as me. And that was what I could play. And I’m changing, I’m a little more sure of myself. I don’t really care as much what people think about me, and I think that probably reads. And so, I’m able to play those roles now. And definitely, it’s definitely a noticeable change in the stuff people are seeing me in.