Jimmi Simpson on Dillard’s Death and Relationship With Negan (Exclusive)

Jimmi Simpson‘s Mason Dillard completely altered the fabric of AMC’s TWD spinoff, The Walking Dead: Dead City in Season 3. Not only was his eccentric survivor a hilarious addition to the series — who knew that Negan (Jeffrey Dean Morgan) needed a buddy to play video games with? — but his turn towards becoming the season’s Big Bad in the latter episodes made it impossible to look away. Warning: Spoilers for The Walking Dead: Dead City Season 3 Finale, Episode 8, “Tenebrae,” ahead!

And so, it’s with a heavy heart that Negan said goodbye to his pal-turned-enemy in the third season ender. At least Dillard is finally with the walkers that he swore he could communicate with, shuffling into the great beyond. Below, TV Insider caught up with Simpson to talk all things Walking Dead.

First, how many times did you break while you had these actors, in walker grab, gnawing on your arm during scenes this season? Did you get used to it after awhile?

Jimmi Simpson: It’s not a matter of breaking. As Jeffrey said in an interview we just did together, we don’t have that much time with a show like The Walking Dead. It’s probably, like, a 10-day shoot that we do in eight. And so both of us had to be as professional as possible, and not let every take with each other crack each other up. But then also with Kristina [Ellery] and Joshua [Hernandez], who play Titicaca and Cockenspiel, they came in like Shakespearean-trained actors. They’re both really brilliant. And they came in so committed and they’d gone through so much work each morning to look so off-putting, and yet this humanity shined through every single time. So, when Titicaca was gnawing on my shoulder, it seems so ridiculous, but I could feel her intention every single time, and Joshua the same, so present.

Had you been a fan of The Walking Dead going into this or did you have to catch up and figure out what was going on?

There was some catching up that I needed to do. The stuff I’d seen, it was just because I’m a bit of a gorehound from the ’80s. And my favorite kind of gore is when it’s just bumped up from reality a little bit. And so, there is a little sense of humor, even though everything is pretty precious in survival mode, generally, on The Walking Dead. But yeah, I was a fan of what everybody was doing.

At what point did you find out that Dillard would be the villain this season? Did you know going into the role? 

I did. So, for Westworld, I had no idea that I was going to be the Man in Black. Which is really fun because as an actor, your job is to withhold the ending. Whereas, here, it was part of the pitch when they came to me about this role. And this was before I had done all of my research. And so Seth Hoffman, the showrunner, saying, “This is the first man who believes he can speak to the walkers,” and then ultimately, the ending, was a huge draw for me because Dillard’s break, like William’s, is based on emotional heartbreak.

And with heartbreak, sometimes you have these passing thoughts of vengeance. “I hope they hurt as much as I do. I hope that they’re feeling the way I’m feeling.” Dillard is going about actively trying to make Negan feel the pain that he feels by this friendship ending.

Robert Clark/AMC

How do you think Dillard feels about Negan in his final moments?

In the very, very final moments, I think Dillard’s aware of the futility of the path that he’s chosen. And it’s just too late. But there’s a moment that is so real for both of them, that Negan’s able to facilitate — Dillard’s natural conclusion being what only Negan and Dillard know is what he needs, which is to actually fall back into the community that he’s felt the closest with in his life. And so this existential sigh of relief that Dillard feels becoming a walker is one of the things that drew me to saying yes to Dillard.

Before Dillard took his final breaths, you also got to do the Negan whistle and hold [Negan’s barbed-wire bat] Lucille. That had to be fun. Did JDM give you any pointers while you were shooting those scenes?

It’s more of observing what Jeffrey had done. And then, you know, [Negan’s] so protective of that bat. Just the act of him allowing Dillard to hold it was like another element of the bonding of those two.

Tell me about shooting the fake sitcom that we see at the top of the episode. How do you interpret that scene from Dillard’s mind?

It’s so clarifying. It’s basically an attempt to let the audience in on how Dillard sees things, and it takes away some of the gore and the awfulness, because Dillard really does see the humanity in all creatures. He does feel that echo of humanity in everyone, and that’s what he sees the most, you know? When Cockenspiel’s arm is falling off, Dillard reacts as if his buddy was just injured in like a tree-chopping incident. It’s the articulation of all of what you see from Dillard prior to that.

Robert Clark/AMC

“Seeing the humanity in all creatures” — you actually have a lot of different creatures that you had to interact with this season. Turkeys, frogs…

I’m a creature lover, so [I enjoyed] getting to know the turkeys, spending time with the frogs, and seeing if I could calm them down enough to get some good takes. And even the maggots, you know, there was always someone on set — not a single maggot could be harmed during the filming. Each one was accounted for. I was just bummed I didn’t get any on-camera time with the coyotes.

Looking back on this season as a whole, did you have any favorite moments from shooting?

When Dillard and Negan both put down their perspective bats. Dillard puts his [undead] friends downstairs and asks him, “You wanna show me that video game you’re always playing?” And Negan’s like, “You wanna see it?” And it’s just two buddies like, “Wait, do we love each other?”

Between Westworld, Dark Matter, and TWD, you’ve got more than a few sci-fi shows under your belt now. Are you looking to continue the trend of doing more sci-fi projects, or do you think that you want to try something different next?

I basically choose roles by reading something and feeling like, “Oh, I’m not sure how to do that.” And then I’m like, “Well, that means I should probably try it.” So, that happens to be, right now, a lot of science fiction. And right now, the world needs a little bit of escape. Predictive sci-fi, where you’re taking things that exist now and you’re kind of painting them as what they could be, that feels like we’re talking about the future in a way that doesn’t really bum us out, because it’s just a little removed from reality. And there’s so much room to play there.

Working on Westworld, on Black Mirror, on Dark Matter, on Dead City, all of these are some of my favorite roles. It’s the roles that got me there, more than the genre, but I love the genre. I’ve loved the genre since I was a little boy reading Ray Bradbury and Isaac Asimov.

The Walking Dead: Dead City, Seasons 1-3, Streaming Now, AMC+