Mason Dillard, the eccentric survivor who bonded over video games with Negan, turned the tables in Season 3 of The Walking Dead: Dead City. Jimmi Simpson spoke with TV Insider about the finale, the walkers, and why Dillard’s descent into villainy felt inevitable.
Dillard went from a funny sidekick to the season’s main antagonist. The twist landed with a dramatic payoff in the third-season finale, Episode 8, “Tenebrae.” Simpson talked about the physical demands of the role, the cast chemistry, and the meaning behind his character’s final moments.
Breaking While Walkers Grab
Simpson faced a literal problem throughout the season: walkers grabbing his arm. The scenes required actors to look convincingly terrified while walkers gnawed on them.
“It’s not a matter of breaking,” Simpson said. “We don’t have that much time with a show like The Walking Dead. It’s probably a 10-day shoot that we do in eight.”
Both Simpson and Jeffrey Dean Morgan had to stay professional, he explained. The cast of Titicaca and Cockenspiel, played by Kristina Ellery and Joshua Hernandez, brought a Shakespearean intensity to their roles.
“They’re both really brilliant,” Simpson said. “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.”
Catching Up With The Walking Dead
Simpson admitted he needed to catch up before taking on Dillard. The show’s history was extensive, and he wanted to understand the world he was entering.
“There was some catching up that I needed to do,” he said. “The stuff I’d seen, it was just because I’m a bit of a gorehound from the ’80s.”
He appreciated the show’s balance of horror and humor. “There is a little sense of humor, even though everything is pretty precious in survival mode, generally, on The Walking Dead,” he noted.
The Villain Pitch
Simpson knew from the start that Dillard would become the season’s villain. The pitch itself sold him.
“For Westworld, I had no idea that I was going to be the Man in Black,” he said. “Which is really fun because as an actor, your job is to withhold the ending.”
Here, the pitch included the reveal. Seth Hoffman, the showrunner, described Dillard as “the first man who believes he can speak to the walkers.” The ending, where Dillard breaks, was based on emotional heartbreak.
“Like William’s, is based on emotional heartbreak,” Simpson said. “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’s plan was simple: make Negan feel the pain of losing their friendship.
Dillard’s Final Feelings
The finale gave Dillard a moment of clarity. Simpson said his character became aware of the futility of his path, but it was too late.
“In the very, very final moments, I think Dillard’s aware of the futility of the path that he’s chosen,” he said. “But there’s a moment that is so real for both of them, that Negan’s able to facilitate.”
Dillard’s natural conclusion was to fall back into the community he felt closest to. Becoming a walker offered him an existential sigh of relief.
“That 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,” Simpson said.
The Negan Whistle And Lucille
Simpson got to play with Negan’s signature weapons in the finale. He held Lucille, the barbed-wire bat, and even did the Negan whistle.
“It’s more of observing what Jeffrey had done,” he said. “And then, you know, [Negan’s] so protective of that bat.”
The act of Negan allowing Dillard to hold Lucille was another element of their bond. Simpson found the scene rewarding, even if it was brief.
The Fake Sitcom Scene
The episode opens with a mock sitcom framing. Simpson saw it as a way to show how Dillard sees the world.
“It’s so clarifying,” he said. “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.”
Dillard sees the humanity in all creatures. Even when Cockenspiel’s arm falls off, Dillard reacts as if his buddy was just injured in a tree-chopping incident.
“It’s the articulation of all of what you see from Dillard prior to that,” Simpson said.
Creature Interactions
Dillard spent the season surrounded by animals. Simpson had to work with turkeys, frogs, and maggots.
“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,” he said.
Each maggot was accounted for during filming. No creature was harmed.
“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,” he said.
He was bummed he didn’t get any on-camera time with the coyotes.
Favorite Moments From The Season
Simpson had a clear favorite from the season. It came when Dillard and Negan both put down their respective bats.
“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,” Simpson recalled.
That moment captured the friendship that defined their arc.
What We Make Of It
Simpson’s interview shows a performer who found joy in the absurdity of the role. He approached the walkers, maggots, and the sitcom framing with genuine enthusiasm.
The character’s journey from comic relief to antagonist is complete. Simpson framed it as Dillard finding peace in his community.
“The existential sigh of relief that Dillard feels becoming a walker is one of the things that drew me to saying yes to Dillard,” he said.
The season ended with Negan saying goodbye to his friend-turned-enemy. Dillard is finally with the walkers he believed he could communicate with.
The Walking Dead: Dead City Season 3 has concluded. Simpson’s performance carried Dillard from amusing sidekick to a character whose choices defined the season.
- Show: The Walking Dead: Dead City
- Season: 3
- Episode: 8, “Tenebrae”
- Main antagonist: Mason Dillard (played by Jimmi Simpson)
- Cast: Jeffrey Dean Morgan (Negan), Kristina Ellery (Titicaca), Joshua Hernandez (Cockenspiel)
Simpson’s account offers a rare glimpse into the creative process behind one of television’s most memorable villains.
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