Lillard debuts as Mr. Charles, who “bends the ear of very powerful people around the world.”

Matthew Lillard previews ‘Cheshire Cat’ Daredevil role and his D&D group that led to the gig

Lillard debuts as Mr. Charles, who "bends the ear of very powerful people around the world."

By Nick Romano

Nick Romano

Nick Romano is a senior editor at ** with 15 years of journalism experience covering entertainment. His work previously appeared in Vanity Fair, Vulture, IGN, and more.

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March 16, 2026 10:30 a.m. ET

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Matthew Lillard as Mr. Charles in 'Daredevil: Born Again' season 2. Credit:

- Matthew Lillard shares he's the Dungeon Master for a *Dungeons & Dragons* group that includes the *Daredevil: Born Again* showrunner.

- Lillard describes his season 2 role of Mr. Charles as having a "Cheshire Cat sort of energy."

- "He's not really interested in Gotham politics. He's interested in world politics."

Picture this: You're a working Hollywood actor and running a *Dungeons & Dragons* group for some of the most prominent names in television.

Seated before you, as the Dungeon Master crafting a fantasy role-playing narrative, are Max Nix, the creator of *Burn Notice* who's currently developing the *Baywatch** *reboot; Elwood Reid, who heads the CBS action-drama *Tracker*; fellow actor Abe Benrubi (*ER*, *Parker Lewis Can't Lose*); Dario Scardapane, showrunner for *Daredevil: Born Again*; and Scardapane's wife, Jen J.

This is very much Matthew Lillard's reality. "I am the Dungeon Master for all these incredibly powerful showrunners in Hollywood," he tells **. "It's hilarious because they are not used to having somebody tell them the story or shape the story for them. So it's been a very interesting journey as we run *Curse of Strahd* [campaign] for the last three years."

Did this situation result in Scardapane creating a role for Lillard, that of Mr. Charles, in *Daredevil: Born Again* season 2 (premiering on Disney+ March 24)? "Kinda," the *Scream 7* and *Cross* actor acknowledges.

Vincent D'Onofrio, Ayelet Zurer, and Matthew Lillard on 'Daredevil: Born Again' season 2.

Jojo Whilden/MARVEL

In truth, Lillard's relationship with Scardapane, and therefore Reid, goes back to *The Bridge*, that FX detective drama fronted by Diane Kruger. Lillard played Daniel Frye, a reporter for the *El Paso Times* with a substance abuse issue, while Reid served as one of the showrunners and Scardapane worked in the writers' room.

"They would allow me to improv stuff and bring idiosyncratic beats to it," Lillard recalls. "And the more that we worked together, the more they trusted me. The more they trusted me, the more I got to play. I think that's what Dario was hoping I would bring to Mr. Charles."

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*Daredevil: Born Again*'s second season, designed as a Part 2 to the season 1 story, depicts the rise of the resistance after Mayor Wilson Fisk (Vincent D'Onofrio), a.k.a. the Kingpin, has taken complete authoritarian control over New York City. As Fisk's anti-vigilante task force abducts dissidents off the street, locking them away in an undisclosed warehouse full of cages, Daredevil (Charlie Cox) becomes a symbol of rebellion for those willing to fight back.

"The story is about power," Brad Winderbaum, the head of Marvel TV, described of the season. "When Wilson Fisk takes over New York, not just as a mayor but as a king in a way, it puts him in a new class of power players on the international stage. Matthew Lillard's character represents that."

Daredevil (Charlie Cox) on 'Daredevil: Born Again' season 2.

Courtesy of Marvel Television

Cox doesn't share scenes with Lillard, as Mr. Charles operates in that upper echelon, but the star called the role "delicious."

"He is somebody who bends the ear of very powerful people around the world. So he's not really interested in Gotham politics. He's interested in world politics," Lillard explains — using the term "Gotham" to describe New York City and not mixing up Marvel comic book locations with DC. "So when he is dealing and trifling with someone like Kingpin, he's not that impressed. That's all I can say, you know? There's this Cheshire Cat sort of energy about him."

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In Lillard's eyes, Scardapane — who plays a bard in the D&D group, by the way — wrote something that allows him to do what he does best: play. He felt it in his many scenes with D'Onofrio, whom Lillard knows from working together on Oz Scott's 2000 drama *Spanish Judges*.

"He's a lot of fun," Lillard says of Mr. Charles. "You sort of can't do too much with him in this world that's really tense and really buttoned-down, and along comes, you know, Matthew Lillard chewing scenery. So for me, it's a lot of fun. I think that he plays well in the world and I'm excited for people to see him."

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