Matthew Lillard Teases His Mysterious “Cheshire Cat” Role in DAREDEVIL: BORN AGAIN Season 2
When Daredevil: Born Again returns for Season 2, it’s bringing in a wildcard that doesn’t punch, bleed, or wear a mask. Instead, Matthew Lillard is stepping into the Marvel Cinematic Universe with a character who plays a completely different game, one rooted in influence, observation, and global power.
Lillard’s debut arrives on March 24, and while fans might expect another street-level player tangled up in Daredevil’s war with Wilson Fisk, Mr. Charles operates on an entirely different level. He isn’t part of the chaos unfolding in New York City. He’s watching it, analyzing it, and maybe even enjoying it.
Trying to pin down who this guy is, Lillard landed on a comparison that says a lot without spelling everything out. “There’s this Cheshire Cat sort of energy about him,” Lillard told Entertainment Weekly.
That description tracks. Mr. Charles sounds like someone who drifts through high-stakes situations with a knowing smile, never rattled, never rushed. While Fisk tightens his grip on the city and Daredevil rises as a symbol of resistance, this guy is playing a much bigger board.
“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 noted, using “Gotham” casually for New York without confusing Marvel and DC territories.
“So when he is dealing and trifling with someone like Kingpin, he’s not that impressed. That’s all I can say, you know?”
That one detail alone flips expectations. Kingpin might be the most dangerous man in New York, but to Mr. Charles, he’s just another piece on the board.
Marvel Television boss Brad Winderbaum gave more context on how this character fits into the bigger picture. As Fisk’s influence grows, it draws attention from players operating on a global scale. Mr. Charles represents that world looking in, and possibly interfering.
Winderbaum also made it clear that Lillard brings a unique energy into a show that’s otherwise grounded and intense.
“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,” he added.
Even without sharing scenes with Charlie Cox’s Daredevil, Lillard still found plenty to work with, especially reuniting with Vincent D’Onofrio, whom he previously worked with on Spanish Judges. That history adds an extra layer to their on-screen dynamic, even if their characters are operating from very different positions of power.
What makes this casting even cooler is how it came together. Lillard spent years as a Dungeon Master in a Dungeons & Dragons campaign that included Daredevil: Born Again showrunner Dario Scardapane.
That creative collaboration eventually led to Scardapane shaping Mr. Charles specifically for Lillard, which explains why the character already feels so tailored and distinct.
So while Season 2 is packed with tension, rebellion, and brutal street-level conflict, Mr. Charles looks like he’ll be something else entirely. A calm presence in the middle of chaos. A man who smiles while everything burns.
That might make him one of the most dangerous players in the entire series.